9183
Context
Xanthine Dehydrogenase Deficiency (Xanthinuria)
The rare genetic disorder, Xanthinuria (also referred to as xanthine oxidase deficiency) results from a deficiency of the enzyme xanthine oxidase. This enzyme deficiency causes the accumulation of: xanthine in the plasma, uric acid in serum or hypoxanthine, uric acid and xanthine in the urine. The disorder has symptoms including arthralgia, hematuria, mental retardation, stomatisis, and urolithiasis.
Disease
PW121976
Center
PathwayVisualizationContext122252
3500
5600
#000099
PathwayVisualization88107
88233
Purine Metabolism
Purines are heterocyclic aromatic organic compounds, consisting of a pyrimidine ring fused to an imidazole ring. Purines, including substituted purines, are the most widely distributed kind of nitrogen-containing heterocycle in nature. The two most important purines are adenine and guanine. Other notable purines are hypoxanthine, xanthine, theobromine, caffeine, uric acid and isoguanine. Purines are found in a number of other important biomolecules, such as ATP, GTP, cyclic AMP, NADH, and coenzyme A. This pathway depicts a number of processes including purine nucleotide biosynthesis, purine degradation and purine salvage. The major site of purine nucleotide synthesis is in the liver. Synthesis of the purine nucleotides begins with PRPP and leads to the first fully formed nucleotide, inosine 5'-monophosphate (IMP). IMP synthesis begins with 5-phospho-α-ribosyl-1-pyrophosphate, PRPP. Through a series of reactions utilizing ATP, tetrahydrofolate (THF) derivatives, glutamine, glycine and aspartate this pathway yields IMP. The rate limiting reaction is catalyzed by glutamine PRPP amidotransferase which drives the reaction with PRPP and glutamine yielding 5-phosphoribosylamine (PRA). 5-phosphoribosylamine is converted to glycinamide ribotide (GAR) then to formyglycinamide ribotide (FGAR). This set of reactions is catalyzed by a trifunctional enzyme containing GAR synthetase, GAR transformylase and AIR synthetase. FGAR is converted to formylglycinamidine-ribonucleotide (FGAM) by formylglycinamide synthase. FGAM is then converted by aminoimidzaole ribotide synthase to 5-aminoimidazole ribotide (AIR) then carboxylated by aminoimidazole ribotide carboxylase to carboxyaminoimidazole ribotide (CAIR). CAIR is then converted to succinylaminoimidazole carboxamide ribotide (SAICAR) by succinylaminoimidazole carboxamide ribotide synthase followed by conversion to AICAR (via adenylsuccinate lyase) then to FAICAR (via aminoimidazole carboxamide ribotide transformylase). FAICAR is finally converted to inosine monophosphate (IMP) by IMP cyclohydrolase. Because of the complexity of this synthetic process, the purine ring is actually composed of atoms derived from many different molecules. The N1 atom arises from the amine group of Asp, the C2 and C8 atoms originate from formate, the N3 and N9 atoms come from the amide group of Gln, the C4, C5 and N7 atoms come from Gly and the C6 atom comes from CO2. IMP represents a branch point for purine biosynthesis, because it can be converted into either AMP or GMP through two distinct reaction pathways. AMP is generated from IMP via adenylsuccinate synthetase (which adds aspartate) and adenylsuccinate lyase. GMP is generated via the action of IMP dehydrogenase and GMP synthase. Catabolism of purine nucleotides ultimately leads to the production of uric acid. Beginning from AMP, the enzymes AMP deaminase and nucleotidase work in concert to generate inosine. Alternately, AMP may be dephosphorylate by nucleotidase and then adenosine deaminase (ADA) converts the free adenosine to inosine. The enzyme purine nucleotide phosphorylase (PNP) converts inosine to hypoxanthine, while xanthine oxidase converts hypoxanthine to xanthine and finally to uric acid. GMP and XMP can also be converted to uric acid via the action of nucleotidase, PNP, guanine deaminase and xanthine oxidase. The synthesis of nucleotides from the purine bases and purine nucleosides takes place in a series of steps known as the salvage pathways. The free purine bases, adenine, guanine, and hypoxanthine, can be reconverted to their corresponding nucleotides by phosphoribosylation. Two key transferase enzymes are involved in the salvage of purines: adenosine phosphoribosyltransferase (APRT), which catalyzes the conversion of adenine to AMP and hypoxanthine-guanine phosphoribosyltransferase (HGPRT), which catalyzes the conversion of hypoxanthine to IMP.
Metabolic
17
108623
99
SubPathway
107759
190
Compound
135
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
2
Platelet
CL:0000233
8
Beta cell
CL:0000639
6
Myocyte
CL:0000187
1
Homo sapiens
9606
Eukaryote
Human
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
2
Bacteria
2
Prokaryote
Bacteria
3
Escherichia coli
562
Prokaryote
19
Schizosaccharomyces pombe
4896
Eukaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
21
Xenopus laevis
8355
Eukaryote
African clawed frog
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
25
Escherichia coli (strain K12)
83333
Prokaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
23
Pseudomonas aeruginosa
287
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
51
Picea sitchensis
3332
Eukaryote
Sitka spruce
5
Cytoplasm
GO:0005737
6
Lysosome
GO:0005764
4
Peroxisome
GO:0005777
3
Mitochondrial Matrix
GO:0005759
2
Mitochondrion
GO:0005739
10
Cell Membrane
GO:0005886
11
Extracellular Space
GO:0005615
16
Lysosomal Lumen
GO:0043202
7
Endoplasmic Reticulum Membrane
GO:0005789
1
Cytosol
GO:0005829
18
Melanosome Membrane
GO:0033162
13
Endoplasmic Reticulum
GO:0005783
25
Golgi apparatus
GO:0005794
14
Mitochondrial Outer Membrane
GO:0005741
12
Mitochondrial Inner Membrane
GO:0005743
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
15
Nucleus
GO:0005634
31
Periplasmic Space
GO:0005620
35
Chloroplast
GO:0009507
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
40
Periplasm
GO:0042597
27
Peroxisome Membrane
GO:0005778
32
Inner Membrane
GO:0070258
19
sarcoplasmic reticulum
GO:0016529
26
Golgi apparatus membrane
GO:0000139
24
Mitochondrial Intermembrane Space
GO:0005758
39
Mitochondrial membrane
GO:0031966
8
Smooth Endoplasmic Reticulum
GO:0005790
1
Liver
BTO:0000759
72
9
4
Adrenal Medulla
BTO:0000049
71
8
25
Intestine
BTO:0000648
28
Stomach
BTO:0001307
155
26
7
Nervous System
BTO:0001484
8
Blood Vessel
BTO:0001102
74
11
11
Heart
BTO:0000562
73
10
24
Brain
BTO:0000142
89
16
2
Endothelium
BTO:0000393
18
Pancreas
BTO:0000988
5
cardiocyte
BTO:0001539
9
Muscle
BTO:0000887
141
18
3
Sympathetic Nervous System
BTO:0001832
8
5
1
1
PW_BS000008
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5
18
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PW_BS000024
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5
12
1
PW_BS000111
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5
5
1
PW_BS000122
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5
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PW_BS000135
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6
1
1
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PW_BS000004
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10
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PW_BS000014
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1
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PW_BS000013
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11
1
PW_BS000015
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1
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PW_BS000010
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18
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1
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1
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7
1
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PW_BS000049
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1
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25
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PW_BS000043
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4
10
1
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PW_BS000024
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14
1
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PW_BS000022
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PW_BS000046
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PW_BS000017
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1
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PW_BS000029
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PW_BS000070
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PW_BS000159
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PW_BS000001
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PW_BS000152
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PW_BS000024
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PW_BS000160
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PW_BS000024
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PW_BS000024
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25
18
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PW_BS000024
215
6
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PW_BS000024
216
4
18
1
PW_BS000024
210
13
18
1
PW_BS000024
212
1
7
18
1
PW_BS000024
222
3
4
1
PW_BS000024
224
2
4
1
PW_BS000024
190
11
18
PW_BS000024
170
18
PW_BS000170
225
35
4
1
PW_BS000024
226
4
4
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PW_BS000024
162
12
18
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PW_BS000162
26
1
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PW_BS000026
277
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2
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PW_BS000024
164
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PW_BS000164
281
1
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36
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34
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PW_BS000065
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PW_BS000024
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PW_BS000024
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11
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PW_BS000024
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PW_BS000024
315
1
23
PW_BS000024
318
31
23
PW_BS000024
322
1
23
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PW_BS000024
293
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1
PW_BS000024
253
5
4
1
PW_BS000024
132
1
12
1
PW_BS000132
133
3
12
1
PW_BS000133
134
12
12
1
PW_BS000134
331
7
12
1
PW_BS000028
332
1
7
12
1
PW_BS000028
333
1
2
12
PW_BS000028
115
10
12
PW_BS000115
334
4
12
1
PW_BS000028
336
1
12
1
PW_BS000028
337
1
16
12
1
PW_BS000028
341
4
1
12
1
PW_BS000028
343
18
12
1
PW_BS000028
347
1
3
12
5
PW_BS000028
329
14
12
1
PW_BS000028
352
25
12
PW_BS000028
353
25
12
7
PW_BS000028
356
25
12
1
PW_BS000028
360
4
10
12
1
PW_BS000028
368
3
60
1
PW_BS000028
370
2
60
1
PW_BS000028
228
36
1
PW_BS000024
119
2
17
1
PW_BS000119
383
7
5
1
PW_BS000100
384
12
5
1
PW_BS000100
390
7
6
1
PW_BS000112
391
12
6
1
PW_BS000112
398
7
17
1
PW_BS000113
232
40
3
PW_BS000024
406
3
5
1
PW_BS000115
407
2
5
1
PW_BS000115
408
4
5
1
PW_BS000115
124
1
5
1
PW_BS000124
412
1
2
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PW_BS000115
405
10
5
PW_BS000115
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11
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PW_BS000115
415
18
5
1
PW_BS000115
414
1
5
5
1
PW_BS000115
425
1
3
5
5
PW_BS000115
429
1
5
1
PW_BS000115
121
12
17
1
PW_BS000121
419
25
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10
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1
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120
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374
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PW_BS000115
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2
17
PW_BS000115
376
10
17
PW_BS000053
137
11
17
PW_BS000137
447
1
7
17
1
PW_BS000115
136
13
17
1
PW_BS000136
448
1
16
17
1
PW_BS000115
451
18
17
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PW_BS000115
450
1
5
17
1
PW_BS000115
460
1
3
17
5
PW_BS000115
464
1
17
1
PW_BS000115
455
25
17
1
PW_BS000115
469
4
10
17
1
PW_BS000115
399
14
17
1
PW_BS000113
471
25
17
PW_BS000115
472
25
17
7
PW_BS000115
297
5
10
1
PW_BS000024
479
3
10
1
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PW_BS000115
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10
1
PW_BS000115
299
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18
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PW_BS000115
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13
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10
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24
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2
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32
1
15
1
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39
7
1
1
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1
14
1
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PW_BS000058
59
27
1
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PW_BS000059
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18
5
1
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PW_BS000066
51
8
1
PW_BS000051
23
15
1
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PW_BS000023
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8
5
1
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2
PW_BS000089
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1033
Diguanosine tetraphosphate
HMDB0001340
Diguanosine tetraphosphate is a diguanosine polyphosphate. Diguanosine polyphosphates (GpnGs) are found in human platelets, among a number of dinucleoside polyphosphates, which vary with respect to the number of phosphate groups and the nucleoside moieties; not only diguanosine polyphosphates (GpnG) are found, but also mixed dinucleoside polyphosphates containing one adenosine and one guanosine moiety (ApnG). The vasoactive nucleotides that can be detected in human plasma contain shorter (n=2-3) and longer (n=4-6) polyphosphate chains. GpnGs have not yet been characterized so far with respect to their effects on kidney vasculature. (PMID: 11159696, 11682456, 11115507).
4130-19-2
C01261
165186
15883
CPD-609
144813
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C3N=C(N)NC4=O)[C@@H](O)[C@H]2O)C(=O)N1
C20H28N10O21P4
InChI=1S/C20H28N10O21P4/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(47-17)1-45-52(37,38)49-54(41,42)51-55(43,44)50-53(39,40)46-2-6-10(32)12(34)18(48-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1
OLGWXCQXRSSQPO-MHARETSRSA-N
{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinic acid
868.3858
868.038094056
-1.90
12
diguanosine tetraphosphate
0
-4
FDB022564
(ppg)2;Bis(5'-guanosyl) tetraphosphate;Bis(guanylyl) diphosphate;G(5')p4(5')g;Gp4g;Gppppg;Guanosine(5')tetraphospho(5')guanosine;P1,p4-bis(5'-guanosyl) tetraphosphate;[5-(2-amino-6-hydroxy-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-[[[[5-(2-amino-6-hydroxy-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-phosphinic acid;Diguanosine tetraphosphate;P(1),p(4)-bis(5'-guanosyl) tetraphosphoric acid;Bis(5'-guanosyl) tetraphosphoric acid;Bis(guanylyl) diphosphoric acid;Diguanosine tetraphosphoric acid;P1,p4-bis(5'-guanosyl) tetraphosphoric acid
PW_C001033
Guan2P4
1731
8
11768
198
78666
111
121845
122
124398
135
1420
Water
HMDB0002111
Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71% of Earth's surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the body's solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the sun's energy to split off water's hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the sun's energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia).
7732-18-5
C00001
962
15377
937
O
H2O
InChI=1S/H2O/h1H2
XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
18.0153
18.010564686
1
water
0
0
FDB013390
Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;Wasser
PW_C001420
H2O
55
8
94
9
109
5
139
4
151
3
162
14
481
13
526
15
624
28
652
10
691
20
770
33
823
18
838
2
1094
31
1377
49
1465
54
1590
43
2018
24
2532
22
2678
60
2727
46
2778
17
2805
29
3143
70
3164
72
3634
61
4598
36
4727
37
4941
93
5030
27
5156
7
5195
97
5214
100
5227
94
5236
103
5297
105
5319
111
5343
113
5355
112
5402
110
5470
123
5483
125
5492
126
5507
127
5534
130
5537
114
5541
129
5591
135
5608
118
5622
108
5691
6
5759
140
5778
101
5841
143
5853
146
5877
107
5890
95
5910
147
5940
151
6032
155
6059
157
6087
161
6123
163
6133
159
6215
1
6218
166
6477
178
6507
180
6600
152
6713
117
6840
188
6888
160
7162
205
7181
207
7193
206
7211
211
7228
213
7238
214
7243
215
7295
198
7350
216
7388
210
7401
212
7467
222
7492
224
7500
190
7588
170
8201
225
8237
226
8414
162
9265
26
11850
277
11922
164
12011
281
12213
285
12250
286
12264
287
12327
249
12520
227
12632
65
12693
290
12705
291
12715
292
13007
298
13019
300
13025
301
13037
302
13261
223
13327
294
15340
308
42327
315
42695
318
43691
322
76914
293
77019
253
77102
132
77131
133
77215
134
77378
331
77397
332
77471
333
77516
115
77536
334
77628
336
77722
337
77759
341
77816
343
77982
347
78071
329
78235
352
78242
353
78270
356
79113
360
80014
368
80039
370
80591
228
80656
119
93830
383
94794
384
110557
390
110639
391
115844
398
119879
232
119915
122
119963
406
120008
407
120046
408
120113
124
120365
412
120430
405
120438
409
120606
415
120794
414
121158
425
121240
429
121351
121
121381
419
121607
434
122118
382
122384
436
122753
120
122797
374
122804
443
123012
446
123064
376
123072
137
123131
447
123142
136
123162
448
123231
451
123384
450
123730
460
123810
464
123940
455
124165
469
124670
399
124938
471
124945
472
125305
297
125353
479
125386
481
125424
482
125480
299
125682
483
125707
478
125745
487
126054
490
126238
495
126273
484
126764
480
126896
501
126963
502
127017
388
127177
208
127199
209
127227
504
127506
507
127576
515
127836
389
128082
395
128176
513
986
Guanosine triphosphate
HMDB0001273
Guanosine triphosphate (GTP) is a guanine nucleotide containing three phosphate groups esterified to the sugar moiety. GTP functions as a carrier of phosphates and pyrophosphates involved in channeling chemical energy into specific biosynthetic pathways. GTP activates the signal transducing G proteins which are involved in various cellular processes including proliferation, differentiation, and activation of several intracellular kinase cascades. Proliferation and apoptosis are regulated in part by the hydrolysis of GTP by small GTPases Ras and Rho. Another type of small GTPase, Rab, plays a role in the docking and fusion of vesicles and may also be involved in vesicle formation. In addition to its role in signal transduction, GTP also serves as an energy-rich precursor of mononucleotide units in the enzymatic biosynthesis of DNA and RNA.
86-01-1
C00044
6830
15996
GTP
6569
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1
C10H16N5O14P3
InChI=1S/C10H16N5O14P3/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1
XKMLYUALXHKNFT-UUOKFMHZSA-N
({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
523.1804
522.990659781
-1.70
8
triphosphate, guanosine
0
-3
FDB022527
5'-gtp;Gtg;Gtp;Guanosine 5'-(tetrahydrogen triphosphate);Guanosine 5'-triphosphate;Guanosine 5'-triphosphorate;Guanosine 5'-triphosphoric acid;Guanosine triphosphate;Guanosine mono(tetrahydrogen triphosphate) (ester);H4gtp;Guanosine-5'-triphosphate
PW_C000986
GTP
81
8
240
4
1939
2
4091
14
4153
73
5006
85
5384
103
6043
155
6103
161
6490
178
7478
222
11753
115
11769
198
11981
151
12725
290
69327
1
76962
225
77144
133
77544
111
77951
132
80025
368
80088
308
80121
164
89113
253
119985
406
120066
122
121204
124
122768
120
122818
135
123774
118
125365
479
125443
297
126480
299
126907
501
126982
205
128051
388
1080
Guanosine monophosphate
HMDB0001397
Guanosine monophosphate, also known as guanylic acid or 5'-GMP, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Guanosine monophosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Guanosine monophosphate has been found throughout most human tissues, and has also been detected in multiple biofluids, such as saliva and blood. Guanosine monophosphate can be found anywhere throughout the human cell, such as in mitochondria, golgi, lysosome, and nucleus. Guanosine monophosphate exists in all living organisms, ranging from bacteria to humans. In humans, guanosine monophosphate is involved in the tigecycline action pathway, the homocarnosinosis pathway, the chloramphenicol action pathway, and the azithromycin action pathway. Guanosine monophosphate is also involved in several metabolic disorders, some of which include adenylosuccinate lyase deficiency, xanthine dehydrogenase deficiency (xanthinuria), adenine phosphoribosyltransferase deficiency (aprt), and myoadenylate deaminase deficiency. Outside of the human body, guanosine monophosphate can be found in a number of food items such as black salsify, oyster mushroom, endive, and redcurrant. This makes guanosine monophosphate a potential biomarker for the consumption of these food products. Guanosine 5\'-monophosphate. A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature.
85-32-5
C00144
6804
17345
GMP
6545
DB01972
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1
C10H14N5O8P
InChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1
RQFCJASXJCIDSX-UUOKFMHZSA-N
{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
363.2206
363.057998961
-2.01
6
guanylate
0
-2
FDB012390
5'-gmp;E 626;Gmp;Guanidine monophosphate;Guanosine 5'-monophosphate;Guanosine 5'-phosphate;Guanosine 5'-phosphorate;Guanosine 5'-phosphoric acid;Guanosine monophosphate;Guanosine-5'-monophosphate;Guanosine-5'-phosphate;Guanosine-phosphate;Guanylate;Guanylic acid;Pg;Guanosine 5'-monophosphoric acid;Guanosine monophosphoric acid;Guanosine-5'-monophosphoric acid
PW_C001080
GSMP
1732
8
1766
49
11770
198
11772
213
78005
111
78668
331
80685
135
120165
122
121849
383
124402
398
125525
297
127060
205
414
Adenosine triphosphate
HMDB0000538
Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).
56-65-5
C00002
5957
15422
ATP
5742
DB00171
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H16N5O13P3
InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
ZKHQWZAMYRWXGA-KQYNXXCUSA-N
({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
507.181
506.995745159
-2.05
7
adenosine triphosphate
0
-3
FDB021813
5'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acid
PW_C000414
ATP
9
2
21
4
60
8
266
16
414
22
478
13
733
32
799
5
934
39
976
3
2105
18
2112
10
2146
49
2156
14
2160
58
2405
59
2434
27
2726
46
2812
29
3029
66
3163
72
3616
61
3617
51
4399
23
4474
31
4768
91
4864
54
5032
89
5035
26
5155
7
5205
97
5215
100
5250
104
5291
101
5313
111
5346
112
5390
103
5406
117
5430
118
5443
120
5542
129
5556
132
5569
133
5603
135
5621
108
5846
143
5854
146
5876
107
5897
147
5924
151
6048
155
6109
161
6230
166
6493
178
6839
188
6870
160
6976
199
7157
205
7184
206
7209
210
7225
213
7229
211
7298
198
7302
216
7390
217
7408
218
7432
163
7481
222
7499
190
8186
225
11847
277
11903
170
12010
281
12039
164
12178
285
12578
226
12691
290
13264
223
15327
308
42326
315
42621
322
42694
318
77028
253
77218
134
77233
329
77468
333
77632
336
78037
332
78041
350
78168
128
78214
351
78240
353
78411
335
78494
115
78850
130
78865
331
78919
334
80028
368
80046
184
80674
119
85629
1
94826
124
113234
94
113282
388
116280
109
119914
122
119992
406
120154
407
120245
382
120362
412
121246
429
121392
123
121397
433
121471
408
121974
410
122065
125
122079
383
122083
405
122402
422
122444
435
122919
399
123009
446
123816
464
123951
447
123956
468
124029
374
124527
444
124616
136
124630
398
124634
376
124943
472
124972
375
125011
470
125304
297
125371
479
125392
299
125515
481
125595
484
126123
485
126220
300
126234
495
126240
478
126547
491
126596
499
126913
501
127123
389
127731
516
127781
395
127796
390
127801
209
128119
508
128167
517
936
Guanosine diphosphate
HMDB0001201
Guanosine 5'-(trihydrogen diphosphate). A guanine nucleotide containing two phosphate groups esterified to the sugar moiety. It is an ester of pyrophosphoric acid with the nucleoside guanosine. GDP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase guanine. GDP is the product of GTP dephosphorylation by GTPases, e.g. the G-proteins that are involved in signal transduction.
146-91-8
C00035
8977
17552
GDP-4-DEHYDRO-6-DEOXY-D-MANNOSE
8630
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1
C10H15N5O11P2
InChI=1S/C10H15N5O11P2/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(25-9)1-24-28(22,23)26-27(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1
QGWNDRXFNXRZMB-UUOKFMHZSA-N
[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
443.2005
443.024329371
-2.00
7
{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
0
-3
FDB022487
5'-gdp;Gdp;Guanosine 5'-(trihydrogen pyrophosphate);Guanosine 5'-diphosphate;Guanosine 5'-pyrophosphate;Guanosine mono(trihydrogen diphosphate);Guanosine pyrophosphate;Guanosine-5'-diphosphate;Guanosine-diphosphate;Ppg;Guanosine diphosphate;Guanosine 5'-diphosphoric acid
PW_C000936
GDP
83
8
238
4
1762
14
2391
2
4154
73
5007
85
5382
103
6041
155
6101
161
6488
178
7476
222
11754
115
11771
211
11823
198
12727
290
13395
151
69322
1
77142
133
77546
111
77952
132
80023
368
80080
308
80122
164
89115
253
119983
406
120068
122
121205
124
121847
405
122766
120
122820
135
123775
118
124400
376
125363
479
125445
297
126905
501
126984
205
1034
Adenosine diphosphate
HMDB0001341
Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.
58-64-0
C00008
6022
16761
ADP
5800
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H15N5O10P2
InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
XTWYTFMLZFPYCI-KQYNXXCUSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
427.2011
427.029414749
-2.12
6
adenosine-diphosphate
0
-2
FDB021817
Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acid
PW_C001034
ADP
23
4
134
8
415
22
482
13
801
5
963
15
978
3
1061
14
1518
2
1901
49
2104
18
2113
10
2161
58
2408
59
2435
27
2728
47
2736
46
2855
29
3165
72
3635
61
4400
23
4476
31
4770
91
5036
26
5157
7
5208
97
5217
100
5315
111
5349
112
5392
103
5446
120
5544
129
5572
133
5624
108
5741
117
5764
101
5849
143
5856
146
5878
107
5899
147
5926
151
6050
155
6111
161
6231
166
6495
178
6700
94
6841
188
6872
160
7159
205
7187
206
7208
210
7226
213
7231
211
7300
198
7303
216
7391
217
7410
218
7433
163
7483
222
8187
225
11851
277
11905
170
12013
281
12180
285
13262
223
15329
308
42328
315
42398
313
42622
322
42696
318
77029
253
77087
132
77216
134
77306
329
77472
333
77663
336
78039
332
78043
350
78170
128
78215
351
78244
353
78414
335
78495
115
78705
331
78849
130
78920
334
80030
368
80622
118
80651
135
80676
119
94827
124
113283
388
116204
109
119944
122
119994
406
120156
407
120318
382
120366
412
121248
429
121394
123
121399
433
121472
408
121899
383
121976
410
122064
125
122085
405
122405
422
122445
435
122973
399
123013
446
123818
464
123953
447
123958
468
124030
374
124452
398
124529
444
124615
136
124636
376
124947
472
124975
375
125012
470
125334
297
125373
479
125492
299
125517
481
125645
484
126125
485
126219
300
126235
495
126242
478
126550
491
126597
499
126915
501
127733
516
127780
395
127797
390
127803
209
128122
508
128168
517
128313
389
423
Magnesium
HMDB0000547
Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.
22537-22-0
C00305
888
18420
13-HYDROXY-MAGNESIUM-PROTOPORP
865
DB01378
[Mg++]
Mg
InChI=1S/Mg/q+2
JLVVSXFLKOJNIY-UHFFFAOYSA-N
magnesium(2+) ion
24.305
23.985041898
0
magnesium(2+) ion
2
2
FDB003518
Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+
PW_C000423
Mg2+
86
8
227
4
268
16
476
2
727
26
811
5
819
18
883
22
936
39
983
3
992
21
1167
46
1483
49
1529
43
1764
14
2124
10
2411
59
2942
23
3126
29
3373
7
4540
31
4774
91
4869
54
4974
56
5253
104
5329
111
5356
112
5376
103
5906
147
5934
151
6038
155
6094
161
6250
166
6484
178
6594
164
6881
160
6979
199
7170
205
7194
206
7227
213
7233
211
7250
214
7310
216
7313
198
7473
222
11763
132
11843
210
12312
225
12324
249
12513
288
12581
226
12729
290
15275
285
15337
308
77137
133
77236
329
77937
336
78393
334
78417
335
78489
115
78522
331
78536
356
78574
130
80020
368
80045
184
80048
372
80623
118
80654
135
80865
15
80965
253
81841
51
93832
383
94900
27
108596
223
110559
390
115687
398
119974
406
120070
122
120247
382
120702
407
120981
408
121181
124
121265
429
121319
419
121924
125
122086
405
122408
422
122759
120
122921
399
123307
119
123546
374
123835
464
123889
455
124477
136
124637
376
124978
375
125447
297
125598
484
125669
479
125777
481
125921
482
125947
299
125973
495
126000
490
126243
478
126553
491
126753
300
127125
389
127164
501
127380
502
127407
388
127451
507
127804
209
128125
508
128347
395
1104
Phosphate
HMDB0001429
Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.
14265-44-2
C00009
1061
18367
CPD-8587
1032
[O-]P([O-])([O-])=O
O4P
InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3
NBIIXXVUZAFLBC-UHFFFAOYSA-K
phosphoric acid
94.9714
94.95342
3
phosphoric acid
0
-2
DBMET00532
FDB022617
Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ion
PW_C001104
Pi
24
4
84
8
814
5
818
18
831
2
980
3
1763
14
1767
49
2500
10
2729
47
2737
46
3129
29
3166
72
3636
61
3851
23
4249
22
4475
31
5031
27
5158
7
5207
97
5216
100
5317
111
5351
112
5381
103
5447
120
5543
129
5573
133
5605
135
5625
108
5693
6
5848
143
5855
146
5911
147
5941
151
6040
155
6100
161
6294
107
6487
178
6691
101
6714
117
6842
188
6889
160
7161
205
7189
206
7212
211
7306
198
7389
210
7402
212
7436
163
7475
222
8196
225
8258
227
10118
241
10134
257
11748
132
11761
115
11773
213
11904
170
11927
164
12014
281
12728
290
13263
223
34819
17
42255
304
42350
315
42435
318
43692
322
77018
253
77194
293
77217
134
77940
336
77966
130
78048
332
78057
329
78245
353
78669
331
80022
368
89279
308
93831
383
94796
384
110558
390
110640
391
113235
94
115845
398
116206
109
119982
406
120069
122
120699
407
121057
124
121216
125
121268
429
121352
121
121409
123
121423
382
121852
405
123304
119
123621
118
123786
136
123838
464
123968
447
123981
399
124405
376
124948
472
125362
479
125446
297
125774
481
125954
299
126221
478
126594
300
126604
298
126723
484
126904
501
127413
388
127783
209
128166
395
128177
513
128315
389
353
Calcium
HMDB0000464
Calcium is essential for the normal growth and maintenance of bones and teeth, and calcium requirements must be met throughout life. Requirements are greatest during periods of growth, such as childhood, during pregnancy and when breast-feeding. Long-term calcium deficiency can lead to osteoporosis, in which the bone deteriorates and there is an increased risk of fractures. Adults need between 1,000 and 1,300 mg of calcium in their daily diet. Calcium is essential for living organisms, particularly in cell physiology, and is the most common metal in many animals. Physiologically, it exists as an ion in the body. Calcium combines with phosphorus to form calcium phosphate in the bones and teeth. It is essential for the normal functioning of nerves and muscles and plays a role in blood coagulation (as factor IV) and in many enzymatic processes. Calcium is an important component of a healthy diet. A deficit can affect bone and tooth formation, while overretention can cause kidney stones. Vitamin D is needed to absorb calcium. Dairy products, such as milk and cheese, are a well-known source of calcium. However, some individuals are allergic to dairy products and even more people, particularly those of non-European descent, are lactose-intolerant, leaving them unable to consume dairy products. Fortunately, many other good sources of calcium exist. These include: seaweeds such as kelp, wakame and hijiki; nuts and seeds (like almonds and sesame); beans; amaranth; collard greens; okra; rutabaga; broccoli; kale; and fortified products such as orange juice and soy milk. Calcium has also been found to assist in the production of lymphatic fluids.
14127-61-8
C00076
271
29108
CA%2b2
266
DB01373
[Ca++]
Ca
InChI=1S/Ca/q+2
BHPQYMZQTOCNFJ-UHFFFAOYSA-N
calcium(2+) ion
40.078
39.962591155
0
calcium(2+) ion
2
2
FDB003513
Ca;Calcium element;Ca(2+);Ca2+;Calcium ion;Calcium, doubly charged positive ion
PW_C000353
Ca2+
276
16
303
8
553
14
601
2
941
15
993
21
997
35
1046
3
1163
46
1164
47
1478
49
1491
42
1552
43
2116
58
2138
17
2796
18
2937
9
3159
71
3160
72
3942
29
4186
66
4782
10
4822
28
5340
111
5780
101
7179
205
7232
211
7258
160
7281
190
11774
213
11837
198
11842
210
12198
164
12215
285
15288
151
15350
308
69336
1
77389
331
77600
115
78154
132
78266
356
78526
345
78724
130
78908
114
80413
74
80589
228
81826
51
120220
122
120465
405
121049
124
121300
418
121377
419
121850
383
121923
125
122370
409
122895
135
123099
376
123613
118
123870
454
123936
455
124403
398
124476
136
124924
137
125571
297
125711
478
125981
489
126009
299
126050
490
126533
495
127203
209
127434
506
127460
388
127502
507
128105
390
767
dGDP
HMDB0000960
dGDP is a derivative of the common nucleic acid GTP, or guanosine triphosphate, in which the -OH (hydroxyl) group on the 2' carbon on the nucleotide's pentose has been removed (hence the deoxy- part of the name). Additionally, the diphosphate of the name indicates that one of the phosphoryl groups of GTP has been removed, most likely by hydrolysis (Wikipedia).
3493-09-2
C00361
439220
28862
DGDP
388359
NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O2)C(=O)N1
C10H15N5O10P2
InChI=1S/C10H15N5O10P2/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(24-6)2-23-27(21,22)25-26(18,19)20/h3-6,16H,1-2H2,(H,21,22)(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1
CIKGWCTVFSRMJU-KVQBGUIXSA-N
[({[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
427.2011
427.029414749
-2.07
6
dGDP
0
-2
FDB022338
2'-deoxy-gdp;2'-deoxyguanosine-5'-diphosphate;5'-dgdp;Deoxyguanosine 5'-diphosphate;Deoxyguanosine diphosphate;Deoxyguanosine-diphosphate;Dgdp;2'-deoxyguanosine 5'-diphosphate;2'-deoxyguanosine 5'-diphosphoric acid;Deoxyguanosine diphosphoric acid
PW_C000767
dGDP
1797
8
11775
198
78670
111
121855
122
124408
135
1112
dGTP
HMDB0001440
Under normal physiologic conditions, deoxyguanosine (dGuo) undergoes phosphorolysis by purine nucleoside phosphorylase (PNP, EC 2.4.2.1, an enzyme involved in the recycling of nucleosides and deoxynucleosides in cellular remodeling). However, when PNP is inhibited, deoxycytidine kinase (dCK, EC 2.7.1.74) shunts unmetabolized dGuo into deoxyguanosine triphosphate (dGTP), which accumulates and blocks DNA synthesis. Deficiency of purine nucleoside phosphorylase results in defective T-cell immunity. A correlation between the degree of T cell inhibition and the level of dCK activity is observed. (PMID: 11287638, 402573).
2564-35-4
C00286
65103
16497
DGTP
58613
NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)N1
C10H16N5O13P3
InChI=1S/C10H16N5O13P3/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(26-6)2-25-30(21,22)28-31(23,24)27-29(18,19)20/h3-6,16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1
HAAZLUGHYHWQIW-KVQBGUIXSA-N
({[({[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
507.181
506.995745159
-1.96
7
dGTP
0
-3
FDB022623
Deoxyguanosine 5'-triphosphate;2'-deoxyguanosine 5'-triphosphate;2'-deoxyguanosine triphosphate;Deoxyguanosine triphosphate;2'-deoxyguanosine 5'-triphosphoric acid;Deoxyguanosine 5'-triphosphoric acid;Deoxyguanosine triphosphoric acid
PW_C001112
dGTP
1802
8
11776
198
78671
111
121856
122
124409
135
822
2'-Deoxyguanosine 5'-monophosphate
HMDB0001044
2'-Deoxyguanosine 5'-monophosphate is a derivative of the common nucleic acid GTP, or guanosine triphosphate, in which the -OH (hydroxyl) group on the 2' carbon on the nucleotide's pentose has been removed (hence the deoxy- part of the name). Additionally, the diphosphate of the name indicates that two of the phosphoryl groups of GTP have been removed, most likely by hydrolysis (Wikipedia).
902-04-5
C00362
65059
16192
DGMP
58570
DB04457
NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1
C10H14N5O7P
InChI=1S/C10H14N5O7P/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(22-6)2-21-23(18,19)20/h3-6,16H,1-2H2,(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1
LTFMZDNNPPEQNG-KVQBGUIXSA-N
{[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
347.2212
347.063084339
-2.11
5
deoxyguanylate
0
-1
FDB022388
2'-dg-5'-mp;2'-deoxy-5'-gmp;2'-deoxy-5'-guanylate;2'-deoxy-5'-guanylic acid;2'-deoxy-gmp;2'-deoxy-guanosine 5'-(dihydrogen phosphate);2'-deoxy-guanosine 5'-phosphate;2'-deoxy-guanosine phosphate;2'-deoxyguanosine 5'-monophosphate;2'-deoxyguanosine 5'-phosphate;2'-deoxyguanosine-5'-phosphate;2'-deoxyguanylate;2'-deoxyguanylic acid;2'-dgmp;Deoxy-gmp;Deoxyguanosine 5'-monophosphate;Deoxyguanosine 5'-phosphate;Deoxyguanosine-phosphate;Guanine riboside;Dgmp;2'-deoxyguanosine 5'-(dihydrogen phosphate);Deoxyguanosine monophosphate;Deoxyguanylic acid
PW_C000822
dGMP
1803
8
11777
198
78672
111
121857
122
124410
135
58
Deoxyguanosine
HMDB0000085
Deoxyguanosine is a nucleoside consisting of the base guanine and the sugar deoxyribose. It is like guanosine, but with one oxygen atom removed. It is a nucleoside component of DNA. Deoxyguanosine can be converted to 8-hydroxy-deoxyguanosine (8-OHdG) due to hydroxyl radical attack at the C8 of guanine. 8-OHdG is a sensitive marker of the DNA damage This damage, if left unrepaired, has been proposed to contribute to mutagenicity and cancer promotion.
961-07-9
C00330
187790
17172
DEOXYGUANOSINE
163230
NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1
C10H13N5O4
InChI=1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1
YKBGVTZYEHREMT-KVQBGUIXSA-N
2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
267.2413
267.096753929
-1.37
4
2-deoxyguanosine
0
0
FDB012064
2'-deoxy-guanosine;2'-deoxyguanosine;2-deoxyguanosine;9-(2-deoxy-b-d-erythro-pentofuranosyl)-guanine;9-(2-deoxy-b-d-erythro-pentofuranosyl)guanine;9-(2-deoxy-beta-delta-erythro-pentofuranosyl)-guanine;9-(2-deoxy-beta-delta-erythro-pentofuranosyl)guanine;Deoxyguanosine;Desoxyguanosine;Guanine deoxy nucleoside;Guanine deoxyriboside;2-amino-9-(2-deoxy-9-beta-d-ribofuranosyl)-9h-purin-6-ol;9-(2-deoxy-beta-d-erythro-pentofuranosyl)-guanine;Dg;2-amino-9-(2-deoxy-9-b-d-ribofuranosyl)-9h-purin-6-ol;2-amino-9-(2-deoxy-9-β-d-ribofuranosyl)-9h-purin-6-ol;9-(2-deoxy-β-d-erythro-pentofuranosyl)-guanine
PW_C000058
doxyG
1806
8
11778
198
78673
111
121858
122
124411
135
170
Pyrophosphate
HMDB0000250
The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.
14000-31-8
C00013
644102
18361
PPI
559142
DB04160
[O-]P([O-])(=O)OP([O-])([O-])=O
O7P2
InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4
XPPKVPWEQAFLFU-UHFFFAOYSA-J
(phosphonooxy)phosphonic acid
173.9433
173.911925378
4
pyrophosphoric acid
0
-3
FDB021918
(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ion
PW_C000170
Ppi
12
2
35
4
63
8
429
23
735
32
882
22
1217
3
1620
49
2410
59
2815
29
4175
14
4868
54
5034
89
5252
104
5294
101
5409
117
5424
103
5433
118
5458
120
5548
111
5559
132
5584
133
5606
135
5655
108
5879
107
6239
166
6978
199
7073
188
7134
163
7272
160
7312
198
7318
213
8275
151
8283
210
11869
161
12002
222
12041
164
12315
225
12323
249
12512
288
12579
226
12695
290
15219
306
15375
18
34760
17
42561
315
42697
318
77235
329
77317
128
77635
336
78416
335
78928
331
79153
112
79950
134
79958
130
80047
372
80417
170
85630
1
94786
384
94814
125
94819
382
98678
223
110634
391
113270
395
113275
389
115527
136
115532
399
119934
122
120017
124
120032
406
120330
410
120936
407
121261
429
121341
121
121486
383
122407
422
122985
444
123502
119
123831
464
124044
398
124977
375
125324
297
125395
299
125410
479
125597
484
125656
485
125876
481
126552
491
126869
205
126935
388
126950
501
127337
206
128124
508
86
Guanine
HMDB0000132
Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA. Guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with conjugated double bonds. Being unsaturated, the bicyclic molecule is planar. The guanine nucleoside is called guanosine. The first isolation of guanine was reported in 1844 from the excreta of sea birds, known as guano, which was used as a source of fertilizer. High affinity binding of guanine nucleotides and the ability to hydrolyze bound GTP to GDP are characteristics of an extended family of intracellular proteins. Guanine nucleotide-binding regulatory proteins may be involved in the activation of phospholipases C and A2 by hormones and other ligands. The binding of hormones to receptors that activate phospholipase C is decreased by guanine nucleotides and these hormones also stimulate a high-affinity GTPase activity in cell membranes. Effects of hormones on phospholipase C activity in cell-free preparations are dependent on the presence of guanine nucleotides. Hypoxanthine-guanine phosphoribosyltransferase (HPRT, EC 2.4.2.8) is a purine salvage enzyme that catalyses the conversion of hypoxanthine and guanine to their respective mononucleotides. Partial deficiency of this enzyme can result in the overproduction of uric acid leading to a severe form of gout, whilst a virtual absence of HPRT activity causes the Lesch-Nyhan syndrome which is characterised by hyperuricaemia, mental retardation, choreoathetosis and compulsive self-mutilation. Peroxynitrite induces DNA base damage predominantly at guanine (G) and 8-oxoguanine (8-oxoG) nucleobases via oxidation reactions. G and 8-oxoG are the most reactive bases toward Peroxynitrite and possibly the major contributors to peroxynitrite-derived genotoxic and mutagenic lesions. The neutral G radical, reacts with NO2 to yield 8-nitroguanine and 5-nitro-4-guanidinohydantoin. (PMID: 16352449, 2435586, 2838362, 1487231).
73-40-5
C00242
764
16235
GUANINE
744
DB02377
NC1=NC(=O)C2=C(N1)N=CN2
C5H5N5O
InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
UYTPUPDQBNUYGX-UHFFFAOYSA-N
2-amino-6,7-dihydro-3H-purin-6-one
151.1261
151.049409807
-1.82
3
2-aminohypoxanthine
0
0
FDB004222
2-amino-1,7-dihydro-6h-purin-6-one;2-amino-1,9-dihydro-6h-purin-6-one;2-amino-1,9-dihydro-purin-6-one;2-amino-3,7-dihydro-6h-purin-6-one;2-amino-6-hydroxy-1h-purine;2-amino-6-hydroxypurine;2-amino-6-purinol;2-amino-hypoxanthine;2-aminohypoxanthine;6-hydroxy-2-aminopurine;C.i. natural white 1;Ci natural white 1;Dew pearl;Gua;Gun;Guanin;Guanine;Guanine enol;Mearlmaid;Mearlmaid aa;Natural white 1;Natural pearl essence;Naturon;Pathocidin;Pearl essence;Stella polaris;2-amino-6-oxopurine;G
PW_C000086
Guanine
1814
8
11779
198
78674
111
121861
122
124414
135
190
Phosphoribosyl pyrophosphate
HMDB0000280
Phosphoribosyl pyrophosphate (PRPP) is a pentosephosphate. The key substance in the biosynthesis of histidine, tryptophan, and purine and pyrimidine nucleotides. It is formed from ribose 5-phosphate by the enzyme ribose-phosphate diphosphokinase. It plays a role in transferring phosphate groups in several reactions. (Wikipedia).
7540-64-9
C00119
7339
17111
PRPP
7062
DB01632
O[C@H]1[C@@H](O)[C@@H](O[P@](O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O
C5H13O14P3
InChI=1S/C5H13O14P3/c6-3-2(1-16-20(8,9)10)17-5(4(3)7)18-22(14,15)19-21(11,12)13/h2-7H,1H2,(H,14,15)(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1
PQGCEDQWHSBAJP-TXICZTDVSA-N
[({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
390.0696
389.95181466
-1.53
7
phosphoribosylpyrophosphate
0
-4
FDB021928
5-phospho-a-d-ribose-1-diphosphate;5-phospho-a-d-ribosyl pyrophosphate;5-phospho-alpha-d-ribose 1-diphosphate;5-phospho-alpha-d-ribose-1-diphosphate;5-phospho-alpha-d-ribosyl pyrophosphate;5-phospho-alpha-d-riobse 1-diphosphate;5-phospho-alpha-delta-ribose 1-diphosphate;5-phospho-alpha-delta-ribose-1-diphosphate;5-phospho-alpha-delta-ribosyl pyrophosphate;5-phosphoribose 1-pyrophosphate;5-phosphoribosyl 1-diphosphate;5-phosphoribosyl a-1-pyrophosphate;5-phosphoribosyl-1-pyrophosphate;5-phosphorylribose 1-a-diphosphate;5-phosphorylribose 1-alpha-diphosphate;5-phosphorylribose 1-pyrophosphate;5-phosphorylribosyl 1-pyrophosphate;Pp-ribose-p;Prpp;Prib-pp;Phosphoribosyl pyrophosphate;Phosphoribosyl-1-pyrophosphate;Phosphoribosyl-pyrophosphate;Phosphoribosylpyrophosphorate;Phosphoribosylpyrophosphoric acid;A-d-5-(dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose;A-d-5-phosphoribosyl 1-pyrophosphate;A-d-ribofuranose 5-phosphate 1-pyrophosphate;A-d-ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate);Alpha-d-5-(dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose;Alpha-d-5-phosphoribosyl 1-pyrophosphate;Alpha-d-ribofuranose 5-phosphate 1-pyrophosphate;Alpha-d-ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate);Alpha-delta-5-(dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose;Alpha-delta-5-phosphoribosyl 1-pyrophosphate;Alpha-delta-ribofuranose 5-phosphate 1-pyrophosphate;5-phosphoribosyl 1-pyrophosphate;5-phosphoribosyl diphosphate;Alpha-d-ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate);Alpha-phosphoribosylpyrophosphoric acid;Phosphoribosylpyrophosphate;5-phospho-a-d-ribose 1-diphosphate;5-phospho-a-d-ribose 1-diphosphoric acid;5-phospho-alpha-d-ribose 1-diphosphoric acid;5-phospho-α-d-ribose 1-diphosphate;5-phospho-α-d-ribose 1-diphosphoric acid;Phosphoribosyl pyrophosphoric acid;5-phosphoribosyl 1-pyrophosphoric acid;5-phosphoribosyl diphosphoric acid;A-d-ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate);A-d-ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid);Alpha-d-ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid);α-d-ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate);α-d-ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid);A-phosphoribosylpyrophosphate;A-phosphoribosylpyrophosphoric acid;Alpha-phosphoribosylpyrophosphate;α-phosphoribosylpyrophosphate;α-phosphoribosylpyrophosphoric acid
PW_C000190
PRPP
1774
2
1815
8
5816
108
11780
198
42663
315
77176
132
78002
111
80680
135
111657
7
120160
122
121950
124
124503
118
125521
297
126346
299
127056
205
127709
388
87
Guanosine
HMDB0000133
Guanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a beta-N9-glycosidic bond. Guanosine can be phosphorylated to become GMP (guanosine monophosphate), cGMP (cyclic guanosine monophosphate), GDP (guanosine diphosphate), and GTP (guanosine triphosphate) (Wikipedia). This nucleoside exerts important neuroprotective and neuromodulator roles in the central nervous system, which may be related to inhibition of the glutamatergic neurotransmission activity. Guanosine is the specific extracellular guanine-based purines effector and its conversion occurs not only in the central nervous system but also peripherally (PMID: 16325434). Guanosine is found to be associated with purine nucleoside phosphorylase (PNP) deficiency, which is an inborn error of metabolism.
118-00-3
C00387
6802
16750
GUANOSINE
6544
DB02857
NC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1
C10H13N5O5
InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1
NYHBQMYGNKIUIF-UUOKFMHZSA-N
2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
283.2407
283.091668551
-1.27
5
guanosine
0
0
FDB003632
2-amino-1,9-dihydro-9-b-d-ribofuranosyl-6h-purin-6-one;2-amino-1,9-dihydro-9-beta-delta-ribofuranosyl-6h-purin-6-one;2-amino-inosine;9-b-d-ribofuranosyl-guanine;9-beta-delta-ribofuranosyl-guanine;Guanosine;Ribonucleoside;Vernine;B-d-ribofuranoside guanine-9;Beta-delta-ribofuranoside guanine-9;2(3h)-imino-9-beta-d-ribofuranosyl-9h-purin-6(1h)-one;2-amino-1,9-dihydro-9-beta-d-ribofuranosyl-6h-purin-6-one;2-amino-9-beta-d-ribofuranosyl-1,9-dihydro-6h-purin-6-one;9-beta-d-ribofuranosyl-guanine;G;Guanine riboside;Guanine-9-beta-d-ribofuranoside;Guanosin;Guo;2(3h)-imino-9-b-d-ribofuranosyl-9h-purin-6(1h)-one;2(3h)-imino-9-β-d-ribofuranosyl-9h-purin-6(1h)-one;2-amino-1,9-dihydro-9-β-d-ribofuranosyl-6h-purin-6-one;2-amino-9-b-d-ribofuranosyl-1,9-dihydro-6h-purin-6-one;2-amino-9-β-d-ribofuranosyl-1,9-dihydro-6h-purin-6-one;9-β-d-ribofuranosyl-guanine;Guanine-9-b-d-ribofuranoside;Guanine-9-β-d-ribofuranoside
PW_C000087
Guo
1817
8
6775
107
6776
108
11781
198
78675
111
121863
122
124416
135
1441
Phosphoric acid
HMDB0002142
Phosphoric acid, also known as orthophosphoric acid or phosphoric(V) acid, is a mineral acid with the chemical formula H3PO4. Alternatively, orthophosphoric acid molecules can combine with themselves to form a variety of compounds referred to as phosphoric acids in a more general way. For a discussion of these, see Phosphoric acids and Phosphates. Appears to exist only as a food additive and produced synthetically. --Wikipedia.
7664-38-2
C00009
1004
26078
979
OP(O)(O)=O
H3O4P
InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)
NBIIXXVUZAFLBC-UHFFFAOYSA-N
phosphoric acid
97.9952
97.976895096
3
phosphoric acid
0
-2
FDB013380
Acide phosphorique (french);Acido fosforico [italian];Acidum phosphoricum;Diphosphate tetrasodium;Fosforzuuroplossingen [dutch];Marphos;Nfb;Ortho- phosphoric acid;Orthophosphoric acid;Phosphoric acid (acd/name 4.0);Phosphorsaeure;Phosphorsaeureloesungen [german];Sodium pyrophosphate;Sodium pyrophosphate decahydrate;Sodium pyrophosphate decahydrate biochemica;Sonac;Tetra-sodium pyrophosphate;Tetrasodium pyrophosphate decahydrate;Tetrasodium pyrophosphate 10-hydrate;White phosphoric acid;[po(oh)3];Acide phosphorique;H3po4;Phosphate;Phosphorsaeureloesungen;Orthophosphate
PW_C001441
PhosfrA
171
8
440
4
483
13
1592
43
1678
2
1902
49
1910
5
4856
3
5913
147
5943
151
6891
160
11782
198
11828
213
11829
216
11852
277
12638
31
77105
132
77330
133
77473
333
77779
111
78000
112
78272
356
78706
331
78707
334
80671
135
80677
119
119918
122
120126
124
120157
407
120344
406
120367
412
121383
419
121900
383
121902
408
122858
118
122994
120
123014
446
123942
455
124453
398
124455
374
125308
297
125493
299
125518
481
125664
479
126056
490
126855
205
127030
388
127053
206
127159
501
127508
507
1146
Ribose 1-phosphate
HMDB0001489
Ribose 1-phosphate is an intermediate in the metabolism of Pyrimidine and the metabolism of Nicotinate and nicotinamide. It is a substrate for Uridine phosphorylase 2, Phosphoglucomutase, Purine nucleoside phosphorylase and Uridine phosphorylase 1. Ribose 1-phosphate can be formed from guanosine through the action of purine nucleoside phosphorylase. Ribose 1-phosphate can also act as a ribose donor in the synthesis of xanthosine as catalyzed by the same enzyme (purine nucleoside phosphorylase). The presence of guanase, which irreversibly converts guanine to xanthine, affects the overall process of guanosine transformation. As a result of this purine pathway, guanosine is converted into xanthosine, thus overcoming the lack of guanosine deaminase in mammals. The activated ribose moiety in Ribose 1-phosphate which stems from the catabolism of purine nucleosides can be transferred to uracil and, in the presence of ATP, used for the synthesis of pyrimidine nucleotides; therefore, purine nucleosides can act as ribose donors for the salvage of pyrimidine bases. (PMID: 9133638).
14075-00-4
C00620
439236
16300
RIBOSE-1P
388373
DB03101
OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H]1O
C5H11O8P
InChI=1S/C5H11O8P/c6-1-2-3(7)4(8)5(12-2)13-14(9,10)11/h2-8H,1H2,(H2,9,10,11)/t2-,3-,4-,5-/m1/s1
YXJDFQJKERBOBM-TXICZTDVSA-N
{[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}phosphonic acid
230.1098
230.01915384
-0.82
5
ribose 1-phosphate
0
-2
FDB022650
1-o-phosphono-d-ribofuranose;D-ribofuranose 1-(dihydrogen phosphate);D-ribofuranose 1-phosphate;D-ribose-1-phosphate;D-ribose-1p;Ribofuranose 1-phosphate;Ribose 1-phosphate;A-d-ribofuranose 1-(dihydrogen phosphate);A-d-ribose 1-phosphate;Alpha-d-ribofuranose 1-(dihydrogen phosphate);Alpha-d-ribofuranose 1-phosphate;Alpha-d-ribose 1-phosphate;D-ribose 1-phosphate;D-ribose 1-phosphoric acid;Ribose 1-phosphoric acid
PW_C001146
Rib-1P
1770
2
1818
8
11783
198
77175
132
78676
111
121864
122
121968
124
124417
135
124521
118
126344
299
127725
388
1042
Deoxyribose 1-phosphate
HMDB0001351
Deoxyribose 1-phosphate belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Deoxyribose 1-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, deoxyribose 1-phosphate is primarily located in the cytoplasm. Deoxyribose 1-phosphate exists in all living organisms, ranging from bacteria to humans. Deoxyribose 1-phosphate participates in a number of enzymatic reactions. In particular, Hypoxanthine and deoxyribose 1-phosphate can be biosynthesized from deoxyinosine through its interaction with the enzyme purine nucleoside phosphorylase. Furthermore, Adenine and deoxyribose 1-phosphate can be biosynthesized from deoxyadenosine through its interaction with the enzyme purine nucleoside phosphorylase. Furthermore, Uracil and deoxyribose 1-phosphate can be biosynthesized from deoxyuridine through its interaction with the enzyme thymidine phosphorylase / uracil phosphorylase. Finally, Thymine and deoxyribose 1-phosphate can be biosynthesized from thymidine; which is catalyzed by the enzyme thymidine phosphorylase / uracil phosphorylase. In humans, deoxyribose 1-phosphate is involved in the thioguanine action pathway, the azathioprine action pathway, the mercaptopurine action pathway, and the purine metabolism pathway. Deoxyribose 1-phosphate is also involved in several metabolic disorders, some of which include the gout or kelley-seegmiller syndrome pathway, purine nucleoside phosphorylase deficiency, UMP synthase deficiency (orotic aciduria), and molybdenum cofactor deficiency. Deoxyribose 1-phosphate is an intermediate in the metabolism of Pyrimidine. It is a substrate for Purine nucleoside phosphorylase and Thymidine phosphorylase.
17210-42-3
C00672
439287
28542
DEOXY-RIBOSE-1P
388420
OC[C@H]1OC(C[C@@H]1O)OP(O)(O)=O
C5H11O7P
InChI=1S/C5H11O7P/c6-2-4-3(7)1-5(11-4)12-13(8,9)10/h3-7H,1-2H2,(H2,8,9,10)/t3-,4+,5?/m0/s1
KBDKAJNTYKVSEK-PYHARJCCSA-N
{[(4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}phosphonic acid
214.1104
214.024239218
-0.76
4
deoxyribose-1-phosphate
0
-2
FDB022571
2-deoxy-d-erythro-pentofuranose 1-phosphate;2-deoxy-d-ribose 1-phosphate;2-deoxy-d-ribose-1-phosphate;2-deoxy-alpha-d-ribose 1-phosphate;2-deoxy-alpha-delta-ribose 1-phosphate;2-deoxy-delta-erythro-pentofuranose 1-phosphate;2-deoxy-delta-ribose 1-phosphate;2-deoxy-delta-ribose-1-phosphate;2-deoxyribofuranose 1-phosphate;D-2-deoxy-ribofuranose 1-phosphate;Deoxyribose 1-phosphate;Deoxyribose-1-phosphate;Delta-2-deoxy-ribofuranose 1-phosphate;2-deoxy-1-o-phosphono-d-erythro-pentofuranose;2-deoxy-1-o-phosphono-d-ribofuranose
PW_C001042
D1P
1801
2
1823
8
11784
198
77189
132
78678
111
121867
122
122198
124
124420
135
124750
118
126358
299
127921
388
198
Xanthine
HMDB0000292
Xanthine is a purine base found in most body tissues and fluids, certain plants, and some urinary calculi. It is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects. (Dorland, 28th ed.).
69-89-6
C00385
1188
17712
XANTHINE
1151
DB02134
O=C1NC2=C(NC=N2)C(=O)N1
C5H4N4O2
InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
LRFVTYWOQMYALW-UHFFFAOYSA-N
2,3,6,7-tetrahydro-1H-purine-2,6-dione
152.1109
152.033425392
-1.49
3
xanthine
0
0
DBMET00499
FDB001977
1h-purine-2,6-diol;2,6(1,3)-purinedion;2,6-dihydroxypurine;2,6-dioxopurine;3,7-dihydro-1h-purine-2,6-dione;3,7-dihydropurine-2,6-dione;9h-purine-2,6(1h,3h)-dione;9h-purine-2,6-diol;Dioxopurine;Isoxanthine;Pseudoxanthine;Purine-2,6(1h,3h)-dione;Purine-2,6-diol;Xanthic oxide;Xanthin;Xanthine
PW_C000198
Xanthin
1830
8
11785
198
12442
151
78679
111
121868
122
124421
135
35
Ammonia
HMDB0000051
Ammonia is a colourless alkaline gas and is one of the most abundant nitrogen-containing compounds in the atmosphere. It is an irritant with a characteristic pungent odor that is widely used in industry. Inasmuch as ammonia is highly soluble in water and, upon inhalation, is deposited in the upper airways, occupational exposures to ammonia have commonly been associated with sinusitis, upper airway irritation, and eye irritation. Acute exposures to high levels of ammonia have also been associated with diseases of the lower airways and interstitial lung. Small amounts of ammonia are naturally formed in nearly all tissues and organs of the vertebrate organism. Ammonia is both a neurotoxin and a metabotoxin. In fact, it is the most common endogenous neurotoxin. A neurotoxin is a compound that causes damage to neural tissue and neural cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Ammonia is recognized to be central in the pathogenesis of a brain condition known as hepatic encephalopathy, which arises from various liver diseases and leads to a build up ammonia in the blood (hyperammonemia). More than 40% of people with cirrhosis develop hepatic encephalopathy. Part of the neurotoxicity of ammonia arises from the fact that it easily crosses the blood-brain barrier and is absorbed and metabolized by the astrocytes, a population of cells in the brain that constitutes 30% of the cerebral cortex. Astrocytes use ammonia when synthesizing glutamine from glutamate. The increased levels of glutamine lead to an increase in osmotic pressure in the astrocytes, which become swollen. There is increased activity of the inhibitory gamma-aminobutyric acid (GABA) system, and the energy supply to other brain cells is decreased. This can be thought of as an example of brain edema. The source of the ammonia leading to hepatic encephalopathy is not entirely clear. The gut produces ammonia, which is metabolized in the liver, and almost all organ systems are involved in ammonia metabolism. Colonic bacteria produce ammonia by splitting urea and other amino acids, however this does not fully explain hyperammonemia and hepatic encephalopathy. The alternative explanation is that hyperammonemia is the result of the intestinal breakdown of amino acids, especially glutamine. The intestines have significant glutaminase activity, predominantly located in the enterocytes. On the other hand, intestinal tissues only have a little glutamine synthetase activity, making it a major glutamine-consuming organ. In addition to the intestine, the kidney is an important source of blood ammonia in patients with liver disease. Ammonia is also taken up by the muscle and brain in hepatic coma, and there is confirmation that ammonia is metabolized in muscle. Excessive formation of ammonia in the brains of Alzheimer's disease patients has also been demonstrated, and it has been shown that some Alzheimer's disease patients exhibit elevated blood ammonia concentrations. Ammonia is the most important natural modulator of lysosomal protein processing. Indeed, there is strong evidence for the involvement of aberrant lysosomal processing of beta-amyloid precursor protein (beta-APP) in the formation of amyloid deposits. Inflammatory processes and activation of microglia are widely believed to be implicated in the pathology of Alzheimer's disease. Ammonia is able to affect the characteristic functions of microglia, such as endocytosis, and cytokine production. Based on these facts, an ammonia-based hypothesis for Alzheimer's disease has been suggested (PMID: 17006913, 16167195, 15377862, 15369278). Chronically high levels of ammonia in the blood are associated with nearly twenty different inborn errors of metabolism including: 3-hydroxy-3-methylglutaryl-CoA lyase deficiency, 3-methyl-crotonylglycinuria, argininemia, argininosuccinic aciduria, beta-ketothiolase deficiency, biotinidase deficiency, carbamoyl phosphate synthetase deficiency, carnitine-acylcarnitine translocase deficiency, citrullinemia type I, hyperinsulinism-hyperammonemia syndrome, hyperornithinemia-hyperammonemia-homocitrullinuria syndrome, isovaleric aciduria, lysinuric protein intolerance, malonic aciduria, methylmalonic aciduria, methylmalonic aciduria due to cobalamin-related disorders, propionic acidemia, pyruvate carboxylase deficiency, and short chain acyl CoA dehydrogenase deficiency (SCAD deficiency). Many of these inborn errors of metabolism are associated with urea cycle disorders or impairment of amino acid metabolism. High levels of ammonia in the blood (hyperammonemia) lead to the activation of NMDA receptors in the brain. This results in the depletion of brain ATP, which in turn leads to the release of glutamate. Ammonia also leads to the impairment of mitochondrial function and calcium homeostasis, thereby decreasing ATP synthesis. Excess ammonia also increases the formation of nitric oxide (NO), which in turn reduces the activity of glutamine synthetase, and thereby decreases the elimination of ammonia in the brain (PMID: 12020609). As a neurotoxin, ammonia predominantly affects astrocytes. Disturbed mitochondrial function and oxidative stress, factors implicated in the induction of the mitochondrial permeability transition, appear to be involved in the mechanism of ammonia neurotoxicity. Ammonia can also affect the glutamatergic and GABAergic neuronal systems, the two prevailing neuronal systems of the cortical structures. All of these effects can lead to irreversible brain damage, coma, and/or death. Infants with urea cycle disorders and hyperammonemia initially exhibit vomiting and increasing lethargy. If untreated, seizures, hypotonia (poor muscle tone, floppiness), respiratory distress (respiratory alkalosis), and coma can occur. Adults with urea cycle disorders and hyperammonemia will exhibit episodes of disorientation, confusion, slurred speech, unusual and extreme combativeness or agitation, stroke-like symptoms, lethargy, and delirium. Ammonia also has toxic effects when an individual is exposed to ammonia solutions. Acute exposure to high levels of ammonia in air may be irritating to skin, eyes, throat, and lungs and cause coughing and burns. Lung damage and death may occur after exposure to very high concentrations of ammonia. Swallowing concentrated solutions of ammonia can cause burns in the mouth, throat, and stomach. Splashing ammonia into eyes can cause burns and even blindness.
7664-41-7
C00014
222
16134
AMMONIA
217
N
H3N
InChI=1S/H3N/h1H3
QGZKDVFQNNGYKY-UHFFFAOYSA-N
ammonia
17.0305
17.026549101
1
ammonia
0
1
FDB003908
Ammonia anhydrous;Ammonia inhalant;Ammonia solution strong [usan];Ammonia water;Ammoniak;Liquid ammonia;Am-fol;Ammonia;Ammonia (conc 20% or greater);Ammonia gas;Ammonia solution;Ammonia solution strong (nf);Ammonia water (jp15);Ammoniac [french];Ammoniaca [italian];Ammoniacum gummi;Ammoniak [german];Ammoniak kconzentrierter;Ammoniakgas;Ammonium ion;Amoniak [polish];Anhydrous ammonia;Aromatic ammonia vaporole;Azane;Nh(3);Nh3;Nitro-sil;Primaeres amin;Sekundaeres amin;Spirit of hartshorn;Tertiaeres amin;[nh3];Ammoniac;Amoniaco;R-717;Ammonia solution strong
PW_C000035
NH3
97
9
112
5
133
8
142
4
438
2
479
13
550
14
1468
54
2533
22
2572
3
5338
111
6016
147
7022
160
7177
205
11786
198
11848
277
11885
215
12708
291
12718
292
76966
225
77046
294
77329
133
77343
132
77469
333
77499
113
77539
334
77597
115
77985
347
77993
112
78072
329
79244
293
80650
135
80657
119
116203
109
119921
122
120049
408
120053
126
120136
407
120343
406
120363
412
120462
405
121046
124
121161
425
122119
382
122800
374
122805
443
122993
120
123010
446
123096
376
123610
118
123733
460
124671
399
125311
297
125427
482
125431
301
125502
481
125663
479
125708
478
126102
299
126274
484
126966
502
126970
207
127039
206
127158
501
127200
209
127600
388
127837
389
1005
Zinc (II) ion
HMDB0001303
Zinc is an essential element, necessary for sustaining all life.Physiologically, it exists as an ion in the body. It is estimated that 3000 of the hundreds of thousands of proteins in the human body contain zinc prosthetic groups. In addition, there are over a dozen types of cells in the human body that secrete zinc ions, and the roles of these secreted zinc signals in medicine and health are now being actively studied. Intriguingly, brain cells in the mammalian forebrain are one type of cell that secretes zinc, along with its other neuronal messenger substances. Cells in the salivary gland, prostate, immune system and intestine are other types that secrete zinc. Obtaining a sufficient zinc intake during pregnancy and in young children is a problem, especially among those who cannot afford a good and varied diet. Brain development is stunted by zinc deficiency in utero and in youth. Zinc is an activator of certain enzymes, such as carbonic anhydrase. Carbonic anhydrase is important in the transport of carbon dioxide in vertebrate blood. Even though zinc is an essential requirement for a healthy body, too much zinc can be harmful. Excessive absorption of zinc can also suppress copper and iron absorption. The free zinc ion in solution is highly toxic to plants, invertebrates, and even vertebrate fish. The Free Ion Activity Model (FIAM) is well-established in the literature, and shows that just micromolar amounts of the free ion kills some organisms.
23713-49-7
C00038
32051
29105
ZN%2b2
29723
DB01593
[Zn++]
Zn
InChI=1S/Zn/q+2
PTFCDOFLOPIGGS-UHFFFAOYSA-N
zinc(2+) ion
65.409
63.929146578
0
zinc(2+) ion
2
2
FDB003729
Zinc;Zinc ion;Dietary zinc;Zinc cation;Zinc, ion (zn2+);Zn(ii);Zn(2+);Zn2+
PW_C001005
Zinc
13
2
38
4
118
8
271
16
529
15
2957
51
3044
68
3120
29
3147
70
5410
117
5425
103
5434
118
5459
120
5560
132
5585
133
5598
135
7449
166
11787
198
12466
226
12724
290
13321
151
76967
225
77401
111
77580
114
77929
336
80400
1
120020
124
120035
406
120060
122
120441
409
121257
429
123075
137
123827
464
125398
299
125413
479
125438
297
125685
483
126938
388
126953
501
126976
205
127180
208
914
Adenosine diphosphate ribose
HMDB0001178
Adenosine diphosphate ribose is a molecule formed into poly(ADP-ribose) or PAR chains by the enzyme poly ADP ribose polymerase or PARP. PARP is found in every cell nucleus. Its main role is to detect and signal single-strand DNA breaks (SSB) to the enzymatic machinery involved in the SSB repair. PARP activation is an immediate cellular response to metabolic, chemical, or radiation-induced DNA SSB damage. Once PARP detects a SSB, it binds to the DNA, and, after a structural change, begins the synthesis of a poly (ADP-ribose) chain (PAR) as a signal for the other DNA-repairing enzymes such as DNA ligase III (LigIII), DNA polymerase beta, and scaffolding proteins such as X-ray cross-complementing gene 1 (XRCC1). After repairing, the PAR chains are degraded via PAR glycohydrolase (PARG). ADP-ribose binds to and activates the TRPM2 ion channel. Adenosine diphosphate ribose is an intermediate in NAD metabolism. The enzyme NAD(P)+ nucleosidase [EC:3.2.2.6] catalyzes the production of this metabolite from nicotinamide adenine dinucleotide phosphate. This reaction is irreversible and occurs in the cytosol.
20762-30-5
C00301
192
16960
ADENOSINE_DIPHOSPHATE_RIBOSE
187
NC1=C2N=CN(C3OC(COP(O)(=O)OP(O)(=O)OCC4OC(O)C(O)C4O)C(O)C3O)C2=NC=N1
C15H23N5O14P2
InChI=1S/C15H23N5O14P2/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(23)8(21)5(32-14)1-30-35(26,27)34-36(28,29)31-2-6-9(22)11(24)15(25)33-6/h3-6,8-11,14-15,21-25H,1-2H2,(H,26,27)(H,28,29)(H2,16,17,18)
SRNWOUGRCWSEMX-UHFFFAOYSA-N
{[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(3,4,5-trihydroxyoxolan-2-yl)methoxy]phosphoryl}oxy)phosphinic acid
559.3157
559.071673493
-2.19
8
adp ribose
0
-2
FDB022468
(rib5)ppa;5-(adenosine 5'-pyrophosphoryl)-d-ribose;A5'pp5rib;Adp ribose;Adp-d-ribose;Adp-rib;Adp-ribose;Adpribose;Adenosine 5'-diphosphoribose;Adenosine diphosphate ribose;Adopprib;Ribose adenosine diphosphate;[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [hydroxy-[(3,4,5-trihydroxyoxolan-2-yl)methoxy]phosphoryl] hydrogen phosphate;D-ribofuranos-5-yl-adp
PW_C000914
ADP-Rib
1837
8
4571
2
11788
198
77997
111
78391
132
80667
135
120149
122
121952
124
124505
118
125511
297
127048
205
127710
388
32
Adenosine monophosphate
HMDB0000045
Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP can be produced during ATP synthesis by the enzyme adenylate kinase. AMP has recently been approved as a 'Bitter Blocker' additive to foodstuffs. When AMP is added to bitter foods or foods with a bitter aftertaste it makes them seem 'sweeter'. This potentially makes lower calorie food products more palatable.
61-19-8
C00020
6083
16027
AMP
5858
DB00131
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1
C10H14N5O7P
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
UDMBCSSLTHHNCD-KQYNXXCUSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
347.2212
347.063084339
-2.02
5
adenylate
0
-2
DBMET00485
FDB021806
5'-amp;5'-adenosine monophosphate;5'-adenylate;5'-adenylic acid;Amp;Adenosine 5'-monophosphate;Adenosine 5'-phosphate;Adenosine 5'-phosphorate;Adenosine 5'-phosphoric acid;Adenosine phosphate;Adenosine-5'-monophosphorate;Adenosine-5'-monophosphoric acid;Adenosine-5-monophosphorate;Adenosine-5-monophosphoric acid;Adenosine-monophosphate;Adenosine-phosphate;Adenovite;Adenylate;Adenylic acid;Cardiomone;Lycedan;Muscle adenylate;Muscle adenylic acid;My-b-den;My-beta-den;Phosaden;Phosphaden;Phosphentaside;5'-o-phosphonoadenosine;Adenosine 5'-(dihydrogen phosphate);Adenosine monophosphate;Adenosine-5'p;Adenosini phosphas;Ado5'p;Fosfato de adenosina;Pa;Pado;Phosphate d'adenosine;5'-adenosine monophosphoric acid;Adenosine phosphoric acid;Adenosine 5'-(dihydrogen phosphoric acid);Adenosine 5'-monophosphoric acid;Adenosine monophosphoric acid;Adenosine-5'-monophosphate;Phosphoric acid d'adenosine
PW_C000032
AMP
11
2
34
4
62
8
270
16
734
32
881
22
1189
14
4572
5
4867
54
5033
89
5251
104
5408
117
5423
103
5432
118
5457
120
5558
132
5583
133
5779
101
5795
108
6977
199
7072
188
11789
198
11868
161
11988
151
12003
222
12580
226
12636
31
12694
290
13331
225
42266
3
42646
315
77234
329
77325
111
78392
334
78809
115
79320
112
80399
1
80684
135
80900
7
119916
122
120016
124
120031
406
120246
382
120888
405
121954
408
122920
399
123464
376
124507
374
125306
297
125394
299
125409
479
125596
484
126853
205
126934
388
126949
501
127124
389
127311
209
127711
502
1191
D-Ribose 5-phosphate
HMDB0001548
D-Ribose 5-phosphate is an important intermediate metabolite in the Pentose phosphate pathway (KEGG, map00030) and in the Purine metabolism pathway (KEGG, map00230). The intracellular ribose 5-phosphate concentration is an important determinant of the rate of de novo purine synthesis. (PMID 6699001).
4300-28-1
C00117
439167
52742
RIBOSE-5P
388313
OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
C5H11O8P
InChI=1S/C5H11O8P/c6-3-2(1-12-14(9,10)11)13-5(8)4(3)7/h2-8H,1H2,(H2,9,10,11)/t2-,3-,4-,5?/m1/s1
KTVPXOYAKDPRHY-SOOFDHNKSA-N
{[(2R,3S,4R)-3,4,5-trihydroxyoxolan-2-yl]methoxy}phosphonic acid
230.1098
230.01915384
-0.84
5
D-ribofuranose 5-phosphate
0
-2
FDB001615
D-ribose 5-phosphate;D-ribose-5-p;D-ribose-5-phosphate;D-ribose-5-phosphorate;D-ribose-5-phosphoric acid;Ribose-5-p;Ribose-5-phosphate;Ribose-5-phosphorate;Ribose-5-phosphoric acid;Ribose-5p;D-ribose 5'-phosphate;Ribose 5-phosphate;D-ribose 5'-phosphoric acid;D-ribofuranose 5-phosphoric acid;D-ribose 5-phosphoric acid;Ribose 5-phosphoric acid
PW_C001191
DRib-5P
1758
2
1838
8
11790
198
13295
225
77171
132
78680
111
121870
122
122183
124
124423
135
124735
118
126340
299
127904
388
882
5-Phosphoribosylamine
HMDB0001128
5-Phosphoribosylamine, also known as 5-p-beta-D-ribosyl-amine or PRA, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. 5-Phosphoribosylamine is soluble (in water) and a moderately acidic compound (based on its pKa). In humans, 5-phosphoribosylamine is involved in the purine metabolism pathway, the azathioprine action pathway, the mercaptopurine action pathway, and the homocarnosinosis pathway. 5-Phosphoribosylamine is also involved in several metabolic disorders, some of which include the AICA-ribosiduria pathway, xanthine dehydrogenase deficiency (xanthinuria), the hyperinsulinism-hyperammonemia syndrome pathway, and 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency. Outside of the human body, 5-phosphoribosylamine can be found in a number of food items such as red bell pepper, apple, chinese chestnut, and wild leek. This makes 5-phosphoribosylamine a potential biomarker for the consumption of these food products. 5-Phosphoribosylamine is a substrate for Amidophosphoribosyltransferase and Trifunctional purine biosynthetic protein adenosine-3.
C03090
439905
37737
5-P-BETA-D-RIBOSYL-AMINE
388939
N[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
C5H12NO7P
InChI=1S/C5H12NO7P/c6-5-4(8)3(7)2(13-5)1-12-14(9,10)11/h2-5,7-8H,1,6H2,(H2,9,10,11)/t2-,3-,4-,5-/m1/s1
SKCBPEVYGOQGJN-TXICZTDVSA-N
{[(2R,3S,4R,5R)-5-amino-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
229.125
229.035138255
-0.78
5
5-phospho-β-D-ribosylamine
0
-1
FDB022441
5-p-beta-d-ribosyl-amine;5-p-beta-delta-ribosyl-amine;5-phospho-d-ribosylamine;5-phospho-beta-d-ribosyl-amine;5-phospho-beta-d-ribosylamine;5-phospho-beta-delta-ribosyl-amine;5-phospho-beta-delta-ribosylamine;5-phospho-delta-ribosylamine;5-phosphoribosylamine;Pra;5-phosphoribosyl-1-amine;5-phospho-b-d-ribosylamine;5-phospho-β-d-ribosylamine
PW_C000882
5-PPRSA
1841
8
11791
198
78001
111
80679
135
120159
122
125520
297
127055
205
95
L-Glutamic acid
HMDB0000148
Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. (http://en.wikipedia.org/wiki/Glutamic_acid).
56-86-0
C00025
33032
16015
GLT
30572
DB00142
N[C@@H](CCC(O)=O)C(O)=O
C5H9NO4
InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
WHUUTDBJXJRKMK-VKHMYHEASA-N
(2S)-2-aminopentanedioic acid
147.1293
147.053157781
-0.26
3
L-glutamic acid
0
-1
FDB012535
(2s)-2-aminopentanedioate;(2s)-2-aminopentanedioic acid;(s)-(+)-glutamate;(s)-(+)-glutamic acid;(s)-2-aminopentanedioate;(s)-2-aminopentanedioic acid;(s)-glutamate;(s)-glutamic acid;1-amino-propane-1,3-dicarboxylate;1-amino-propane-1,3-dicarboxylic acid;1-aminopropane-1,3-dicarboxylate;1-aminopropane-1,3-dicarboxylic acid;2-aminoglutarate;2-aminoglutaric acid;2-aminopentanedioate;2-aminopentanedioic acid;Aciglut;Aminoglutarate;Aminoglutaric acid;E;Glt;Glu;Glusate;Glut;Glutacid;Glutamicol;Glutamidex;Glutaminate;Glutaminic acid;Glutaminol;Glutaton;L-(+)-glutamate;L-(+)-glutamic acid;L-glu;L-glutamate;L-glutaminate;L-glutaminic acid;L-a-aminoglutarate;L-a-aminoglutaric acid;L-alpha-aminoglutarate;L-alpha-aminoglutaric acid;A-aminoglutarate;A-aminoglutaric acid;A-glutamate;A-glutamic acid;Alpha-aminoglutarate;Alpha-aminoglutaric acid;Alpha-glutamate;Alpha-glutamic acid;Acide glutamique;Acido glutamico;Acidum glutamicum;Glutamate;Glutamic acid;L-glutaminsaeure
PW_C000095
Glu
16
2
44
3
65
8
119
1
138
4
164
14
969
9
1105
42
1448
50
1456
26
1462
54
5323
111
5344
113
5415
117
5439
118
5565
132
5631
107
5632
108
5859
105
6006
147
6071
157
6191
94
6531
85
6838
187
6844
188
7092
72
7093
71
7165
205
7182
207
7514
224
7518
151
8208
225
8373
220
11792
198
11855
161
12004
222
12621
31
12683
289
12697
290
42348
315
42349
318
42845
320
77020
253
77332
133
77525
112
77971
346
77977
327
77981
347
78291
345
80649
135
120023
124
120040
122
120086
407
120347
406
120692
126
120816
418
121147
423
121153
424
121157
425
122833
119
122997
120
123299
443
123401
454
123719
458
123725
459
123729
460
125401
299
125418
297
125457
481
125667
479
125769
301
125802
489
126941
388
126995
206
127162
501
127257
506
500
L-Glutamine
HMDB0000641
Glutamine (Gln) is one of the 20 amino acids encoded by the standard genetic code. Its side chain is an amide; it is formed by replacing a side-chain hydroxyl of glutamic acid with an amine functional group. glutamine is found in foods high in proteins, such as fish, red meat, beans, and dairy products. glutamine is a supplement that is used in weightlifting, bodybuilding, endurance and other sports, as well as by those who suffer from muscular cramps or pain particularly elderly people. The main use of glutamine within the diet of either group is as a means of replenishing the body's stores of amino acids that have been used during exercise or everyday activities. Studies which are looking into problems with excessive consumption of glutamine thus far have proved inconclusive. However, normal supplementation is healthy mainly because glutamine is supposed to be supplemented after prolonged periods of exercise (for example, a workout or exercise in which amino acids are required for use) and replenishes amino acid stores; this being the main reason glutamine is recommended during fasting or for people who suffer from physical trauma, immune deficiencies, or cancer. There is a significant body of evidence that links glutamine-enriched diets with intestinal effects; aiding maintenance of gut barrier function, intestinal cell proliferation and differentiation, as well as generally reducing septic morbidity and the symptoms of Irritable Bowel Syndrome. The reason for such "cleansing" properties is thought to stem from the fact that the intestinal extraction rate of glutamine is higher than that for other amino acids, and is therefore thought to be the most viable option when attempting to alleviate conditions relating to the gastrointestinal tract. These conditions were discovered after comparing plasma concentration within the gut between glutamine-enriched and non glutamine-enriched diets. However, even though glutamine is thought to have "cleansing" properties and effects, it is unknown to what extent glutamine has clinical benefits, due to the varied concentrations of glutamine in varieties of food. It is also known that glutamine has various effects in reducing healing time after operations. Hospital waiting times after abdominal surgery are reduced by providing parenteral nutrition regimens containing amounts of glutamine to patients. Clinical trials have revealed that patients on supplementation regimes containing glutamine have improved nitrogen balances, generation of cysteinyl-leukotrienes from polymorphonuclear neutrophil granulocytes and improved lymphocyte recovery and intestinal permeability (in postoperative patients) - in comparison to those who had no glutamine within their dietary regime; all without any side-effects. (http://en.wikipedia.org/wiki/glutamine).
56-85-9
C00064
5961
18050
GLN
5746
DB00130
N[C@@H](CCC(N)=O)C(O)=O
C5H10N2O3
InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1
ZDXPYRJPNDTMRX-VKHMYHEASA-N
(2S)-2-amino-4-carbamoylbutanoic acid
146.1445
146.069142196
-0.17
3
L-glutamine
0
0
FDB012164
(2s)-2,5-diamino-5-oxopentanoate;(2s)-2,5-diamino-5-oxopentanoic acid;(2s)-2-amino-4-carbamoylbutanoate;(2s)-2-amino-4-carbamoylbutanoic acid;(s)-2,5-diamino-5-oxopentanoate;(s)-2,5-diamino-5-oxopentanoic acid;2-aminoglutaramic acid;Cebrogen;Glavamin;Glumin;Glutamic acid 5-amide;Glutamic acid amide;Glutamine;L-(+)-glutamine;L-2-aminoglutaramic acid;L-2-aminoglutaramidic acid;L-glutamic acid 5-amide;L-glutamic acid gamma-amide;L-glutamid;L-glutamide;L-glutamin;L-glutamine;L-glutaminsaeure-5-amid;Levoglutamid;Levoglutamida;Levoglutamide;Levoglutamidum;Levoglutamina;Polyglutamine;Stimulina;Gamma-glutamine;Q;Glutamate 5-amide;Glutamate amide
PW_C000500
Gln
61
8
443
4
2701
2
3021
15
5658
107
5659
108
6068
157
6846
166
6847
3
8390
225
11793
198
12692
290
42352
318
42353
315
77016
253
77296
111
77333
133
78395
132
79164
114
79264
116
80652
135
113207
94
116207
109
120038
122
120348
406
121219
409
121961
124
122998
120
123789
137
124514
118
125416
297
125668
479
126359
299
126812
483
126956
205
127163
501
127718
388
128411
208
78
Glycine
HMDB0000123
Glycine is a simple, nonessential amino acid, although experimental animals show reduced growth on low-glycine diets. The average adult ingests 3 to 5 grams of glycine daily. Glycine is involved in the body's production of DNA, phospholipids and collagen, and in release of energy. Glycine levels are effectively measured in plasma in both normal patients and those with inborn errors of glycine metabolism. (http://www.dcnutrition.com/AminoAcids/) Nonketotic hyperglycinaemia (OMIM 606899) is an autosomal recessive condition caused by deficient enzyme activity of the glycine cleavage enzyme system (EC 2.1.1.10). The glycine cleavage enzyme system comprises four proteins: P-, T-, H- and L-proteins (EC 1.4.4.2, EC 2.1.2.10 and EC 1.8.1.4 for P-, T- and L-proteins). Mutations have been described in the GLDC (OMIM 238300), AMT (OMIM 238310), and GCSH (OMIM 238330) genes encoding the P-, T-, and H-proteins respectively. The glycine cleavage system catalyses the oxidative conversion of glycine into carbon dioxide and ammonia, with the remaining one-carbon unit transferred to folate as methylenetetrahydrofolate. It is the main catabolic pathway for glycine and it also contributes to one-carbon metabolism. Patients with a deficiency of this enzyme system have increased glycine in plasma, urine and cerebrospinal fluid (CSF) with an increased CSF: plasma glycine ratio. (PMID 16151895).
56-40-6
C00037
5257127
15428
GLY
730
DB00145
NCC(O)=O
C2H5NO2
InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)
DHMQDGOQFOQNFH-UHFFFAOYSA-N
2-aminoacetic acid
75.0666
75.032028409
0.87
2
glycine
0
0
FDB000484
2-aminoacetate;2-aminoacetic acid;Aciport;Amino-acetate;Amino-acetic acid;Aminoacetate;Aminoacetic acid;Aminoethanoate;Aminoethanoic acid;Glicoamin;Glycocoll;Glycolixir;Glycosthene;Gyn-hydralin;Padil;Aminoessigsaeure;G;Gly;Glycin;Glykokoll;Glyzin;H2n-ch2-cooh;Hgly;Leimzucker
PW_C000078
Gly
31
4
179
8
1812
2
1881
27
2829
29
5420
103
5454
120
5580
133
5640
107
5641
108
5863
105
6007
147
7014
160
7439
3
7441
166
7442
15
11794
198
11872
161
12429
151
15233
222
42419
318
42420
315
77644
336
77742
111
78022
132
78304
351
80708
135
120028
406
120097
122
120117
124
121687
429
122283
435
122850
118
124236
464
124837
470
125406
479
125466
297
125484
299
126448
499
126946
501
127003
205
127021
388
128018
517
1355
Glycineamideribotide
HMDB0002022
Glycinamidoribotide conversion to N-formylglycinamide ribonucleotide is the third reaction of the de novo purine biosynthesis, a reaction catalyzed by the enzyme Glycinamide ribonucleotide transformylase (EC 2.1.2.2), with concomitant conversion of 10-formyltetrahydrofolate to tetrahydrofolate. (PMID: 9143358). Glycineamideribotide formation is stimulated by Luteinizing hormone (LH) and Chorionic gonadotropin (HCG) via activation of Glc-6-P-dehydrogenase (EC 1.1.1.49). (PMID: 4366083).
10074-18-7
C03838
160913
18349
5-PHOSPHO-RIBOSYL-GLYCINEAMIDE
141370
NCC(=O)N[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
C7H15N2O8P
InChI=1S/C7H15N2O8P/c8-1-4(10)9-7-6(12)5(11)3(17-7)2-16-18(13,14)15/h3,5-7,11-12H,1-2,8H2,(H,9,10)(H2,13,14,15)/t3-,5-,6-,7-/m1/s1
OBQMLSFOUZUIOB-SHUUEZRQSA-N
{[(2R,3S,4R,5R)-5-(2-aminoacetamido)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
286.1764
286.056601978
-1.29
6
glycineamide ribonucleotide
0
-1
FDB022801
5'-phosphoribosyl-glycineamide;5'-phosphoribosylglycinamide;5'-phosphoribosylglycineamide;Gar;Glycinamide ribonucleotide;Glycineamide ribonucleotide;N(1)-(5-phospho-d-ribosyl)glycinamide;N-glycyl-5-o-phosphono-d-ribofuranosylamine;N1-(5-phospho-d-ribosyl)glycinamide
PW_C001355
Glyadbt
1843
8
11795
198
78682
111
121873
122
124426
135
774
10-Formyltetrahydrofolate
HMDB0000972
10-Formyltetrahydrofolate (10-CHO-THF) is form of tetrahydrofolate that acts as a donor of formyl groups in anabolism. In particular, 10-CHO-THF is used as a substrate in a number of formyltransferase reactions. It plays an important role in purine biosynthesis, where 10-CHO-THF is a substrate for phosphoribosylaminoimidazolecarboxamide formyltransferase, as well as in the formylation of the methionyl initiator tRNA (fMet-tRNA), when 10-CHO-THF is a substrate for methionyl-tRNA formyltransferase. 10-Formyltetrahydrofolate is a substrate for Trifunctional purine biosynthetic protein adenosine-3, Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase (mitochondrial), 10-formyltetrahydrofolate dehydrogenase, Folylpolyglutamate synthase (mitochondrial), Bifunctional purine biosynthesis protein PURH and C-1-tetrahydrofolate synthase (cytoplasmic).
2800-34-2
C00234
122347
15637
10-FORMYL-THF
109092
NC1=NC(=O)C2=C(NCC(CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)N1
C20H23N7O7
InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t11?,13-/m0/s1
AUFGTPPARQZWDO-YUZLPWPTSA-N
(2S)-2-[(4-{N-[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid
473.4393
473.165896125
-3.15
7
(2S)-2-[(4-{N-[(2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid
0
-2
FDB022345
10-formyl-(6rs)-tetrahydrofolic acid;10-formyl-h4pteglu1;10-formyl-thf;10-formyl-tetrahydrofolate;10-formyltetrahydrofolate;10-formyltetrahydrofolic acid;10-formyltetrahydropteroylglutamate;10-formyltetrahydropteroylglutamic acid;10-fthf;N-[p-[n-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-glutamate;N-[p-[n-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-glutamic acid;N-[p-[n-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-l-glutamate;N-[p-[n-[(2-amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-l-glutamic acid;N10-formyl-5,6,7,8-tetrahydrofolate;N10-formyl-5,6,7,8-tetrahydrofolic acid;N10-formyltetrahydrofolate;N10-formyltetrahydrofolic acid;N10-formyltetrahydropteroylglutamate;N10-formyl-h4f;N10-formyl-thf
PW_C000774
10-FTHF
947
8
979
3
1918
2
5316
111
5350
112
7160
205
7188
206
7440
166
11796
198
78322
132
120671
122
120698
407
122301
124
123285
135
123303
119
124853
118
125754
297
125773
481
126467
299
128037
388
1221
Tetrahydrofolic acid
HMDB0001846
Tetrahydrofolate is a soluble coenzyme (vitamin B9) that is synthesized de novo by plants and microorganisms, and absorbed from the diet by animals. It is composed of three distinct parts: a pterin ring, a p-ABA (p-aminobenzoic acid) and a polyglutamate chain with a number of residues varying between 1 and 8. Only the tetra-reduced form of the molecule serves as a coenzyme for C1 transfer reactions. In biological systems, the C1-units exist under various oxidation states and the different tetrahydrofolate derivatives constitute a family of related molecules named indistinctly under the generic term folate. (PMID 16042593). Folate is important for cells and tissues that rapidly divide. Cancer cells divide rapidly, and drugs that interfere with folate metabolism are used to treat cancer. Methotrexate is a drug often used to treat cancer because it inhibits the production of the active form, tetrahydrofolate. Unfortunately, methotrexate can be toxic, producing side effects such as inflammation in the digestive tract that make it difficult to eat normally. -- Wikipedia; Signs of folic acid deficiency are often subtle. Diarrhea, loss of appetite, and weight loss can occur. Additional signs are weakness, sore tongue, headaches, heart palpitations, irritability, and behavioral disorders. Women with folate deficiency who become pregnant are more likely to give birth to low birth weight and premature infants, and infants with neural tube defects. In adults, anemia is a sign of advanced folate deficiency. In infants and children, folate deficiency can slow growth rate. Some of these symptoms can also result from a variety of medical conditions other than folate deficiency. It is important to have a physician evaluate these symptoms so that appropriate medical care can be given. -- Wikipedia; Folinic acid is a form of folate that can help 'rescue' or reverse the toxic effects of methotrexate. Folinic acid is not the same as folic acid. Folic acid supplements have little established role in cancer chemotherapy. There have been cases of severe adverse effects of accidental substitution of folic acid for folinic acid in patients receiving methotrexate cancer chemotherapy. It is important for anyone receiving methotrexate to follow medical advice on the use of folic or folinic acid supplements. -- Wikipedia. Low concentrations of folate, vitamin B12, or vitamin B6 may increase the level of homocysteine, an amino acid normally found in blood. There is evidence that an elevated homocysteine level is an independent risk factor for heart disease and stroke. The evidence suggests that high levels of homocysteine may damage coronary arteries or make it easier for blood clotting cells called platelets to clump together and form a clot. However, there is currently no evidence available to suggest that lowering homocysteine with vitamins will reduce your risk of heart disease. Clinical intervention trials are needed to determine whether supplementation with folic acid, vitamin B12 or vitamin B6 can lower your risk of developing coronary heart disease. -- Wikipedia.
135-16-0
C00101
13781857
20506
THF
18714427
DB00116
NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)N2)N1
C19H23N7O6
InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11-,12?/m0/s1
MSTNYGQPCMXVAQ-PXYINDEMSA-N
2-{[4-({[(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
445.4292
445.170981503
-3.22
8
2-{[4-({[(6S)-2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
0
-2
FDB022705
(6s)-tetrahydrofolate;(6s)-tetrahydrofolic acid;5,6,7,8-tetrahydrofolate;5,6,7,8-tetrahydrofolic acid;Tetra-h-folate;Tetrahydrafolate;Tetrahydrofolate;Tetrahydrofolic acid;Tetrahydropteroyl mono-l-glutamate;Tetrahydropteroylglutamate
PW_C001221
THFA
448
4
571
8
975
3
1809
2
5307
111
5347
112
5601
135
5786
108
6009
147
7066
188
7151
205
7185
206
7583
163
11797
198
42640
315
77336
133
78118
132
120352
406
120482
122
120696
407
122166
124
123001
120
123301
119
124718
118
125673
479
125749
297
125771
481
126324
299
127168
501
127886
388
1007
5'-Phosphoribosyl-N-formylglycinamide
HMDB0001308
5'-Phosphoribosyl-N-formylglycineamide (also known as FGAR or N-Formyl-GAR) is a substrate for Phosphoribosylformylglycinamidine synthase. It is involved in aminoimidazole ribonucleotide biosynthesis and plays a vital role in purine metabolism as well as the conversion of glutamine to glutamate. 5'-Phosphoribosyl-N-formylglycineamide is described as a glycinamide ribonucleotide having a phosphate group at the 5-position and a formyl group on the glycine nitrogen.
349-34-8
C04376
130805
5-P-RIBOSYL-N-FORMYLGLYCINEAMIDE
115687
O[C@H]1[C@@H](O)[C@H](NC(=O)CNC=O)O[C@@H]1COP(O)(O)=O
C8H15N2O9P
InChI=1S/C8H15N2O9P/c11-3-9-1-5(12)10-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H,9,11)(H,10,12)(H2,15,16,17)/t4-,6-,7-,8-/m1/s1
VDXLUNDMVKSKHO-XVFCMESISA-N
{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoacetamido)oxolan-2-yl]methoxy}phosphonic acid
314.1865
314.0515166
-1.68
6
[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoacetamido)oxolan-2-yl]methoxyphosphonic acid
0
-2
FDB022544
5'-p-ribosyl-n-formylglycineamide;5'-phosphoribosyl-n-formylglycinamide;5'-phosphoribosyl-n-formylglycineamide;5'-phosphoribosyl-formylglycinamide;5-phosphoribosyl-n-formalglycineamide;Fgar;N(2)-formyl-n(1)-(5-phospho-d-ribosyl)glycinamide;N-formyl-gar;N-formylglycinamide ribonucleotide;N2-formyl-n1-(5-phospho-d-ribosyl)glycinamide
PW_C001007
5PPNFG
1845
8
11798
198
78684
111
121875
122
124428
135
791
Phosphoribosylformylglycineamidine
HMDB0000999
Phosphoribosylformylglycineamidine, also known as fgam, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. Phosphoribosylformylglycineamidine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Phosphoribosylformylglycineamidine exists in all living organisms, ranging from bacteria to humans. In humans, phosphoribosylformylglycineamidine is involved in the mercaptopurine action pathway, the purine metabolism pathway, the azathioprine action pathway, and the thioguanine action pathway. Phosphoribosylformylglycineamidine is also involved in several metabolic disorders, some of which include xanthine dehydrogenase deficiency (xanthinuria), myoadenylate deaminase deficiency, molybdenum cofactor deficiency, and the gout or kelley-seegmiller syndrome pathway. Outside of the human body, phosphoribosylformylglycineamidine can be found in a number of food items such as winter savory, rambutan, mountain yam, and guava. This makes phosphoribosylformylglycineamidine a potential biomarker for the consumption of these food products. 5-Phosphoribosyl-n-formylglycineamidine is a substrate for Glucosamine-6-phosphate isomerase.
37721-04-3
C04640
440417
18413
5-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINE
7830994
O[C@H]1[C@@H](O)[C@H](NC(=N)CNC=O)O[C@@H]1COP(O)(O)=O
C8H16N3O8P
InChI=1S/C8H16N3O8P/c9-5(1-10-3-12)11-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H2,9,11)(H,10,12)(H2,15,16,17)/t4-,6-,7-,8-/m1/s1
PMCOGCVKOAOZQM-XVFCMESISA-N
{[(2R,3S,4R,5R)-5-[N-(carbamimidoylmethyl)formamido]-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
313.2017
313.067501015
-1.31
6
[(2R,3S,4R,5R)-5-[N-(carbamimidoylmethyl)formamido]-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
0
-1
FDB022360
5'-phosphoribosyl-n-formyl glycineamidine;5'-phosphoribosylformylglycinamidine;5-phosphoribosyl-n-formylglycineamidine;Fgam;N-(2-amino-2-iminoethyl)-n-(5-o-phosphono-b-d-ribofuranosyl)-formamide;N-(2-amino-2-iminoethyl)-n-(5-o-phosphono-beta-delta-ribofuranosyl)-formamide;1-(5'-phosphoribosyl)-n-formylglycinamidine;5'-phosphoribosyl-n-formylglycinamidine;2-(formamido)-n1-(5-phospho-d-ribosyl)acetamidine
PW_C000791
FGAM
1846
8
11799
198
78685
111
121876
122
124429
135
2699
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate
HMDB0006273
5-amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate is an intermediate in purine metabolism. 5-amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate is converted from aminoimidazole ribotide via phosphoribosylaminoimidazole carboxylase [EC: 4.1.1.21].
C04751
165388
28413
PHOSPHORIBOSYL-CARBOXY-AMINOIMIDAZOLE
144983
NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(O)=O
C9H14N3O9P
InChI=1S/C9H14N3O9P/c10-7-4(9(15)16)11-2-12(7)8-6(14)5(13)3(21-8)1-20-22(17,18)19/h2-3,5-6,8,13-14H,1,10H2,(H,15,16)(H2,17,18,19)/t3-,5-,6-,8-/m1/s1
XFVULMDJZXYMSG-ZIYNGMLESA-N
5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazole-4-carboxylic acid
339.1959
339.046765573
-2.08
6
5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazole-4-carboxylic acid
0
-2
FDB023871
1-(5'-phosphoribosyl)-4-carboxy-5-aminoimidazole;1-(5'-phosphoribosyl)-5-amino-4-carboxyimidazole;1-(5'-phosphoribosyl)-5-amino-4-imidazolecarboxylate;1-(5-phospho-d-ribosyl)-5-amino-4-imidazolecarboxylate;4-carboxy-5-aminoimidazole ribonucleotide;5'-phosphoribosyl-4-carboxy-5-aminoimidazole;5'-phosphoribosyl-5-amino-4-imidazolecarboxylate;5'phosphoribosyl-4-carboxy-5-aminoimidazole;5-amino-1-(5-phospho-d-ribosyl)imidazole-4-carboxylic acid;5-amino-4-carboxyimidazole ribonucleotide;5-amino-4-imidazolecarboxylic acid ribonucleotide;5-aminoimidazole carboxilic acid ribonucleotice;5-aminoimidazole-4-carboxilic acid ribonucleotide;Carboxyaminoimidazole ribonucleotide;5-amino-1-(5-phospho-d-ribosyl)imidazole-4-carboxylate;1-(5'-phosphoribosyl)-5-amino-4-imidazolecarboxylic acid;1-(5-phospho-d-ribosyl)-5-amino-4-imidazolecarboxylic acid;5'-phosphoribosyl-5-amino-4-imidazolecarboxylic acid
PW_C002699
CR
1849
8
11800
198
78687
111
121878
122
124431
135
955
5-Aminoimidazole ribonucleotide
HMDB0001235
5-aminoimidazole ribonucleotide (AIR), is an intermediate of purine nucleotide biosynthesis. It is also the precursor to 4-amino-2-methyl-5-hydroxymethylpyrimidine (HMP), the first product of pyrimidine biosynthesis. This reaction is mediated by the enzyme HMP-P kinase (ThiD). HMP is a precursor of thiamine phosphate (TMP), and subsequently to thiamine pyrophosphate (TPP). TPP is an essential cofactor in all living systems that plays a central role in metabolism. (PMID: 15326535). 5-Aminoimidazole ribonucleotide is a substrate for a number of proteins including: Scaffold attachment factor B2, Multifunctional protein ADE2, Pulmonary surfactant-associated protein B, Tumor necrosis factor receptor superfamily member 25, Pulmonary surfactant-associated protein C, Serine/threonine-protein kinase Chk1, Vinexin, Trifunctional purine biosynthetic protein adenosine-3, Antileukoproteinase 1 and Scaffold attachment factor B.
25635-88-5
C03373
161500
28843
5-PHOSPHORIBOSYL-5-AMINOIMIDAZOL
141854
NC1=CN=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
C8H14N3O7P
InChI=1S/C8H14N3O7P/c9-5-1-10-3-11(5)8-7(13)6(12)4(18-8)2-17-19(14,15)16/h1,3-4,6-8,12-13H,2,9H2,(H2,14,15,16)/t4-,6-,7-,8-/m1/s1
PDACUKOKVHBVHJ-XVFCMESISA-N
{[(2R,3S,4R,5R)-5-(5-amino-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
295.1864
295.056936329
-1.94
5
5-aminoimidazole ribotide
0
-1
FDB022504
1-(5'-phosphoribosyl)-5-aminoimidazole;1-(5-phospho-d-ribosyl)-5-aminoimidazole;5'-phosphoribosyl-5-aminoimidazole;5-amino-1-(5-phospho-d-ribosyl)imidazole;5-aminoimidazole ribonucleotide;5-aminoimidazole ribotide;Air;Aminoimidazole ribotide
PW_C000955
5-AnRbn
1848
8
11801
198
78688
111
121879
122
124432
135
1316
Carbon dioxide
HMDB0001967
Carbon dioxide is a colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbon dioxide is produced during respiration by all animals, fungi and microorganisms that depend on living and decaying plants for food, either directly or indirectly. It is, therefore, a major component of the carbon cycle. Additionally, carbon dioxide is used by plants during photosynthesis to make sugars which may either be consumed again in respiration or used as the raw material to produce polysaccharides such as starch and cellulose, proteins and the wide variety of other organic compounds required for plant growth and development. When inhaled at concentrations much higher than usual atmospheric levels, it can produce a sour taste in the mouth and a stinging sensation in the nose and throat. These effects result from the gas dissolving in the mucous membranes and saliva, forming a weak solution of carbonic acid. Carbon dioxide is used by the food industry, the oil industry, and the chemical industry. Carbon dioxide is used to produce carbonated soft drinks and soda water. Traditionally, the carbonation in beer and sparkling wine comes about through natural fermentation, but some manufacturers carbonate these drinks artificially.
124-38-9
C00011
280
16526
274
O=C=O
CO2
InChI=1S/CO2/c2-1-3
CURLTUGMZLYLDI-UHFFFAOYSA-N
methanedione
44.0095
43.989829244
0.63
0
carbon dioxide
0
0
DBMET00423
FDB014084
Carbon oxide;Carbon-12 dioxide;Carbonic acid anhydride;Carbonic acid gas;Carbonic anhydride;[co2];Co2;E 290;E-290;E290;R-744
PW_C001316
CO2
50
8
121
1
204
4
480
13
503
18
640
3
677
31
695
20
806
5
1133
43
1638
49
1745
2
2551
17
3144
70
5283
103
5320
111
5750
108
5771
101
5968
100
6026
155
6078
161
6471
178
6637
107
6922
190
7017
160
7035
163
7061
188
7163
205
7308
198
7333
213
7461
222
7530
210
8215
225
8223
151
9158
249
11849
277
11908
170
12464
226
12688
290
42626
315
43523
318
76994
293
77122
133
77170
132
77470
333
77739
112
77750
129
77763
341
78077
134
78405
356
78427
334
78941
331
79227
130
80008
368
80675
119
80717
135
94836
384
113291
391
115549
121
119954
406
120089
122
120155
407
120364
412
120556
414
120833
419
120922
124
120991
408
121284
125
121505
383
122744
120
123011
446
123190
450
123418
455
123489
118
123556
374
123855
136
124063
398
125344
479
125460
297
125516
481
125824
490
125870
299
125931
482
126280
480
126887
501
127052
206
127277
507
127331
388
127390
502
123
L-Aspartic acid
HMDB0000191
Aspartic acid (Asp, D), also known as aspartate, the name of its anion, is one of the 20 natural proteinogenic amino acids which are the building blocks of proteins. As its name indicates, aspartic acid is the carboxylic acid analog of asparagine. As a neurotransmitter, aspartic acid may provide resistance to fatigue and thus lead to endurance, although the evidence to support this idea is not strong (Wikipedia). Aspartic acid is a nonessential amino acid that is made from glutamic acid by enzymes using vitamin B6. The amino acid has important roles in the urea cycle and DNA metabolism. Aspartic acid is a major excitatory neurotransmitter, which is sometimes found to be increased in epileptic and stroke patients. It is decreased in depressed patients and in patients with brain atrophy. Aspartic acid supplements are being evaluated. Five grams can raise blood levels. Magnesium and zinc may be natural inhibitors of some of the actions of aspartic acid. Aspartic acid, with the amino acid phenylalanine, is a part of a new natural sweetener, aspartame. This sweetener is an advance in artificial sweeteners, and is probably safe in normal doses to all except phenylketonurics. The jury is still out on the long-term effects it has on many brain neurohormones. Aspartic acid may be a significant immunostimulant of the thymus and can protect against some of the damaging effects of radiation. Many claims have been made for the special value of administering aspartic acid in the form of potassium and magnesium salts. Since aspartic acid is relatively nontoxic, studies are now in progress to elucidate its pharmacological and therapeutic roles (http://www.dcnutrition.com/AminoAcids).
56-84-8
C00049
44367445
17053
L-ASPARTATE
5745
DB00128
N[C@@H](CC(O)=O)C(O)=O
C4H7NO4
InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1
CKLJMWTZIZZHCS-REOHCLBHSA-N
(2S)-2-aminobutanedioic acid
133.1027
133.037507717
0.03
3
L-aspartic acid
0
-1
FDB012567
Asp;(+)-aspartate;(+)-aspartic acid;(2s)-aspartate;(2s)-aspartic acid;(l)-aspartate;(l)-aspartic acid;(r)-2-aminosuccinate;(s)-(+)-aspartate;(s)-(+)-aspartic acid;(s)-2-aminosuccinate;(s)-2-aminosuccinic acid;(s)-aminobutanedioate;(s)-aminobutanedioic acid;(s)-aspartate;(s)-aspartic acid;(s)-amino-butanedioate;(s)-amino-butanedioic acid;2-amino-3-methylsuccinate;2-amino-3-methylsuccinic acid;2-aminosuccinate;2-aminosuccinic acid;Aminosuccinate;Asparagate;Asparagic acid;Asparaginate;Asparaginic acid;Asparatate;Aspartate;H-asp-oh;L-(+)-aspartate;L-(+)-aspartic acid;L-aminosuccinate;L-aminosuccinic acid;L-asparagate;L-asparagic acid;L-asparaginate;L-asparaginic acid;L-aspartate;Alpha-aminosuccinate;Alpha-aminosuccinic acid;(s)-2-aminobutanedioic acid;Aspartic acid;D;L-asparaginsaeure;(s)-2-aminobutanedioate
PW_C000123
Asp
48
8
93
9
1101
3
1103
4
1104
42
1994
2
5663
107
5664
108
6851
188
7570
160
8185
225
11802
198
12686
290
12704
291
42363
318
42364
315
77323
111
77510
132
77532
113
78288
133
78289
345
79307
112
80699
135
119878
232
119881
117
120037
122
120421
124
120809
406
120813
418
123057
118
123394
120
123398
454
125415
297
125795
479
125799
489
126955
205
127250
501
127254
506
127555
388
637
SAICAR
HMDB0000797
SAICAR (or (S)-2-[5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate) is a substrate for the multifunctional protein ADE2. SAICAR is an intermediate in purine metabolism. SAICAR is converted from 5-amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate via phosphoribosylaminoimidazole-succinocarboxamide synthase (EC: 6.3.2.6) or SAICAR synthase. This enzyme catalyses the seventh step out of ten in the biosynthesis of purine nucleotides. The appearance of succinylaminoimidazolecarboxamide riboside (SAICAriboside) and succinyladenosine (S-Ado) in cerebrospinal fluid, in urine, and, to a lesser extent, in plasma is characteristic of a heritable deficiency known as adenylosuccinate lyase deficiency. Adenylosuccinate lyase deficiency is responsible for a range of symptoms that involve psychomotor retardation, often accompanied by epileptic seizures, and autistic features. When present in sufficiently high levels, SAICAR can act as an oncometabolite, a metabotoxin, and an acidogen. An oncometabolite is a compound that promotes tumour growth and survival. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. As an oncometabolite, high levels of SAICAR stimulate pyruvate kinase isoform M2 and promote cancer cell survival in glucose-limited conditions such as aerobic glycolysis (PMID: 23086999). As an organic acid, SAICAR is associated with acidosis. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated adenylosuccinate lyase deficiency. Many affected children with organic acidemias experience intellectual disability or delayed development.
3031-95-6
C04823
160666
18319
P-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE
141175
NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](CC(O)=O)C(O)=O
C13H19N4O12P
InChI=1S/C13H19N4O12P/c14-10-7(11(22)16-4(13(23)24)1-6(18)19)15-3-17(10)12-9(21)8(20)5(29-12)2-28-30(25,26)27/h3-5,8-9,12,20-21H,1-2,14H2,(H,16,22)(H,18,19)(H,23,24)(H2,25,26,27)/t4-,5+,8+,9+,12+/m0/s1
NAQGHJTUZRHGAC-ZZZDFHIKSA-N
(2S)-2-({5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-4-yl}formamido)butanedioic acid
454.2833
454.073708604
-2.42
8
saicar
0
-4
FDB022251
(s)-2-(5-amino-1-(5-phospho-d-ribosyl)imidazole-4-carboxamido)succinate;(s)-2-(5-amino-1-(5-phospho-d-ribosyl)imidazole-4-carboxamido)succinic acid;(s)-2-(5-amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinate;(s)-2-(5-amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinic acid;(s)-2-[5-amino-1-(5-phospho-d-ribosyl)imidazole-4-carboxamido]succinate;(s)-2-[5-amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinate;1-(5'-phosphoribosyl)-4-(n-succinocarboxamide)-5-aminoimidazole;1-(5'-phosphoribosyl)-5-amino-4-(n-succinocarboxamide)-imidazole;1-(5'-phosphoribosyl)-5-amino-4-(n-succinocarboxamide)-imidazole' 1-(5'-phosphoribosyl)-4-(n-succinocarboxamide)-5-aminoimidazole;5'-phosphoribosyl-4-(n-succinocarboxamide)-5-aminoimidazole;5'-phosphoribosyl-4-(n-succinocarbozamide)-5-aminoimidazole;5-amino-4-imidazole-n-succinocarboxamide ribonucleotide;L-n-[(5-amino-1-b-d-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate);L-n-[(5-amino-1-beta-delta-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate);N-(5-amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphate;N-[5-amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartate;N-[5-amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartic acid;Phosphoribosylaminoimidazolesuccinocarboxamide;Saicar;Saicariboside;Succino-aicar;Succinylaminoimidazole carboxamide riboside;(2s)-2-[5-amino-1-(5-phospho-beta-d-ribosyl)imidazole-4-carboxamido]succinic acid;Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphate;Succinylaminoimidazolecarboxamide ribose-5'-phosphate
PW_C000637
SAICAR
1851
8
11803
198
78690
111
121881
122
124434
135
88
Fumaric acid
HMDB0000134
Fumaric acid is a precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase. Fumarate is converted by fumarase to malate. A fumarate is a salt or ester of the organic compound fumaric acid, a dicarboxylic acid. (wikipedia).
110-17-8
C00122
21883788
18012
FUM
10197150
DB04299
OC(=O)\C=C\C(O)=O
C4H4O4
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
VZCYOOQTPOCHFL-OWOJBTEDSA-N
(2E)-but-2-enedioic acid
116.0722
116.010958616
-0.68
2
fumaric acid
0
-2
FDB003291
(2e)-but-2-enedioate;(2e)-but-2-enedioic acid;(e)-2-butenedioate;(e)-2-butenedioic acid;2-(e)-butenedioate;2-(e)-butenedioic acid;Allomaleate;Allomaleic acid;Boletate;Boletic acid;Fc 33;Fumarate;Fumaric acid;Lichenate;Lichenic acid;Sodium fumarate;Trans-1,2-ethylenedicarboxylate;Trans-1,2-ethylenedicarboxylic acid;Trans-2-butenedioate;Trans-2-butenedioic acid;Trans-butenedioate;Trans-butenedioic acid;(2e)-2-butenedioic acid;E297;Fumarsaeure;Trans-but-2-enedioic acid;(2e)-2-butenedioate;Trans-but-2-enedioate
PW_C000088
Fumarat
102
8
254
17
2004
2
5053
4
5388
102
6047
156
6107
162
6458
107
6459
108
6492
179
6763
117
6837
166
7480
223
9065
151
11804
198
12713
290
42400
322
42496
318
42497
315
77148
134
77466
111
79107
132
80027
369
117808
133
119989
384
120043
122
121599
124
122661
406
122772
121
122794
135
124157
118
125236
120
125369
480
125421
297
126793
479
126911
391
126960
205
127565
388
128391
501
1168
AICAR
HMDB0001517
AICAR also known as ZMP is an analog of AMP that is capable of stimulating AMP-dependent protein kinase activity(AMPK). AICAR is an intermediate in the generation of inosine monophosphate. AICAR is being clinically used to treat and protect against cardiac ischemic injury. AICAR can enter cardiac cells to inhibit adenosine kinase and adenosine deaminase. It enhances the rate of nucleotide re-synthesis increasing adenosine generation from adenosine monophosphate only during conditions of myocardial ischemia. AICAR increases glucose uptake by inducing translocation of GLUT4 and/or by activating the p38 MAPK pathway.
3031-94-5
C04677
65110
18406
AICAR
58620
DB01700
NC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
C9H15N4O8P
InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1
NOTGFIUVDGNKRI-UUOKFMHZSA-N
{[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
338.2112
338.062749988
-2.08
6
aica ribonucleotide
0
-2
FDB001213
5'-p-ribosyl-5-amino-4-imidazole carboxamide;5'-phosphoribosyl-5-amino-4-imidazole carboxamide;5-amino-4-imidazolecarboxamide ribotide;Aica ribonucleotide;Aminoimidazole carboxamide ribonucleotide;Z-nucleotide;1-(5'-phosphoribosyl)-5-amino-4-imidazolecarboxamide;5'-phospho-ribosyl-5-amino-4-imidazole carboxamide;5'-phosphoribosyl-5-amino-4-imidazolecarboxamide;5-amino-1-(5-phospho-d-ribosyl)imidazole-4-carboxamide;5-aminoimidazole-4-carboxamide ribotide;5-phosphoribosyl-4-carbamoyl-5-aminoimidazole;Acadesine 5'-monophosphate;Aica-ribonucleotide;Aicar
PW_C001168
AICAR
1852
8
11805
198
78691
111
121882
122
124435
135
1111
Phosphoribosyl formamidocarboxamide
HMDB0001439
Phosphoribosyl formamidocarboxamide, also known as faicar, belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. Phosphoribosyl formamidocarboxamide is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, phosphoribosyl formamidocarboxamide is primarily located in the cytoplasm and mitochondria. Phosphoribosyl formamidocarboxamide exists in all living organisms, ranging from bacteria to humans. In humans, phosphoribosyl formamidocarboxamide is involved in the azathioprine action pathway, the mercaptopurine action pathway, the thioguanine action pathway, and the purine metabolism pathway. Phosphoribosyl formamidocarboxamide is also involved in several metabolic disorders, some of which include xanthine dehydrogenase deficiency (xanthinuria), the gout or kelley-seegmiller syndrome pathway, myoadenylate deaminase deficiency, and adenylosuccinate lyase deficiency. Outside of the human body, phosphoribosyl formamidocarboxamide can be found in a number of food items such as kai-lan, apricot, cupuaçu, and pomes. This makes phosphoribosyl formamidocarboxamide a potential biomarker for the consumption of these food products. This compound is an intermediate in purine metabolism, where it is the byproduct of phosphoribosylaminoimidazolecarboxamide formyltransferase (EC 2.1.2.3) and IMP cyclohydrolase (EC 3.5.4.10). It is also a byproduct of Ligases (EC 6.3.4.-).
C04734
166760
18381
PHOSPHORIBOSYL-FORMAMIDO-CARBOXAMIDE
145893
NC(=O)C1=C(NC=O)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
C10H15N4O9P
InChI=1S/C10H15N4O9P/c11-8(18)5-9(13-3-15)14(2-12-5)10-7(17)6(16)4(23-10)1-22-24(19,20)21/h2-4,6-7,10,16-17H,1H2,(H2,11,18)(H,13,15)(H2,19,20,21)/t4-,6-,7-,10-/m1/s1
ABCOOORLYAOBOZ-KQYNXXCUSA-N
{[(2R,3S,4R,5R)-5-(4-carbamoyl-5-formamido-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
366.2213
366.05766461
-2.23
6
[(2R,3S,4R,5R)-5-(4-carbamoyl-5-formamidoimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
0
-2
FDB022622
5'-phosphoribosyl-5-formamido-4-imidazole carboxamide;5'-p-ribosyl-5-formamido-4-imidazole carboxamide;5-amino-1-(5-phospho-d-ribosyl)imidazole-4-carboxamide;5-formamido-1-(5-phospho-d-ribosyl)imidazole-4-carboxamide;5-formamido-1-(5-phosphoribosyl)-imidazole-4-carboxamide;5-phosphoribosyl-5-formamido-4-imid-carboxamide;Phosphoribosyl-formamido-carboxamide;1-(5'-phosphoribosyl)-5-formamido-4-imidazolecarboxamide;5'-phosphoribosyl-5-formamido-4-imidazolecarboxamide;5-formamido-1-(5-phosphoribosyl)imidazole-4-carboxamide;Faicar
PW_C001111
FosbFca
1853
8
11806
198
78693
111
121883
122
124436
135
114
Inosinic acid
HMDB0000175
Inosinic acid is a purine nucleotide which has hypoxanthine as the base and one phosphate group esterified to the sugar moiety. Inosinic acid is a nucleotide present in muscle and other tissues. It is formed by the deamination of AMP and when hydrolysed produces inosine. Inosinic acid is the ribonucleotide of hypoxanthine and is the first compound formed during the synthesis of purine. (Wikipedia).
131-99-7
C00130
8582
17202
IMP
8264
O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CNC2=O
C10H13N4O8P
InChI=1S/C10H13N4O8P/c15-6-4(1-21-23(18,19)20)22-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,11,12,17)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
GRSZFWQUAKGDAV-KQYNXXCUSA-N
{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-6,9-dihydro-1H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid
348.206
348.047099924
-2.06
5
inosine-5'-monophosphate
0
-2
FDB021901
5'-imp;5'-inosinate;5'-inosine monophosphate;5'-inosinic acid;Imp;Inosine 5'-monophosphate;Inosine 5'-phosphate;Inosine monophosphate;Inosine-5'-monophosphate;2'-inosine-5'-monophosphate;Hypoxanthosine 5'-monophosphate;Inosinic acid;Ribosylhypoxanthine monophosphate;2'-inosine-5'-monophosphoric acid;5'-inosine monophosphoric acid;Hypoxanthosine 5'-monophosphoric acid;Inosine 5'-monophosphoric acid;Inosine 5'-phosphoric acid;Inosine monophosphoric acid;Inosinate;Ribosylhypoxanthine monophosphoric acid
PW_C000114
Imp
82
8
11807
198
12438
151
12726
290
77545
111
120067
122
122819
135
125444
297
126983
205
1196
Xanthylic acid
HMDB0001554
Xanthylic acid is an important metabolic intermediate in the Purine Metabolism, and is a product or substrate of the enzymes Inosine monophosphate dehydrogenase (EC 1.1.1.205), Hypoxanthine phosphoribosyltransferase (EC 2.4.2.8), Xanthine phosphoribosyltransferase (EC 2.4.2.22), 5'-Ribonucleotide phosphohydrolase (EC 3.1.3.5), Ap4A hydrolase (EC 3.6.1.17), Nucleoside-triphosphate diphosphatase (EC 3.6.1.19), Phosphoribosylamine-glycine ligase (EC 6.3.4.1), and glutamine amidotransferase (EC 6.3.5.2). (KEGG) Xanthylic acid can also be used in quantitative measurements of the Inosine monophosphate dehydrogenase enzyme activities in purine metabolism. This measurement is important for optimal thiopurine therapy for children with acute lymphoblastic leukaemia (ALL). (PMID: 16725387).
523-98-8
C00655
73323
15652
XANTHOSINE-5-PHOSPHATE
66054
O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O
C10H13N4O9P
InChI=1S/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1
DCTLYFZHFGENCW-UUOKFMHZSA-N
{[(2R,3S,4R,5R)-5-(2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
364.2054
364.042014546
-2.17
6
xanthosine monophosphate
0
-2
FDB022687
(9-d-ribosylxanthine)-5'-phosphate;5'-xanthonylate monophosphate;Xmp;Xanthosine 5'-phosphate;Xanthosine-5'-p;Xanthosine-5'-phosphate;Xanthosine monophosphate;Xanthylic acid;(9-d-ribosylxanthine)-5'-phosphoric acid;5'-xanthylate;Xanthosine 5'-phosphoric acid;Xanthosine monophosphoric acid;Xanthylate
PW_C001196
XntylcA
1857
8
11808
198
78004
111
80683
135
120164
122
125524
297
127059
205
721
NAD
HMDB0000902
NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).
53-84-9
C00003
5893
15846
NAD
5682
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H28N7O14P2
InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BAWFJGJZGIEFAR-NNYOXOHSSA-O
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
664.433
664.116946663
-2.59
8
1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
1
-1
FDB022309
3-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nad
PW_C000721
NAD
140
4
150
3
353
8
651
10
1114
2
1134
43
1273
5
1466
54
2229
49
2779
17
2835
29
3107
9
4807
18
4813
18
4819
28
4902
6
4960
31
5167
95
5238
103
5334
111
5360
112
5469
123
5482
125
5590
135
5610
118
5696
100
5738
108
5827
141
5912
147
5942
151
6024
155
6072
157
6076
161
6385
1
6469
178
6772
117
6890
160
7012
188
7097
163
7174
205
7197
206
7405
198
7459
222
8241
226
8359
225
9085
224
11819
216
12322
249
13006
298
13018
300
13256
223
42404
322
42619
315
77104
132
77120
133
77209
134
77370
331
77650
336
77667
334
77702
332
77709
130
77915
113
77983
347
78406
356
80006
368
80690
119
93825
124
110552
388
112750
166
112853
94
119929
122
119952
406
120171
407
120834
419
120984
408
121159
425
121242
126
121259
429
121817
383
122614
384
122742
120
123130
447
123141
136
123419
455
123549
374
123731
460
123812
443
123829
464
124370
398
125187
121
125319
297
125342
479
125530
481
125806
299
125825
490
125924
482
126515
495
126765
480
126885
501
127278
507
127383
502
128089
390
128360
391
128428
395
1144
NADH
HMDB0001487
NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).
58-68-4
C00004
439153
16908
NADH
388299
DB00157
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O14P2
InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BOPGDPNILDQYTO-NNYOXOHSSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid
665.441
665.124771695
-2.35
8
NADH
0
-2
FDB022649
1,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotide
PW_C001144
NADH
143
4
153
3
490
8
648
10
1115
2
1275
5
1469
54
2230
49
2781
17
2836
29
3109
9
4806
18
4812
18
4821
28
4904
6
4959
31
5169
95
5240
103
5332
111
5358
112
5466
123
5479
125
5593
135
5698
100
5737
108
5829
141
5915
147
5945
151
6027
155
6079
161
6387
1
6472
178
6771
117
6893
160
7011
188
7099
163
7172
205
7195
206
7462
222
8244
226
8360
225
9086
224
11809
198
11821
216
12320
249
13003
298
13015
300
13255
223
42403
322
42618
315
77107
132
77123
133
77208
134
77371
331
77651
336
77668
334
77700
332
77707
130
77917
113
77986
347
80009
368
80691
119
93822
124
110549
388
112854
94
115838
118
119955
406
120172
407
120378
122
120986
408
121162
425
121244
126
121693
429
121818
383
122616
384
122745
120
123127
447
123138
136
123551
374
123734
460
123814
443
124242
464
124371
398
125189
121
125345
479
125531
481
125762
297
125808
299
125926
482
126516
495
126767
480
126888
501
127385
502
128090
390
128362
391
128429
395
457
Potassium
HMDB0000586
Potassium is an essential electrolyte. Potassium balance is crucial for regulating the excitability of nerves and muscles and so critical for regulating contractility of cardiac muscle. Although the most important changes seen in the presence of deranged potassium are cardiac, smooth muscle is also affected with increasing muscle weakness, a feature of both hyperkalaemia and hypokalaemia. Physiologically, it exists as an ion in the body. Potassium (K+) is a positively charged electrolyte, cation, which is present throughout the body in both intracellular and extracellular fluids. The majority of body potassium, >90%, are intracellular. It moves freely from intracellular fluid (ICF) to extracellular fluid (ECF) and vice versa when adenosine triphosphate increases the permeability of the cell membrane. It is mainly replaced inside or outside the cells by another cation, sodium (Na+). The movement of potassium into or out of the cells is linked to certain body hormones and also to certain physiological states. Standard laboratory tests measure ECF potassium. Potassium enters the body rapidly during food ingestion. Insulin is produced when a meal is eaten; this causes the temporary movement of potassium from ECF to ICF. Over the ensuing hours, the kidneys excrete the ingested potassium and homeostasis is returned. In the critically ill patient, suffering from hyperkalaemia, this mechanism can be manipulated beneficially by administering high concentration (50%) intravenous glucose. Insulin can be added to the glucose, but glucose alone will stimulate insulin production and cause movement of potassium from ECF to ICF. The stimulation of alpha receptors causes increased movement of potassium from ICF to ECF. A noradrenaline infusion can elevate serum potassium levels. An adrenaline infusion, or elevated adrenaline levels, can lower serum potassium levels. Metabolic acidosis causes a rise in extracellular potassium levels. In this situation, excess of hydrogen ions (H+) are exchanged for intracellular potassium ions, probably as a result of the cellular response to a falling blood pH. Metabolic alkalosis causes the opposite effect, with potassium moving into the cells. (PMID: 17883675).
24203-36-9
C00238
813
29103
K%2b
791
DB01345
[K+]
K
InChI=1S/K/q+1
NPYPAHLBTDXSSS-UHFFFAOYSA-N
potassium(1+) ion
39.0983
38.963706861
0
potassium(1+) ion
1
1
FDB003521
K+;Kalium;Potassium;Potassium (k+);Potassium (ion);Potassium cation;Potassium ion;Potassium ion (k+);Potassium ion (k1+);Potassium ion(+);Potassium ion(1+);Potassium monocation;Potassium(+);Potassium(1+);Potassium(1+) ion;Potassium(i) cation;K(+)
PW_C000457
K+
573
8
931
19
1926
2
2095
15
3033
66
3161
72
3162
71
3613
51
3614
61
5921
147
5952
151
6902
160
11810
198
15222
306
77023
225
77115
132
77610
111
78241
326
78246
353
120484
122
121198
124
123105
135
123768
118
124944
452
124949
472
125860
297
125965
299
127322
205
127421
388
143
NADP
HMDB0000217
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).
53-59-8
C00006
5886
18009
NAD(P)
5675
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O17P3
InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
XJLXINKUBYWONI-NNYOXOHSSA-O
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
744.4129
744.083277073
-2.27
9
1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
1
-3
FDB021908
Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acid
PW_C000143
NADP
183
8
191
3
768
5
780
10
824
18
839
2
1611
29
1617
49
4685
31
4796
14
4801
14
5308
111
5790
108
6017
147
6132
159
6273
35
6778
117
7069
188
7105
163
7152
205
7206
160
7317
213
7346
210
7562
212
7589
170
8197
225
8220
151
8419
224
11811
198
11897
211
12008
222
12152
164
12249
286
12597
226
12650
249
42344
315
43745
322
76913
293
77164
132
77384
331
77396
332
77461
130
77515
115
77624
336
77814
334
77870
112
80713
119
113165
94
120106
407
120429
405
120450
122
120604
408
120618
123
121142
125
121277
429
121401
124
121485
383
123063
376
123084
135
123229
374
123243
447
123713
136
123848
464
123960
118
124043
398
125473
481
125694
297
125743
482
126215
299
126528
495
127010
206
127225
502
127570
388
128100
390
146
NADPH
HMDB0000221
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).
53-57-6
C00005
22833512
16474
NADPH
17215925
NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O
C21H30N7O17P3
InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m0/s1
ACFIXJIJDZMPPO-NCHANQSKSA-N
{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
745.4209
745.091102105
-2.14
9
[(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
0
-4
FDB021909
2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reduced
PW_C000146
NADPH
185
8
190
3
778
10
796
5
821
18
837
2
1609
29
1615
49
4687
31
4793
14
4797
14
5310
111
5789
108
5972
147
6128
159
6271
35
6779
117
7068
188
7103
163
7154
205
7205
160
7315
213
7345
210
7559
212
7591
170
8194
225
8219
151
8421
224
11812
198
11893
211
12006
222
12150
164
12245
286
12596
226
12648
249
42343
315
43746
322
76911
293
77166
132
77385
331
77394
332
77460
130
77504
112
77511
115
77623
336
80712
119
113164
94
120105
407
120425
405
120452
122
120616
123
121141
125
121275
429
121402
124
121483
383
123059
376
123086
135
123241
447
123712
136
123846
464
123961
118
124041
398
125472
481
125696
297
126214
299
126529
495
127009
206
127572
388
128101
390
203
Xanthosine
HMDB0000299
Biological Source: Xanthosine is produced by guanine-free mutants of bacteria e.g. Bacillus subtilis, Aerobacter aerogenes. Also reported from seeds of Trifolium alexandrinum Physical Description: Prismatic cryst. (H2O) (Chemnetbase) The deamination product of guanosine. Xanthosine monophosphate is an intermediate in purine metabolism, formed from IMP, and forming GMP.(Wikipedia). Xanthylic acid can be used in quantitative measurements of the Inosine monophosphate dehydrogenase enzyme activities in purine metabolism, as recommended to ensure optimal thiopurine therapy for children with acute lymphoblastic leukaemia (ALL). (PMID: 16725387).
146-80-5
C01762
64959
18107
58484
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O
C10H12N4O6
InChI=1S/C10H12N4O6/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19)/t3-,5-,6-,9-/m1/s1
UBORTCNDUKBEOP-UUOKFMHZSA-N
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purine-2,6-diol
284.2255
284.075684136
-1.01
5
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purine-2,6-diol
0
0
FDB001604
3,9-dihydro-9-d-ribofuranosyl-1h-purine-2,6-dione;3,9-dihydro-9-b-d-ribofuranosyl-1h-purine-2,6-dione;3,9-dihydro-9-beta-delta-ribofuranosyl-1h-purine-2,6-dione;3,9-dihydro-9-delta-ribofuranosyl-1h-purine-2,6-dione;9-d-ribofuranosylxanthine;9-b-d-ribofuranosylxanthine;9-beta-delta-ribofuranosylxanthine;9-delta-ribofuranosylxanthine;Xanthosine;9-beta-d-ribofuranosyl-3,9-dihydro-1h-purine-2,6-dione;9-beta-d-ribofuranosylxanthine;Xanthine 9-beta-d-ribofuranoside;Xanthine riboside;9-b-d-ribofuranosyl-3,9-dihydro-1h-purine-2,6-dione;9-β-d-ribofuranosyl-3,9-dihydro-1h-purine-2,6-dione;9-β-d-ribofuranosylxanthine;Xanthine 9-b-d-ribofuranoside;Xanthine 9-β-d-ribofuranoside
PW_C000203
Xanthos
1861
8
6773
107
6774
108
11813
198
43740
318
43741
315
78695
111
121888
122
124441
135
127
Inosine
HMDB0000195
Inosine is a purine nucleoside that has hypoxanthine linked by the N9 nitrogen to the C1 carbon of ribose. It is an intermediate in the degradation of purines and purine nucleosides to uric acid and in pathways of purine salvage. It also occurs in the anticodon of certain transfer RNA molecules. (Dorland, 28th ed).
58-63-9
C00294
6021
17596
INOSINE
5799
DB04335
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1NC=NC2=O
C10H12N4O5
InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1
UGQMRVRMYYASKQ-KQYNXXCUSA-N
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one
268.2261
268.080769514
-1.27
4
inosine
0
0
DBMET00496
FDB011802
(-)-inosine;1,9-dihydro-9-b-d-ribofuranosyl-6h-purin-6-one;1,9-dihydro-9-beta-d-ribofuranosyl-6h-purin-6-one;1,9-dihydro-9-beta-delta-ribofuranosyl-6h-purin-6-one;9-b-d-ribofuranosyl-hypoxanthine;9-b-d-ribofuranosylhypoxanthine;9-beta-d-ribofuranosyl-hypoxanthine;9-beta-d-ribofuranosylhypoxanthine;9-beta-delta-ribofuranosyl-hypoxanthine;9-beta-delta-ribofuranosylhypoxanthine;9beta-d-ribofuranosylhypoxanthine;9beta-delta-ribofuranosylhypoxanthine;Atorel;Hxr;Hypoxanthine 9-beta-d-ribofuranoside;Hypoxanthine 9-beta-delta-ribofuranoside;Hypoxanthine d-riboside;Hypoxanthine nucleoside;Hypoxanthine ribonucleoside;Hypoxanthine riboside;Hypoxanthine-9 beta-d-ribofuranoside;Hypoxanthine-9 beta-delta-ribofuranoside;Hypoxanthine-9-d-ribofuranoside;Hypoxanthine-9-beta-d-ribofuranoside;Hypoxanthine-9-beta-delta-ribofuranoside;Hypoxanthine-9-delta-ribofuranoside;Hypoxanthine-ribose;Hypoxanthosine;Indole-3-carboxaldehyde;Ino;Inosie;Iso-prinosine;Oxiamin;Panholic-l;Pantholic-l;Ribonosine;Selfer;Trophicardyl;Beta-d-ribofuranoside hypoxanthine-9;Beta-inosine;Beta-delta-ribofuranoside hypoxanthine-9;9-beta-d-ribofuranosyl-9h-purin-6-ol;I;Inosin;Inosina;Inosinum;9-b-d-ribofuranosyl-9h-purin-6-ol;9-β-d-ribofuranosyl-9h-purin-6-ol;9-β-d-ribofuranosylhypoxanthine
PW_C000127
Inosine
1862
8
11814
198
12439
151
78696
111
121889
122
124442
135
102
Hypoxanthine
HMDB0000157
Hypoxanthine is a naturally occurring purine derivative and a reaction intermediate in the metabolism of adenosine and in the formation of nucleic acids by the salvage pathway. Hypoxanthine is also a spontaneous deamination product of adenine. Lesch-Nyhan disease is caused by deficiency of the purine salvage enzyme hypoxanthine-guanine phosphoribosyltransferase. (OMIN 308000).
68-94-0
C00262
790
17368
HYPOXANTHINE
768
DB04076
OC1=NC=NC2=C1NC=N2
C5H4N4O
InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
FDGQSTZJBFJUBT-UHFFFAOYSA-N
7H-purin-6-ol
136.1115
136.03851077
-1.02
2
6-hydroxypurine
0
0
DBMET00493
FDB003949
1,7-dihydro-6h-purin-6-one;1,7-dihydro-6h-purine-6-one;1h,7h-hypoxanthine;3h-purin-6-ol;4-hydroxy-1h-purine;6(1h)-purinone;6-hydroxy-1h-purine;6-hydroxypurine;6-oxopurine;7h-purin-6-ol;9h-purin-6(1h)-one;9h-purin-6-ol;Hypoxanthine enol;Purin-6(1h)-one;Purin-6(3h)-one;Purin-6-ol;Purine-6-ol;Sarcine;Sarkin;Sarkine;Hyp
PW_C000102
Hyp
1863
8
11815
198
12440
151
78697
111
121890
122
124443
135
1065
Oxygen
HMDB0001377
Oxygen is the third most abundant element in the universe after hydrogen and helium and the most abundant element by mass in the Earth's crust. Diatomic oxygen gas constitutes 20.9% of the volume of air. All major classes of structural molecules in living organisms, such as proteins, carbohydrates, and fats, contain oxygen, as do the major inorganic compounds that comprise animal shells, teeth, and bone. Oxygen in the form of O2 is produced from water by cyanobacteria, algae and plants during photosynthesis and is used in cellular respiration for all living organisms. Green algae and cyanobacteria in marine environments provide about 70% of the free oxygen produced on earth and the rest is produced by terrestrial plants. Oxygen is used in mitochondria to help generate adenosine triphosphate (ATP) during oxidative phosphorylation. For animals, a constant supply of oxygen is indispensable for cardiac viability and function. To meet this demand, an adult human, at rest, inhales 1.8 to 2.4 grams of oxygen per minute. This amounts to more than 6 billion tonnes of oxygen inhaled by humanity per year. At a resting pulse rate, the heart consumes approximately 8-15 ml O2/min/100 g tissue. This is significantly more than that consumed by the brain (approximately 3 ml O2/min/100 g tissue) and can increase to more than 70 ml O2/min/100 g myocardial tissue during vigorous exercise. As a general rule, mammalian heart muscle cannot produce enough energy under anaerobic conditions to maintain essential cellular processes; thus, a constant supply of oxygen is indispensable to sustain cardiac function and viability. However, the role of oxygen and oxygen-associated processes in living systems is complex, and they and can be either beneficial or contribute to cardiac dysfunction and death (through reactive oxygen species). Reactive oxygen species (ROS) are a family of oxygen-derived free radicals that are produced in mammalian cells under normal and pathologic conditions. Many ROS, such as the superoxide anion (O2-)and hydrogen peroxide (H2O2), act within blood vessels, altering mechanisms mediating mechanical signal transduction and autoregulation of cerebral blood flow. Reactive oxygen species are believed to be involved in cellular signaling in blood vessels in both normal and pathologic states. The major pathway for the production of ROS is by way of the one-electron reduction of molecular oxygen to form an oxygen radical, the superoxide anion (O2-). Within the vasculature there are several enzymatic sources of O2-, including xanthine oxidase, the mitochondrial electron transport chain, and nitric oxide (NO) synthases. Studies in recent years, however, suggest that the major contributor to O2- levels in vascular cells is the membrane-bound enzyme NADPH-oxidase. Produced O2- can react with other radicals, such as NO, or spontaneously dismutate to produce hydrogen peroxide (H2O2). In cells, the latter reaction is an important pathway for normal O2- breakdown and is usually catalyzed by the enzyme superoxide dismutase (SOD). Once formed, H2O2 can undergo various reactions, both enzymatic and nonenzymatic. The antioxidant enzymes catalase and glutathione peroxidase act to limit ROS accumulation within cells by breaking down H2O2 to H2O. Metabolism of H2O2 can also produce other, more damaging ROS. For example, the endogenous enzyme myeloperoxidase uses H2O2 as a substrate to form the highly reactive compound hypochlorous acid. Alternatively, H2O2 can undergo Fenton or Haber-Weiss chemistry, reacting with Fe2+/Fe3+ ions to form toxic hydroxyl radicals (-.OH). (PMID: 17027622, 15765131).
7782-44-7
C00007
977
15379
CPD-6641
952
O=O
O2
InChI=1S/O2/c1-2
MYMOFIZGZYHOMD-UHFFFAOYSA-N
oxidanone
31.9988
31.989829244
0
singlet oxygen
0
0
FDB022589
Dioxygen;Molecular oxygen;O2;Oxygen;Oxygen molecule;[oo];Dioxygene;Disauerstoff;E 948;E-948;E948
PW_C001065
O2
95
9
110
5
245
16
500
18
505
8
549
14
625
28
638
3
649
10
674
31
688
20
754
15
763
4
769
33
836
2
1375
49
2016
24
2531
22
2803
29
4260
42
4747
13
5467
123
5480
125
5493
126
5508
127
5809
108
5973
147
6129
159
7006
188
7032
163
7050
160
7319
213
7533
210
7560
212
8395
151
11816
216
11864
198
11883
215
11894
211
12057
225
12063
164
12247
286
12279
226
12325
249
12706
291
12716
292
13004
298
13016
300
13026
301
13038
302
13260
223
42276
17
42657
315
76910
293
77044
294
77214
134
77350
111
77363
130
77377
331
77395
332
77497
113
77512
115
77537
334
77626
336
77723
337
77736
112
77747
129
77756
341
77805
114
77812
133
78070
329
78151
132
78381
345
78805
343
79111
360
120047
408
120383
122
120426
405
120542
407
120553
414
120594
409
120601
406
120883
415
121045
124
121104
383
121605
434
121656
429
122117
382
122573
418
122689
384
122798
374
122822
443
123027
135
123060
376
123128
447
123139
136
123163
448
123176
119
123187
450
123219
137
123226
120
123459
451
123609
118
123669
398
124163
469
124214
464
124669
399
125145
454
125275
121
125425
482
125706
478
125731
483
125737
297
125740
479
125884
481
126100
299
126272
484
126522
495
126721
489
126825
480
126964
502
126986
207
127198
209
127214
208
127219
205
127222
501
127305
504
127345
206
127557
388
127574
515
127835
389
128081
395
128095
390
128312
506
128432
391
1783
Hydrogen peroxide
HMDB0003125
Hydrogen peroxide (H2O2) is a very pale blue liquid which appears colourless in a dilute solution, slightly more viscous than water. It is a weak acid. It has strong oxidizing properties and is therefore a powerful bleaching agent that is mostly used for bleaching paper, but has also found use as a disinfectant and as an oxidizer. Hydrogen peroxide in the form of carbamide peroxide is widely used for tooth whitening (bleaching), both in professionally- and in self-administered products. Hydrogen peroxide (H2O2) is a well-documented component of living cells. It plays important roles in host defense and oxidative biosynthetic reactions. In addition there is growing evidence that at low levels, H2O2 also functions as a signaling agent, particularly in higher organisms. H2O2 has increasingly been viewed as an important cellular signaling agent in its own right, capable of modulating both contractile and growth-promoting pathways with more far-reaching effects. Due to the accumulation of hydrogen peroxide in the skin of patients with the depigmentation disorder vitiligo, the human epidermis cannot have the normal capacity for autocrine synthesis, transport and degradation of acetylcholine as well as the muscarinic (m1-m5) and nicotinic signal transduction in keratinocytes and melanocytes. Accumulating evidence suggests that hydrogen peroxide (H(2)O(2)) plays an important role in cancer development. Experimental data have shown that cancer cells produce high amounts of H(2)O(2). An increase in the cellular levels of H(2)O(2) has been linked to several key alterations in cancer, including DNA alterations, cell proliferation, apoptosis resistance, metastasis, angiogenesis and hypoxia-inducible factor 1 (HIF-1) activation. (PMID: 17150302, 17335854, 16677071, 16607324, 16514169).
7722-84-1
C00027
784
16240
HYDROGEN-PEROXIDE
763
OO
H2O2
InChI=1S/H2O2/c1-2/h1-2H
MHAJPDPJQMAIIY-UHFFFAOYSA-N
peroxol
34.0147
34.005479308
2
hydrogen peroxide
0
0
FDB014562
Adeka super el;Albone;Albone 35;Albone ds;Anti-keim 50;Asepticper;Baquashock;Cix;Clarigel gold;Crestal whitestrips;Crystacide;Dentasept;Deslime lp;Hioxyl;Hipox;Hybrite;Hydrogen dioxide;Hydrogen peroxide;Inhibine;Lase peroxide;Lensan a;Magic bleaching;Metrokur;Mirasept;Nite white excel 2;Odosat d;Opalescence xtra;Oxigenal;Oxydol;Oxyfull;Oxysept;Oxysept i;Pegasyl;Perhydrol;Perone;Peroxaan;Peroxclean;Quasar brite;Select bleach;Superoxol;T-stuff;Whiteness hp;Whitespeed;Xtra white;[oh(oh)];Dihydrogen dioxide;H2o2;Hooh
PW_C001783
H2O2
98
9
113
5
188
8
551
14
627
28
755
15
1243
3
1691
2
1749
51
2534
22
3818
10
4749
13
4752
31
5495
126
5502
123
5510
127
5810
108
6005
147
7038
163
8396
151
11817
216
11886
215
12461
226
12709
291
12719
292
13028
301
13035
298
13040
302
13405
222
42658
315
77022
225
77047
294
77079
293
77500
113
77540
334
77598
115
77720
332
77725
337
77806
114
77810
111
77819
326
78073
329
78152
132
78598
112
120050
408
120102
122
120463
405
120595
409
120609
416
120954
407
121047
124
122120
382
122801
374
122814
443
122839
135
123097
376
123157
447
123165
448
123220
137
123234
452
123520
119
123611
118
124672
399
125428
482
125469
297
125709
478
125732
483
125748
488
125895
481
126103
299
126275
484
126967
502
126978
207
127006
205
127201
209
127215
208
127230
505
127356
206
127601
388
127838
389
964
FAD
HMDB0001248
FAD, also known as flavitan or adeflavin, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. FAD is a drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD is slightly soluble (in water) and a moderately acidic compound (based on its pKa). FAD has been found in human liver and muscle tissues, and has also been detected in multiple biofluids, such as feces and blood. Within the cell, FAD is primarily located in the cytoplasm, mitochondria, endoplasmic reticulum and peroxisome. FAD exists in all living organisms, ranging from bacteria to humans. In humans, FAD is involved in the risedronate action pathway, the ibandronate action pathway, the valine, leucine and isoleucine degradation pathway, and the pyrimidine metabolism pathway. FAD is also involved in several metabolic disorders, some of which include the oncogenic action OF L-2-hydroxyglutarate in hydroxygluaricaciduria pathway, gaba-transaminase deficiency, 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency, and the saccharopinuria/hyperlysinemia II pathway. FAD is a condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972).
146-14-5
C00016
643975
16238
FAD
559059
DB03147
CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)CO[P@](O)(=O)O[P@@](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2
C27H33N9O15P2
InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1
VWWQXMAJTJZDQX-UYBVJOGSSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
785.5497
785.157134455
-2.27
9
flavine-adenine dinucleotide
0
-3
FDB022511
1h-purin-6-amine flavin dinucleotide;1h-purin-6-amine flavine dinucleotide;Adenine-flavin dinucleotide;Adenine-flavine dinucleotide;Adenine-riboflavin dinuceotide;Adenine-riboflavin dinucleotide;Adenine-riboflavine dinucleotide;Fad;Flamitajin b;Flanin f;Flavin adenine dinucleotide;Flavin adenine dinucleotide oxidized;Flavin-adenine dinucleotide;Flavine adenosine diphosphate;Flavine-adenine dinucleotide;Flavitan;Flaziren;Isoalloxazine-adenine dinucleotide;Riboflavin 5'-adenosine diphosphate;Riboflavin-adenine dinucleotide;Riboflavine-adenine dinucleotide;Adeflavin
PW_C000964
FAD
99
9
114
5
186
8
192
3
216
4
253
17
628
28
825
18
840
2
1188
14
1489
42
1612
29
1622
49
2133
58
2536
22
3723
26
4602
36
4688
31
4741
13
4758
10
4881
6
5268
103
5285
102
5335
111
5496
126
5511
127
5613
118
6030
155
6054
156
6082
161
6116
162
6390
1
6475
178
6499
179
6666
107
7039
163
7175
205
7321
213
7465
222
7487
223
9076
224
11818
216
11887
215
11899
211
12296
225
12328
249
12443
151
12519
227
12595
226
12710
291
12720
292
13029
301
13041
302
43623
318
77080
293
77126
133
77152
134
77501
113
77507
112
77518
115
77541
334
77615
132
77726
337
78054
329
78375
345
78930
331
79222
336
79272
358
80012
368
80034
369
80714
119
119958
406
119999
384
120051
408
120107
407
120432
405
120453
122
120490
124
121278
429
121298
418
121417
382
121489
383
122748
120
122776
121
122802
374
122823
443
123066
376
123087
135
123166
448
123849
464
123868
454
123976
399
124047
398
125348
479
125378
480
125429
482
125474
481
125697
297
125979
489
126107
299
126277
484
126891
501
126920
391
126968
502
126987
207
127011
206
127310
209
127432
506
127602
388
127840
389
195
Uric acid
HMDB0000289
Uric acid is a heterocyclic purine derivative that is the final oxidation product of purine metabolism. It is produced by the enzyme xanthine oxidase, which oxidizes oxypurines such as xanthine into uric acid. In most mammals, except humans and higher primates, the enzyme uricase further oxidizes uric acid to allantoin. Uric acid is also the end product of nitrogen metabolism in birds and reptiles. In such species, it is excreted in feces as a dry mass. Humans produce only small quantities of uric acid with excess accumulation leading to a type of arthritis known as gout. The loss of uricase in higher primates parallels the similar loss of the ability to synthesize ascorbic acid vitamin C. This may be because in higher primates uric acid partially replaces ascorbic acid.
69-93-2
C00366
1175
17775
URATE
1142
DB01696
O=C1NC2=C(N1)C(=O)NC(=O)N2
C5H4N4O3
InChI=1S/C5H4N4O3/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h(H4,6,7,8,9,10,11,12)
LEHOTFFKMJEONL-UHFFFAOYSA-N
2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
168.1103
168.028340014
-1.98
4
uric acid
0
0
DBMET00498
FDB015350
1h-purine-2,6,8-triol;2,6,8-trihydroxypurine;2,6,8-trioxopurine;2,6,8-trioxypurine;Lithate;Lithic acid;Purine-2,6,8(1h,3h,9h)-trione;Urate;Uric acid
PW_C000195
Urate
1873
5
11820
216
12444
151
12459
226
78699
334
121892
408
124445
374
50
Deoxyinosine
HMDB0000071
Deoxyinosine is a nucleoside that is formed when hypoxanthine is attached to a deoxyribose ring (also known as a ribofuranose) via a beta-N9-glycosidic bond. Deoxyinosine is found in DNA while Inosine is found in RNA. Inosine is a nucleic acid important for RNA editing. Adenosine deaminase (ADA) catalyzes the conversion of adenosine and deoxyadenosine to inosine and deoxyinosine, respectively. ADA-deficient individuals suffer from severe combined immunodeficiency (SCID) and are unable to produce significant numbers of mature T or B lymphocytes. This occurs as a consequence of the accumulation of ADA substrates or their metabolites. Inosine is also an intermediate in a chain of purine nucleotides reactions required for muscle movements.
890-38-0
C05512
65058
28997
DEOXYINOSINE
58569
OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC2=O
C10H12N4O4
InChI=1S/C10H12N4O4/c15-2-6-5(16)1-7(18-6)14-4-13-8-9(14)11-3-12-10(8)17/h3-7,15-16H,1-2H2,(H,11,12,17)/t5-,6+,7+/m0/s1
VGONTNSXDCQUGY-RRKCRQDMSA-N
9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-ol
252.23
252.085854882
-1.40
3
2'-deoxy-inosine
0
0
FDB012323
2'-deoxyinosine;2-deoxy-inosine;9-(2-deoxy-b-d-erythro-pentofuranosyl)-1,9-dihydro-6h-purin-6-one;9-(2-deoxy-b-d-erythro-pentofuranosyl)-hypoxanthine;9-(2-deoxy-beta-d-erythro-pentofuranosyl)-hypoxanthine;9-(2-deoxy-beta-delta-erythro-pentofuranosyl)-1,9-dihydro-6h-purin-6-one;9-(2-deoxy-beta-delta-erythro-pentofuranosyl)-hypoxanthine;D-ino;Deoxyinosine;Delta-ino;9-(2-deoxy-beta-d-erythro-pentofuranosyl)-9h-purin-6-ol;9-(2-deoxy-b-d-erythro-pentofuranosyl)-9h-purin-6-ol;9-(2-deoxy-β-d-erythro-pentofuranosyl)-9h-purin-6-ol
PW_C000050
D-Ino
1875
8
11822
198
78700
111
121893
122
124446
135
413
Adenylsuccinic acid
HMDB0000536
Adenylsuccinic acid, also known as adenylosuccinate or aspartyl adenylate, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Adenylsuccinic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, adenylsuccinic acid is primarily located in the cytoplasm and mitochondria. In humans, adenylsuccinic acid is involved in the aspartate metabolism pathway, the azathioprine action pathway, the mercaptopurine action pathway, and the purine metabolism pathway. Adenylsuccinic acid is also involved in several metabolic disorders, some of which include myoadenylate deaminase deficiency, the lesch-nyhan syndrome (LNS) pathway, adenylosuccinate lyase deficiency, and the hypoacetylaspartia pathway. Adenylsuccinic acid is a substrate of the enzyme adenylosuccinase [EC 4.3.2.2] in purine metabolism pathway. The accumulation of adenylsuccinic acid in body fluids occurs due to a deficiency of adenylosuccinase. (KEGG; PMID 8412002).
19046-78-7
C03794
440122
15919
389122
O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN=C2NC(CC(O)=O)C(O)=O
C14H18N5O11P
InChI=1S/C14H18N5O11P/c20-7(21)1-5(14(24)25)18-11-8-12(16-3-15-11)19(4-17-8)13-10(23)9(22)6(30-13)2-29-31(26,27)28/h3-6,9-10,13,22-23H,1-2H2,(H,20,21)(H,24,25)(H,15,16,18)(H2,26,27,28)/t5?,6-,9-,10-,13-/m1/s1
OFBHPPMPBOJXRT-DPXQIYNJSA-N
2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-9H-purin-6-yl}amino)butanedioic acid
463.2934
463.074042955
-2.29
7
adenylosuccinate
0
-4
FDB022101
6-succino-5'-adenylate;6-succino-5'-adenylic acid;Adenyl-succinic acid;Adenylosuccinate;Adenylosuccinic acid;Adenylsuccinate;Adenylsuccinic acid;Aspartyl adenylate;D-ribofuranosyl)-9h-purin-6-yl];D-ribofuranosyl-9h-purin-6-yl) mono(dihydrogen phosphate) (ester);N(6)-(1,2-dicarboxyethyl)-amp;Succinyl amp;Succinyladenosine 5'-monophosphate;Succinyladenosine monophosphorate;Succinyladenosine monophosphoric acid;N6-(1,2-dicarboxyethyl)-amp
PW_C000413
Asuca
85
8
11824
198
12712
290
77534
111
120042
122
122793
135
125420
297
126959
205
34
Adenosine
HMDB0000050
Adenosine is a nucleoside that is composed of adenine and D-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. For instance, adenosine plays an important role in energy transfer as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate (cAMP). Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously adenosine causes transient heart block in the AV node. Due to the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent. Overdoses of adenosine intake (as a drug) can lead to several side effects including chest pain, feeling faint, shortness of breath, and tingling of the senses. Serious side effects include a worsening dysrhythmia and low blood pressure. When present in sufficiently high levels, adenosine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of adenosine are associated with adenosine deaminase deficiency. Adenosine is a precursor to deoxyadenosine, which is a precursor to dATP. A buildup of dATP in cells inhibits ribonucleotide reductase and prevents DNA synthesis, so cells are unable to divide. Since developing T cells and B cells are some of the most mitotically active cells, they are unable to divide and propagate to respond to immune challenges. High levels of deoxyadenosine also lead to an increase in S-adenosylhomocysteine, which is toxic to immature lymphocytes.
58-61-7
C00212
60961
16335
ADENOSINE
54923
DB00640
NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1
C10H13N5O4
InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
OIRDTQYFTABQOQ-KQYNXXCUSA-N
(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
267.2413
267.096753929
-1.28
4
adenosine
0
0
FDB003554
1-(6-amino-9h-purin-9-yl)-1-deoxy-beta-d-ribofuranose;1-(6-amino-9h-purin-9-yl)-1-deoxy-beta-delta-ribofuranose;6-amino-9beta-d-ribofuranosyl-9h-purine;6-amino-9beta-delta-ribofuranosyl-9h-purine;9-beta-d-arabinofuranosyladenine;9-beta-d-ribofuranosidoadenine;9-beta-d-ribofuranosyl-9h-purin-6-amine;9-beta-d-ribofuranosyladenine;9-beta-delta-arabinofuranosyladenine;9-beta-delta-ribofuranosidoadenine;9-beta-delta-ribofuranosyl-9h-purin-6-amine;9-beta-delta-ribofuranosyladenine;9beta-d-ribofuranosyladenine;9beta-d-ribofuranosyl-9h-purin-6-amine;9beta-delta-ribofuranosyladenine;9beta-delta-ribofuranosyl-9h-purin-6-amine;Adenine nucleoside;Adenine riboside;Adenine-9beta-d-ribofuranoside;Adenine-9beta-delta-ribofuranoside;Adenocard;Adenocor;Adenoscan;Adenosin;Boniton;Myocol;Nucleocardyl;Sandesin;B-d-adenosine;Beta-adenosine;Beta-d-adenosine;Beta-delta-adenosine;(2r,3r,4s,5r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;6-amino-9-beta-d-ribofuranosyl-9h-purine;Ade-rib;Adenine deoxyribonucleoside;Adenyldeoxyriboside;Ado;Deoxyadenosine;Desoxyadenosine;6-amino-9-b-d-ribofuranosyl-9h-purine;6-amino-9-β-d-ribofuranosyl-9h-purine;9-b-d-ribofuranosidoadenine;9-β-d-ribofuranosidoadenine;9-b-d-ribofuranosyl-9h-purin-6-amine;9-β-d-ribofuranosyl-9h-purin-6-amine;β-d-adenosine
PW_C000034
Adenosi
352
8
1896
2
4013
15
5609
118
6769
107
6770
108
11825
198
12526
249
43737
315
43738
318
77612
132
78702
111
119928
122
120487
124
122722
135
125318
297
126459
299
126864
205
128029
388
24
Adenine
HMDB0000034
Adenine is a purine base. Adenine is found in both DNA and RNA. Adenine is a fundamental component of adenine nucleotides. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose; it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions. Purine inborn errors of metabolism (IEM) are serious hereditary disorders, which should be suspected in any case of neonatal fitting, failure to thrive, recurrent infections, neurological deficit, renal disease, self-mutilation and other manifestations. Investigation usually starts with uric acid (UA) determination in urine and plasma. (OMIM 300322, 229600, 603027, 232400, 232600, 232800, 201450, 220150, 232200, 162000, 164050, 278300). (PMID: 17052198, 17520339).
73-24-5
C00147
190
16708
ADENINE
185
DB00173
NC1=C2NC=NC2=NC=N1
C5H5N5
InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
GFFGJBXGBJISGV-UHFFFAOYSA-N
7H-purin-6-amine
135.1267
135.054495185
-1.07
2
vitamin B4
0
0
FDB012266
1,6-dihydro-6-iminopurine;1h-purin-6-amine;1h-purine-6-amine;3,6-dihydro-6-iminopurine;6-amino-1h-purine;6-amino-3h-purine;6-amino-7h-purine;6-amino-9h-purine;6-amino-purine;6-aminopurine;9h-purin-6-amine;9h-purin-6-yl-amin;9h-purin-6-ylamine;9h-purine-6-amine;Ade;Adenin;Adenine;Adeninimine;Vitamin b4;A
PW_C000024
Adenine
1892
8
6760
107
6761
108
11826
198
12524
227
12530
249
43735
318
43736
315
78703
111
121897
122
124450
135
68
Deoxyadenosine
HMDB0000101
Deoxyadenosine is a derivative of the nucleoside adenosine. It is composed of adenine attached to a deoxyribose moiety via a N9-glycosidic bond. Deoxyribose differs from ribose by the absence of oxygen in the 3' position of its ribose ring. Deoxyadenosine is a critical component of DNA. When present in sufficiently high levels, deoxyadensoine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of deoxyadenosine are associated with adenosine deaminase (ADA) deficiency, an inborn error of metabolism. ADA deficiency damages the immune system and causes severe combined immunodeficiency (SCID). People with SCID lack virtually all immune protection from bacteria, viruses, and fungi. They are prone to repeated and persistent infections that can be very serious or life-threatening. These infections are often caused by "opportunistic" organisms that ordinarily do not cause illness in people with a normal immune system. The main symptoms of ADA deficiency are pneumonia, chronic diarrhea, and widespread skin rashes. The mechanism by which dATP functions as an immunotoxin is as follows: because deoxyadenosine is a precursor to dATP, a buildup of dATP in cells inhibits ribonucleotide reductase and prevents DNA synthesis, so cells are unable to divide. Since developing T cells and B cells are some of the most mitotically active cells, they are unable to divide and propagate to respond to immune challenges. High levels of deoxyadenosine also lead to an increase in S-adenosylhomocysteine, which is toxic to immature lymphocytes.
958-09-8
C00559
13730
17256
13135
NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1
C10H13N5O3
InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1
OLXZPDWKRNYJJZ-RRKCRQDMSA-N
(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
251.2419
251.101839307
-1.37
3
2-deoxyadenosine
0
0
FDB021894
1-(6-amino-9h-purin-9-yl)-1,2-dideoxy-b-d-ribofuranose;1-(6-amino-9h-purin-9-yl)-1,2-dideoxy-beta-d-ribofuranose;1-(6-amino-9h-purin-9-yl)-1,2-dideoxy-beta-delta-ribofuranose;2'-deoxyadenosine;2-deoxyadenosine;9-(2-deoxy-b-d-erythro-pentofuranosyl)-9h-purin-6-amine;9-(2-deoxy-b-d-erythro-pentofuranosyl)adenine;9-(2-deoxy-b-d-ribofuranosyl)-9h-purin-6-amine;9-(2-deoxy-beta-d-erythro-pentofuranosyl)-9h-purin-6-amine;9-(2-deoxy-beta-d-erythro-pentofuranosyl)adenine;9-(2-deoxy-beta-d-ribofuranosyl)-9h-purin-6-amine;9-(2-deoxy-beta-delta-erythro-pentofuranosyl)-9h-purin-6-amine;9-(2-deoxy-beta-delta-erythro-pentofuranosyl)adenine;9-(2-deoxy-beta-delta-ribofuranosyl)-9h-purin-6-amine;Adenine deoxyribonucleoside;Adenine deoxyribose;Adenine-9 2-deoxy-b-d-erythro-pentofuranoside;Adenine-9 2-deoxy-beta-d-erythro-pentofuranoside;Adenine-9 2-deoxy-beta-delta-erythro-pentofuranoside;Adenyldeoxyriboside;Da;Deoxyadenosine;Desoxyadenosine;(2r,3s,5r)-5-(6-amino-9h-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol;5-(6-amino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-ol;9-(2-deoxy-β-d-erythro-pentofuranosyl)adenine;9-(2-deoxy-β-d-ribofuranosyl)-9h-purin-6-amine
PW_C000068
DA
1895
8
11827
198
78704
111
121898
122
124451
135
41
cAMP
HMDB0000058
cAMP or cyclic AMP is an adenine nucleotide containing one phosphate group which is esterified to both the 3'- and 5'-positions of the sugar moiety. It is a second messenger and a key intracellular regulator, functioning as a mediator of activity for a number of hormones, including epinephrine, glucagon, and ACTH. cAMP is synthesized from ATP by adenylate cyclase. Adenylate cyclase is located at the cell membranes. Adenylate cyclase is activated by the hormones glucagon and adrenaline and by G protein. Liver adenylate cyclase responds more strongly to glucagon, and muscle adenylate cyclase responds more strongly to adrenaline. cAMP decomposition into AMP is catalyzed by the enzyme phosphodiesterase.
60-92-4
C00575
6076
17489
CAMP
5851
DB02527
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O
C10H12N5O6P
InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
IVOMOUWHDPKRLL-KQYNXXCUSA-N
(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
329.2059
329.052519653
-1.96
3
(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2,7-dihydroxy-tetrahydro-4H-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
0
-1
FDB001497
Cyclic AMP;3'5'-cyclic amp;6-(6-amino-9h-purin-9-yl)tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide;Acrasin;Adenosine 3',5'-cyclic monophosphate;Adenosine 3',5'-cyclic phosphate;Adenosine 3',5'-cyclophosphate;Adenosine 3',5'-monophosphate;Adenosine 3,5'-cyclic monophosphorate;Adenosine 3,5'-cyclic monophosphoric acid;Adenosine cyclic monophosphate;Adenosine cyclic-monophosphate;Adenosine-cyclic-phosphate;Adenosine-cyclic-phosphoric-acid;Cyclic 3',5'-amp;Cyclic 3',5'-adenylate;Cyclic 3',5'-adenylic acid;Cyclic amp;Cyclic adenosine 3',5'-phosphate;Camp;Adenosine 3',5'-phosphate;Adenosine-3',5'-cyclic-monophosphate;Cyclic adenylic acid;Adenosine 3',5'-cyclic monophosphoric acid;Adenosine 3',5'-cyclic phosphoric acid;Adenosine 3',5'-phosphoric acid;Adenosine-3',5'-cyclic-monophosphoric acid;Cyclic adenylate
PW_C000041
cAMP
267
16
475
2
935
39
1000
21
1916
8
4174
14
11830
198
78709
111
80044
184
121904
122
124457
135
724
Deoxyadenosine monophosphate
HMDB0000905
Adenosine is a nucleoside comprised of adenine attached to a ribose (ribofuranose) moiety via a -N9-glycosidic bond. Deoxyadenosine monophosphate is a derivative of the common nucleic acid ATP, or adenosine triphosphate, in which the -OH (hydroxyl) group on the 2' carbon on the nucleotide's pentose has been removed (hence the deoxy- part of the name). Additionally, the monophosphate of the name indicates that two of the phosphoryl groups of GTP have been removed, most likely by hydrolysis. Deoxyadenosine monophosphate is abbreviated dAMP. (Wikipedia).
653-63-4
C00360
12599
17713
DAMP
12079
NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1
C10H14N5O6P
InChI=1S/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1
KHWCHTKSEGGWEX-RRKCRQDMSA-N
{[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
331.2218
331.068169717
-2.09
4
DAMP
0
-2
FDB022311
2'-deoxy-5'-adenylate;2'-deoxy-5'-adenylic acid;2'-deoxy-amp;2'-deoxy-adenosine 5'-phosphorate;2'-deoxy-adenosine 5'-phosphoric acid;2'-deoxyadenosine 5'-monophosphate;2'-deoxyadenosine 5'-phosphate;2'-deoxyadenosine monophosphate;2'-deoxyadenosine-5'-monophosphate;2'-deoxyadenosine-5'-phosphate;2'-deoxyadenylate;2'-deoxyadenylic acid;2'-damp;Deoxy-5'-adenylate;Deoxy-5'-adenylic acid;Deoxy-amp;Deoxyadenosine 5'-monophosphate;Deoxyadenosine 5'-phosphate;Deoxyadenosine monophosphate;Deoxyadenosine-phosphate;Deoxyadenylate;Deoxyadenylic acid;Pda;Damp;2'-deoxy-5'-adenosine monophosphate;2'-deoxyadenosine 5'-(dihydrogen phosphate);2'-deoxy-5'-adenosine monophosphoric acid;2'-deoxyadenosine 5'-(dihydrogen phosphoric acid);2'-deoxyadenosine 5'-monophosphoric acid;2'-deoxyadenosine 5'-phosphoric acid;2'-deoxyadenosine monophosphoric acid;2'-deoxyadenosine-5'-monophosphoric acid;Deoxyadenosine 5'-monophosphoric acid;Deoxyadenosine 5'-phosphoric acid;Deoxyadenosine monophosphoric acid
PW_C000724
dAMP
1929
8
11831
198
78710
111
121906
122
124459
135
1161
dADP
HMDB0001508
dADP belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside diphosphates. These are purine nucleotides with diphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. dADP is slightly soluble (in water) and a moderately acidic compound (based on its pKa). dADP has been found throughout most human tissues. Within the cell, dADP is primarily located in the mitochondria, nucleus and cytoplasm. In humans, dADP is involved in the purine metabolism pathway, the thioguanine action pathway, the azathioprine action pathway, and the mercaptopurine action pathway. dADP is also involved in several metabolic disorders, some of which include xanthine dehydrogenase deficiency (xanthinuria), adenine phosphoribosyltransferase deficiency (aprt), the xanthinuria type I pathway, and the xanthinuria type II pathway. Deoxyadenosine diphosphate has been identified in the mononuclear cells of a patient affected with in inherited adenosine deaminase deficiency (OMIM 102700) (PMID 6980023), and in in mononuclear cells of hemodialyzed patients. (PMID 11461945).
2793-06-8
C00206
53477733
16174
DADP
NC1=NC=NC2=C1N=CN2C1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O1
C10H15N5O9P2
InChI=1S/C10H15N5O9P2/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(23-7)2-22-26(20,21)24-25(17,18)19/h3-7,16H,1-2H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)/t5-,6+,7?/m0/s1
DAEAPNUQQAICNR-GFCOJPQKSA-N
[({[(2R,3S)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
411.2017
411.034500127
-2.17
5
{[(2R,3S)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
0
-2
FDB022662
2'-deoxyadenosine-5'-diphosphate;Deoxyadenosine diphosphate;Dadp
PW_C001161
dADP
1925
8
11832
198
78711
111
121907
122
124460
135
1177
Deoxyadenosine triphosphate
HMDB0001532
Deoxyadenosine triphosphate (dATP) is a purine nucleoside triphosphate used in cells for DNA synthesis. A nucleoside triphosphate is a molecule type that contains a nucleoside with three phosphates bound to it. dATP contains the sugar deoxyribose, a precursor to DNA synthesis whereby the two existing phosphate groups are cleaved with the remaining deoxyadenosine monophosphate being incorporated into DNA during replication. Due to its enzymatic incorporation into DNA, photoreactive dATP analogs such as N6-[4-azidobenzoyl–(2-aminoethyl)]-2′-deoxyadenosine-5′-triphosphate (AB-dATP) and N6-[4-[3-(trifluoromethyl)-diazirin-3-yl]benzoyl-(2-aminoethyl)]-2′-deoxyadenosine-5′-triphosphate (DB-dATP) have been used for DNA photoaffinity labeling. When present in sufficiently high levels, dATP can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of deoxyadenosine triphosphate are associated with adenosine deaminase (ADA) deficiency, an inborn error of metabolism. ADA deficiency damages the immune system and causes severe combined immunodeficiency (SCID). People with SCID lack virtually all immune protection from bacteria, viruses, and fungi. They are prone to repeated and persistent infections that can be very serious or life-threatening. These infections are often caused by "opportunistic" organisms that ordinarily do not cause illness in people with a normal immune system. The main symptoms of ADA deficiency are pneumonia, chronic diarrhea, and widespread skin rashes. The mechanism by which dATP functions as an immunotoxin is as follows: a buildup of dATP in cells inhibits ribonucleotide reductase and prevents DNA synthesis, so cells are unable to divide. Since developing T cells and B cells are some of the most mitotically active cells, they are unable to divide and propagate to respond to immune challenges.
1927-31-7
C00131
15993
16284
DATP
15194
NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1
C10H16N5O12P3
InChI=1S/C10H16N5O12P3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(25-7)2-24-29(20,21)27-30(22,23)26-28(17,18)19/h3-7,16H,1-2H2,(H,20,21)(H,22,23)(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1
SUYVUBYJARFZHO-RRKCRQDMSA-N
({[({[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
491.1816
491.000830537
-2.11
6
dATP
0
-3
FDB022674
2'-Deoxy-5'-ATP;2'-Deoxy-ATP;2'-Deoxyadenosine 5'-triphosphate;2'-Deoxyadenosine triphosphate;Deoxy-ATP;Deoxyadenosine 5'-triphosphate;Deoxyadenosine triphosphate;Deoxyadenosine-triphosphate;dATP;2'-Deoxyadenosine 5'-triphosphoric acid;Deoxyadenosine 5'-triphosphoric acid;Deoxyadenosine triphosphoric acid
PW_C001177
doATP
1930
8
11833
198
12227
151
78712
111
121908
122
124461
135
7218
Guanosine 2',3'-cyclic phosphate
HMDB0011629
2',3'-Cyclic GMP is a cyclic guanosine derivative that is a precursor to 3'-GMP. The enzyme 2'3'-cyclic-nucleotide 2'-phosphodiesterase (E.C. 3.1.4.16) catalyses the hydrolysis of both 2',3'-cyclic AMP and 2',3'-cyclic GMP into 3'-AMP and 3'-GMP, respectively, at the 3'-terminal of RNA. 2',3'-cyclic phosphate termini are produced, as either intermediates or final products, during RNA cleavage by many different endoribonucleases. The enzyme RNA 3'-phosphate cyclase also converts the 3'-terminal phosphate in RNA into the 2',3'-cyclic phosphodiester in the ATP-dependent reaction which involves formation of the covalent cyclase-AMP and the RNA-N3' pp5' A intermediates (PMID: 10397337). This enzyme could be involved in the maintenance of cyclic ends in tRNA splicing intermediates or in the cyclization of the 3' end of U6 snRNA (PMID: 9184239). Guanosine-2',3'-cyclic phosphate is capable of blocking DNA synthesis in vitro (PMID: 7528887). 2', 3'-cGMP seems to preferentially stimulate mature T-cells while 3', 5'-cGMP preferentially acts on B-cells (PMID: 163786).
634-02-6
C06194
92823
28181
CPD-3709
83792
NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12
C10H12N5O7P
InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-6-5(3(1-16)20-9)21-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1
UASRYODFRYWBRC-UUOKFMHZSA-N
9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-2-amino-6,9-dihydro-3H-purin-6-one
345.2053
345.047434275
-1.99
4
9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-2-amino-3H-purin-6-one
0
-1
C06194
2',3' cgmp;2',3'-cyclic gmp;2',3'-cgmp;Cyclic 2',3'-(hydrogen phosphate)-guanosine;Cyclic guanosine 2',3'-monophosphate;Guanosine 2',3'-cyclic monophosphate;Guanosine 2',3'-cyclic phosphate;Guanosine cyclic 2',3'-(hydrogen phosphate);Guanosine cyclic-2',3'-monophosphate;O(2'),o(3')-hydroxyphosphoryl-guanosine;Cyclic guanosine 2',3'-monophosphoric acid;Guanosine 2',3'-cyclic monophosphoric acid;Guanosine 2',3'-cyclic phosphoric acid;Guanosine cyclic 2',3'-(hydrogen phosphoric acid);Guanosine cyclic-2',3'-monophosphoric acid
PW_C007218
23CGMP
1931
8
11834
198
78713
111
80276
2
121909
122
124462
135
1799
Heme
HMDB0003178
Heme is the color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins. A heme or haem is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. Not all porphyrins contain iron, but a substantial fraction of porphyrin-containing metalloproteins have heme as their prosthetic subunit; these are known as hemoproteins.
14875-96-8
C00032
17627
HEME_A
24604415
DB02577
CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C=C)C8=[N+]7[Fe--]4(N2C1=C8)N56)C(C)=C3CCC(O)=O
C34H32FeN4O4
InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;
KABFMIBPWCXCRK-RGGAHWMASA-L
4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide
616.487
616.177297665
-5.48
2
4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide
0
-2
FDB016272
(protoporphyrinato)iron;Ferroheme;Ferroheme b;Ferroprotoheme;Ferroprotoporphyrin;Ferroprotoporphyrin ix;Ferrous protoheme;Ferrous protoheme ix;Haem;Hem;Heme;Iron protoporphyrin;Iron protoporphyrin ix;Iron(ii) protoporphyrin ix;Protoferroheme;Protohaem;Protoheme;Protoheme ix;Reduced hematin
PW_C001799
Heme
247
16
308
10
324
8
608
2
766
5
1244
3
1354
49
1413
36
1963
18
2806
29
2938
9
3238
11
3367
26
3421
14
3734
4
4043
31
4823
28
5170
95
5472
123
5485
125
5517
129
5830
141
6246
78
6283
1
6597
151
7044
160
7060
161
7326
213
11835
198
11898
211
12065
164
13009
298
13021
300
42278
17
76915
293
76931
249
77351
111
77364
130
77367
331
77398
332
77517
115
77629
336
77813
334
78380
133
78602
132
78963
112
79932
134
120431
405
120603
408
120955
407
121085
383
121658
429
121746
124
121910
122
122570
406
122691
384
123065
376
123133
447
123144
136
123228
374
123521
119
123650
398
124216
464
124297
118
124463
135
125142
120
125277
121
125742
482
125896
481
126196
299
126499
297
126512
495
126718
479
126827
480
127224
502
127357
206
127632
388
128070
205
128083
395
128086
390
128309
501
128434
391
1846
IDP
HMDB0003335
IDP, also known as riboxin or 5'-idp, belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. IDP is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, IDP is primarily located in the mitochondria and nucleus. IDP exists in all living organisms, ranging from bacteria to humans. In humans, IDP is involved in the thioguanine action pathway, the azathioprine action pathway, the purine metabolism pathway, and the mercaptopurine action pathway. IDP is also involved in several metabolic disorders, some of which include the xanthinuria type I pathway, the gout or kelley-seegmiller syndrome pathway, xanthine dehydrogenase deficiency (xanthinuria), and the AICA-ribosiduria pathway. IDP is an inosine nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety.
86-04-4
C00104
644173
17808
IDP
559208
O[C@@H]1[C@@H](COP(O)(=O)OP(O)(O)=O)OC([C@@H]1O)N1C=NC2=C1NC=NC2=O
C10H14N4O11P2
InChI=1S/C10H14N4O11P2/c15-6-4(1-23-27(21,22)25-26(18,19)20)24-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,21,22)(H,11,12,17)(H2,18,19,20)/t4-,6-,7-,10?/m1/s1
JPXZQMKKFWMMGK-VTHZCTBJSA-N
[({[(2R,3S,4R)-3,4-dihydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
428.1859
428.013430334
-2.00
6
{[(2R,3S,4R)-3,4-dihydroxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
0
-3
FDB023146
5'-idp;Idp;Inosine 5'-(trihydrogen diphosphate);Inosine 5'-(trihydrogen pyrophosphate);Inosine 5'-diphosphate;Inosine 5'-pyrophosphate;Inosine diphosphate;Inosine pyrophosphate;Riboxin;Riboxine
PW_C001846
IDP
1935
8
11836
198
78715
111
121914
122
124467
135
121
Inosine triphosphate
HMDB0000189
Inosine triphosphate (ITP) is an intermediate in the purine metabolism pathway. Relatively high levels of ITP in red cells are found in individuals as result of deficiency of inosine triphosphatase (EC 3.1.3.56, ITPase) ITPase is a cytosolic nucleoside triphosphate pyrophosphohydrolase specific for ITP catalysis to inosine monophosphate (IMP) and deoxy-inosine triphosphate (dITP) to deoxy-inosine monophosphate. ITPase deficiency is not associated with any defined pathology other than the characteristic and abnormal accumulation of ITP in red blood cells. Nevertheless, ITPase deficiency may have pharmacogenomic implications, and the abnormal metabolism of 6-mercaptopurine in ITPase-deficient patients may lead to thiopurine drug toxicity. ITPase's function is not clearly understood but possible roles for ITPase could be to prevent the accumulation of rogue nucleotides which would be otherwise incorporated into DNA and RNA, or compete with nucleotides such as GTP in signalling processes. (PMID : 170291, 1204209, 17113761, 17924837).
132-06-9
C00081
8583
16039
ITP
8265
O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN=C2O
C10H15N4O14P3
InChI=1S/C10H15N4O14P3/c15-6-4(1-25-30(21,22)28-31(23,24)27-29(18,19)20)26-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,21,22)(H,23,24)(H,11,12,17)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
HAEJPQIATWHALX-KQYNXXCUSA-N
({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-9H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
508.1658
507.979760744
-2.03
7
({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxypurin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
0
-3
FDB021902
2'-inosine-5'-triphosphate;5'-itp;5-itp;Itp;Itt;Inosine 5;Inosine 5'-(tetrahydrogen triphosphate);Inosine 5'-triphosphate;Inosine 5(tetrahydrogen triphosphate);Inosine 5-triphopshate;Inosine triphosphate;Inosine tripolyphosphate;O(5')-(tetrahydroxytriphosphoryl)inosine;2'-inosine-5'-triphosphoric acid;Inosine 5'-triphosphoric acid;Inosine triphosphoric acid;Inosine tripolyphosphoric acid
PW_C000121
Ino3P
1937
8
11838
198
78716
111
121916
122
124469
135
1801
5-Aminoimidazole-4-carboxamide
HMDB0003192
5-Aminoimidazole-4-carboxamide is an imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. Compounded with orotic acid, it is used to treat liver diseases. -- Pubchem.
360-97-4
C04051
9679
2030
CPD-3762
9298
NC(=O)C1=C(N)N=CN1
C4H6N4O
InChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8)
DVNYTAVYBRSTGK-UHFFFAOYSA-N
4-amino-1H-imidazole-5-carboxamide
126.1166
126.054160834
-0.01
3
4-aminoimidazole-5-carboxamide
0
0
FDB023121
4-amino-5-imidazolecarboxamide;4-aminoimidazole-5-carboxamide;4-carbamoyl-5-aminoimidazole;4-carboxamido-5-aminoimidazole;5-amino-1h-imidazole-4-carboxamide;5-amino-4-imidazolecarboxamide;5-amino-imidazole-4-carboxamide;5-aminoimidazol-4-carboxamide;5-aminoimidazole-4-carboxamide ribotide;Aic;Aica;Aicar;Colahepat;4-amino-5-carbamoylimidazole;5(4)-amino-4(5)-imidazolecarboxamide;5-amino-4-imidazolecarboxyamide
PW_C001801
5Ai4Ca
1938
8
11839
198
78717
111
121917
122
124470
135
40707
Disulfide
HMDB0061376
Disulfides, also known as HSSH or hydrogen sulfide, belongs to the class of inorganic compounds known as other non-metal sulfides. These are inorganic compounds containing a sulfur atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen belongs to the class of other non-metals. Outside of the human body, disulfides can be found in soft-necked garlic. This makes disulfides a potential biomarker for the consumption of this food product.
13465-07-1
108196
33114
97274
SS
H2S2
InChI=1S/H2S2/c1-2/h1-2H
BWGNESOTFCXPMA-UHFFFAOYSA-N
dithioperoxol
66.146
65.959791444
2
disulfane
0
0
Hssh;Disulphane
PW_C040707
Disulfi
4710
2
11840
160
78719
132
121919
124
124472
118
8133
Fe3+
HMDB0012943
Fe3+, also known as ferric ion or fe(iii), belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. Fe3+ exists in all living organisms, ranging from bacteria to humans. 2,3-Dihydroxybenzoylserine and fe3+ can be biosynthesized from ferric enterobactin through its interaction with the enzyme enterochelin esterase. Outside of the human body, fe3+ can be found in a number of food items such as bamboo shoots, catjang pea, chickpea, and orange bell pepper. This makes fe3+ a potential biomarker for the consumption of these food products. The major activity of supplemental iron is in the prevention and treatment of iron deficiency anemia. Iron has putative immune-enhancing, anticarcinogenic and cognition-enhancing activities.
20074-52-6
C14819
29936
29034
CPD-10134
27815
[Fe+3]
Fe
InChI=1S/Fe/q+3
VTLYFUHAOXGGBS-UHFFFAOYSA-N
iron(3+) ion
55.845
55.934942133
0
iron(3+) ion
3
3
C14819
Fe(iii);Ferric ion;Iron(3+);Fe (iii) ion;Fe(3+);Ferric iron;Iron, ion (fe(3+))
PW_C008133
Fe3+
1230
3
1296
8
1420
49
1997
2
7042
163
11841
160
12675
151
77431
111
77450
331
78599
112
78721
132
120949
407
121013
122
121127
383
121593
124
123515
119
123578
135
123696
398
124151
118
125890
481
127351
206
127559
388
16649
Bis(5'-nucleosyl)-tetraphosphatase [asymmetrical]
Q6PEC0
Asymmetrically hydrolyzes Ap4A to yield AMP and ATP. Plays a major role in maintaining homeostasis (By similarity).
Nudt2
17
3.6.1.17
124399
135
16654
Nucleoside diphosphate kinase 6
O88426
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate.
Nme6
17
2.7.4.6
124401
135
124761
118
16659
Ectonucleoside triphosphate diphosphohydrolase 5
Q6P6S9
Uridine diphosphatase (UDPase) that promotes protein N-glycosylation and ATP level regulation. UDP hydrolysis promotes protein N-glycosylation and folding in the endoplasmic reticulum, as well as elevated ATP consumption in the cytosol via an ATP hydrolysis cycle. Together with CMPK1 and AK1, constitutes an ATP hydrolysis cycle that converts ATP to AMP and results in a compensatory increase in aerobic glycolysis. The nucleotide hydrolyzing preference is GDP > IDP > UDP, but not any other nucleoside di-, mono- or triphosphates, nor thiamine pyrophosphate. Plays a key role in the AKT1-PTEN signaling pathway by promoting glycolysis in proliferating cells in response to phosphoinositide 3-kinase (PI3K) signaling (By similarity).
Entpd5
17
3.6.1.6; 3.6.1.42
124404
398
124478
136
16664
Ectonucleoside triphosphate diphosphohydrolase 8
Q5DRK1
Canalicular ectonucleoside NTPDase responsible for the main hepatic NTPDase activity. Ectonucleoside NTPDases catalyze the hydrolysis of gamma- and beta-phosphate residues of nucleotides, playing a central role in concentration of extracellular nucleotides. Has activity toward ATP, ADP, UTP and UDP, but not toward AMP (By similarity).
Entpd8
17
3.6.1.5
124406
376
124468
135
16668
Guanylate kinase 1, isoform CRA_b
Q71RR7
Guk1
17
124407
135
16673
5'-nucleotidase domain-containing protein 2
Q5M7U9
Nt5dc2
17
3.1.3.-
124412
135
124502
118
16678
Deoxycytidine kinase
P48769
Required for the phosphorylation of the deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA).
Dck
17
2.7.1.74
124413
119
16680
Adenine phosphoribosyltransferase
P36972
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
Aprt
17
2.4.2.7
124415
135
16686
Purine nucleoside phosphorylase
A6KEC5
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Pnp
17
2.4.2.1
124418
135
124500
118
16692
Hypoxanthine-guanine phosphoribosyltransferase
Q62926
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway (By similarity).
Hprt1
17
2.4.2.8
124419
135
16695
Guanine deaminase
Q9WTT6
Catalyzes the hydrolytic deamination of guanine, producing xanthine and ammonia.
Gda
17
3.5.4.3
124422
135
124771
118
16698
ADP-sugar pyrophosphatase
Q6AY63
Enzyme that can either act as an ADP-sugar pyrophosphatase in absence of diphosphate or catalyze the synthesis of ATP in presence of diphosphate. In absence of diphosphate, hydrolyzes with similar activities various modified nucleoside diphosphates such as ADP-ribose, ADP-mannose, ADP-glucose, 8-oxo-GDP and 8-oxo-dGDP. Can also hydrolyze other nucleotide sugars with low activity. In presence of diphosphate, mediates the synthesis of ATP in the nucleus by catalyzing the conversion of ADP-ribose to ATP and ribose 5-phosphate. Nuclear ATP synthesis takes place when dephosphorylated at Thr-45. Nuclear ATP generation is required for extensive chromatin remodeling events that are energy-consuming. Does not play a role in U8 snoRNA decapping activity. Binds U8 snoRNA.
Nudt5
17
3.6.1.13; 3.6.1.58; 2.7.7.96
124424
135
16702
Ribose-phosphate pyrophosphokinase 1
Q5M8A4
Catalyzes the synthesis of phosphoribosylpyrophosphate (PRPP) that is essential for nucleotide synthesis.
Prps1
17
2.7.6.1
124425
135
124739
118
14628
Amidophosphoribosyltransferase
P35433
Ppat
17
2.4.2.14
80682
135
16711
Trifunctional purine biosynthetic protein adenosine-3
G3V918
Gart
17
6.3.4.13; 6.3.3.1; 2.1.2.2
124427
135
124471
118
16716
Phosphoribosylformylglycinamidine synthase
A0A0G2JTN4
Pfas
17
124430
135
16717
Multifunctional protein ADE2
P51583
Paics
17
6.3.2.6; 4.1.1.21
124433
135
14985
Adenylosuccinate lyase
D3ZW08
Adsl
17
4.3.2.2
122795
135
16724
Bifunctional purine biosynthesis protein PURH
Q6IN16
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.
Atic
17
2.1.2.3; 3.5.4.10
124437
135
16728
Inosine triphosphate pyrophosphatase
D3ZW55
Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Itpa
17
3.6.1.9
124438
135
124763
118
14629
GMP synthase [glutamine-hydrolyzing]
Q4V7C6
Gmps
17
6.3.5.2
80686
135
16733
Inosine-5'-monophosphate dehydrogenase 1
D3ZLZ7
Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in the development of malignancy and the growth progression of some tumors.
Impdh1
17
1.1.1.205
124439
135
16737
GMP reductase 1
Q9Z244
Catalyzes the irreversible NADPH-dependent deamination of GMP to IMP. It functions in the conversion of nucleobase, nucleoside and nucleotide derivatives of G to A nucleotides, and in maintaining the intracellular balance of A and G nucleotides.
Gmpr
17
1.7.1.7
124440
135
15441
Xanthine dehydrogenase/oxidase
Q63157
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species.
Xdh
17
1.17.1.4; 1.17.3.2
123154
443
123169
448
124444
374
16743
Adenylosuccinate synthetase isozyme 2
D4AEP0
Plays an important role in the de novo pathway and in the salvage pathway of purine nucleotide biosynthesis. Catalyzes the first commited step in the biosynthesis of AMP from IMP.
Adss
17
6.3.4.4
124447
135
16745
AMP deaminase 1
Q6LDJ4
AMP deaminase plays a critical role in energy metabolism.
Ampd1
17
3.5.4.6
124448
135
16750
Adenosine deaminase
Q920P6
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events. Acts as a positive regulator of T-cell coactivation, by binding DPP4. Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion. Enhances dendritic cell immunogenicity by affecting dendritic cell costimulatory molecule expression and cytokines and chemokines secretion. Enhances CD4+ T-cell differentiation and proliferation. Acts as a positive modulator of adenosine receptors ADORA1 and ADORA2A, by enhancing their ligand affinity via conformational change. Stimulates plasminogen activation. Plays a role in male fertility. Plays a protective role in early postimplantation embryonic development.
Ada
17
3.5.4.4
124449
135
16754
Adenylate kinase isoenzyme 1
Q9JJN3
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Also displays broad nucleoside diphosphate kinase activity. Plays an important role in cellular energy homeostasis and in adenine nucleotide metabolism.
Ak1
17
2.7.4.3; 2.7.4.6
124454
135
16759
ATPase family AAA domain-containing protein 1
B3STU2
ATPase that plays a critical role in regulating the surface expression of AMPA receptors (AMPAR), thereby regulating synaptic plasticity and learning and memory. Required for NMDA-stimulated AMPAR internalization and inhibition of GRIA1 and GRIA2 recycling back to the plasma membrane; these activities are ATPase-dependent.
Atad1
17
3.6.1.3
124456
374
16762
cAMP-specific 3',5'-cyclic phosphodiesterase 4D
Q8CG06
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Pde4d
17
3.1.4.53
124458
135
132617
551
16770
Guanylate cyclase soluble subunit alpha-2
Q54A43
Has guanylyl cyclase on binding to the beta-1 subunit.
Gucy1a2
17
4.6.1.2
124464
135
16776
Guanylate cyclase soluble subunit beta-1
Q8CH88
Mediates responses to nitric oxide (NO) by catalyzing the biosynthesis of the signaling molecule cGMP.
Gucy1b1
17
4.6.1.2
124465
135
16779
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A
Q9QYJ5
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. Can hydrolyze both cAMP and cGMP, but has higher affinity for cAMP and is more efficient with cAMP as substrate.
Pde10a
17
3.1.4.17; 3.1.4.35
124466
135
16785
Thioredoxin
P11232
Participates in various redox reactions through the reversible oxidation of its active center dithiol to a disulfide and catalyzes dithiol-disulfide exchange reactions (By similarity). Plays a role in the reversible S-nitrosylation of cysteine residues in target proteins, and thereby contributes to the response to intracellular nitric oxide. Nitrosylates the active site Cys of CASP3 in response to nitric oxide (NO), and thereby inhibits caspase-3 activity. Induces the FOS/JUN AP-1 DNA binding activity in ionizing radiation (IR) cells through its oxidation/reduction status and stimulates AP-1 transcriptional activity (By similarity).
Txn
17
124473
118
16793
Ribonucleoside-diphosphate reductase
Q5U2Q5
Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides.
Rrm1
17
1.17.4.1
124474
118
16795
Ribonucleoside-diphosphate reductase subunit M2
Q4KLN6
Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides (By similarity). Inhibits Wnt signaling (By similarity).
Rrm2
17
1.17.4.1
124475
118
14998
Adenylosuccinate synthetase isozyme 1
M0R629
Component of the purine nucleotide cycle (PNC), which interconverts IMP and AMP to regulate the nucleotide levels in various tissues, and which contributes to glycolysis and ammoniagenesis. Catalyzes the first commited step in the biosynthesis of AMP from IMP.
Adssl1
17
6.3.4.4
122821
135
7758
Unknown
Unknown
17
3.1.1.1, 3.1.1.56
5435
118
5460
120
80644
375
80655
135
80666
376
123808
443
123811
464
124957
473
124970
121
125260
398
131937
444
131983
470
132254
119
132257
529
132260
457
132605
137
132607
447
132609
138
132610
136
132612
452
132616
549
132621
552
132622
462
132623
553
132624
555
133143
400
135385
465
9231
Bis(5'-nucleosyl)-tetraphosphatase [asymmetrical]
17
PW_P009231
17487
16649
1
9232
Nucleoside diphosphate kinase 6
17
PW_P009232
17488
16654
1
9233
Ectonucleoside triphosphate diphosphohydrolase 5
17
PW_P009233
17489
16659
1
9234
Ectonucleoside triphosphate diphosphohydrolase 8
17
PW_P009234
17490
16664
1
9235
Guanylate kinase
17
PW_P009235
17491
16668
1
9236
Cytosolic purine 5'-nucleotidase
17
PW_P009236
17492
16673
4
9237
Deoxyguanosine kinase
17
PW_P009237
17493
16678
2
9238
Adenine phosphoribosyltransferase
17
PW_P009238
17494
16680
2
9240
Purine nucleoside phosphorylase
17
PW_P009240
17496
16686
3
9239
Hypoxanthine-guanine phosphoribosyltransferase
17
PW_P009239
17495
16692
4
9241
Guanine deaminase
17
PW_P009241
17497
16695
2
9242
ADP-sugar pyrophosphatase
17
PW_P009242
17498
16698
2
9243
Ribose-phosphate pyrophosphokinase 3
17
PW_P009243
17499
16702
2
7763
Amidophosphoribosyltransferase
17
PW_P007763
15775
14628
4
9244
Trifunctional purine biosynthetic protein adenosine-3
17
PW_P009244
17500
16711
1
9245
Phosphoribosylformylglycinamidine synthase
17
PW_P009245
17501
16716
1
9246
Multifunctional protein ADE2
17
PW_P009246
17502
16717
8
8827
Adenylosuccinate lyase
17
PW_P008827
17078
14985
4
9247
Bifunctional purine biosynthesis protein PURH
17
PW_P009247
17503
16724
2
9248
Inosine triphosphate pyrophosphatase
17
PW_P009248
17504
16728
2
7764
GMP synthase [glutamine-hydrolyzing]
17
PW_P007764
15776
14629
2
9249
Inosine-5'-monophosphate dehydrogenase 1
17
PW_P009249
17505
16733
4
9250
GMP reductase 1
17
PW_P009250
17506
16737
4
8919
Xanthine dehydrogenase/oxidase
17
PW_P008919
17171
15441
2
8834
Adenylosuccinate synthetase isozyme 2
17
PW_P008834
17085
16743
2
9251
AMP deaminase 1
17
PW_P009251
17507
16745
4
9252
Adenosine deaminase
17
PW_P009252
17508
16750
1
9253
Adenylate kinase isoenzyme 1
17
PW_P009253
17509
16754
9254
ATPase family AAA domain-containing protein 1
17
PW_P009254
17510
16759
1
9255
cAMP-specific 3',5'-cyclic phosphodiesterase 4D
17
PW_P009255
17511
16762
9259
Guanylate cyclase
17
PW_P009259
17515
16770
1
17516
16776
1
9260
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A
17
PW_P009260
17517
16779
2
9261
Thioredoxin Disulfide
17
PW_P009261
17518
16785
1
9262
Thioredoxin
17
PW_P009262
17519
16785
1
9263
Ribonucleoside-diphosphate reductase 1
17
PW_P009263
17520
16793
1
17521
16795
1
8833
Adenylosuccinate synthetase isozyme 1
17
PW_P008833
17084
14998
2
9256
Adenylate cyclase type 2
17
PW_P009256
17512
7758
1
9257
Guanine nucleotide-binding protein alpha
17
PW_P009257
17513
7758
1
147657
false
PW_R147657
Right
550646
1033
1
Compound
false
550647
1420
1
Compound
true
550648
986
1
Compound
false
550649
1080
1
Compound
true
137917
9231
3.6.1.17
147658
false
PW_R147658
Both
550650
414
1
Compound
true
550651
936
1
Compound
false
550652
1034
1
Compound
true
550653
986
1
Compound
false
137918
9232
2.7.4.6
147659
false
PW_R147659
Right
550654
936
1
Compound
false
550655
1420
1
Compound
true
550656
1080
1
Compound
false
550657
1104
1
Compound
true
137919
9233
147660
false
PW_R147660
Right
550658
986
1
Compound
false
550659
1420
1
Compound
true
550660
936
1
Compound
false
550661
1104
1
Compound
true
137920
9234
3.6.1.5
137921
9233
147661
false
PW_R147661
Both
550662
414
1
Compound
true
550663
1080
1
Compound
false
550664
1034
1
Compound
true
550665
936
1
Compound
false
137922
9235
2.7.4.8
147662
false
PW_R147662
Right
550666
414
1
Compound
true
550667
767
1
Compound
false
550668
1034
1
Compound
true
550669
1112
1
Compound
false
137923
9232
2.7.4.6
147663
false
PW_R147663
Both
550670
414
1
Compound
true
550671
822
1
Compound
false
550672
1034
1
Compound
true
550673
767
1
Compound
false
137924
9235
2.7.4.8
147664
false
PW_R147664
Both
550674
822
1
Compound
false
550675
1420
1
Compound
true
550676
58
1
Compound
false
550677
1104
1
Compound
true
137925
9236
3.1.3.5
147665
false
PW_R147665
Both
550678
414
1
Compound
true
550679
58
1
Compound
false
550680
1034
1
Compound
true
550681
822
1
Compound
false
137926
9237
2.7.1.113
147666
false
PW_R147666
Both
550682
1080
1
Compound
false
550683
170
1
Compound
true
550684
86
1
Compound
false
550685
190
1
Compound
true
137927
9238
2.4.2.7
137928
9239
2.4.2.8
147667
false
PW_R147667
Right
550686
1080
1
Compound
false
550687
1420
1
Compound
true
550688
87
1
Compound
false
550689
1441
1
Compound
true
137929
9236
3.1.3.5
147668
false
PW_R147668
Both
550690
87
1
Compound
false
550691
1104
1
Compound
true
550692
86
1
Compound
false
550693
1146
1
Compound
true
137930
9240
2.4.2.1
147669
false
PW_R147669
Both
550694
58
1
Compound
false
550695
1104
1
Compound
true
550696
86
1
Compound
false
550697
1042
1
Compound
true
137931
9240
2.4.2.1
147670
false
PW_R147670
Right
550698
86
1
Compound
false
550699
1420
1
Compound
true
550700
198
1
Compound
false
550701
35
1
Compound
true
137932
9241
3.5.4.3
147671
false
PW_R147671
Right
550702
914
1
Compound
false
550703
1420
1
Compound
true
550704
32
1
Compound
true
550705
1191
1
Compound
false
137933
9242
147672
false
PW_R147672
Both
550706
1191
1
Compound
false
550707
414
1
Compound
true
550708
190
1
Compound
false
550709
32
1
Compound
true
137934
9243
2.7.6.1
110922
false
PW_R110922
Both
403555
882
1
Compound
false
403556
170
1
Compound
true
403557
95
1
Compound
true
403558
500
1
Compound
true
403559
190
1
Compound
false
403560
1420
1
Compound
true
101163
7763
2.4.2.14
147673
false
PW_R147673
Right
550710
414
1
Compound
true
550711
882
1
Compound
false
550712
78
1
Compound
true
550713
1034
1
Compound
true
550714
1104
1
Compound
true
550715
1355
1
Compound
false
137935
9244
147674
false
PW_R147674
Right
550716
774
1
Compound
true
550717
1355
1
Compound
false
550718
1221
1
Compound
true
550719
1007
1
Compound
false
137936
9244
147675
false
PW_R147675
Right
550720
414
1
Compound
true
550721
1007
1
Compound
false
550722
500
1
Compound
true
550723
1420
1
Compound
true
550724
1034
1
Compound
true
550725
1441
1
Compound
true
550726
791
1
Compound
false
550727
95
1
Compound
true
137937
9245
6.3.5.3
147676
false
PW_R147676
Both
550728
2699
1
Compound
false
550729
955
1
Compound
false
550730
1316
1
Compound
true
137938
9246
147677
false
PW_R147677
Both
550731
414
1
Compound
true
550732
2699
1
Compound
false
550733
123
1
Compound
true
550734
1034
1
Compound
true
550735
1441
1
Compound
true
550736
637
1
Compound
false
137939
9246
147678
false
PW_R147678
Both
550737
637
1
Compound
false
550738
88
1
Compound
true
550739
1168
1
Compound
false
137940
8827
4.3.2.2
147679
false
PW_R147679
Both
550740
774
1
Compound
true
550741
1168
1
Compound
false
550742
1221
1
Compound
true
550743
1111
1
Compound
false
137941
9247
147680
false
PW_R147680
Both
550744
114
1
Compound
false
550745
1420
1
Compound
true
550746
1111
1
Compound
false
137942
9247
147681
false
PW_R147681
Right
550747
986
1
Compound
false
550748
1420
1
Compound
true
550749
1080
1
Compound
false
550750
170
1
Compound
true
137943
9248
3.6.1.19
147682
false
PW_R147682
Right
550751
414
1
Compound
true
550752
1196
1
Compound
false
550753
35
1
Compound
true
550754
32
1
Compound
true
550755
170
1
Compound
true
550756
1080
1
Compound
false
137944
7764
6.3.5.2
147683
false
PW_R147683
Right
550757
114
1
Compound
false
550758
721
1
Compound
true
550759
1420
1
Compound
true
550760
1196
1
Compound
false
550761
1144
1
Compound
true
137945
9249
1.1.1.205
147684
false
PW_R147684
Both
550762
114
1
Compound
false
550763
35
1
Compound
true
550764
143
1
Compound
true
550765
1080
1
Compound
false
550766
146
1
Compound
true
137946
9250
1.7.1.7
147685
false
PW_R147685
Right
550767
1196
1
Compound
false
550768
1420
1
Compound
true
550769
203
1
Compound
false
550770
1104
1
Compound
true
137947
9236
3.1.3.5
147686
false
PW_R147686
Both
550771
203
1
Compound
false
550772
1104
1
Compound
true
550773
198
1
Compound
false
550774
1146
1
Compound
true
137948
9240
2.4.2.1
147687
false
PW_R147687
Right
550775
114
1
Compound
false
550776
1420
1
Compound
true
550777
127
1
Compound
false
550778
1104
1
Compound
true
137949
9236
3.1.3.5
147688
false
PW_R147688
Both
550779
1196
1
Compound
false
550780
170
1
Compound
true
550781
198
1
Compound
false
550782
190
1
Compound
true
137950
9239
2.4.2.8
147689
false
PW_R147689
Both
550783
127
1
Compound
false
550784
1104
1
Compound
true
550785
102
1
Compound
false
550786
1146
1
Compound
true
137951
9240
2.4.2.1
147690
false
PW_R147690
Both
550787
114
1
Compound
false
550788
170
1
Compound
true
550789
102
1
Compound
false
550790
190
1
Compound
true
137952
9239
2.4.2.8
147691
false
PW_R147691
Right
550791
102
1
Compound
false
550792
1065
1
Compound
true
550793
1420
1
Compound
true
550794
198
1
Compound
false
550795
1783
1
Compound
true
137953
8919
147692
false
PW_R147692
Right
550796
198
1
Compound
false
550797
721
1
Compound
true
550798
1420
1
Compound
true
550799
195
1
Compound
false
550800
1144
1
Compound
true
137954
8919
147693
false
PW_R147693
Both
550801
50
1
Compound
false
550802
1104
1
Compound
true
550803
102
1
Compound
false
550804
1042
1
Compound
true
137955
9240
2.4.2.1
147004
false
PW_R147004
Both
547938
986
1
Compound
true
547939
114
1
Compound
false
547940
123
1
Compound
false
547941
936
1
Compound
true
547942
1104
1
Compound
true
547943
413
1
Compound
false
137167
8833
6.3.4.4
137168
8834
6.3.4.4
147694
false
PW_R147694
Both
550805
32
1
Compound
false
550806
1420
1
Compound
true
550807
114
1
Compound
false
550808
35
1
Compound
true
137956
9251
3.5.4.6
146998
false
PW_R146998
Both
547912
413
1
Compound
false
547913
88
1
Compound
true
547914
32
1
Compound
false
137161
8827
4.3.2.2
147695
false
PW_R147695
Right
550809
34
1
Compound
false
550810
1420
1
Compound
true
550811
127
1
Compound
false
550812
35
1
Compound
true
137957
9252
3.5.4.4
147696
false
PW_R147696
Both
550813
34
1
Compound
false
550814
1104
1
Compound
true
550815
24
1
Compound
false
550816
1146
1
Compound
true
137958
9240
2.4.2.1
147697
false
PW_R147697
Both
550817
68
1
Compound
false
550818
1104
1
Compound
true
550819
24
1
Compound
false
550820
1042
1
Compound
true
137959
9240
2.4.2.1
147698
false
PW_R147698
Both
550821
68
1
Compound
false
550822
1420
1
Compound
true
550823
50
1
Compound
false
550824
35
1
Compound
true
137960
9252
3.5.4.4
147699
false
PW_R147699
Both
550825
32
1
Compound
false
550826
170
1
Compound
true
550827
24
1
Compound
false
550828
190
1
Compound
true
137961
9238
2.4.2.7
147700
false
PW_R147700
Both
550829
1034
1
Compound
false
550830
1420
1
Compound
true
550831
32
1
Compound
false
550832
1441
1
Compound
true
137962
9233
147701
false
PW_R147701
Right
550833
414
1
Compound
false
550834
32
1
Compound
false
550835
1034
2
Compound
false
137963
9253
147702
false
PW_R147702
Right
550836
414
1
Compound
false
550837
1420
1
Compound
true
550838
1034
1
Compound
false
550839
1441
1
Compound
true
137964
9254
3.6.1.3
147703
false
PW_R147703
Right
550840
41
1
Compound
false
550841
1420
1
Compound
true
550842
32
1
Compound
false
137965
9255
3.1.4.53
147704
false
PW_R147704
Right
550843
414
1
Compound
false
550844
41
1
Compound
false
550845
170
1
Compound
true
137966
9256
4.6.1.1
137967
9257
147705
false
PW_R147705
Both
550846
414
1
Compound
true
550847
724
1
Compound
false
550848
1034
1
Compound
true
550849
1161
1
Compound
false
137968
9253
147706
false
PW_R147706
Both
550850
724
1
Compound
false
550851
1420
1
Compound
true
550852
68
1
Compound
false
550853
1441
1
Compound
true
137969
9236
3.1.3.5
147707
false
PW_R147707
Both
550854
414
1
Compound
true
550855
1161
1
Compound
false
550856
1034
1
Compound
true
550857
1177
1
Compound
false
137970
9232
2.7.4.6
147708
false
PW_R147708
Right
550858
986
1
Compound
false
550859
7218
1
Compound
false
550860
170
1
Compound
true
137971
9259
4.6.1.2
147709
false
PW_R147709
Right
550861
7218
1
Compound
false
550862
1420
1
Compound
true
550863
1080
1
Compound
false
137972
9260
147710
false
PW_R147710
Right
550864
1846
1
Compound
false
550865
1420
1
Compound
true
550866
114
1
Compound
false
550867
1104
1
Compound
true
137973
9234
3.6.1.5
147711
false
PW_R147711
Right
550868
121
1
Compound
false
550869
1420
1
Compound
true
550870
114
1
Compound
false
550871
170
1
Compound
true
137974
9248
3.6.1.19
147712
false
PW_R147712
Both
550872
414
1
Compound
true
550873
1846
1
Compound
false
550874
1034
1
Compound
true
550875
121
1
Compound
false
137975
9232
2.7.4.6
147713
false
PW_R147713
Right
550876
121
1
Compound
false
550877
1420
1
Compound
true
550878
1846
1
Compound
false
550879
1104
1
Compound
true
137976
9234
3.6.1.5
147714
false
PW_R147714
Both
550880
1168
1
Compound
false
550881
170
1
Compound
true
550882
1801
1
Compound
false
550883
190
1
Compound
true
137977
9238
2.4.2.7
147715
false
PW_R147715
Right
550884
414
1
Compound
true
550885
791
1
Compound
false
550886
1034
1
Compound
true
550887
1104
1
Compound
true
550888
955
1
Compound
false
137978
9244
147716
false
PW_R147716
Both
550889
1161
1
Compound
false
550890
9261
1
ProteinComplex
true
550891
1420
1
Compound
true
550892
1034
1
Compound
false
550893
9262
1
ProteinComplex
true
137979
9263
1.17.4.1
147717
false
PW_R147717
Right
550894
1161
1
Compound
false
550895
1104
1
Compound
true
550896
1177
1
Compound
false
550897
1420
1
Compound
true
137980
9233
147718
false
PW_R147718
Both
550898
767
1
Compound
false
550899
9261
1
ProteinComplex
true
550900
1420
1
Compound
true
550901
936
1
Compound
false
550902
9262
1
ProteinComplex
true
137981
9263
1.17.4.1
2661852
1033
135
81
false
460
550
10
regular
200
190
2661853
1420
135
49
false
695
780
10
regular
78
78
2661854
986
135
81
false
460
1130
10
regular
200
190
2661855
1080
135
81
false
700
940
10
regular
200
190
2661856
414
135
42
false
629
1510
10
regular
50
30
2661857
936
376
81
false
459
1580
10
regular
200
190
2661858
1034
135
43
false
625
1355
10
regular
50
30
2661859
423
135
9
false
564
1405
10
regular
100
25
2661860
1420
398
49
false
755
1480
10
regular
78
78
2661861
1080
398
81
false
1369
1578
10
regular
200
190
2661862
1104
398
46
false
1025
1505
10
regular
44
43
2661863
353
398
9
false
865
1565
10
regular
100
25
2661864
423
398
9
false
864
1635
10
regular
100
25
2661865
1420
376
49
false
405
1325
10
regular
78
78
2661866
1104
376
46
false
413
1498
10
regular
44
43
2661867
353
376
9
false
340
1455
10
regular
100
25
2661868
414
135
42
false
1099
1908
10
regular
50
30
2661869
1034
135
43
false
849
1910
10
regular
50
30
2661870
414
135
42
false
639
2380
10
regular
50
30
2661871
767
135
81
false
459
2165
10
regular
200
190
2661872
1034
135
43
false
644
2535
10
regular
50
30
2661873
1112
135
81
false
459
2610
10
regular
200
190
2661874
423
135
9
false
569
2430
10
regular
100
25
2661875
414
135
42
false
984
2585
10
regular
50
30
2661876
822
135
81
false
804
2645
10
regular
200
200
2661877
1034
135
43
false
979
2430
10
regular
50
30
2661878
1420
135
49
false
979
2865
10
regular
78
78
2661879
58
135
81
false
803
3105
10
regular
200
190
2661880
1104
135
46
false
981
3048
10
regular
44
43
2661881
423
135
9
false
914
3007
10
regular
100
25
2661882
414
119
42
false
463
3050
10
regular
50
30
2661883
1034
119
43
false
474
2850
10
regular
50
30
2661884
170
135
45
false
1039
1951
10
regular
63
43
2661885
86
135
3
false
1418
2618
10
regular
100
100
2661886
190
135
81
false
888
2118
10
regular
200
190
2661887
1420
135
49
false
1539
1813
10
regular
78
78
2661888
87
135
81
false
1368
2098
10
regular
200
190
2661889
1441
135
46
false
1561
1991
10
regular
44
43
2661890
423
135
9
false
1364
1948
10
regular
100
25
2661891
1104
135
46
false
1352
2301
10
regular
44
43
2661892
1146
135
3
false
1308
2448
10
regular
100
110
2661893
170
135
45
false
1824
1956
10
regular
63
43
2661894
190
135
81
false
1833
2113
10
regular
200
190
2661895
423
135
9
false
1651
2103
10
regular
100
25
2661896
1104
135
46
false
1322
3028
10
regular
44
43
2661897
1042
135
3
false
1283
2738
10
regular
100
110
2661898
1420
135
49
false
1693
2773
10
regular
78
78
2661899
198
135
3
false
2148
2656
10
regular
100
100
2661900
35
135
63
false
1964
2772
10
regular
78
78
2661901
1005
135
9
false
1808
2653
10
regular
100
25
2661902
914
135
81
false
825
550
10
regular
200
190
2661903
1420
135
49
false
1040
720
10
regular
78
78
2661904
32
135
44
false
1305
725
10
regular
50
30
2661905
1191
135
81
false
1390
550
10
regular
200
190
2661906
414
135
42
false
1640
720
10
regular
50
30
2661907
190
135
81
false
1970
550
10
regular
200
190
2661908
32
135
44
false
1860
725
10
regular
50
30
2661909
423
135
9
false
1730
595
10
regular
100
25
2661910
882
135
81
false
2595
548
10
regular
200
190
2661911
170
135
45
false
2463
546
10
regular
63
43
2661912
95
135
3
false
2435
706
10
regular
100
110
2661913
500
135
3
false
2215
705
10
regular
100
100
2661914
1420
135
49
false
2230
515
10
regular
78
78
2661915
423
135
9
false
2325
668
10
regular
100
25
2661916
414
135
42
false
2865
548
10
regular
50
30
2661917
78
135
3
false
2825
718
10
regular
100
100
2661918
1034
135
43
false
3105
551
10
regular
50
30
2661919
1104
135
46
false
3118
719
10
regular
44
43
2661920
1355
135
81
false
3235
550
10
regular
200
190
2661921
774
135
81
false
3445
375
10
regular
200
190
2661922
1221
135
81
false
3710
375
10
regular
200
190
2661923
1007
135
81
false
3925
545
10
regular
200
200
2661924
414
135
42
false
4225
545
10
regular
50
30
2661925
500
135
3
true
4200
695
10
regular
100
100
2661926
1420
135
49
false
4135
505
10
regular
78
78
2661927
1034
135
43
false
4465
543
10
regular
50
30
2661928
1441
135
46
false
4538
536
10
regular
44
43
2661929
791
135
81
false
4615
552
10
regular
200
190
2661930
95
135
3
true
4455
697
10
regular
100
110
2661931
2699
135
81
false
5149
1094
10
regular
200
210
2661932
955
135
81
false
5150
549
10
regular
200
200
2661933
1316
135
52
false
5088
795
10
regular
78
78
2661934
414
135
42
false
5004
1099
10
regular
50
30
2661935
123
135
3
false
4984
1269
10
regular
100
110
2661936
1034
135
43
false
4744
1102
10
regular
50
30
2661937
1441
135
46
false
4742
1270
10
regular
44
43
2661938
637
135
81
false
4444
1101
10
regular
200
190
2661939
88
135
3
false
4064
1276
10
regular
100
100
2661940
1168
135
81
false
3794
1101
10
regular
200
190
2661941
774
135
81
false
3544
926
10
regular
200
190
2661942
1221
135
81
false
3304
926
10
regular
200
190
2661943
1111
135
81
false
3049
1096
10
regular
200
200
2661944
114
135
81
false
2964
1581
10
regular
200
190
2661945
1420
135
49
false
3204
1446
10
regular
78
78
2661946
1420
135
49
false
895
1360
10
regular
78
78
2661947
170
135
45
false
1142
1368
10
regular
63
43
2661948
423
135
9
false
979
1340
10
regular
100
25
2661949
414
135
42
false
1954
1580
10
regular
50
30
2661950
1196
135
81
false
2099
1580
10
regular
200
190
2661951
35
135
63
false
1935
1741
10
regular
78
78
2661952
32
135
44
false
1714
1580
10
regular
50
30
2661953
170
135
45
false
1707
1743
10
regular
63
43
2661954
721
135
59
false
2724
1576
10
regular
50
30
2661955
1420
135
49
false
2724
1736
10
regular
78
78
2661956
1144
135
60
false
2499
1575
10
regular
50
30
2661957
457
135
9
false
2594
1706
10
regular
100
25
2661958
35
135
63
false
2310
1549
10
regular
78
78
2661959
143
135
61
false
2279
1416
10
regular
50
30
2661960
146
135
62
false
2059
1418
10
regular
50
30
2661961
1420
135
49
false
2059
1810
10
regular
78
78
2661962
203
135
81
false
2098
2100
10
regular
200
190
2661963
1104
135
46
false
2096
1998
10
regular
44
43
2661964
423
135
9
false
2089
1950
10
regular
100
25
2661965
1104
135
46
false
2077
2313
10
regular
44
43
2661966
1146
135
3
false
2018
2456
10
regular
100
110
2661967
1420
135
49
false
3129
1796
10
regular
78
78
2661968
127
135
81
false
2963
2101
10
regular
200
190
2661969
1104
135
46
false
3141
1974
10
regular
44
43
2661970
423
135
9
false
2954
1941
10
regular
100
25
2661971
170
135
45
false
2519
2028
10
regular
63
43
2661972
190
135
81
false
2538
2206
10
regular
200
190
2661973
423
135
9
false
2321
2195
10
regular
100
25
2661974
1104
135
46
false
3137
2339
10
regular
44
43
2661975
102
135
3
false
3015
2656
10
regular
100
100
2661976
1146
135
3
false
3135
2491
10
regular
100
110
2661977
170
135
45
false
2684
2024
10
regular
63
43
2661978
423
135
9
false
2846
2201
10
regular
100
25
2661979
1065
374
65
false
2736
2574
10
regular
78
78
2661980
1420
374
49
false
2750
2761
10
regular
78
78
2661981
1783
374
56
false
2494
2574
10
regular
78
78
2661982
964
374
9
false
2601
2733
10
regular
100
25
2661983
721
374
59
false
2468
2951
10
regular
50
30
2661984
1420
374
49
false
2348
2841
10
regular
78
78
2661985
195
374
3
false
2883
2831
10
regular
100
100
2661986
1144
374
60
false
2713
2951
10
regular
50
30
2661987
964
374
9
false
2578
2906
10
regular
100
25
2661988
50
135
81
false
2964
3141
10
regular
200
190
2661989
1104
135
46
false
3157
3034
10
regular
44
43
2661990
1042
135
3
false
3150
2796
10
regular
100
110
2661991
986
135
54
false
3329
1506
10
regular
50
30
2661992
123
135
3
false
3304
1276
10
regular
100
110
2661993
936
135
53
false
3574
1509
10
regular
50
30
2661994
1104
135
46
false
3577
1337
10
regular
44
43
2661995
413
135
81
false
3704
1353
10
regular
200
190
2661996
423
135
9
false
3424
1401
10
regular
100
25
2661997
32
135
81
false
3704
1770
10
regular
200
190
2661998
1420
135
49
false
3534
1735
10
regular
78
78
2661999
35
135
63
false
3310
1734
10
regular
78
78
2662000
1005
135
9
false
3414
1810
10
regular
100
25
2662001
88
135
3
false
3629
1665
10
regular
100
100
2662002
34
135
81
false
3703
2100
10
regular
200
190
2662003
1420
135
49
false
3498
2045
10
regular
78
78
2662004
35
135
63
false
3264
2044
10
regular
78
78
2662005
1005
135
9
false
3373
2145
10
regular
100
25
2662006
1104
135
46
false
3677
2353
10
regular
44
43
2662007
24
135
3
false
3755
2655
10
regular
100
100
2662008
1146
135
3
false
3620
2495
10
regular
100
110
2662009
68
135
81
false
3704
3140
10
regular
200
190
2662010
1104
135
46
false
3672
3033
10
regular
44
43
2662011
1042
135
3
false
3620
2805
10
regular
100
110
2662012
1420
135
49
false
3489
3090
10
regular
78
78
2662013
35
135
63
false
3255
3084
10
regular
78
78
2662014
1005
135
9
false
3364
3185
10
regular
100
25
2662015
170
135
45
false
4039
2183
10
regular
63
43
2662016
190
135
81
false
4055
2415
10
regular
200
190
2662017
1034
398
81
false
4494
2214
10
regular
200
190
2662018
1420
398
49
false
4374
2079
10
regular
78
78
2662019
1441
398
46
false
4137
2285
10
regular
44
43
2662020
353
398
9
false
4229
2244
10
regular
100
25
2662021
423
398
9
false
4224
2174
10
regular
100
25
2662022
414
135
81
false
4494
1770
10
regular
200
190
2662023
1420
374
49
false
4954
1995
10
regular
78
78
2662024
1441
374
46
false
4963
2247
10
regular
44
43
2662025
41
135
81
false
4119
1430
10
regular
200
190
2662026
1420
135
49
false
4034
1605
10
regular
78
78
2662027
1005
135
9
false
4239
1700
10
regular
100
25
2662028
170
135
45
false
4624
1508
10
regular
63
43
2662029
414
135
42
false
4659
3069
10
regular
50
30
2662030
724
135
81
false
4494
3139
10
regular
200
190
2662031
1034
135
43
false
4654
2929
10
regular
50
30
2662032
1161
135
81
false
4494
2704
10
regular
200
190
2662033
1420
135
49
false
4279
3094
10
regular
78
78
2662034
1441
135
46
false
4062
3120
10
regular
44
43
2662035
423
135
9
false
4159
3264
10
regular
100
25
2662036
414
135
42
false
4779
2619
10
regular
50
30
2662037
1034
135
43
false
5009
2619
10
regular
50
30
2662038
1177
135
81
false
5139
2704
10
regular
200
190
2662039
423
135
9
false
4869
2679
10
regular
100
25
2662040
7218
135
81
false
1370
1058
10
regular
200
200
2662041
170
135
45
false
1103
1051
10
regular
63
43
2662042
1799
135
9
false
960
1110
10
regular
100
25
2662043
1420
135
49
false
1545
1278
10
regular
78
78
2662044
1005
135
9
false
1515
1400
10
regular
100
25
2662045
423
135
9
false
1330
1395
10
regular
100
25
2662046
1846
135
81
false
2154
900
10
regular
200
190
2662047
1420
135
49
false
2094
1160
10
regular
78
78
2662048
1104
135
46
false
2132
1346
10
regular
44
43
2662049
353
135
9
false
2144
1295
10
regular
100
25
2662050
121
135
81
false
2893
896
10
regular
200
190
2662051
1420
135
49
false
2848
1216
10
regular
78
78
2662052
170
135
45
false
2864
1394
10
regular
63
43
2662053
423
135
9
false
2858
1308
10
regular
100
25
2662054
414
135
42
false
2484
830
10
regular
50
30
2662055
1034
135
43
false
2703
826
10
regular
50
30
2662056
423
135
9
false
2563
870
10
regular
100
25
2662057
1420
135
49
false
2698
1121
10
regular
78
78
2662058
1104
135
46
false
2482
1125
10
regular
44
43
2662059
353
135
9
false
2563
1016
10
regular
100
25
2662060
170
135
45
false
3977
861
10
regular
63
43
2662061
1801
135
81
false
4389
880
10
regular
200
190
2662062
190
135
81
false
4149
720
10
regular
200
190
2662063
414
118
42
false
4845
565
10
regular
50
30
2662064
1034
118
43
false
5080
560
10
regular
50
30
2662065
1104
118
46
false
5090
695
10
regular
44
43
2662066
1420
118
49
false
4669
2589
10
regular
78
78
2662067
40707
118
9
false
4334
2589
10
regular
100
25
2662068
8133
118
9
false
4449
2494
10
regular
100
25
2662069
1104
136
46
false
4772
2924
10
regular
44
43
2662070
1420
136
49
false
5049
2929
10
regular
78
78
2662071
353
136
9
false
4871
2881
10
regular
100
25
2662072
423
136
9
false
4871
2806
10
regular
100
25
2662073
1420
118
49
false
609
2025
10
regular
78
78
2662074
40707
118
9
false
384
1985
10
regular
100
25
2662075
8133
118
9
false
604
1902
10
regular
100
25
929938
16649
135
2
false
485
895
8
subunit
regular
150
70
929939
16654
135
2
false
484
1410
8
subunit
regular
150
70
929940
16659
398
2
false
844
1580
8
subunit
regular
150
70
929941
16664
376
2
false
255
1410
8
subunit
regular
150
70
929942
16668
135
2
false
929
1813
8
subunit
regular
150
70
929943
16654
135
2
false
484
2440
8
subunit
regular
150
70
929944
16668
135
2
false
829
2487
8
subunit
regular
150
70
929945
16673
135
8
false
834
2942
8
subunit
regular
140
85
929946
16678
119
6
false
513
2922
8
protein
regular
160
80
929947
16680
135
6
false
1096
2048
8
subunit
regular
160
80
929948
16673
135
8
false
1399
1888
8
subunit
regular
140
85
929949
16686
135
16
false
1384
2363
8
subunit
regular
170
90
929950
16692
135
8
false
1686
2038
8
subunit
regular
140
85
929951
16686
135
16
false
1384
2881
8
subunit
regular
170
90
929952
16695
135
6
false
1788
2668
8
subunit
regular
160
80
929953
16698
135
6
false
1125
605
8
subunit
regular
160
80
929954
16702
135
2
false
1705
610
8
subunit
regular
150
70
929955
14628
135
8
false
2305
603
8
subunit
regular
140
85
929956
16711
135
2
false
2930
608
8
subunit
regular
150
70
929957
16711
135
2
false
3605
610
8
subunit
regular
150
70
929958
16716
135
2
false
4300
610
8
subunit
regular
150
70
929959
16717
135
7
false
5154
889
8
subunit
regular
190
85
929960
16717
135
7
false
4794
1159
8
subunit
regular
190
85
929961
14985
135
2
false
4159
1161
8
subunit
regular
150
70
929962
16724
135
2
false
3449
1161
8
subunit
regular
150
70
929963
16724
135
2
false
3074
1373
8
subunit
regular
150
70
929964
16728
135
6
false
979
1270
8
subunit
regular
160
80
929965
14629
135
6
false
1779
1635
8
subunit
regular
160
80
929966
16733
135
8
false
2569
1636
8
subunit
regular
140
85
929967
16737
135
8
false
2126
1463
8
subunit
regular
140
85
929968
16673
135
8
false
2129
1890
8
subunit
regular
140
85
929969
16686
135
16
false
2114
2375
8
subunit
regular
170
90
929970
16673
135
8
false
2994
1876
8
subunit
regular
140
85
929971
16692
135
8
false
2361
2130
8
subunit
regular
140
85
929972
16686
135
16
false
2979
2408
8
subunit
regular
170
90
929973
16692
135
8
false
2766
2136
8
subunit
regular
140
85
929974
15441
374
6
false
2571
2668
8
subunit
regular
160
80
929975
15441
374
6
false
2543
2841
8
subunit
regular
160
80
929976
16686
135
16
false
2979
2908
8
subunit
regular
170
90
929977
16743
135
6
false
3399
1406
8
subunit
regular
160
80
929978
16745
135
8
false
3394
1825
8
subunit
regular
140
85
929979
14985
135
2
false
3729
1606
8
subunit
regular
150
70
929980
16750
135
2
false
3348
2160
8
subunit
regular
150
70
929981
16686
135
16
false
3719
2417
8
subunit
regular
170
90
929982
16686
135
16
false
3719
2907
8
subunit
regular
170
90
929983
16750
135
2
false
3339
3200
8
subunit
regular
150
70
929984
16680
135
6
false
3886
2300
8
subunit
regular
160
80
929985
16659
398
2
false
4204
2189
8
subunit
regular
150
70
929986
16754
135
2
false
4519
2057
8
subunit
regular
150
70
929987
16759
374
2
false
4804
2119
8
subunit
regular
150
70
929988
16762
135
6
false
4139
1700
8
subunit
regular
160
80
929989
16754
135
2
false
4519
2979
8
subunit
regular
150
70
929990
16673
135
8
false
4134
3194
8
subunit
regular
140
85
929991
16654
135
2
false
4844
2689
8
subunit
regular
150
70
929992
16770
135
97
false
935
1145
8
none
regular
150
70
929993
16776
135
2
false
935
1120
8
protein
regular
150
70
929994
16779
135
6
false
1390
1370
8
subunit
regular
160
80
929995
16664
135
2
false
2179
1245
8
subunit
regular
150
70
929996
16728
135
6
false
2913
1298
8
subunit
regular
160
80
929997
16654
135
2
false
2543
880
8
subunit
regular
150
70
929998
16664
135
2
false
2543
1031
8
subunit
regular
150
70
929999
16680
135
6
false
4039
938
8
subunit
regular
160
80
930000
16711
118
2
false
4915
615
8
subunit
regular
150
70
930001
16785
118
99
false
4334
2599
8
subunit
regular
150
70
930002
16785
118
99
false
4334
2404
8
subunit
regular
150
70
930003
16793
118
2
false
4544
2484
8
subunit
regular
150
70
930004
16795
118
2
false
4519
2499
8
subunit
regular
150
70
930005
16659
136
2
false
4851
2821
8
subunit
regular
150
70
930006
16785
118
99
false
359
1995
8
subunit
regular
150
70
930007
16785
118
99
false
359
1795
8
subunit
regular
150
70
930008
16793
118
97
false
504
1917
8
subunit
regular
150
70
930009
16795
118
2
false
484
1897
8
subunit
regular
150
70
794307
9231
88107
135
926398
929938
794308
9232
88107
135
926399
929939
32954
2661859
3625508
Cofactor
794309
9233
88107
398
926400
929940
32955
2661863
3625513
Cofactor
32956
2661864
3625514
Cofactor
794310
9234
88107
376
926401
929941
32957
2661867
3625519
Cofactor
794311
9235
88107
135
926402
929942
794312
9232
88107
135
926403
929943
32958
2661874
3625528
Cofactor
794313
9235
88107
135
926404
929944
794314
9236
88107
135
926405
929945
32959
2661881
3625537
Cofactor
794315
9237
88107
119
926406
929946
794316
9238
88107
135
926407
929947
794317
9236
88107
135
926408
929948
32960
2661890
3625550
Cofactor
794318
9240
88107
135
926409
929949
794319
9239
88107
135
926410
929950
32961
2661895
3625559
Cofactor
794320
9240
88107
135
926411
929951
794321
9241
88107
135
926412
929952
32962
2661901
3625568
Cofactor
794322
9242
88107
135
926413
929953
794323
9243
88107
135
926414
929954
32963
2661909
3625577
Cofactor
794324
7763
88107
135
926415
929955
32964
2661915
3625584
Cofactor
794325
9244
88107
135
926416
929956
794326
9244
88107
135
926417
929957
794327
9245
88107
135
926418
929958
794328
9246
88107
135
926419
929959
794329
9246
88107
135
926420
929960
794330
8827
88107
135
926421
929961
794331
9247
88107
135
926422
929962
794332
9247
88107
135
926423
929963
794333
9248
88107
135
926424
929964
32965
2661948
3625626
Cofactor
794334
7764
88107
135
926425
929965
794335
9249
88107
135
926426
929966
32966
2661957
3625638
Cofactor
794336
9250
88107
135
926427
929967
794337
9236
88107
135
926428
929968
32967
2661964
3625648
Cofactor
794338
9240
88107
135
926429
929969
794339
9236
88107
135
926430
929970
32968
2661970
3625657
Cofactor
794340
9239
88107
135
926431
929971
32969
2661973
3625662
Cofactor
794341
9240
88107
135
926432
929972
794342
9239
88107
135
926433
929973
32970
2661978
3625671
Cofactor
794343
8919
88107
374
926434
929974
32971
2661982
3625677
Cofactor
794344
8919
88107
374
926435
929975
32972
2661987
3625683
Cofactor
794345
9240
88107
135
926436
929976
794346
8834
88107
135
926437
929977
32973
2661996
3625694
Cofactor
794347
9251
88107
135
926438
929978
32974
2662000
3625699
Cofactor
794348
8827
88107
135
926439
929979
794349
9252
88107
135
926440
929980
32975
2662005
3625707
Cofactor
794350
9240
88107
135
926441
929981
794351
9240
88107
135
926442
929982
794352
9252
88107
135
926443
929983
32976
2662014
3625720
Cofactor
794353
9238
88107
135
926444
929984
794354
9233
88107
398
926445
929985
32977
2662020
3625729
Cofactor
32978
2662021
3625730
Cofactor
794355
9253
88107
135
926446
929986
794356
9254
88107
374
926447
929987
794357
9255
88107
135
926448
929988
32979
2662027
3625741
Cofactor
794358
9253
88107
135
926449
929989
794359
9236
88107
135
926450
929990
32980
2662035
3625754
Cofactor
794360
9232
88107
135
926451
929991
32981
2662039
3625759
Cofactor
794361
9259
88107
135
926452
929992
926453
929993
32982
2662042
3625763
Cofactor
794362
9260
88107
135
926454
929994
32983
2662044
3625767
Cofactor
32984
2662045
3625768
Cofactor
794363
9234
88107
135
926455
929995
32985
2662049
3625773
Cofactor
794364
9248
88107
135
926456
929996
32986
2662053
3625778
Cofactor
794365
9232
88107
135
926457
929997
32987
2662056
3625783
Cofactor
794366
9234
88107
135
926458
929998
32988
2662059
3625788
Cofactor
794367
9238
88107
135
926459
929999
794368
9244
88107
118
926460
930000
794369
9261
88107
118
926461
930001
32989
2662067
3625801
Cofactor
794370
9262
88107
118
926462
930002
794371
9263
88107
118
926463
930003
926464
930004
32990
2662068
3625804
Cofactor
794372
9233
88107
136
926465
930005
32991
2662071
3625809
Cofactor
32992
2662072
3625810
Cofactor
794373
9261
88107
118
926466
930006
32993
2662074
3625814
Cofactor
794374
9262
88107
118
926467
930007
794375
9263
88107
118
926468
930008
926469
930009
32994
2662075
3625817
Cofactor
2877847
M150 150 L150 200 L200 150 z
10
true
18
3586509
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M150 150 L150 200 L200 150 z
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3625727
M3910 1946 C3963 1989 4174 2224 4204 2224
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3625729
M150 150 L150 200 L200 150 z
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3625730
M150 150 L150 200 L200 150 z
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3625731
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3625732
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3625733
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3625734
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3625735
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3625736
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3625737
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3625739
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3625740
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M3944 1745 L3944 1795 L3994 1745 z
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3625790
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3625791
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3625792
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3625793
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3625794
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3625795
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M150 150 L150 200 L200 150 z
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3625812
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3625813
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3625814
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3625816
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3625817
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792226
88107
147657
135
3206565
2661852
3625500
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3206566
2661853
3625501
Left
3206567
2661854
3625502
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3206568
2661855
3625503
Right
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137917
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792227
88107
147658
135
3206569
2661856
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Left
3206570
2661857
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Left
3206571
2661858
3625506
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3206572
2661854
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Right
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137918
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792228
88107
147659
398
3206573
2661857
3625509
Left
3206574
2661860
3625510
Left
3206575
2661861
3625511
Right
3206576
2661862
3625512
Right
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137919
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792229
88107
147660
376
3206577
2661854
3625515
Left
3206578
2661865
3625516
Left
3206579
2661857
3625517
Right
3206580
2661866
3625518
Right
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137920
794310
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88107
147661
135
3206581
2661868
3625520
Left
3206582
2661861
3625521
Left
3206583
2661869
3625522
Right
3206584
2661857
3625523
Right
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137922
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792231
88107
147662
135
3206585
2661870
3625524
Left
3206586
2661871
3625525
Left
3206587
2661872
3625526
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3206588
2661873
3625527
Right
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137923
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88107
147663
135
3206589
2661875
3625529
Left
3206590
2661876
3625530
Left
3206591
2661877
3625531
Right
3206592
2661871
3625532
Right
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137924
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88107
147664
135
3206593
2661876
3625533
Left
3206594
2661878
3625534
Left
3206595
2661879
3625535
Right
3206596
2661880
3625536
Right
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137925
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88107
147665
119
3206597
2661882
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Left
3206598
2661879
3625539
Left
3206599
2661883
3625540
Right
3206600
2661876
3625541
Right
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137926
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88107
147666
135
3206601
2661861
3625542
Left
3206602
2661884
3625543
Left
3206603
2661885
3625544
Right
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2661886
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Right
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137927
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88107
147667
135
3206605
2661861
3625546
Left
3206606
2661887
3625547
Left
3206607
2661888
3625548
Right
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2661889
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Right
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137929
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88107
147668
135
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2661888
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Left
3206610
2661891
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Left
3206611
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Right
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88107
147666
135
3206613
2661861
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Left
3206614
2661893
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Left
3206615
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2661894
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Right
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137928
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88107
147669
135
3206617
2661879
3625560
Left
3206618
2661896
3625561
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3206619
2661885
3625562
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3206620
2661897
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Right
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137931
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88107
147670
135
3206621
2661885
3625564
Left
3206622
2661898
3625565
Left
3206623
2661899
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Right
3206624
2661900
3625567
Right
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137932
794321
792241
88107
147671
135
3206625
2661902
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Left
3206626
2661903
3625570
Left
3206627
2661904
3625571
Right
3206628
2661905
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Right
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137933
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792242
88107
147672
135
3206629
2661905
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Left
3206630
2661906
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Left
3206631
2661907
3625575
Right
3206632
2661908
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Right
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137934
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792243
88107
110922
135
3206633
2661910
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Left
3206634
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Left
3206635
2661912
3625580
Left
3206636
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Right
3206637
2661907
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Right
3206638
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Right
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101163
794324
792244
88107
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135
3206639
2661916
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Left
3206640
2661910
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Left
3206641
2661917
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Left
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Right
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Right
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Right
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137935
794325
792245
88107
147674
135
3206645
2661921
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Left
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2661920
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Left
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2661922
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Right
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137936
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792246
88107
147675
135
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2661924
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Left
3206650
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Left
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2661925
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Left
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2661926
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Right
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2661928
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Right
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2661929
3625601
Right
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2661930
3625602
Right
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137937
794327
792247
88107
147676
135
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2661931
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Left
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2661932
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Right
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2661933
3625605
Right
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137938
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792248
88107
147677
135
3206660
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Left
3206661
2661931
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Left
3206662
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Left
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Right
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Right
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Right
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137939
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792249
88107
147678
135
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2661938
3625612
Left
3206667
2661939
3625613
Right
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2661940
3625614
Right
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137940
794330
792250
88107
147679
135
3206669
2661941
3625615
Left
3206670
2661940
3625616
Left
3206671
2661942
3625617
Right
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2661943
3625618
Right
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137941
794331
792251
88107
147680
135
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2661944
3625619
Left
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2661945
3625620
Left
3206675
2661943
3625621
Right
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137942
794332
792252
88107
147681
135
3206676
2661854
3625622
Left
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2661946
3625623
Left
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2661861
3625624
Right
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2661947
3625625
Right
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137943
794333
792253
88107
147682
135
3206680
2661949
3625627
Left
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2661950
3625628
Left
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2661951
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Left
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3625630
Right
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3625631
Right
3206685
2661861
3625632
Right
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137944
794334
792254
88107
147683
135
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2661944
3625633
Left
3206687
2661954
3625634
Left
3206688
2661955
3625635
Left
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3625636
Right
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2661956
3625637
Right
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137945
794335
792255
88107
147684
135
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2661944
3625639
Left
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2661958
3625640
Left
3206693
2661959
3625641
Left
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2661861
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Right
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Right
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137946
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792256
88107
147685
135
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2661950
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Left
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2661961
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Left
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Right
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Right
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137947
794337
792257
88107
147686
135
3206700
2661962
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Left
3206701
2661965
3625650
Left
3206702
2661899
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Right
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2661966
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Right
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137948
794338
792258
88107
147687
135
3206704
2661944
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Left
3206705
2661967
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Left
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2661968
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Right
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2661969
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Right
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137949
794339
792259
88107
147688
135
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2661950
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Left
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2661971
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Left
3206710
2661899
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Right
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2661972
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Right
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137950
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792260
88107
147689
135
3206712
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Left
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2661974
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Left
3206714
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Right
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Right
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137951
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88107
147690
135
3206716
2661944
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Left
3206717
2661977
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Left
3206718
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Right
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2661972
3625670
Right
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137952
794342
792262
88107
147691
374
3206720
2661975
3625672
Left
3206721
2661979
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Left
3206722
2661980
3625674
Left
3206723
2661899
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Right
3206724
2661981
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Right
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137953
794343
792263
88107
147692
374
3206725
2661899
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Left
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Left
3206727
2661984
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Left
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Right
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Right
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137954
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792264
88107
147693
135
3206730
2661988
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Left
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2661989
3625685
Left
3206732
2661975
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Right
3206733
2661990
3625687
Right
748744
137955
794345
792265
88107
147004
135
3206734
2661991
3625688
Left
3206735
2661944
3625689
Left
3206736
2661992
3625690
Left
3206737
2661993
3625691
Right
3206738
2661994
3625692
Right
3206739
2661995
3625693
Right
748745
137168
794346
792266
88107
147694
135
3206740
2661997
3625695
Left
3206741
2661998
3625696
Left
3206742
2661944
3625697
Right
3206743
2661999
3625698
Right
748746
137956
794347
792267
88107
146998
135
3206744
2661995
3625700
Left
3206745
2662001
3625701
Right
3206746
2661997
3625702
Right
748747
137161
794348
792268
88107
147695
135
3206747
2662002
3625703
Left
3206748
2662003
3625704
Left
3206749
2661968
3625705
Right
3206750
2662004
3625706
Right
748748
137957
794349
792269
88107
147696
135
3206751
2662002
3625708
Left
3206752
2662006
3625709
Left
3206753
2662007
3625710
Right
3206754
2662008
3625711
Right
748749
137958
794350
792270
88107
147697
135
3206755
2662009
3625712
Left
3206756
2662010
3625713
Left
3206757
2662007
3625714
Right
3206758
2662011
3625715
Right
748750
137959
794351
792271
88107
147698
135
3206759
2662009
3625716
Left
3206760
2662012
3625717
Left
3206761
2661988
3625718
Right
3206762
2662013
3625719
Right
748751
137960
794352
792272
88107
147699
135
3206763
2661997
3625721
Left
3206764
2662015
3625722
Left
3206765
2662007
3625723
Right
3206766
2662016
3625724
Right
748752
137961
794353
792273
88107
147700
398
3206767
2662017
3625725
Left
3206768
2662018
3625726
Left
3206769
2661997
3625727
Right
3206770
2662019
3625728
Right
748753
137962
794354
792274
88107
147701
135
3206771
2662022
3625731
Left
3206772
2661997
3625732
Left
3206773
2662017
3625733
Right
748754
137963
794355
792275
88107
147702
374
3206774
2662022
3625734
Left
3206775
2662023
3625735
Left
3206776
2662017
3625736
Right
3206777
2662024
3625737
Right
748755
137964
794356
792276
88107
147703
135
3206778
2662025
3625738
Left
3206779
2662026
3625739
Left
3206780
2661997
3625740
Right
748756
137965
794357
792277
88107
147704
135
3206781
2662022
3625742
Left
3206782
2662025
3625743
Right
3206783
2662028
3625744
Right
792278
88107
147705
135
3206784
2662029
3625746
Left
3206785
2662030
3625747
Left
3206786
2662031
3625748
Right
3206787
2662032
3625749
Right
748757
137968
794358
792279
88107
147706
135
3206788
2662030
3625750
Left
3206789
2662033
3625751
Left
3206790
2662009
3625752
Right
3206791
2662034
3625753
Right
748758
137969
794359
792280
88107
147707
135
3206792
2662036
3625755
Left
3206793
2662032
3625756
Left
3206794
2662037
3625757
Right
3206795
2662038
3625758
Right
748759
137970
794360
792281
88107
147708
135
3206796
2661854
3625760
Left
3206797
2662040
3625761
Right
3206798
2662041
3625762
Right
748760
137971
794361
792282
88107
147709
135
3206799
2662040
3625764
Left
3206800
2662043
3625765
Left
3206801
2661861
3625766
Right
748761
137972
794362
792283
88107
147710
135
3206802
2662046
3625769
Left
3206803
2662047
3625770
Left
3206804
2661944
3625771
Right
3206805
2662048
3625772
Right
748762
137973
794363
792284
88107
147711
135
3206806
2662050
3625774
Left
3206807
2662051
3625775
Left
3206808
2661944
3625776
Right
3206809
2662052
3625777
Right
748763
137974
794364
792285
88107
147712
135
3206810
2662054
3625779
Left
3206811
2662046
3625780
Left
3206812
2662055
3625781
Right
3206813
2662050
3625782
Right
748764
137975
794365
792286
88107
147713
135
3206814
2662050
3625784
Left
3206815
2662057
3625785
Left
3206816
2662046
3625786
Right
3206817
2662058
3625787
Right
748765
137976
794366
792287
88107
147714
135
3206818
2661940
3625789
Left
3206819
2662060
3625790
Left
3206820
2662061
3625791
Right
3206821
2662062
3625792
Right
748766
137977
794367
792288
88107
147715
118
3206822
2662063
3625793
Left
3206823
2661929
3625794
Left
3206824
2662064
3625795
Right
3206825
2662065
3625796
Right
3206826
2661932
3625797
Right
748767
137978
794368
792289
88107
147716
118
3206827
2662032
3625798
Left
3206828
2662066
3625799
Left
3206829
2662017
3625800
Right
16649
794369
3625802
Left
16650
794370
3625803
Right
748768
137979
794371
792290
88107
147717
136
3206830
2662032
3625805
Left
3206831
2662069
3625806
Left
3206832
2662038
3625807
Right
3206833
2662070
3625808
Right
748769
137980
794372
792291
88107
147718
118
3206834
2661871
3625811
Left
3206835
2662073
3625812
Left
3206836
2661857
3625813
Right
16651
794373
3625815
Left
16652
794374
3625816
Right
748770
137981
794375
108237
108623
88107
14
false
1995
850
16
regular
105096
2661907
3625818
Right
185081
13
375
2855
0.9
0.9
0
2
1
490
240
185082
66
735
1430
1.1
1.1
0
2
3
280
360
185083
67
2420
2625
1.0
1.0
0
2
4
399
340
185084
66
4110
2025
1.0
1.0
0
2
3
280
360
185085
66
4745
2620
1.0
1.0
0
2
3
280
360
185086
67
4670
1970
1.0
1.0
0
2
4
399
340
368541
M331 440 C331 390 381 340 431 340 C1932 340 3882 340 5383 340 C5433 340 5483 390 5483 440 C5483 1308 5483 2437 5483 3305 C5483 3355 5433 3405 5383 3405 C3882 3405 1932 3405 431 3405 C381 3405 331 3355 331 3305 C331 2437 331 1308 331 440
1
true
6
5152.0
3065.0
447343
15
Endoplasmic Reticulum
835
1465
20
1.0
1.0
160
15
447344
15
Peroxisome
2555
2750
20
1.0
1.0
160
15
447345
15
Endoplasmic Reticulum
4165
2060
20
1.0
1.0
160
15
447346
15
Peroxisome
4920
2180
20
1.0
1.0
160
15
447347
15
Intracellular Space
840
410
20
1.0
1.0
160
15
447348
15
Extracellular Space
830
160
20
1.0
1.0
160
15
447349
15
Mitochondria
390
2980
20
1.0
1.0
160
15
Xanthine Dehydrogenase Deficiency (Xanthinuria)
The rare genetic disorder, Xanthinuria (also referred to as xanthine oxidase deficiency) results from a deficiency of the enzyme xanthine oxidase. This enzyme deficiency causes the accumulation of: xanthine in the plasma, uric acid in serum or hypoxanthine, uric acid and xanthine in the urine. The disorder has symptoms including arthralgia, hematuria, mental retardation, stomatisis, and urolithiasis.
Disease
PW_X009183
Complete
Context9183
49761
102
Compound
Increased
49762
198
Compound
Increased
49763
15441
Protein
Mutated
278059
13176819
XANTHINURIA. Nutr Rev. 1954 Jul;12(7):200-2.
9183
Context