99
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
PW000080
Center
PathwayVisualizationContext80
3650
5400
#000099
PathwayVisualization62
91
Purine Metabolism
Purine is a water soluble, organic compound. Purines, including purines that have been substituted, are the most widely distributed kind of nitrogen-containing heterocycle in nature. The two most important purines are adenine and guanine. Other notable examples are hypoxanthine, xanthine, theobromine, caffeine, uric acid and isoguanine. This pathway depicts a number of processes including purine nucleotide biosynthesis, purine degradation and purine salvage. The main organ where purine nucleotides are created is the liver. This process starts as
5-phospho-α-ribosyl-1-pyrophosphate, or PRPP, and creates inosine 5’-monophosphate, or IMP. Following a series of reactions, PRPP uses compounds such as tetrahydrofolate derivatives, glycine and ATP, and IMP is produced as a result. Glutamine PRPP amidotransferase catalyzes PRPP into 5-phosphoribosylamine, or 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 tosuccinylaminoimidazole 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 creates a fork in the road for the creation of purine, as it can either become GMP or AMP. 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. Purine nucleotides being catabolized creates 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. Nucleotide creation stemming from the purine bases and purine nucleosides happens in steps that are called the “salvage pathways”. The free purine bases phosphoribosylated and reconverted to their respective nucleotides.
Metabolic
1
132
99
SubPathway
205
190
Compound
8
111
Lehninger, A.L. Lehninger principles of biochemistry (4th ed.) (2005). New York: W.H Freeman.
91
Pathway
112
Salway, J.G. Metabolism at a glance (3rd ed.) (2004). Alden, Mass.: Blackwell Pub.
91
Pathway
279610
30441833
Garcia-Gil M, Camici M, Allegrini S, Pesi R, Petrotto E, Tozzi MG: Emerging Role of Purine Metabolizing Enzymes in Brain Function and Tumors. Int J Mol Sci. 2018 Nov 14;19(11). pii: ijms19113598. doi: 10.3390/ijms19113598.
91
Pathway
279611
22531138
Davies O, Mendes P, Smallbone K, Malys N: Characterisation of multiple substrate-specific (d)ITP/(d)XTPase and modelling of deaminated purine nucleotide metabolism. BMB Rep. 2012 Apr;45(4):259-64.
91
Pathway
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
12
Astrocyte
CL:0000127
18
Erythrocyte
CL:0000232
21
Theca Cell
CL:0000503
22
Granulosa Cell
CL:0000501
19
Sertoli Cell
CL:0000216
14
Parietal Cell
CL:0000162
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
138
human
0046323
Eukaryote
196
Homo
1924
Eukaryote
Human
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
56
Basal Cell Membrane
GO:0009925
22
post-synaptic membrane
GO:0045211
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
6
Kidney
BTO:0000671
71
8
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
26
Lung
BTO:0000763
35
Ovary
BTO:0000975
34
Testis
BTO:0001363
14
Eye
BTO:0000439
153
24
8
5
1
1
PW_BS000008
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PW_BS000024
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PW_BS000180
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PW_BS000152
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PW_BS000024
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PW_BS000170
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8
5
PW_BS000115
488
8
10
PW_BS000115
505
8
6
PW_BS000115
358
39
12
PW_BS000028
186
12
2
1
PW_BS000024
11
1
8
1
1
PW_BS000011
78
8
1
1
PW_BS000078
833
5
138
1
PW_BS000548
1076
1
1
18
PW_BS000578
840
7
138
1
PW_BS000549
844
13
138
1
PW_BS000549
839
10
138
PW_BS000549
841
2
138
1
PW_BS000549
1008
1
196
1
PW_BS000577
843
1
138
1
PW_BS000549
393
1
5
1
PW_BS000173
842
4
138
1
PW_BS000549
818
5
1
2
PW_BS000548
41
8
1
1
PW_BS000041
792
7
1
PW_BS000527
607
26
1
PW_BS000501
817
8
5
1
2
PW_BS000548
183
26
10
1
1
PW_BS000024
948
35
1
21
PW_BS000563
949
35
1
22
PW_BS000563
946
34
1
19
PW_BS000563
970
28
56
1
14
PW_BS000567
67
18
10
1
8
PW_BS000067
832
6
56
1
1
PW_BS000548
1049
14
22
1
6
PW_BS000577
1014
11
10
1
4
PW_BS000577
789
24
1
1
3
PW_BS000524
965
24
22
1
3
PW_BS000566
787
24
10
1
3
PW_BS000524
1138
8
10
1
6
PW_BS000581
48
1
1
3
PW_BS000048
1056
9
1
1
6
PW_BS000578
830
11
1
1
1
PW_BS000548
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
140674
790
140675
834
140755
185
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
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
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
140770
891
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
140773
891
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
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
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
140676
790
140677
834
140695
50
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=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)N1
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
OP(O)(=O)OP(O)(O)=O
H4O7P2
InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)
XPPKVPWEQAFLFU-UHFFFAOYSA-N
(phosphonooxy)phosphonic acid
177.9751
177.943225506
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
140772
891
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](OP(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
140771
891
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
O[C@H]1O[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-AIHAYLRMSA-N
{[(2R,3S,4R,5S)-3,4,5-trihydroxyoxolan-2-yl]methoxy}phosphonic acid
230.1098
230.01915384
-0.84
5
α-D-ribose 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
140738
84
140739
597
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-[(4-hydroxy-2-imino-1,2,5,6,7,8-hexahydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid
473.4393
473.165896125
-3.15
8
(2S)-2-[(4-{N-[(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid
0
-1
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)-4-hydroxy-2-imino-1,2,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
445.4292
445.170981503
-3.22
9
2-{[4-({[(6S)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
0
-1
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
NC(=N)CN(C=O)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
C8H16N3O8P
InChI=1S/C8H16N3O8P/c9-5(10)1-11(3-12)8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H3,9,10)(H2,15,16,17)/t4-,6-,7-,8-/m1/s1
WQXXBAWHDQWCKL-XVFCMESISA-N
{[(2R,3S,4R,5R)-5-[N-(carbamimidoylmethyl)formamido]-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
313.203
313.067501485
-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
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
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
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
140798
185
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
C21H27N7O14P2
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)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BAWFJGJZGIEFAR-NNYOXOHSSA-N
1-[(2R,3R,4S,5R)-5-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono}oxy)(hydroxy)phosphoryl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-(C-hydroxycarbonimidoyl)-1lambda5-pyridin-1-ylium
663.4251
663.109121631
-2.52
8
1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-(C-hydroxycarbonimidoyl)-1lambda5-pyridin-1-ylium
0
-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
140757
185
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
140759
185
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
140680
834
140681
790
140687
781
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](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H28N7O17P3
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)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
XJLXINKUBYWONI-NNYOXOHSSA-N
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 phosphono)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
743.405
743.075452041
-2.22
8
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 phosphono}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
0
-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
140709
168
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=C2N=CN=C3N)[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-/m1/s1
ACFIXJIJDZMPPO-NNYOXOHSSA-N
{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2R,3S,4R,5R)-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
nadph
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
140706
168
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=C(O)N=CN=C12
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
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
dioxygen
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)COP(O)(=O)OP(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
140790
185
140799
186
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=C2N=CN([C@H]3C[C@H](O)[C@@H](CO)O3)C2=NC=N1
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
[H][C@@]12COP(O)(=O)O[C@@]1([H])[C@@H](O)[C@@H](O2)N1C=NC2=C1N=CN=C2N
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
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
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
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
140718
18
40711
4Fe-4S
HMDB0061380
Tetrakis(λ¹-iron(1+) ion) tetrasulfane tetrasulfanide belongs to the class of inorganic compounds known as transition 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 is a transition metal.
33723
S.S.S.S.[SH-].[SH-].[SH-].[SH-].[Fe+].[Fe+].[Fe+].[Fe+]
Fe4H12S8
InChI=1S/4Fe.8H2S/h;;;;8*1H2/q4*+1;;;;;;;;/p-4
WBBXSFIKFJDGSG-UHFFFAOYSA-J
tetrakis(lambda1-iron(1+) ion) tetrasulfane tetrasulfanide
491.96
491.610214
0
tetrakis(lambda1-iron(1+) ion) tetrasulfane tetrasulfanide
0
1
PW_C040711
4Fe-4S
4738
3
4859
8
5051
4
5065
2
5403
110
6060
157
6124
163
6508
180
7493
224
12618
164
77160
112
78003
111
80040
370
80681
135
117797
133
117828
132
120009
407
120161
122
122658
406
122673
124
122784
119
125233
120
125248
118
125387
481
125522
297
126790
479
126806
299
126928
206
127057
205
128387
501
128404
388
40558
2Fe-2S
HMDB0061344
Bis(λ²-iron(2+) ion) disulfane tetrasulfanide belongs to the class of inorganic compounds known as transition 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 is a transition metal.
S.S.[SH-].[SH-].[SH-].[SH-].[Fe++].[Fe++]
Fe2H8S6
InChI=1S/2Fe.6H2S/h;;6*1H2/q2*+2;;;;;;/p-4
MZMMVZPHZTYDNI-UHFFFAOYSA-J
bis(lambda2-iron(2+) ion) disulfane tetrasulfanide
312.11
311.764899
0
bis(lambda2-iron(2+) ion) disulfane tetrasulfanide
0
2
PW_C040558
2Fe2S
3742
2
4012
8
4257
17
4389
3
4626
5
4754
31
4829
9
4837
28
5056
4
5497
126
5512
127
7046
160
13030
301
13042
302
77715
113
77727
337
78377
134
78386
132
79207
112
117811
133
121586
407
121795
124
122567
384
122664
406
123152
443
123167
448
124144
119
124346
118
125140
121
125239
120
126189
299
126715
480
126796
479
127680
388
128306
391
128394
501
1491
Molybdopterin
HMDB0002206
Molybdenum cofactor is a cofactor required for the activity of enzymes such as sulfite oxidase, xanthine oxidoreductase, and aldehyde oxidase. It is a coordination complex formed between molybdopterin (which, despite the name, does not contain molybdenum) and an oxide of molybdenum. Molybdopterins, in turn, are synthesized from guanosine triphosphate. Molybdenum cofactor functions directly in ethylbenzene dehydrogenase, glyceraldehyde-3-phosphate ferredoxin oxidoreductase, and respiratory arsenate reductase. In animals and plants these enzymes use molybdenum bound at the active site in a tricyclic molybdenum cofactor. All molybdenum-using enzymes so far identified in nature use this cofactor The simplest structure of molybdopterin contains a pyranopterin coordinated to molybdenum. The pyranopterin structure is a fused ring system containing a pyran fused to pterin. In addition, the pyran ring is substituted with two thiols and an alkyl phosphate. In molybdopterin, the thiols coordinate to molybdenum. In some cases, the alkyl phosphate group is replaced by an alkyl diphosphate nucleotide. -- Wikipedia.
73508-07-3
C05924
23304237
21437
CPD0-1882
4883416
O.O.[Mo++].[H]C1(COP(O)([O-])=O)OC2([H])NC3=C(NC2([H])C(S)=C1S)C([O-])=NC(=N)N3
C10H16MoN5O8PS2
InChI=1S/C10H14N5O6PS2.Mo.2H2O/c11-10-14-7-4(8(16)15-10)12-3-6(24)5(23)2(21-9(3)13-7)1-20-22(17,18)19;;;/h2-3,9,12,23-24H,1H2,(H2,17,18,19)(H4,11,13,14,15,16);;2*1H2/q;+2;;/p-2
VUKICSJFFDCESC-UHFFFAOYSA-L
molybdenum(2+) ion 8-[(hydrogen phosphonooxy)methyl]-2-imino-6,7-disulfanyl-1H,2H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-4-olate dihydrate
525.31
526.923197
-2.74
7
molybdenum(2+) ion 8-[(hydrogen phosphonooxy)methyl]-2-imino-6,7-disulfanyl-1H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-4-olate dihydrate
0
-2
FDB022906
Moco;Molybdenum cofactor;Molybdenum enzyme molybdenum cofactor;Molybdoenzyme molybdenum-containing cofactor;Nitrate reductase molybdenum cofactor;Pterin molybdenum cofactor
PW_C001491
mlyBdpn
1684
8
1704
2
3918
26
3953
29
4388
3
4627
5
4753
31
4830
9
4838
28
5498
126
5513
127
12038
151
13031
301
13043
302
77716
113
77728
337
78385
132
79206
112
121585
407
121794
124
123153
443
123168
448
124143
119
124345
118
126108
299
127679
388
588
Bis(5'-nucleosyl)-tetraphosphatase [asymmetrical]
P50583
Asymmetrically hydrolyzes Ap4A to yield AMP and ATP. Plays a major role in maintaining homeostasis.
HMDBP00621
NUDT2
9p13
AL356494
1
3.6.1.17
1733
8
140387
833
110
Nucleoside diphosphate kinase 6
O75414
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. Inhibitor of p53-induced apoptosis.
HMDBP00114
NME6
3p21
U90449
1
2.7.4.6
1680
8
2714
2
136743
3
139661
23
140388
833
142988
1076
822
Ectonucleoside triphosphate diphosphohydrolase 5
O75356
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. Also hydrolyzes GDP and IDP 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).
HMDBP00879
ENTPD5
14q24
BC130487
1
3.6.1.6; 3.6.1.42
1765
14
1768
49
4713
18
140389
840
140425
844
2891
Ectonucleoside triphosphate diphosphohydrolase 8
Q5MY95
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.
HMDBP07670
ENTPD8
9q34.3
AY903953
1
3.6.1.5
1772
14
1936
8
139704
2
140390
839
140420
833
873
Guanylate kinase
Q16774
Essential for recycling GMP and indirectly, cGMP.
HMDBP00930
GUK1
1q32-q41
AK303845
1
2.7.4.8
1773
8
140043
2
140391
833
143039
1076
2368
Cytosolic purine 5'-nucleotidase
P49902
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
HMDBP03750
NT5C2
10q24.32
BC001595
1
3.1.3.5
1807
8
2345
2
140392
833
140510
1
142990
1076
713
Deoxyguanosine kinase, mitochondrial
Q16854
Required for the phosphorylation of several deoxyribonucleosides and certain nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
HMDBP00766
DGUOK
2p13
AC073046
1
2.7.1.113
1808
3
140393
841
429
Adenine phosphoribosyltransferase
P07741
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
HMDBP00438
APRT
16q24
BC107151
1
2.4.2.7
1816
8
139703
2
140394
833
2369
Purine nucleoside phosphorylase
P00491
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.
HMDBP03752
PNP
14q13.1
AY817667
1
2.4.2.1
1819
8
2342
2
136565
7
140395
833
140513
1
142075
26
142577
1008
458
Hypoxanthine-guanine phosphoribosyltransferase
P00492
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.
HMDBP00475
HPRT1
Xq26.1
M12452
1
2.4.2.8
1820
8
3624
2
4080
7
139728
26
140396
833
654
Guanine deaminase
Q9Y2T3
Catalyzes the hydrolytic deamination of guanine, producing xanthine and ammonia (By similarity).
HMDBP00690
GDA
9q21.13
AF095286
1
3.5.4.3
1831
8
2739
2
140397
833
140511
1
142078
26
594
ADP-sugar pyrophosphatase
Q9UKK9
Hydrolyzes with similar activities ADP-ribose ADP-mannose, ADP-glucose, 8-oxo-GDP and 8-oxo-dGDP. Can also hydrolyze other nucleotide sugars with low activity.
HMDBP00627
NUDT5
10p14
CH471072
1
3.6.1.13; 3.6.1.58
1839
8
139671
2
140398
833
537
Ribose-phosphate pyrophosphokinase 3
P21108
Catalyzes the synthesis of phosphoribosylpyrophosphate (PRPP) that is essential for nucleotide synthesis.
HMDBP00566
PRPS1L1
7p21.1
M57423
1
2.7.6.1
1775
2
1840
8
140399
833
143062
1008
325
Amidophosphoribosyltransferase
Q06203
HMDBP00331
PPAT
4q12
U00238
1
2.4.2.14
1842
8
3756
2
140400
833
324
Trifunctional purine biosynthetic protein adenosine-3
P22102
HMDBP00330
GART
21q22.11
CH471079
1
6.3.4.13; 6.3.3.1; 2.1.2.2
1844
8
4706
2
140401
833
140421
843
140426
393
143025
1076
798
Phosphoribosylformylglycinamidine synthase
O15067
HMDBP00853
PFAS
17p13.1
BC167158
1
6.3.5.3
1847
8
139672
2
140402
833
143027
1076
837
Multifunctional protein ADE2
P22234
HMDBP00894
PAICS
4q12
AC068620
1
6.3.2.6; 4.1.1.21
1850
8
139673
2
140403
833
143031
1076
554
Adenylosuccinate lyase
P30566
HMDBP00585
ADSL
22q13.2
S60710
1
4.3.2.2
103
8
139685
2
140404
833
143032
1076
825
Bifunctional purine biosynthesis protein PURH
P31939
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.
HMDBP00882
ATIC
2q35
AB062403
1
2.1.2.3; 3.5.4.10
1854
8
139686
2
140405
833
143033
1076
422
Inosine triphosphate pyrophosphatase
Q9BY32
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.
HMDBP00431
ITPA
20p
AL109976
1
3.6.1.19
1855
8
2717
2
140406
833
560
GMP synthase [glutamine-hydrolyzing]
P49915
Involved in the de novo synthesis of guanine nucleotides which are not only essential for DNA and RNA synthesis, but also provide GTP, which is involved in a number of cellular processes important for cell division.
HMDBP00592
GMPS
3q24
BC012178
1
6.3.5.2
1858
8
3709
2
140407
833
143038
1076
826
Inosine-5'-monophosphate dehydrogenase 1
P20839
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.
HMDBP00883
IMPDH1
7q31.3-q32
AC010655
1
1.1.1.205
1859
8
3633
2
140408
833
649
GMP reductase 1
P36959
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.
HMDBP00685
GMPR
6p23
AL009031
1
1.7.1.7
1860
8
140409
833
176
Xanthine dehydrogenase/oxidase
P47989
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. Has also low oxidase activity towards aldehydes (in vitro).
HMDBP00181
XDH
2p23.1
U39487
1
1.17.1.4; 1.17.3.2
629
28
1872
5
3748
2
4003
8
4831
9
4964
31
139918
301
139923
302
140410
842
140512
1
142077
26
823
Adenylosuccinate synthetase isozyme 2
P30520
Plays an important role in the de novo pathway and in the salvage pathway of purine nucleotide biosynthesis. Catalyzes the first committed step in the biosynthesis of AMP from IMP.
HMDBP00880
ADSS
1q44
X66503
1
6.3.4.4
1876
8
140411
833
142346
2
623
AMP deaminase 1
P23109
AMP deaminase plays a critical role in energy metabolism.
HMDBP00657
AMPD1
1p13
AL096773
1
3.5.4.6
1877
8
140412
833
629
Adenosine deaminase
P00813
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.
HMDBP00664
ADA
20q13.12
X02190
1
3.5.4.4
1891
8
139687
2
140013
15
140413
833
140515
1
142076
26
533
Adenylate kinase isoenzyme 1
P00568
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Small ubiquitous enzyme involved in energy metabolism and nucleotide synthesis that is essential for maintenance and cell growth.
HMDBP00562
AK1
9q34.1
BC001116
1
2.7.4.3; 2.7.4.6
724
26
1907
8
3554
2
4762
31
4771
91
140414
833
143044
1076
5270
ATPase family AAA domain-containing protein 1
Q8NBU5
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 (By similarity).
HMDBP11625
ATAD1
10q23.31
AK027506
1
3.6.1.3
1911
5
5114
2
140415
842
603
cAMP-specific 3',5'-cyclic phosphodiesterase 4D
Q08499
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
HMDBP00636
PDE4D
5q12
BC008390
1
3.1.4.53
272
16
1917
8
3045
68
80401
1
137006
51
140011
818
140416
833
2404
Adenylate cyclase type 10
Q96PN6
Soluble adenylyl cyclase that has a critical role in mammalian spermatogenesis. Produces the cAMP which mediates in part the cAMP-responsive nuclear factors indispensable for maturation of sperm in the epididymis. Induces capacitation, the maturational process that sperm undergo prior to fertilization. May be the bicarbonate sensor. Involved in ciliary beat regulation.
HMDBP04127
ADCY10
1q24
Z97876
1
4.6.1.1
269
16
477
2
937
39
1168
46
1923
8
80268
14
136190
41
136378
74
139719
792
139829
607
140009
817
140010
818
140609
183
140998
73
141493
948
141518
949
141570
946
141845
26
141918
970
141938
67
142198
832
142781
1049
142811
1014
143042
789
143068
965
143093
787
143309
1138
144181
72
1007
Guanylate cyclase soluble subunit alpha-2
P33402
Has guanylyl cyclase on binding to the beta-1 subunit.
Isoform 2 acts as a negative regulator of guanylyl cyclase activity as it forms non-functional heterodimers with the beta subunits.
HMDBP01072
GUCY1A2
11q21-q22
BC130488
1
4.6.1.2
1932
8
80279
2
139967
48
140417
833
143016
1056
1001
Guanylate cyclase soluble subunit beta-1
Q02153
HMDBP01064
GUCY1B3
4q31.3-q33
BC047620
1
4.6.1.2
1933
8
80280
2
139968
48
140418
833
141580
830
143019
1056
571
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A
Q9Y233
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.
HMDBP00604
PDE10A
6q26
AL160160
1
3.1.4.17; 3.1.4.35
1934
8
140419
833
5803
Thioredoxin
P10599
TXN
1
4711
2
140422
843
143040
1076
104
Ribonucleoside-diphosphate reductase large subunit
P23921
Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides.
HMDBP00108
RRM1
11p15.5
X59543
1
1.17.4.1
1798
8
4712
2
136738
166
139667
23
140423
843
142994
1076
107
Ribonucleoside-diphosphate reductase subunit M2
P31350
Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides. Inhibits Wnt signaling.
HMDBP00111
RRM2
2p25-p24
AY032750
1
1.17.4.1
1799
8
2750
2
136739
166
139668
23
140424
843
143041
1076
827
Adenylosuccinate synthetase isozyme 1
Q8N142
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 committed step in the biosynthesis of AMP from IMP (By similarity).
HMDBP00884
ADSSL1
14q32.33
BX248286
1
6.3.4.4
87
8
142345
2
143043
1076
864
Adenylate cyclase type 2
Q08462
This is a membrane-bound, calmodulin-insensitive adenylyl cyclase.
HMDBP00921
ADCY2
5p15.3
AB028983
1
4.6.1.1
3829
2
4173
14
136381
74
139735
777
139845
48
140537
789
140601
183
140899
898
141495
948
142983
1073
143085
787
144285
8
1601
Guanine nucleotide-binding protein G(s) subunit alpha isoforms short
P63092
Guanine nucleotide-binding proteins (G proteins) are involved as modulators or transducers in various transmembrane signaling systems. The G(s) protein is involved in hormonal regulation of adenylate cyclase:it activates the cyclase in response to beta-adrenergic stimuli
HMDBP01781
GNAS
20q13.3
M14631
1
3810
2
4139
14
4158
73
5011
85
5162
8
135588
599
139731
777
139935
43
139987
48
140363
658
140890
898
140893
899
141483
949
141487
946
143229
789
143306
1138
144176
72
469
Bis(5'-nucleosyl)-tetraphosphatase [asymmetrical]
1
PW_P000469
492
588
1
457
Nucleoside diphosphate kinase 6
1
PW_P000457
480
110
1
217
423
1
485
Ectonucleoside triphosphate diphosphohydrolase 5
1
PW_P000485
508
822
1
232
353
1
233
423
1
470
Ectonucleoside triphosphate diphosphohydrolase 8
1
PW_P000470
493
2891
1
224
353
1
487
Guanylate kinase
1
PW_P000487
510
873
1
496
Cytosolic purine 5'-nucleotidase
1
PW_P000496
520
2368
4
241
423
4
497
Deoxyguanosine kinase
1
PW_P000497
521
713
2
498
Adenine phosphoribosyltransferase
1
PW_P000498
522
429
2
500
Purine nucleoside phosphorylase
1
PW_P000500
524
2369
3
499
Hypoxanthine-guanine phosphoribosyltransferase
1
PW_P000499
523
458
4
242
423
8
501
Guanine deaminase
1
PW_P000501
525
654
2
243
1005
1
502
ADP-sugar pyrophosphatase
1
PW_P000502
526
594
2
488
Ribose-phosphate pyrophosphokinase 3
1
PW_P000488
511
537
2
235
423
1
37
Amidophosphoribosyltransferase
1
PW_P000037
38
325
4
23
423
4
461
40711
4
132
1
503
Trifunctional purine biosynthetic protein adenosine-3
1
PW_P000503
527
324
1
504
Phosphoribosylformylglycinamidine synthase
1
PW_P000504
528
798
1
505
Multifunctional protein ADE2
1
PW_P000505
529
837
8
16
Adenylosuccinate lyase
1
PW_P000016
17
554
4
101
1
506
Bifunctional purine biosynthesis protein PURH
1
PW_P000506
530
825
2
507
Inosine triphosphate pyrophosphatase
1
PW_P000507
531
422
2
244
423
2
508
GMP synthase [glutamine-hydrolyzing]
1
PW_P000508
532
560
2
509
Inosine-5'-monophosphate dehydrogenase 1
1
PW_P000509
533
826
4
246
457
1
510
GMP reductase 1
1
PW_P000510
534
649
4
189
Xanthine dehydrogenase/oxidase
1
PW_P000189
207
176
2
85
964
1
391
40558
2
392
1491
2
513
Adenylosuccinate synthetase isozyme 2
1
PW_P000513
537
823
2
247
423
2
514
AMP deaminase 1
1
PW_P000514
538
623
4
248
1005
4
516
Adenosine deaminase
1
PW_P000516
540
629
1
249
1005
1
204
Adenylate kinase isoenzyme 1
1
PW_P000204
222
533
520
ATPase family AAA domain-containing protein 1
1
PW_P000520
544
5270
1
69
cAMP-specific 3',5'-cyclic phosphodiesterase 4D
1
PW_P000069
83
603
41
1005
1
67
Adenylate cyclase type 10
1
PW_P000067
81
2404
1
40
423
2
521
Guanylate cyclase
1
PW_P000521
545
1007
1
546
1001
1
252
1799
1
522
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A
1
PW_P000522
547
571
2
253
1005
2
254
423
2
1101
Thioredoxin Disulfide
1
PW_P001101
1262
5803
1
458
40707
1
1100
Thioredoxin
1
PW_P001100
1261
5803
1
491
Ribonucleoside-diphosphate reductase 1
1
PW_P000491
514
104
1
515
107
1
238
8133
2
13
Adenylosuccinate synthetase isozyme 1
1
PW_P000013
14
827
2
10
423
2
80
8
122
Adenylate cyclase type 2
1
PW_P000122
140
864
1
57
423
2
465
24
121
Guanine nucleotide-binding protein alpha
1
PW_P000121
139
1601
1
464
20
162
false
PW_R000162
Right
728
1033
1
Compound
false
729
1420
1
Compound
true
730
986
1
Compound
false
731
1080
1
Compound
true
653
469
3.6.1.17
403
false
PW_R000403
Both
1656
414
1
Compound
true
1657
936
1
Compound
false
1658
1034
1
Compound
true
1659
986
1
Compound
false
617
457
2.7.4.6
186
false
PW_R000186
Right
823
936
1
Compound
false
824
1420
1
Compound
true
825
1080
1
Compound
false
826
1104
1
Compound
true
695
485
235
false
PW_R000235
Right
1019
986
1
Compound
false
1020
1420
1
Compound
true
1021
936
1
Compound
false
1022
1104
1
Compound
true
655
470
3.6.1.5
694
485
360
false
PW_R000360
Both
1493
414
1
Compound
true
1494
1080
1
Compound
false
1495
1034
1
Compound
true
1496
936
1
Compound
false
697
487
2.7.4.8
405
false
PW_R000405
Right
1664
414
1
Compound
true
1665
767
1
Compound
false
1666
1034
1
Compound
true
1667
1112
1
Compound
false
710
457
2.7.4.6
1056
false
PW_R001056
Both
4077
414
1
Compound
true
4078
822
1
Compound
false
4079
1034
1
Compound
true
4080
767
1
Compound
false
712
487
2.7.4.8
69
false
PW_R000069
Both
265
822
1
Compound
false
266
1420
1
Compound
true
267
58
1
Compound
false
268
1104
1
Compound
true
715
496
3.1.3.5
226
false
PW_R000226
Both
978
414
1
Compound
true
979
58
1
Compound
false
980
1034
1
Compound
true
981
822
1
Compound
false
716
497
2.7.1.113
1060
false
PW_R001060
Both
4089
1080
1
Compound
false
4090
170
1
Compound
true
4091
86
1
Compound
false
4092
190
1
Compound
true
718
498
2.4.2.7
719
499
2.4.2.8
66
false
PW_R000066
Right
253
1080
1
Compound
false
254
1420
1
Compound
true
255
87
1
Compound
false
256
1441
1
Compound
true
720
496
3.1.3.5
469
false
PW_R000469
Both
1947
87
1
Compound
false
1948
1104
1
Compound
true
1949
86
1
Compound
false
1950
1146
1
Compound
true
721
500
2.4.2.1
1061
false
PW_R001061
Both
4094
58
1
Compound
false
4095
1104
1
Compound
true
4096
86
1
Compound
false
4097
1042
1
Compound
true
722
500
2.4.2.1
302
false
PW_R000302
Right
1275
86
1
Compound
false
1276
1420
1
Compound
true
1277
198
1
Compound
false
1278
35
1
Compound
true
725
501
3.5.4.3
1064
false
PW_R001064
Right
4106
914
1
Compound
false
4107
1420
1
Compound
true
4108
32
1
Compound
true
4109
1191
1
Compound
false
726
502
1043
false
PW_R001043
Both
4026
1191
1
Compound
false
4027
414
1
Compound
true
4028
190
1
Compound
false
4029
32
1
Compound
true
698
488
2.7.6.1
44
false
PW_R000044
Both
166
882
1
Compound
false
167
170
1
Compound
true
168
95
1
Compound
true
169
500
1
Compound
true
170
190
1
Compound
false
171
1420
1
Compound
true
44
37
2.4.2.14
483
false
PW_R000483
Right
2005
414
1
Compound
true
2006
882
1
Compound
false
2007
78
1
Compound
true
2008
1034
1
Compound
true
2009
1104
1
Compound
true
2010
1355
1
Compound
false
728
503
1065
false
PW_R001065
Right
4110
774
1
Compound
true
4111
1355
1
Compound
false
4112
1221
1
Compound
true
4113
1007
1
Compound
false
729
503
485
false
PW_R000485
Right
2016
414
1
Compound
true
2017
1007
1
Compound
false
2018
500
1
Compound
true
2019
1420
1
Compound
true
2020
1034
1
Compound
true
2021
1441
1
Compound
true
2022
791
1
Compound
false
2023
95
1
Compound
true
730
504
6.3.5.3
486
false
PW_R000486
Both
2024
2699
1
Compound
false
2025
955
1
Compound
false
2026
1316
1
Compound
true
732
505
487
false
PW_R000487
Both
2027
414
1
Compound
true
2028
2699
1
Compound
false
2029
123
1
Compound
true
2030
1034
1
Compound
true
2031
1441
1
Compound
true
2032
637
1
Compound
false
733
505
489
false
PW_R000489
Both
2036
637
1
Compound
false
2037
88
1
Compound
true
2038
1168
1
Compound
false
734
16
4.3.2.2
1066
false
PW_R001066
Both
4114
774
1
Compound
true
4115
1168
1
Compound
false
4116
1221
1
Compound
true
4117
1111
1
Compound
false
735
506
490
false
PW_R000490
Both
2039
114
1
Compound
false
2040
1420
1
Compound
true
2041
1111
1
Compound
false
736
506
1067
false
PW_R001067
Right
4118
986
1
Compound
false
4119
1420
1
Compound
true
4120
1080
1
Compound
false
4121
170
1
Compound
true
737
507
3.6.1.19
1068
false
PW_R001068
Right
4122
414
1
Compound
true
4123
1196
1
Compound
false
4124
35
1
Compound
true
4125
32
1
Compound
true
4126
170
1
Compound
true
4127
1080
1
Compound
false
739
508
6.3.5.2
335
false
PW_R000335
Right
1391
114
1
Compound
false
1392
721
1
Compound
true
1393
1420
1
Compound
true
1394
1196
1
Compound
false
1395
1144
1
Compound
true
740
509
1.1.1.205
1069
false
PW_R001069
Both
4128
114
1
Compound
false
4129
35
1
Compound
true
4130
143
1
Compound
true
4131
1080
1
Compound
false
4132
146
1
Compound
true
741
510
1.7.1.7
72
false
PW_R000072
Right
277
1196
1
Compound
false
278
1420
1
Compound
true
279
203
1
Compound
false
280
1104
1
Compound
true
742
496
3.1.3.5
472
false
PW_R000472
Both
1960
203
1
Compound
false
1961
1104
1
Compound
true
1962
198
1
Compound
false
1963
1146
1
Compound
true
743
500
2.4.2.1
65
false
PW_R000065
Right
249
114
1
Compound
false
250
1420
1
Compound
true
251
127
1
Compound
false
252
1104
1
Compound
true
744
496
3.1.3.5
1070
false
PW_R001070
Both
4133
1196
1
Compound
false
4134
170
1
Compound
true
4135
198
1
Compound
false
4136
190
1
Compound
true
745
499
2.4.2.8
468
false
PW_R000468
Both
1943
127
1
Compound
false
1944
1104
1
Compound
true
1945
102
1
Compound
false
1946
1146
1
Compound
true
746
500
2.4.2.1
1071
false
PW_R001071
Both
4137
114
1
Compound
false
4138
170
1
Compound
true
4139
102
1
Compound
false
4140
190
1
Compound
true
747
499
2.4.2.8
578
false
PW_R000578
Right
2418
102
1
Compound
false
2419
1065
1
Compound
true
2420
1420
1
Compound
true
2421
198
1
Compound
false
2422
1783
1
Compound
true
751
189
579
false
PW_R000579
Right
2423
198
1
Compound
false
2424
721
1
Compound
true
2425
1420
1
Compound
true
2426
195
1
Compound
false
2427
1144
1
Compound
true
752
189
1075
false
PW_R001075
Both
4153
50
1
Compound
false
4154
1104
1
Compound
true
4155
102
1
Compound
false
4156
1042
1
Compound
true
754
500
2.4.2.1
13
false
PW_R000013
Both
61
986
1
Compound
true
62
114
1
Compound
false
63
123
1
Compound
false
64
936
1
Compound
true
65
1104
1
Compound
true
66
413
1
Compound
false
14
13
6.3.4.4
755
513
6.3.4.4
144
false
PW_R000144
Both
627
32
1
Compound
false
628
1420
1
Compound
true
629
114
1
Compound
false
630
35
1
Compound
true
756
514
3.5.4.6
16
false
PW_R000016
Both
77
413
1
Compound
false
78
88
1
Compound
true
79
32
1
Compound
false
17
16
4.3.2.2
94
false
PW_R000094
Right
368
34
1
Compound
false
369
1420
1
Compound
true
370
127
1
Compound
false
371
35
1
Compound
true
761
516
3.5.4.4
467
false
PW_R000467
Both
1939
34
1
Compound
false
1940
1104
1
Compound
true
1941
24
1
Compound
false
1942
1146
1
Compound
true
763
500
2.4.2.1
1081
false
PW_R001081
Both
4174
68
1
Compound
false
4175
1104
1
Compound
true
4176
24
1
Compound
false
4177
1042
1
Compound
true
765
500
2.4.2.1
95
false
PW_R000095
Both
372
68
1
Compound
false
373
1420
1
Compound
true
374
50
1
Compound
false
375
35
1
Compound
true
767
516
3.5.4.4
1083
false
PW_R001083
Both
4182
32
1
Compound
false
4183
170
1
Compound
true
4184
24
1
Compound
false
4185
190
1
Compound
true
768
498
2.4.2.7
250
false
PW_R000250
Both
1071
1034
1
Compound
false
1072
1420
1
Compound
true
1073
32
1
Compound
false
1074
1441
1
Compound
true
770
485
354
false
PW_R000354
Right
1470
414
1
Compound
false
1471
32
1
Compound
false
1472
1034
2
Compound
false
773
204
165
false
PW_R000165
Right
740
414
1
Compound
false
741
1420
1
Compound
true
742
1034
1
Compound
false
743
1441
1
Compound
true
775
520
3.6.1.3
441
false
PW_R000441
Right
1834
41
1
Compound
false
1835
1420
1
Compound
true
1836
32
1
Compound
false
777
69
3.1.4.53
596
false
PW_R000596
Right
2516
414
1
Compound
false
2517
41
1
Compound
false
4200
170
1
Compound
true
80
122
4.6.1.1
1994
121
1090
false
PW_R001090
Both
4208
414
1
Compound
true
4209
724
1
Compound
false
4210
1034
1
Compound
true
4211
1161
1
Compound
false
781
204
70
false
PW_R000070
Both
269
724
1
Compound
false
270
1420
1
Compound
true
271
68
1
Compound
false
272
1441
1
Compound
true
782
496
3.1.3.5
1091
false
PW_R001091
Both
4212
414
1
Compound
true
4213
1161
1
Compound
false
4214
1034
1
Compound
true
4215
1177
1
Compound
false
783
457
2.7.4.6
1092
false
PW_R001092
Right
4216
986
1
Compound
false
4217
7218
1
Compound
false
4218
170
1
Compound
true
784
521
4.6.1.2
1093
false
PW_R001093
Right
4219
7218
1
Compound
false
4220
1420
1
Compound
true
4221
1080
1
Compound
false
785
522
1094
false
PW_R001094
Right
4222
1846
1
Compound
false
4223
1420
1
Compound
true
4224
114
1
Compound
false
4225
1104
1
Compound
true
786
470
3.6.1.5
1095
false
PW_R001095
Right
4226
121
1
Compound
false
4227
1420
1
Compound
true
4228
114
1
Compound
false
4229
170
1
Compound
true
787
507
3.6.1.19
1096
false
PW_R001096
Both
4230
414
1
Compound
true
4231
1846
1
Compound
false
4232
1034
1
Compound
true
4233
121
1
Compound
false
788
457
2.7.4.6
1097
false
PW_R001097
Right
4234
121
1
Compound
false
4235
1420
1
Compound
true
4236
1846
1
Compound
false
4237
1104
1
Compound
true
789
470
3.6.1.5
1098
false
PW_R001098
Both
4238
1168
1
Compound
false
4239
170
1
Compound
true
4240
1801
1
Compound
false
4241
190
1
Compound
true
790
498
2.4.2.7
484
false
PW_R000484
Right
2011
414
1
Compound
true
2012
791
1
Compound
false
2013
1034
1
Compound
true
2014
1104
1
Compound
true
2015
955
1
Compound
false
731
503
1089
false
PW_R001089
Both
4203
1161
1
Compound
false
4204
1101
1
ProteinComplex
true
4205
1420
1
Compound
true
4206
1034
1
Compound
false
4207
1100
1
ProteinComplex
true
780
491
1.17.4.1
2295
false
PW_R002295
Right
8444
1161
1
Compound
false
8445
1104
1
Compound
true
8446
1177
1
Compound
false
8447
1420
1
Compound
true
2191
485
1046
false
PW_R001046
Both
4036
767
1
Compound
false
4037
1101
1
ProteinComplex
true
4038
1420
1
Compound
true
4039
936
1
Compound
false
4040
1100
1
ProteinComplex
true
701
491
1.17.4.1
2939
1033
8
81
false
310
450
10
regular
200
190
2940
1420
8
49
false
510
665
10
regular
78
78
2941
986
8
81
false
310
1030
10
regular
200
190
2942
1080
8
81
false
550
840
10
regular
200
190
3014
936
14
81
false
309
1480
10
regular
200
190
3018
414
8
42
false
479
1410
10
regular
50
30
3019
1034
8
43
false
475
1255
10
regular
50
30
3020
423
8
9
false
354
1300
20
regular
100
25
3021
1420
49
49
false
605
1440
10
regular
78
78
3022
1080
49
81
false
1219
1478
10
regular
200
190
3023
1104
49
46
false
875
1465
10
regular
44
43
3024
353
49
9
false
720
1525
10
regular
100
25
3025
423
49
9
false
719
1595
10
regular
100
25
3033
1420
14
49
false
255
1225
10
regular
78
78
3034
1104
14
46
false
263
1408
10
regular
44
43
3035
353
14
9
false
130
1295
20
regular
100
25
3036
414
8
42
false
949
1808
10
regular
50
30
3037
1034
8
43
false
699
1810
10
regular
50
30
3110
767
8
81
false
309
2065
10
regular
200
190
3117
414
8
42
false
489
2280
10
regular
50
30
3118
1034
8
43
false
494
2435
10
regular
50
30
3119
1112
8
81
false
309
2510
10
regular
200
190
3120
423
8
9
false
364
2330
19
regular
100
25
3124
414
8
42
false
829
2480
10
regular
50
30
3125
822
8
81
false
654
2545
10
regular
200
200
3126
1034
8
43
false
829
2315
10
regular
50
30
3128
1420
8
49
false
829
2765
10
regular
78
78
3129
58
8
81
false
653
3005
10
regular
200
190
3130
1104
8
46
false
831
2948
10
regular
44
43
3131
423
8
9
false
709
2842
19
regular
100
25
3132
414
3
42
false
368
2950
10
regular
50
30
3133
1034
3
43
false
379
2750
10
regular
50
30
3139
170
8
45
false
859
1846
10
regular
63
43
3140
86
8
81
false
1223
2508
10
regular
200
190
3141
190
8
81
false
733
2018
10
regular
200
190
3148
1420
8
49
false
1389
1713
10
regular
78
78
3149
87
8
81
false
1223
1998
10
regular
200
190
3150
1441
8
46
false
1411
1891
10
regular
44
43
3151
423
8
9
false
1264
1788
19
regular
100
25
3152
1104
8
46
false
1202
2201
10
regular
44
43
3153
1146
8
81
false
1048
2313
10
regular
200
190
3154
170
8
45
false
1674
1856
10
regular
63
43
3155
190
8
81
false
1683
2013
10
regular
200
190
3156
423
8
9
false
1561
1933
19
regular
100
25
3161
1104
8
46
false
1167
2973
10
regular
44
43
3162
1042
8
81
false
1018
2663
10
regular
200
190
3171
1420
8
49
false
1543
2673
10
regular
78
78
3172
198
8
81
false
1948
2506
10
regular
200
190
3173
35
8
63
false
1814
2672
10
regular
78
78
3174
1005
8
9
false
1668
2553
10
regular
100
25
3211
914
8
81
false
650
345
10
regular
200
190
3212
1420
8
49
false
875
505
10
regular
78
78
3213
32
8
44
false
1150
525
10
regular
50
30
3214
1191
8
81
false
1235
345
10
regular
200
190
3215
414
8
42
false
1450
500
10
regular
50
30
3216
190
8
81
false
1735
345
10
regular
200
190
3217
32
8
44
false
1660
505
10
regular
50
30
3218
423
8
9
false
1535
395
10
regular
100
25
3219
882
8
81
false
2435
348
10
regular
200
190
3220
170
8
45
false
2263
336
10
regular
63
43
3221
95
8
81
false
2220
511
10
regular
200
190
3222
500
8
81
false
1940
510
10
regular
200
190
3223
1420
8
49
false
2015
320
10
regular
78
78
3224
423
8
9
false
2115
398
10
regular
100
25
3225
414
8
42
false
2715
358
10
regular
50
30
3226
78
8
81
false
2640
508
10
regular
200
190
3227
1034
8
43
false
2945
356
10
regular
50
30
3228
1104
8
46
false
2963
519
10
regular
44
43
3229
1355
8
81
false
3075
350
10
regular
200
190
3230
774
8
81
false
3255
545
10
regular
200
190
3231
1221
8
81
false
3570
550
10
regular
200
190
3232
1007
8
81
false
3770
345
10
regular
200
200
3233
414
8
42
false
4065
350
10
regular
50
30
3234
500
8
3
true
4050
595
10
regular
100
100
3235
1420
8
49
false
3975
295
10
regular
78
78
3236
1034
8
43
false
4315
348
10
regular
50
30
3237
1441
8
46
false
4383
331
10
regular
44
43
3238
791
8
81
false
4455
347
10
regular
200
190
3239
95
8
3
true
4305
597
10
regular
100
110
3243
955
8
81
false
4995
344
10
regular
200
200
3244
2699
8
81
false
4994
994
10
regular
200
210
3245
1316
8
52
false
4938
635
10
regular
78
78
3246
414
8
42
false
4854
999
10
regular
50
30
3247
123
8
81
false
4789
1164
10
regular
200
190
3248
1034
8
43
false
4574
1002
10
regular
50
30
3249
1441
8
46
false
4577
1165
10
regular
44
43
3250
637
8
81
false
4294
1001
10
regular
200
190
3251
88
8
81
false
3854
1156
10
regular
200
190
3252
1168
8
81
false
3644
1001
10
regular
200
190
3253
774
8
81
false
3394
826
10
regular
200
190
3254
1221
8
81
false
3154
826
10
regular
200
190
3255
1111
8
81
false
2899
996
10
regular
200
200
3256
114
8
81
false
2814
1481
10
regular
200
190
3257
1420
8
49
false
3054
1346
10
regular
78
78
3262
1420
8
49
false
745
1260
10
regular
78
78
3263
170
8
45
false
992
1268
10
regular
63
43
3264
423
8
9
false
864
1170
10
regular
100
25
3269
414
8
42
false
1804
1480
10
regular
50
30
3270
1196
8
81
false
1949
1480
10
regular
200
190
3271
35
8
63
false
1785
1641
10
regular
78
78
3272
32
8
44
false
1564
1480
10
regular
50
30
3273
170
8
45
false
1557
1643
10
regular
63
43
3274
721
8
59
false
2574
1476
10
regular
50
30
3275
1420
8
49
false
2574
1636
10
regular
78
78
3276
1144
8
60
false
2349
1475
10
regular
50
30
3277
457
8
9
false
2444
1531
10
regular
100
25
3278
35
8
63
false
2160
1464
10
regular
78
78
3279
143
8
61
false
2129
1316
10
regular
50
30
3280
146
8
62
false
1909
1318
10
regular
50
30
3281
1420
8
49
false
1909
1710
10
regular
78
78
3282
203
8
81
false
1948
2000
10
regular
200
190
3283
1104
8
46
false
1946
1898
10
regular
44
43
3284
423
8
9
false
2009
1785
19
regular
100
25
3289
1104
8
46
false
1927
2213
10
regular
44
43
3290
1146
8
81
false
1743
2336
10
regular
200
190
3291
1420
8
49
false
2979
1696
10
regular
78
78
3292
127
8
81
false
2813
2001
10
regular
200
190
3293
1104
8
46
false
2991
1874
10
regular
44
43
3294
423
8
9
false
2869
1771
19
regular
100
25
3295
170
8
45
false
2369
1928
10
regular
63
43
3296
190
8
81
false
2388
2106
10
regular
200
190
3297
423
8
9
false
2231
2025
19
regular
100
25
3298
1104
8
46
false
2987
2239
10
regular
44
43
3299
102
8
81
false
2815
2506
10
regular
200
190
3300
1146
8
81
false
3020
2356
10
regular
200
190
3301
170
8
45
false
2534
1924
10
regular
63
43
3302
423
8
9
false
2641
2036
19
regular
100
25
3318
1065
5
65
false
2516
2469
10
regular
78
78
3319
1420
5
49
false
2530
2656
10
regular
78
78
3320
1783
5
56
false
2274
2469
10
regular
78
78
3321
964
5
9
false
2381
2558
10
regular
100
25
3322
721
5
59
false
2278
2866
10
regular
50
30
3323
1420
5
49
false
2198
2896
10
regular
78
78
3324
195
5
81
false
2613
2701
10
regular
200
190
3325
1144
5
60
false
2518
2871
10
regular
50
30
3326
964
5
9
false
2383
2761
10
regular
100
25
3330
50
8
81
false
2814
3041
10
regular
200
190
3331
1104
8
46
false
3007
2934
10
regular
44
43
3332
1042
8
81
false
3020
2661
10
regular
200
190
3336
986
8
54
false
3179
1406
10
regular
50
30
3337
123
8
81
false
3104
1111
10
regular
200
190
3338
936
8
53
false
3424
1409
10
regular
50
30
3339
1104
8
46
false
3427
1237
10
regular
44
43
3340
413
8
81
false
3554
1253
10
regular
200
190
3341
423
8
9
false
3274
1301
10
regular
100
25
3342
32
8
81
false
3554
1770
10
regular
200
190
3343
1420
8
49
false
3384
1735
10
regular
78
78
3344
35
8
63
false
3160
1734
10
regular
78
78
3345
1005
8
9
false
3264
1810
10
regular
100
25
3352
88
8
81
false
3349
1535
10
regular
200
190
3362
34
8
81
false
3553
2000
10
regular
200
190
3363
1420
8
49
false
3348
1945
10
regular
78
78
3364
35
8
63
false
3114
1944
10
regular
78
78
3365
1005
8
9
false
3223
2045
10
regular
100
25
3366
1104
8
46
false
3527
2253
10
regular
44
43
3367
24
8
81
false
3555
2510
10
regular
200
190
3368
1146
8
81
false
3345
2370
10
regular
200
190
3372
68
8
81
false
3554
3040
10
regular
200
190
3373
1104
8
46
false
3522
2943
10
regular
44
43
3374
1042
8
81
false
3345
2660
10
regular
200
190
3378
1420
8
49
false
3339
2990
10
regular
78
78
3379
35
8
63
false
3105
2994
10
regular
78
78
3380
1005
8
9
false
3214
3085
10
regular
100
25
3386
170
8
45
false
3899
2113
10
regular
63
43
3387
190
8
81
false
3920
2315
10
regular
200
190
3393
1034
49
81
false
4344
2124
10
regular
200
190
3394
1420
49
49
false
4224
1994
10
regular
78
78
3395
1441
49
46
false
3987
2200
10
regular
44
43
3396
353
49
9
false
4079
2159
10
regular
100
25
3397
423
49
9
false
4074
2089
10
regular
100
25
3411
414
8
81
false
4344
1690
10
regular
200
190
3412
1420
5
49
false
4804
1895
10
regular
78
78
3413
1441
5
46
false
4813
2147
10
regular
44
43
3422
41
8
81
false
3969
1355
10
regular
200
190
3423
1420
8
49
false
3884
1565
10
regular
78
78
3424
1005
8
9
false
4024
1655
19
regular
100
25
3429
170
8
45
false
4409
1453
10
regular
63
43
3430
423
8
9
false
4394
1552
19
regular
100
25
3434
1161
8
81
false
4344
2604
10
regular
200
190
3443
414
8
42
false
4509
2969
10
regular
50
30
3444
724
8
81
false
4344
3039
10
regular
200
190
3445
1034
8
43
false
4504
2829
10
regular
50
30
3446
1420
8
49
false
4129
2994
10
regular
78
78
3447
1441
8
46
false
3912
3020
10
regular
44
43
3448
423
8
9
false
4014
3094
10
regular
100
25
3449
414
8
42
false
4629
2519
10
regular
50
30
3450
1034
8
43
false
4859
2519
10
regular
50
30
3451
1177
8
81
false
4989
2604
10
regular
200
190
3452
423
8
9
false
4719
2579
10
regular
100
25
3453
7218
8
81
false
1220
958
10
regular
200
200
3454
170
8
45
false
953
951
10
regular
63
43
3455
1799
8
9
false
810
1010
10
regular
100
25
3456
1420
8
49
false
1395
1178
10
regular
78
78
3457
1005
8
9
false
1275
1255
19
regular
100
25
3458
423
8
9
false
1275
1350
19
regular
100
25
3459
1846
8
81
false
2004
800
10
regular
200
190
3460
1420
8
49
false
1944
1060
10
regular
78
78
3461
1104
8
46
false
1982
1246
10
regular
44
43
3462
353
8
9
false
2054
1130
19
regular
100
25
3463
121
8
81
false
2743
796
10
regular
200
190
3464
1420
8
49
false
2698
1116
10
regular
78
78
3465
170
8
45
false
2714
1294
10
regular
63
43
3466
423
8
9
false
2793
1198
19
regular
100
25
3467
414
8
42
false
2334
730
10
regular
50
30
3468
1034
8
43
false
2553
726
10
regular
50
30
3469
423
8
9
false
2413
770
10
regular
100
25
3470
1420
8
49
false
2548
1021
10
regular
78
78
3471
1104
8
46
false
2332
1025
10
regular
44
43
3472
353
8
9
false
2413
916
10
regular
100
25
3473
170
8
45
false
3827
761
10
regular
63
43
3474
1801
8
81
false
4239
780
10
regular
200
190
3475
190
8
81
false
3999
620
10
regular
200
190
10092
414
2
42
false
4690
365
10
regular
50
30
10093
1034
2
43
false
4925
360
10
regular
50
30
10094
1104
2
46
false
4935
495
10
regular
44
43
10124
1420
2
49
false
4519
2489
10
regular
78
78
10125
40707
2
9
false
4204
2489
10
regular
100
25
10126
8133
2
9
false
4394
2384
19
regular
100
25
10127
1104
18
46
false
4622
2824
10
regular
44
43
10128
1420
18
49
false
4899
2829
10
regular
78
78
10129
353
18
9
false
4721
2781
10
regular
100
25
10130
423
18
9
false
4721
2706
10
regular
100
25
10131
1420
2
49
false
459
1925
10
regular
78
78
10132
40707
2
9
false
234
1885
10
regular
100
25
10133
8133
2
9
false
364
1782
19
regular
100
25
1086
588
8
2
false
335
795
8
subunit
regular
150
70
1115
110
8
2
false
334
1310
8
subunit
regular
150
70
1116
822
49
2
false
694
1540
8
subunit
regular
150
70
1119
2891
14
2
false
105
1310
8
subunit
regular
150
70
1120
873
8
2
false
779
1713
8
subunit
regular
150
70
1144
110
8
2
false
334
2340
8
subunit
regular
150
70
1146
873
8
2
false
679
2377
8
subunit
regular
150
70
1149
2368
8
8
false
684
2842
8
subunit
regular
140
85
1150
713
3
6
false
418
2822
8
protein
regular
160
80
1152
429
8
6
false
921
1948
8
subunit
regular
160
80
1154
2368
8
8
false
1249
1793
8
subunit
regular
140
85
1155
2369
8
16
false
1239
2263
8
subunit
regular
170
90
1156
458
8
8
false
1536
1938
8
subunit
regular
140
85
1158
2369
8
16
false
1239
2831
8
subunit
regular
170
90
1161
654
8
6
false
1638
2563
8
subunit
regular
160
80
1172
594
8
6
false
965
400
8
subunit
regular
160
80
1173
537
8
2
false
1510
405
8
subunit
regular
150
70
1174
325
8
8
false
2105
403
8
subunit
regular
140
85
1175
324
8
2
false
2795
408
8
subunit
regular
150
70
1176
324
8
2
false
3440
410
8
subunit
regular
150
70
1177
798
8
2
false
4140
410
8
subunit
regular
150
70
1179
837
8
7
false
4999
724
8
subunit
regular
190
85
1180
837
8
7
false
4644
1059
8
subunit
regular
190
85
1181
554
8
2
false
4009
1061
8
subunit
regular
150
70
1182
825
8
2
false
3299
1061
8
subunit
regular
150
70
1183
825
8
2
false
2924
1273
8
subunit
regular
150
70
1185
422
8
6
false
829
1170
8
subunit
regular
160
80
1190
560
8
6
false
1629
1535
8
subunit
regular
160
80
1191
826
8
8
false
2419
1536
8
subunit
regular
140
85
1192
649
8
8
false
1976
1363
8
subunit
regular
140
85
1193
2368
8
8
false
1979
1790
8
subunit
regular
140
85
1195
2369
8
16
false
1964
2275
8
subunit
regular
170
90
1196
2368
8
8
false
2844
1776
8
subunit
regular
140
85
1197
458
8
8
false
2211
2030
8
subunit
regular
140
85
1198
2369
8
16
false
2829
2308
8
subunit
regular
170
90
1199
458
8
8
false
2616
2041
8
subunit
regular
140
85
1204
176
5
6
false
2351
2563
8
subunit
regular
160
80
1205
176
5
6
false
2353
2756
8
subunit
regular
160
80
1207
2369
8
16
false
2829
2808
8
subunit
regular
170
90
1209
823
8
6
false
3249
1306
8
subunit
regular
160
80
1210
623
8
8
false
3244
1825
8
subunit
regular
140
85
1214
554
8
2
false
3579
1506
8
subunit
regular
150
70
1218
629
8
2
false
3198
2060
8
subunit
regular
150
70
1219
2369
8
16
false
3569
2317
8
subunit
regular
170
90
1221
2369
8
16
false
3569
2817
8
subunit
regular
170
90
1223
629
8
2
false
3189
3100
8
subunit
regular
150
70
1225
429
8
6
false
3761
2200
8
subunit
regular
160
80
1228
822
49
2
false
4054
2104
8
subunit
regular
150
70
1235
533
8
2
false
4369
1992
8
subunit
regular
150
70
1236
5270
5
2
false
4654
2019
8
subunit
regular
150
70
1240
603
8
6
false
3989
1660
8
subunit
regular
160
80
1243
2404
8
2
false
4369
1557
8
subunit
regular
150
70
1250
533
8
2
false
4369
2879
8
subunit
regular
150
70
1251
2368
8
8
false
3984
3094
8
subunit
regular
140
85
1252
110
8
2
false
4694
2589
8
subunit
regular
150
70
1253
1007
8
97
false
785
1045
8
none
regular
150
70
1254
1001
8
2
false
785
1020
8
protein
regular
150
70
1255
571
8
6
false
1240
1270
8
subunit
regular
160
80
1256
2891
8
2
false
2029
1145
8
subunit
regular
150
70
1257
422
8
6
false
2763
1198
8
subunit
regular
160
80
1258
110
8
2
false
2393
780
8
subunit
regular
150
70
1259
2891
8
2
false
2393
931
8
subunit
regular
150
70
1260
429
8
6
false
3889
838
8
subunit
regular
160
80
5519
324
2
2
false
4755
410
8
subunit
regular
150
70
5544
5803
2
99
false
4184
2499
8
subunit
regular
150
70
5545
5803
2
99
false
4184
2304
8
subunit
regular
150
70
5546
104
2
2
false
4394
2384
8
subunit
regular
150
70
5547
107
2
2
false
4369
2399
8
subunit
regular
150
70
5548
822
18
2
false
4701
2721
8
subunit
regular
150
70
5549
5803
2
99
false
209
1895
8
subunit
regular
150
70
5550
5803
2
99
false
209
1695
8
subunit
regular
150
70
5551
104
2
97
false
354
1817
8
subunit
regular
150
70
5552
107
2
2
false
334
1797
8
subunit
regular
150
70
1032
469
62
8
1079
1086
1061
457
62
8
1108
1115
517
3020
4478
Cofactor
1062
485
62
49
1109
1116
518
3024
4483
Cofactor
519
3025
4484
Cofactor
1065
470
62
14
1112
1119
522
3035
4499
Cofactor
1066
487
62
8
1113
1120
1088
457
62
8
1137
1144
542
3120
4623
Cofactor
1090
487
62
8
1139
1146
1093
496
62
8
1142
1149
543
3131
4641
Cofactor
1094
497
62
3
1143
1150
1096
498
62
8
1145
1152
1098
496
62
8
1147
1154
546
3151
4665
Cofactor
1099
500
62
8
1148
1155
1100
499
62
8
1149
1156
547
3156
4674
Cofactor
1102
500
62
8
1151
1158
1105
501
62
8
1154
1161
551
3174
4698
Cofactor
1116
502
62
8
1165
1172
1117
488
62
8
1166
1173
560
3218
4754
Cofactor
1118
37
62
8
1167
1174
561
3224
4761
Cofactor
1119
503
62
8
1168
1175
1120
503
62
8
1169
1176
1121
504
62
8
1170
1177
1123
505
62
8
1172
1179
1124
505
62
8
1173
1180
1125
16
62
8
1174
1181
1126
506
62
8
1175
1182
1127
506
62
8
1176
1183
1129
507
62
8
1178
1185
563
3264
4814
Cofactor
1133
508
62
8
1183
1190
1134
509
62
8
1184
1191
567
3277
4833
Cofactor
1135
510
62
8
1185
1192
1136
496
62
8
1186
1193
568
3284
4843
Cofactor
1138
500
62
8
1188
1195
1139
496
62
8
1189
1196
569
3294
4858
Cofactor
1140
499
62
8
1190
1197
570
3297
4863
Cofactor
1141
500
62
8
1191
1198
1142
499
62
8
1192
1199
571
3302
4872
Cofactor
1147
189
62
5
1197
1204
573
3321
4899
Cofactor
1148
189
62
5
1198
1205
574
3326
4905
Cofactor
1150
500
62
8
1200
1207
1152
513
62
8
1202
1209
576
3341
4925
Cofactor
1153
514
62
8
1203
1210
577
3345
4930
Cofactor
1157
16
62
8
1207
1214
1161
516
62
8
1211
1218
580
3365
4962
Cofactor
1162
500
62
8
1212
1219
1164
500
62
8
1214
1221
1166
516
62
8
1216
1223
582
3380
4984
Cofactor
1168
498
62
8
1218
1225
1171
485
62
49
1221
1228
586
3396
5006
Cofactor
587
3397
5007
Cofactor
1178
204
62
8
1228
1235
1179
520
62
5
1229
1236
1183
69
62
8
1233
1240
593
3424
5053
Cofactor
1186
67
62
8
1236
1243
595
3430
5064
Cofactor
1191
204
62
8
1243
1250
1192
496
62
8
1244
1251
601
3448
5093
Cofactor
1193
457
62
8
1245
1252
602
3452
5098
Cofactor
1194
521
62
8
1246
1253
1247
1254
603
3455
5102
Cofactor
1195
522
62
8
1248
1255
604
3457
5106
Cofactor
605
3458
5107
Cofactor
1196
470
62
8
1249
1256
606
3462
5112
Cofactor
1197
507
62
8
1250
1257
607
3466
5117
Cofactor
1198
457
62
8
1251
1258
608
3469
5122
Cofactor
1199
470
62
8
1252
1259
609
3472
5127
Cofactor
1200
498
62
8
1253
1260
4521
503
62
2
5490
5519
4534
1101
62
2
5515
5544
2020
10125
16048
Cofactor
4535
1100
62
2
5516
5545
4536
491
62
2
5517
5546
5518
5547
2021
10126
16051
Cofactor
4537
485
62
18
5519
5548
2022
10129
16056
Cofactor
2023
10130
16057
Cofactor
4538
1101
62
2
5520
5549
2024
10132
16061
Cofactor
4539
1100
62
2
5521
5550
4540
491
62
2
5522
5551
5523
5552
2025
10133
16064
Cofactor
4355
M410 640 C410 670 410 765 410 795
5
false
18
4356
M510 704 C424 704 410 765 410 795
5
false
18
4357
M410 1030 C410 1000 410 895 410 865
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4358
M550 935 C464 935 410 895 410 865
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4474
M479 1425 C456 1425 409 1410 409 1380
5
false
18
true
M 616.0096189432334 1527.5 L 629 1520 L 616.0096189432334 1512.5
false
4475
M409 1480 C409 1450 409 1410 409 1380
5
false
18
true
M 551.5 1567.0096189432334 L 559 1580 L 566.5 1567.0096189432334
false
4476
M475 1270 C450 1270 409 1280 409 1310
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4477
M410 1220 C410 1250 409 1280 409 1310
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4478
M0 50 L0 100 L50 50 z
10
true
18
4479
M509 1575 C552 1575 641 1575 694 1575
5
false
18
4480
M644 1518 C644 1542 664 1575 694 1575
5
false
18
4481
M1219 1573 C1137 1573 874 1575 844 1575
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4482
M897 1508 C897 1536 874 1575 844 1575
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4483
M0 50 L0 100 L50 50 z
10
true
18
4484
M0 50 L0 100 L50 50 z
10
true
18
4495
M310 1125 C230 1127 182 1223 180 1310
5
false
18
4496
M255 1264 C233 1264 180 1280 180 1310
5
false
18
4497
M309 1575 C231 1571 184 1473 180 1380
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4498
M263 1429.5 C224 1428.5 180 1410 180 1380
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4499
M0 50 L0 100 L50 50 z
10
true
18
4500
M974 1808 C974 1781 959 1748 929 1748
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4501
M1214 1650 C1164 1685 1121 1745 929 1748
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4502
M724 1810 C724 1783 749 1748 779 1748
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4503
M514 1650 C560 1698 611 1740 779 1748
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4619
M489 2295 C466 2295 409 2310 409 2340
5
false
18
4620
M409 2255 C409 2285 409 2310 409 2340
5
false
18
4621
M494 2450 C465 2450 409 2440 409 2410
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4622
M409 2510 C409 2480 409 2440 409 2410
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4623
M0 50 L0 100 L50 50 z
10
true
18
4628
M829 2495 C803 2495 754 2477 754 2447
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4629
M754 2545 C754 2515 754 2477 754 2447
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4630
M829 2330 C805 2330 754 2347 754 2377
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4631
M509 2160 C590 2160 754 2296 754 2377
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4637
M754 2745 C754 2789 754 2812 754 2842
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4638
M829 2804 C804 2804 754 2812 754 2842
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4639
M753 3005 C753 2957 754 2957 754 2927
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4640
M831 2969.5 C802 2969.5 754 2957 754 2927
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4641
M0 50 L0 100 L50 50 z
10
true
18
4642
M418 2965 C461 2965 498 2932 498 2902
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4643
M653 3100 C514 3097 498 2932 498 2902
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4644
M429 2765 C466 2765 498 2792 498 2822
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4645
M654 2645 C533 2644 498 2792 498 2822
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4651
M1218 1666 C1141 1707 1001 1892 1001 1948
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4652
M922 1867.5 C992 1867.5 1001 1918 1001 1948
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4653
M1223 2603 C997 2601 1000 2389 1001 2028
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4654
M933 2113 C1000 2116 1001 2058 1001 2028
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4661
M1319 1668 C1319 1698 1319 1763 1319 1793
5
false
18
4662
M1389 1752 C1367 1752 1319 1763 1319 1793
5
false
18
4663
M1323 1998 C1323 1968 1319 1908 1319 1878
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4664
M1411 1912.5 C1387 1912.5 1319 1908 1319 1878
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4665
M1119 1803 L1119 1853 L1169 1803 z
10
true
18
4666
M1323 2188 C1323 2218 1324 2233 1324 2263
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4667
M1246 2222.5 C1282 2222.5 1324 2233 1324 2263
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4668
M1323 2508 C1323 2478 1324 2383 1324 2353
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4669
M1248 2408 C1290 2408 1324 2383 1324 2353
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4670
M1422 1664 C1499 1712 1606 1893 1606 1938
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4671
M1674 1877.5 C1635 1876.5 1606 1908 1606 1938
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4672
M1423 2603 C1592 2525 1606 2214 1606 2023
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
4673
M1683 2108 C1643 2108 1606 2053 1606 2023
5
false
18
true
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4896
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M0 50 L0 100 L50 50 z
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M0 50 L0 100 L50 50 z
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M0 50 L0 100 L50 50 z
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M0 50 L0 100 L50 50 z
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M0 50 L0 100 L50 50 z
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M0 50 L0 100 L50 50 z
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933
62
162
8
3302
2939
4355
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2940
4356
Left
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2941
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Right
3305
2942
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Right
873
653
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62
403
8
3395
3018
4474
Left
3396
3014
4475
Left
3397
3019
4476
Right
3398
2941
4477
Right
907
617
1061
964
62
186
49
3399
3014
4479
Left
3400
3021
4480
Left
3401
3022
4481
Right
3402
3023
4482
Right
908
695
1062
967
62
235
14
3411
2941
4495
Left
3412
3033
4496
Left
3413
3014
4497
Right
3414
3034
4498
Right
911
655
1065
968
62
360
8
3415
3036
4500
Left
3416
3022
4501
Left
3417
3037
4502
Right
3418
3014
4503
Right
912
697
1066
990
62
405
8
3506
3117
4619
Left
3507
3110
4620
Left
3508
3118
4621
Right
3509
3119
4622
Right
934
710
1088
992
62
1056
8
3514
3124
4628
Left
3515
3125
4629
Left
3516
3126
4630
Right
3517
3110
4631
Right
936
712
1090
995
62
69
8
3522
3125
4637
Left
3523
3128
4638
Left
3524
3129
4639
Right
3525
3130
4640
Right
939
715
1093
996
62
226
3
3526
3132
4642
Left
3527
3129
4643
Left
3528
3133
4644
Right
3529
3125
4645
Right
940
716
1094
998
62
1060
8
3534
3022
4651
Left
3535
3139
4652
Left
3536
3140
4653
Right
3537
3141
4654
Right
942
718
1096
1000
62
66
8
3543
3022
4661
Left
3544
3148
4662
Left
3545
3149
4663
Right
3546
3150
4664
Right
944
720
1098
1001
62
469
8
3547
3149
4666
Left
3548
3152
4667
Left
3549
3140
4668
Right
3550
3153
4669
Right
945
721
1099
1002
62
1060
8
3551
3022
4670
Left
3552
3154
4671
Left
3553
3140
4672
Right
3554
3155
4673
Right
946
719
1100
1004
62
1061
8
3559
3129
4680
Left
3560
3161
4681
Left
3561
3140
4682
Right
3562
3162
4683
Right
948
722
1102
1007
62
302
8
3571
3140
4694
Left
3572
3171
4695
Left
3573
3172
4696
Right
3574
3173
4697
Right
951
725
1105
1015
62
1064
8
3605
3211
4746
Left
3606
3212
4747
Left
3607
3213
4748
Right
3608
3214
4749
Right
959
726
1116
1016
62
1043
8
3609
3214
4750
Left
3610
3215
4751
Left
3611
3216
4752
Right
3612
3217
4753
Right
960
698
1117
1017
62
44
8
3613
3219
4755
Left
3614
3220
4756
Left
3615
3221
4757
Left
3616
3222
4758
Right
3617
3216
4759
Right
3618
3223
4760
Right
961
44
1118
1018
62
483
8
3619
3225
4763
Left
3620
3219
4764
Left
3621
3226
4765
Left
3622
3227
4766
Right
3623
3228
4767
Right
3624
3229
4768
Right
962
728
1119
1019
62
1065
8
3625
3230
4769
Left
3626
3229
4770
Left
3627
3231
4771
Right
3628
3232
4772
Right
963
729
1120
1020
62
485
8
3629
3233
4773
Left
3630
3232
4774
Left
3631
3234
4775
Left
3632
3235
4776
Left
3633
3236
4777
Right
3634
3237
4778
Right
3635
3238
4779
Right
3636
3239
4780
Right
964
730
1121
1022
62
486
8
3642
3244
4786
Left
3643
3243
4787
Right
3644
3245
4788
Right
966
732
1123
1023
62
487
8
3645
3246
4789
Left
3646
3244
4790
Left
3647
3247
4791
Left
3648
3248
4792
Right
3649
3249
4793
Right
3650
3250
4794
Right
967
733
1124
1024
62
489
8
3651
3250
4795
Left
3652
3251
4796
Right
3653
3252
4797
Right
968
734
1125
1025
62
1066
8
3654
3253
4798
Left
3655
3252
4799
Left
3656
3254
4800
Right
3657
3255
4801
Right
969
735
1126
1026
62
490
8
3658
3256
4802
Left
3659
3257
4803
Left
3660
3255
4804
Right
970
736
1127
1028
62
1067
8
3665
2941
4810
Left
3666
3262
4811
Left
3667
3022
4812
Right
3668
3263
4813
Right
972
737
1129
1030
62
1068
8
3673
3269
4822
Left
3674
3270
4823
Left
3675
3271
4824
Left
3676
3272
4825
Right
3677
3273
4826
Right
3678
3022
4827
Right
976
739
1133
1031
62
335
8
3679
3256
4828
Left
3680
3274
4829
Left
3681
3275
4830
Left
3682
3270
4831
Right
3683
3276
4832
Right
977
740
1134
1032
62
1069
8
3684
3256
4834
Left
3685
3278
4835
Left
3686
3279
4836
Left
3687
3022
4837
Right
3688
3280
4838
Right
978
741
1135
1033
62
72
8
3689
3270
4839
Left
3690
3281
4840
Left
3691
3282
4841
Right
3692
3283
4842
Right
979
742
1136
1035
62
472
8
3697
3282
4850
Left
3698
3289
4851
Left
3699
3172
4852
Right
3700
3290
4853
Right
981
743
1138
1036
62
65
8
3701
3256
4854
Left
3702
3291
4855
Left
3703
3292
4856
Right
3704
3293
4857
Right
982
744
1139
1037
62
1070
8
3705
3270
4859
Left
3706
3295
4860
Left
3707
3172
4861
Right
3708
3296
4862
Right
983
745
1140
1038
62
468
8
3709
3292
4864
Left
3710
3298
4865
Left
3711
3299
4866
Right
3712
3300
4867
Right
984
746
1141
1039
62
1071
8
3713
3256
4868
Left
3714
3301
4869
Left
3715
3299
4870
Right
3716
3296
4871
Right
985
747
1142
1044
62
578
5
3735
3299
4894
Left
3736
3318
4895
Left
3737
3319
4896
Left
3738
3172
4897
Right
3739
3320
4898
Right
990
751
1147
1045
62
579
5
3740
3172
4900
Left
3741
3322
4901
Left
3742
3323
4902
Left
3743
3324
4903
Right
3744
3325
4904
Right
991
752
1148
1047
62
1075
8
3749
3330
4910
Left
3750
3331
4911
Left
3751
3299
4912
Right
3752
3332
4913
Right
993
754
1150
1049
62
13
8
3757
3336
4919
Left
3758
3256
4920
Left
3759
3337
4921
Left
3760
3338
4922
Right
3761
3339
4923
Right
3762
3340
4924
Right
995
755
1152
1050
62
144
8
3763
3342
4926
Left
3764
3343
4927
Left
3765
3256
4928
Right
3766
3344
4929
Right
996
756
1153
1054
62
16
8
3777
3340
4944
Left
3778
3352
4945
Right
3779
3342
4946
Right
1000
17
1157
1058
62
94
8
3791
3362
4958
Left
3792
3363
4959
Left
3793
3292
4960
Right
3794
3364
4961
Right
1004
761
1161
1059
62
467
8
3795
3362
4963
Left
3796
3366
4964
Left
3797
3367
4965
Right
3798
3368
4966
Right
1005
763
1162
1061
62
1081
8
3803
3372
4971
Left
3804
3373
4972
Left
3805
3367
4973
Right
3806
3374
4974
Right
1007
765
1164
1063
62
95
8
3811
3372
4980
Left
3812
3378
4981
Left
3813
3330
4982
Right
3814
3379
4983
Right
1009
767
1166
1066
62
1083
8
3819
3342
4990
Left
3820
3386
4991
Left
3821
3367
4992
Right
3822
3387
4993
Right
1011
768
1168
1069
62
250
49
3829
3393
5002
Left
3830
3394
5003
Left
3831
3342
5004
Right
3832
3395
5005
Right
1014
770
1171
1074
62
354
8
3846
3411
5026
Left
3847
3342
5027
Left
3848
3393
5028
Right
1021
773
1178
1075
62
165
5
3849
3411
5029
Left
3850
3412
5030
Left
3851
3393
5031
Right
3852
3413
5032
Right
1022
775
1179
1079
62
441
8
3864
3422
5050
Left
3865
3423
5051
Left
3866
3342
5052
Right
1026
777
1183
1082
62
596
8
3871
3411
5061
Left
3872
3422
5062
Right
3873
3429
5063
Right
1029
80
1186
1087
62
1090
8
3887
3443
5085
Left
3888
3444
5086
Left
3889
3445
5087
Right
3890
3434
5088
Right
1034
781
1191
1088
62
70
8
3891
3444
5089
Left
3892
3446
5090
Left
3893
3372
5091
Right
3894
3447
5092
Right
1035
782
1192
1089
62
1091
8
3895
3449
5094
Left
3896
3434
5095
Left
3897
3450
5096
Right
3898
3451
5097
Right
1036
783
1193
1090
62
1092
8
3899
2941
5099
Left
3900
3453
5100
Right
3901
3454
5101
Right
1037
784
1194
1091
62
1093
8
3902
3453
5103
Left
3903
3456
5104
Left
3904
3022
5105
Right
1038
785
1195
1092
62
1094
8
3905
3459
5108
Left
3906
3460
5109
Left
3907
3256
5110
Right
3908
3461
5111
Right
1039
786
1196
1093
62
1095
8
3909
3463
5113
Left
3910
3464
5114
Left
3911
3256
5115
Right
3912
3465
5116
Right
1040
787
1197
1094
62
1096
8
3913
3467
5118
Left
3914
3459
5119
Left
3915
3468
5120
Right
3916
3463
5121
Right
1041
788
1198
1095
62
1097
8
3917
3463
5123
Left
3918
3470
5124
Left
3919
3459
5125
Right
3920
3471
5126
Right
1042
789
1199
1096
62
1098
8
3921
3252
5128
Left
3922
3473
5129
Left
3923
3474
5130
Right
3924
3475
5131
Right
1043
790
1200
3034
62
484
2
9639
10092
15995
Left
9640
3238
15996
Left
9641
10093
15997
Right
9642
10094
15998
Right
9643
3243
15999
Right
3073
731
4521
3037
62
1089
2
9650
3434
16045
Left
9651
10124
16046
Left
9652
3393
16047
Right
735
4534
16049
Left
736
4535
16050
Right
3076
780
4536
3038
62
2295
18
9653
3434
16052
Left
9654
10127
16053
Left
9655
3451
16054
Right
9656
10128
16055
Right
3077
2191
4537
3039
62
1046
2
9657
3110
16058
Left
9658
10131
16059
Left
9659
3014
16060
Right
737
4538
16062
Left
738
4539
16063
Right
3078
701
4540
167
132
62
14
false
1760
660
16
regular
141
3216
4762
Right
143
13
310
2780
0.7
0.7
0
2
1
490
240
144
66
585
1330
1.1
1.1
0
2
3
280
360
147
67
2215
2470
1.3
1.3
0
2
4
399
340
152
66
3960
1940
1.0
1.0
0
2
3
280
360
862
66
4595
2520
1.0
1.0
0
2
3
280
360
863
67
4520
1870
1.0
1.0
0
2
4
399
340
187448
1370
2780
2.5
2.5
0
2
14
327
267
479763
1005
630
1.0
1.0
0
2
1
490
240
201
M177 226 C177 176 227 126 277 126 C1762 126 3694 126 5179 126 C5229 126 5279 176 5279 226 C5279 1195 5279 2456 5279 3425 C5279 3475 5229 3525 5179 3525 C3694 3525 1762 3525 277 3525 C227 3525 177 3475 177 3425 C177 2456 177 1195 177 226
1
true
6
5102.0
3399.0
191
235
Endoplasmic Reticulum
550
1305
20
1.9
1.9
200
15
193
235
Peroxisome
2180
2625
20
1.6
1.6
200
15
194
235
Endoplasmic Reticulum
3920
1870
20
1.9
1.9
200
15
195
235
Peroxisome
4660
1785
20
1.6
1.6
200
15
197
235
Intracellular Space
625
175
20
1.9
1.9
200
15
198
235
Extracellular Space
675
5
20
1.6
1.6
200
15
803
235
Mitochondria
1085
565
20
1.6
1.6
200
15
892010
235
Cytosol
1430
810
20
2.5
2.5
200
15
892011
235
Mitochondria
205
2865
20
1.3
1.3
200
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_X000099
Context99
444
102
Compound
Increased
445
198
Compound
Increased
446
176
Protein
Mutated
755
[Uniprot: P47989](http://www.uniprot.org/uniprot/P47989)
99
Context
756
[OMIM: Entry 278300](http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=278300)
99
Context
757
Engelke, U., van der Graaf, M., Heerschap, A., Hoenderop, S., Moolenaar, S., Morava, E., Wevers, R. Handbook of 1H-NMR spectroscopy in inborn errors of metabolism: body fluid NMR spectroscopy and in vivo MR spectroscopy (2nd ed) (2007) p.101 Heilbronn: SPS Verlagsgesellschaft
99
Context
758
5629078
Cifuentes Delatte L, Castro-Mendoza H: [Familial xanthinuria]. Rev Clin Esp. 1967 Nov 30;107(4):244-56.
99
Context
759
927625
Frayha RA, Salti IS, Arnaout A, Khatchadurian A, Uthman SM: Hereditary xanthinuria: report on three patients and short review of the literature. Nephron. 1977;19(6):328-32. doi: 10.1159/000180910.
99
Context
760
3755469
Carpenter TO, Lebowitz RL, Nelson D, Bauer S: Hereditary xanthinuria presenting in infancy with nephrolithiasis. J Pediatr. 1986 Aug;109(2):307-9.
99
Context
761
861350
Auscher C, Pasquier C, de Gery A, Weissenbach R, Delbarre F: Xanthinuria : study of a large kindred with familial urolithiasis and gout. Biomedicine. 1977 Mar;27(2):57-9.
99
Context
278057
13176819
XANTHINURIA. Nutr Rev. 1954 Jul;12(7):200-2. doi: 10.1111/j.1753-4887.1954.tb03284.x.
99
Context