100
Pathway
Pyrimidine Metabolism
A group of heterocyclic aromatic organic compound, pyrimidines are similar in structure to benzene and pyridine and count the nucleic acids cytosine, thymine, and uracil as structural derivatives. The following pathway illustrates a many pyrimidine-associated processes such as nucleotide biosynthesis, degradation, and salvage. This pathway depicts a number of pyrimidine-related processes such as nucleotide biosynthesis, degradation, and salvage. For pyrimidine nucleotide biosynthesis, carbamoyl phosphate derived from the action of carbamoyl phosphate synthetase II (CPS-II) on glutamine and bicarbonate is converted into carbamoyl aspartate by aspartate transcarbamoylase, ATCase. Dihydroorotic acid is subsequently generated by the action of carbamoyl aspartate dehydrogenase on carbamoyl aspartate. Dihydroorotate dehydrogenase then converts dihydroorotic acid to orotic acid. From this point, orotate phosphoribosyltransferase incorporates phosphoribosyl pyrophosphate into (PRPP) to produce orotidine monophosphate. Orotidine-5’-phosphate carboxylase subsequently converts orotidine monophosphate into uridine monophosphate (UMP). UMP is further phosphorylated twice to form UTP; the first instance by uridylate kinase and the second instance by ubiquitous nucleoside diphosphate kinase. UTP moves into the CTP synthesis pathway with the action of CTP synthase which aminates the molecule.
The uridine nucleotides are also feedstock for the de novo thymine nucleotides synthesis pathway. DeoxyUMP which is derived from UDP or CDP metabolism is transformed by the action of thymidylate synthase into deoxyTMP of which the methyl group is sourced from N5,N10-methylene THF. THF is subsequently regenerated from DHF via dihydrofolate reductase (DHFR) which is essential for the continuation of thymidylate synthase activity. Serine hydroxymethyl transferase then acts on THF to regenerate N5,N10-THF.
Pyrimidine synthesis is a comparatively simpler process than purine synthesis due to a couple of factors; pyrimidine ring structure is assembled as a free base rather being derived from PRPP and there is no branch in the pyrimidine synthesis pathway as opposed to the purine synthesis pathway. For thymidine, the action of thymidine kinase on it (or alternatively deoxyuridine) plays an important role in what is referred to as the salvage pathway to dTTP synthesis. However to form dTMP, the action of thymine phosphorylase and thymidine kinase is required. For deoxycytidine, deoxycytidine kinase is required (deoxycytidine also acts on deoxyadenosine and deoxyguanosine). For uracil, UMP can be formed by the action of uridine phosphorylase and uridine kinase on uracil. Pyrimidine catabolism ultimately results in the formation of the waste products of urea, H2O, and CO2. The product of cytosine breakdown, uracil, can be broken down to N-carbamoyl-β-alanine which can be catabolized into β-alanine. The product of thymine breakdown is β-aminoisobutyrate. The transamination of α-ketoglutarate to glutamate requires both of these breakdown products (β-alanine and β-aminoisobutyrate) to act as amine group donors. The products of this transamination can move through a further reaction that produces malonyl-CoA or methylmalonyl-CoA, a precursor for succinyl-CoA which is used in the Krebs cycle.
Metabolic
PW000160
Center
PathwayVisualizationContext175
4500
3900
#000099
PathwayVisualization105
100
Pyrimidine Metabolism
A group of heterocyclic aromatic organic compound, pyrimidines are similar in structure to benzene and pyridine and count the nucleic acids cytosine, thymine, and uracil as structural derivatives. The following pathway illustrates a many pyrimidine-associated processes such as nucleotide biosynthesis, degradation, and salvage. This pathway depicts a number of pyrimidine-related processes such as nucleotide biosynthesis, degradation, and salvage. For pyrimidine nucleotide biosynthesis, carbamoyl phosphate derived from the action of carbamoyl phosphate synthetase II (CPS-II) on glutamine and bicarbonate is converted into carbamoyl aspartate by aspartate transcarbamoylase, ATCase. Dihydroorotic acid is subsequently generated by the action of carbamoyl aspartate dehydrogenase on carbamoyl aspartate. Dihydroorotate dehydrogenase then converts dihydroorotic acid to orotic acid. From this point, orotate phosphoribosyltransferase incorporates phosphoribosyl pyrophosphate into (PRPP) to produce orotidine monophosphate. Orotidine-5’-phosphate carboxylase subsequently converts orotidine monophosphate into uridine monophosphate (UMP). UMP is further phosphorylated twice to form UTP; the first instance by uridylate kinase and the second instance by ubiquitous nucleoside diphosphate kinase. UTP moves into the CTP synthesis pathway with the action of CTP synthase which aminates the molecule.
The uridine nucleotides are also feedstock for the de novo thymine nucleotides synthesis pathway. DeoxyUMP which is derived from UDP or CDP metabolism is transformed by the action of thymidylate synthase into deoxyTMP of which the methyl group is sourced from N5,N10-methylene THF. THF is subsequently regenerated from DHF via dihydrofolate reductase (DHFR) which is essential for the continuation of thymidylate synthase activity. Serine hydroxymethyl transferase then acts on THF to regenerate N5,N10-THF.
Pyrimidine synthesis is a comparatively simpler process than purine synthesis due to a couple of factors; pyrimidine ring structure is assembled as a free base rather being derived from PRPP and there is no branch in the pyrimidine synthesis pathway as opposed to the purine synthesis pathway. For thymidine, the action of thymidine kinase on it (or alternatively deoxyuridine) plays an important role in what is referred to as the salvage pathway to dTTP synthesis. However to form dTMP, the action of thymine phosphorylase and thymidine kinase is required. For deoxycytidine, deoxycytidine kinase is required (deoxycytidine also acts on deoxyadenosine and deoxyguanosine). For uracil, UMP can be formed by the action of uridine phosphorylase and uridine kinase on uracil. Pyrimidine catabolism ultimately results in the formation of the waste products of urea, H2O, and CO2. The product of cytosine breakdown, uracil, can be broken down to N-carbamoyl-β-alanine which can be catabolized into β-alanine. The product of thymine breakdown is β-aminoisobutyrate. The transamination of α-ketoglutarate to glutamate requires both of these breakdown products (β-alanine and β-aminoisobutyrate) to act as amine group donors. The products of this transamination can move through a further reaction that produces malonyl-CoA or methylmalonyl-CoA, a precursor for succinyl-CoA which is used in the Krebs cycle.
Metabolic
1
328
DNA reaction
SubPathway
499
192
Compound
2
500
57
Compound
2
501
201
Compound
2
502
1189
Compound
2
329
3
SubPathway
503
40
Compound
2
335
RNA reaction
SubPathway
527
790
Compound
2
528
1035
Compound
2
340
7
SubPathway
533
500
Compound
2
343
78
SubPathway
536
862
Compound
2
344
99
SubPathway
537
190
Compound
2
345
86
SubPathway
538
1993
Compound
2
107
Lehninger, A.L. Lehninger principles of biochemistry (4th ed.) (2005). New York: W.H Freeman.
100
Pathway
108
Salway, J.G. Metabolism at a glance (3rd ed.) (2004). Alden, Mass.: Blackwell Pub.
100
Pathway
1
Cell
CL:0000000
2
Platelet
CL:0000233
5
Hepatocyte
CL:0000182
3
Neuron
CL:0000540
4
Cardiomyocyte
CL:0000746
8
Beta cell
CL:0000639
7
Epithelial Cell
CL:0000066
6
Myocyte
CL:0000187
18
Erythrocyte
CL:0000232
1
Homo sapiens
9606
Eukaryote
Human
3
Escherichia coli
562
Prokaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
23
Pseudomonas aeruginosa
287
Prokaryote
12
Mus musculus
10090
Eukaryote
Mouse
17
Rattus norvegicus
10116
Eukaryote
Rat
5
Bos taurus
9913
Eukaryote
Cattle
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
2
Bacteria
2
Prokaryote
Bacteria
19
Schizosaccharomyces pombe
4896
Eukaryote
21
Xenopus laevis
8355
Eukaryote
African clawed frog
25
Escherichia coli (strain K12)
83333
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
5
Cytoplasm
GO:0005737
3
Mitochondrial Matrix
GO:0005759
1
Cytosol
GO:0005829
11
Extracellular Space
GO:0005615
31
Periplasmic Space
GO:0005620
2
Mitochondrion
GO:0005739
35
Chloroplast
GO:0009507
32
Inner Membrane
GO:0070258
14
Mitochondrial Outer Membrane
GO:0005741
15
Nucleus
GO:0005634
4
Peroxisome
GO:0005777
13
Endoplasmic Reticulum
GO:0005783
7
Endoplasmic Reticulum Membrane
GO:0005789
10
Cell Membrane
GO:0005886
27
Peroxisome Membrane
GO:0005778
12
Mitochondrial Inner Membrane
GO:0005743
6
Lysosome
GO:0005764
16
Lysosomal Lumen
GO:0043202
18
Melanosome Membrane
GO:0033162
25
Golgi Apparatus
GO:0005794
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
40
Periplasm
GO:0042597
19
Sarcoplasmic Reticulum
GO:0016529
24
Mitochondrial Intermembrane Space
GO:0005758
26
Golgi Apparatus Membrane
GO:0000139
39
Mitochondrial membrane
GO:0031966
2
Endothelium
BTO:0000393
1
Liver
BTO:0000759
72
9
7
Nervous System
BTO:0001484
18
Pancreas
BTO:0000988
25
Intestine
BTO:0000648
8
Blood Vessel
BTO:0001102
74
11
4
Adrenal Medulla
BTO:0000049
71
8
28
Stomach
BTO:0001307
155
26
11
Heart
BTO:0000562
73
10
6
Kidney
BTO:0000671
71
8
5
cardiocyte
BTO:0001539
9
Muscle
BTO:0000887
141
18
3
Sympathetic Nervous System
BTO:0001832
8
5
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51
1
PW_BS000024
195
13
18
PW_BS000024
168
32
1
PW_BS000168
102
12
3
1
PW_BS000102
156
12
24
1
PW_BS000156
179
12
21
1
PW_BS000179
358
39
12
PW_BS000028
369
12
60
1
PW_BS000028
186
12
2
1
PW_BS000024
289
2
49
1
PW_BS000024
19
3
5
1
3
PW_BS000019
961
1
2
1
5
PW_BS000564
55
1
12
1
5
PW_BS000055
1076
1
1
18
PW_BS000578
833
5
138
1
PW_BS000548
843
1
138
1
PW_BS000549
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
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
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
463
Hydrogen carbonate
HMDB0000595
Bicarbonate, or hydrogen carbonate, is a simple single carbon molecule that plays surprisingly important roles in diverse biological processes. Among these are photosynthesis, the Krebs cycle, whole-body and cellular pH regulation, and volume regulation. Since bicarbonate is charged it is not permeable to lipid bilayers. Mammalian membranes thus contain bicarbonate transport proteins to facilitate the specific transmembrane movement of HCO3(-). Bicarbonate ion is an anion that consists of one central carbon atom surrounded by three oxygen atoms in a trigonal planar arrangement, with a hydrogen atom attached to one of the oxygens. The bicarbonate ion carries a negative one formal charge and is the conjugate base of carbonic acid, H2CO3. The carbonate radical is an elusive and strong one-electron oxidant. Bicarbonate in equilibrium with carbon dioxide constitutes the main physiological buffer. The bicarbonate-carbon dioxide pair stimulates the oxidation, peroxidation and nitration of several biological targets. The demonstration that the carbonate radical existed as an independent species in aqueous solutions at physiological pH and temperature renewed the interest in the pathophysiological roles of this radical and related species. The carbonate radical has been proposed to be a key mediator of the oxidative damage resulting from peroxynitrite production, xanthine oxidase turnover and superoxide dismutase1 peroxidase activity. The carbonate radical has also been proposed to be responsible for the stimulatory effects of the bicarbonate-carbon dioxide pair on oxidations mediated by hydrogen peroxide/transition metal ions. The ultimate precursor of the carbonate radical anion being bicarbonate, carbon dioxide, peroxymonocarbonate or complexes of transition metal ions with bicarbonate-derived species remains a matter of debate. The carbonate radical mediates some of the pathogenic effects of peroxynitrite. The carbonate radical as the oxidant produced from superoxide dismutase (EC 1.15.1.1, SOD1) peroxidase activity. Peroxymonocarbonate is a biological oxidant, whose existence is in equilibrium with hydrogen peroxide and bicarbonate. (PMID: 17505962, 17215880).
71-52-3
C00288
769
17544
HCO3
749
OC(O)=O
CH2O3
InChI=1S/CH2O3/c2-1(3)4/h(H2,2,3,4)
BVKZGUZCCUSVTD-UHFFFAOYSA-N
carbonic acid
62.0248
62.00039393
0.57
2
carbonic acid
0
-1
FDB022134
Bicarbonate;Bicarbonate (hco3-);Bicarbonate anion;Bicarbonate ion;Bicarbonate ion (hco31-);Bicarbonate ions;Carbonate;Carbonate (hco31-);Carbonate ion (hco31-);Carbonic acid;Hydrocarbonate(1-);Hydrogen carbonate;Hydrogen carbonate (hco3-);Hydrogen carbonate anion;Hydrogen carbonate ion;Hydrogen carbonate ion (hco3-);Hydrogencarbonate;Hydrogentrioxocarbonate;Monohydrogen carbonate;[co2(oh)](-);Acid carbonate;Hco3(-);Hydrogen carbonic acid;Acid carbonic acid;Bicarbonic acid;Bicarbonic acid ion
PW_C000463
HCO3
22
4
1687
8
2393
3
2397
2
2613
15
3145
70
5391
103
5445
120
5571
133
6049
155
6110
161
6494
178
7482
222
9092
224
77959
112
78630
132
78762
111
80029
368
119993
406
121209
407
121436
122
121557
124
123779
119
123994
135
124115
118
125372
479
126059
297
126360
299
126541
481
126914
501
127511
205
127922
388
128114
206
862
Carbamoyl phosphate
HMDB0001096
Carbamoyl phosphate is a precursor of both arginine and pyrimidine biosynthesis. It is a labile and potentially toxic intermediate. Carbamoyl phosphate is a molecule that is involved in ridding the body of excess nitrogen in the urea cycle, and also in the synthesis of pyrimidines. It is produced from carbon dioxide, ammonia, and phosphate (from ATP) by the enzyme carbamoyl phosphate synthase. -- Wikipedia.
590-55-6
C00169
278
17672
CARBAMOYL-P
272
NC(=O)OP(O)(O)=O
CH4NO5P
InChI=1S/CH4NO5P/c2-1(3)7-8(4,5)6/h(H2,2,3)(H2,4,5,6)
FFQKYPRQEYGKAF-UHFFFAOYSA-N
(carbamoyloxy)phosphonic acid
141.0199
140.982708755
-0.96
3
carbamoyl-phosphate
0
-2
FDB022424
Carbamic acid monoanhydride with phosphorate;Carbamic acid monoanhydride with phosphoric acid;Carbamoyl-p;Carbamoyl-phosphate;Carbamoylphosphate;Carbamyl phosphate;Carbamyl-phosphate;Aminocarbonyl dihydrogen phosphate;Carbamic phosphoric monoanhydride;Carbamoyl phosphate;Monocarbamoyl phosphate;Phosphoric acid mono(formamide)ester;Aminocarbonyl dihydrogen phosphoric acid;Carbamoyl phosphoric acid;Carbamoyl phosphoric acid;Carbamyl phosphoric acid;Monocarbamoyl phosphoric acid;Phosphate mono(formamide)ester
PW_C000862
CarbmP
89
8
441
4
2702
2
9268
13
11853
161
12730
290
77331
133
77547
111
78725
132
80672
135
120092
122
120345
406
122199
124
122995
120
124751
118
125462
297
125665
479
126361
299
126999
205
127160
501
127923
388
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
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
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
662
Ureidosuccinic acid
HMDB0000828
Ureidosuccinic acid, also known as L-ureidosuccinate or carbamyl-L-aspartate, belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Ureidosuccinic acid exists as a solid, soluble (in water), and a weakly acidic compound (based on its pKa). Ureidosuccinic acid has been found in human prostate tissue, and has also been primarily detected in saliva. Within the cell, ureidosuccinic acid is primarily located in the cytoplasm. Ureidosuccinic acid exists in all living organisms, ranging from bacteria to humans. In humans, ureidosuccinic acid is involved in the aspartate metabolism pathway and the pyrimidine metabolism pathway. Ureidosuccinic acid is also involved in several metabolic disorders, some of which include the canavan disease pathway, UMP synthase deficiency (orotic aciduria), dihydropyrimidinase deficiency, and Beta ureidopropionase deficiency. Outside of the human body, ureidosuccinic acid can be found in a number of food items such as green vegetables, celeriac, pepper (c. frutescens), and italian sweet red pepper. This makes ureidosuccinic acid a potential biomarker for the consumption of these food products. Ureidosuccinic acid is an intermediary product in pyrimidine biosynthesis.
13184-27-5
C00438
93072
15859
CARBAMYUL-L-ASPARTATE
84022
DB04252
NC(=O)N[C@@H](CC(O)=O)C(O)=O
C5H8N2O5
InChI=1S/C5H8N2O5/c6-5(12)7-2(4(10)11)1-3(8)9/h2H,1H2,(H,8,9)(H,10,11)(H3,6,7,12)/t2-/m0/s1
HLKXYZVTANABHZ-REOHCLBHSA-N
(2S)-2-(carbamoylamino)butanedioic acid
176.1274
176.043321376
-0.92
4
carbamylaspartic acid
0
-2
FDB022269
2-ureidobutanedioate;2-ureidobutanedioic acid;Carbamoylaspartic acid;Carbamyl-l-aspartic acid;Carbamylaspartic acid;L-n-carbamoylaspartic acid;L-ureidosuccinate;L-ureidosuccinic acid;N-(aminocarbonyl)-l-aspartic acid;N-carbamoyl-l-aspartate;N-carbamoyl-l-aspartic acid;N-carbamoyl-s-aspartic acid;N-carbamoylaspartate;N-carbamoylaspartic acid;Ncd;Ureidosuccinate;Carbamyl-l-aspartate;(2s)-2-(carbamoylamino)butanedioate;N-(aminocarbonyl)-l-aspartate;N-carbamoyl-s-aspartate
PW_C000662
USuccA
90
8
2705
2
12731
290
77548
111
78726
132
120093
122
122201
124
122837
135
124753
118
125463
297
126363
299
127000
205
127925
388
1852
L-Dihydroorotic acid
HMDB0003349
L-Dihydroorotic acid, also known as (S)-4,5-dihydroorotate or dihydro-L-orotate, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. L-Dihydroorotic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Within the cell, L-dihydroorotic acid is primarily located in the cytoplasm and mitochondria. In humans, L-dihydroorotic acid is involved in the pyrimidine metabolism pathway. L-Dihydroorotic acid is also involved in several metabolic disorders, some of which include dihydropyrimidinase deficiency, UMP synthase deficiency (orotic aciduria), the mngie (mitochondrial neurogastrointestinal encephalopathy) pathway, and Beta ureidopropionase deficiency. Outside of the human body, L-dihydroorotic acid can be found in a number of food items such as custard apple, chicory, fox grape, and tarragon. This makes L-dihydroorotic acid a potential biomarker for the consumption of these food products. L-Dihydroorotic acid is an intermediate in the metabolism of Pyrimidine. It is a substrate for Dihydroorotate dehydrogenase (mitochondrial).
5988-19-2
C00337
439216
17025
DI-H-OROTATE
388355
DB02129
OC(=O)[C@@H]1CC(=O)NC(=O)N1
C5H6N2O4
InChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)/t2-/m0/s1
UFIVEPVSAGBUSI-REOHCLBHSA-N
(4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid
158.1121
158.03275669
-1.10
3
L-dihydroorotic acid
0
-1
FDB023149
(s)-4,5-dihydroorotate;(s)-dihydroorotate;Dihydro-l-orotate;Dihydro-l-orotic acid;L-dihydroorotate;L-dihydroorotic acid;(s)-4,5-dihydroorotic acid
PW_C001852
L-Dhoa
2706
2
78727
132
122202
124
124754
118
126364
299
127926
388
1860
Quinone
HMDB0003364
Quinone is also called 1,4-benzoquinone or cyclohexadienedione. Quinones are oxidized derivatives of aromatic compounds and are often readily made from reactive aromatic compounds with electron-donating substituents such as phenols and catechols, which increase the nucleophilicity of the ring and contributes to the large redox potential needed to break aromaticity. Derivatives of quinones are common constituents of biologically relevant molecules. Some serve as electron acceptors in electron transport chains such as those in photosynthesis (plastoquinone, phylloquinone), and aerobic respiration (ubiquinone). Quinone is a common constituent of biologically relevant molecules (e.g. Vitamin K1 is phylloquinone). A natural example of quinones as oxidizing agents is the spray of bombardier beetles. Hydroquinone is reacted with hydrogen peroxide to produce a fiery blast of steam, a strong deterent in the animal world.
106-51-4
C00472
4650
16509
CPD-8130
4489
O=C1C=CC(=O)C=C1
C6H4O2
InChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H
AZQWKYJCGOJGHM-UHFFFAOYSA-N
cyclohexa-2,5-diene-1,4-dione
108.0948
108.021129372
-0.38
0
quinone
0
0
FDB005755
1,4-benzoquine;1,4-benzoquinone;1,4-cyclohexadiene dioxide;1,4-cyclohexadienedione;1,4-diossibenzene;1,4-dioxy-benzol;1,4-dioxybenzene;2,5-cyclohexadiene-1,4-dione;2,5-cyclohexadiene-1-4-dione;Benzo-1,4-quinone;Benzo-chinon;Benzoquinone;Benzoquinone [un2587];Chinon;Chinone;Cyclohexadiene-1,4-dione;Cyclohexadienedione;Eldoquin;Para-benzoquinone;Para-quinone;Quinone1,4-benzoquinone;Semiquinone anion;Semiquinone radicals;P-benzoquinone;P-chinon;P-quinone;1,4-benzochinon;Quinone
PW_C001860
Quinone
1184
33
2707
2
3835
14
4622
22
4900
3
5891
95
78031
112
78051
329
78728
132
78806
343
120758
407
120884
415
121414
382
122203
124
123355
119
123460
451
123973
399
124755
118
125790
481
126365
299
127245
206
127306
504
127928
388
151
Orotic acid
HMDB0000226
Orotic acid is a minor dietary constituent. Indeed, until it was realized that it could be synthesized by humans, orotic acid was known as vitamin B-13. The richest dietary sources of orotic acid are cow's milk and other dairy products as well as root vegetables such as carrots and beets. Dietary intake probably contributes to a basal rate of orotic acid excretion in urine because fasting decreases excretion by ~50%. However, it is now apparent that most urinary orotic acid is synthesized in the body, where it arises as an intermediate in the pathway for the synthesis of pyrimidine nucleotides. Orotic acid is converted to UMP by UMP synthase, a multifunctional protein with both orotate phosphoribosyltransferase and orotidylate decarboxylase activity. The most frequently observed inborn error of pyrimidine nucleotide synthesis is a mutation of the multifunctional protein UMP synthase (UMP synthase deficiency or orotic aciduria). This disorder prevents the conversion of orotic acid to UMP, and thus to other pyrimidines. As a result, plasma orotic acid accumulates to high concentrations, and increased quantities appear in the urine. Indeed, urinary orotic acid is so markedly increased in individuals harboring a mutation in UMP synthase that orotic acid crystals can form in the urine. The urinary concentration of orotic acid in individuals suffering from orotic aciduria can be of the order of millimoles per millimole creatinine. By comparison, the urinary level in unaffected individuals is ~ 1 µmol/mmol creatinine (PMID: 17513443). Orotic aciduria is characterized by megaloblastic anemia and orotic acid crystalluria that is frequently associated with some degree of physical and mental retardation. These features respond to appropriate pyrimidine replacement therapy and most cases appear to have a good prognosis. When present in sufficiently high levels, orotic acid can act as an acidogen and a metabotoxin. 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. Chronically high levels of orotic acid are associated with at least seven inborn errors of metabolism, including argininemia, LPI syndrome (lysinuric protein intolerance), hyperornithinemia-hyperammonemia-homocitrullinuria (HHH), OTC deficiency, citrullinemia type I, purine nucleoside phosphorylase deficiency, and orotic aciduria. Orotic acid is an organic acid. 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 abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures.
65-86-1
C00295
967
16742
OROTATE
942
DB02262
OC(=O)C1=CC(=O)NC(=O)N1
C5H4N2O4
InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
PXQPEWDEAKTCGB-UHFFFAOYSA-N
2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
156.0963
156.017106626
-1.54
3
orotic acid
0
-1
FDB012327
1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid;1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidecarboxylic acid;1,2,3,6-tetrahydro-2,6-dioxopyrimidin-4-carbonsaeure;2,6-dihydroxy-4-pyrimidinecarboxylic acid;2,6-dihydroxypyrimidine-4-carboxylic acid;2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid;2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid;6-carboxy-2,4-dihydroxypyrimidine;6-carboxyuracil;6-uracilcarboxylic acid;Acide orotique;Acido orotico;Acidum oroticum;Animal galactose factor;Lactinium;Molkensaeure;Oro;Orodin;Oropur;Orotate;Orotic acid;Orotonin;Orotonsan;Orotsaeure;Orotsaure;Oroturic;Orotyl;Uracil-6-carbosaeure;Uracil-6-carboxylate;Uracil-6-carboxylic acid;Vitamin b13;Whey factor
PW_C000151
Orotate
2708
2
78729
132
122204
124
124756
118
126366
299
127929
388
1170
Flavin Mononucleotide
HMDB0001520
Flavin mononucleotide (FMN), or riboflavin-5?-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase as well as cofactor in biological blue-light photo receptors. During the catalytic cycle, the reversible interconversion of oxidized (FMN), semiquinone (FMNH) and reduced (FMNH2) forms occurs in the various oxidoreductases. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers. Flavin mononucleotide is also used as an orange-red food colour additive. It is the principal form in which riboflavin is found in cells and tissues.
146-17-8
C00061
643976
17621
FMN
559060
DB03247
CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=NC(=O)NC(=O)C1=N2
C17H21N4O9P
InChI=1S/C17H21N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H,20,25,26)(H2,27,28,29)/t11-,12+,14-/m0/s1
FVTCRASFADXXNN-SCRDCRAPSA-N
{[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}phosphonic acid
456.3438
456.104614802
-2.83
6
riboflavin 5'-phosphate
0
-3
FDB001984
Fmn;Flanin;Flavine mononucleotide;Flavol;Riboflavin;Riboflavin 5'-monophosphate;Riboflavin 5'-phosphate;Riboflavin mononucleotide;Riboflavin monophosphate;Riboflavin phosphate;Riboflavin-5'-phosphate na;Riboflavin-5-phosphate;Riboflavine 5'-monophosphate;Riboflavine 5'-phosphate;Riboflavine dihydrogen phosphate;Riboflavine monophosphate;Riboflavine phosphate;Riboflavine-5'-phosphate;Vitamin b2 phosphate;Flavin mononucleotide;Riboflavin 5'-(dihydrogen phosphate)
PW_C001170
FlvnMnt
539
8
1190
14
1692
2
4961
31
5772
101
11900
211
12313
225
77519
115
77590
111
78730
132
120433
405
120454
122
121929
124
123067
376
123088
135
124482
118
125698
297
126104
299
127190
205
127312
209
127686
388
140703
49
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
144
Orotidylic acid
HMDB0000218
Orotidylic acid (OMP), is a pyrimidine nucleotide which is the last intermediate in the biosynthesis of uridine monophosphate. Decarboxylation by Orotidylate decarboxylase affords Uridine 5'-phosphate which is the route to Uridine and its derivatives de novo and consequently one of the most important processes in nucleic acid synthesis (Dictionary of Organic Compounds). In humans, the enzyme UMP synthase converts OMP into uridine 5'- monophosphate. If UMP synthase is defective, orotic aciduria can result. (Wikipedia).
2149-82-8
C01103
160617
15842
OROTIDINE-5-PHOSPHATE
141140
DB02957
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C(=O)NC(=O)C=C1C(O)=O
C10H13N2O11P
InChI=1S/C10H13N2O11P/c13-5-1-3(9(16)17)12(10(18)11-5)8-7(15)6(14)4(23-8)2-22-24(19,20)21/h1,4,6-8,14-15H,2H2,(H,16,17)(H,11,13,18)(H2,19,20,21)/t4-,6-,7-,8-/m1/s1
KYOBSHFOBAOFBF-XVFCMESISA-N
3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
368.1908
368.02569578
-1.63
6
6-carboxy-5'-uridylic acid
0
-3
FDB012321
1,2,3,6-tetrahydro-2,6-dioxo-3-(5-o-phosphono-b-d-ribofuranosyl)-4-pyrimidinecarboxylate;1,2,3,6-tetrahydro-2,6-dioxo-3-(5-o-phosphono-b-d-ribofuranosyl)-4-pyrimidinecarboxylic acid;1,2,3,6-tetrahydro-2,6-dioxo-3-(5-o-phosphono-beta-delta-ribofuranosyl)-4-pyrimidinecarboxylate;1,2,3,6-tetrahydro-2,6-dioxo-3-(5-o-phosphono-beta-delta-ribofuranosyl)-4-pyrimidinecarboxylic acid;2,6-dioxo-3-(5-o-phosphono-beta-d-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid;2,6-dioxo-3-(5-o-phosphono-beta-delta-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid;5'-(dihydrogen phosphate) 6-carboxy-uridine;5'-(dihydrogen phosphate) orotidine;5'-omp;5'-phosphate orotidine;5-(dihydrogen phosphate)orotidine;6-carboxy-5'-uridylate;6-carboxy-5'-uridylic acid;Omp;Ometoprim;Omp (nucleotide);Orotidine 5'-(dihydrogen phosphate);Orotidine 5'-monophosphate;Orotidine 5'-phosphate;Orotidine monophosphate;Orotidine-5'-phosphate;Orotidylate;Orotidylic acid;Orotidine 5'-phosphoric acid;Orotidine 5'-(dihydrogen phosphoric acid)
PW_C000144
OMP
2710
2
3450
3
78097
112
78731
132
122144
407
122206
124
124696
119
124758
118
126301
481
126368
299
127865
206
127931
388
194
Uridine 5'-monophosphate
HMDB0000288
5'-Uridylic acid. A uracil nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position. Uridine 5'-monophosphate is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside uridine. UMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase uracil. (Wikipedia).
58-97-9
C00105
6030
16695
UMP
5808
DB03685
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=CC(=O)NC1=O
C9H13N2O9P
InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
DJJCXFVJDGTHFX-XVFCMESISA-N
{[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
324.1813
324.035866536
-1.43
5
uridine monophosphate
0
-2
FDB007508
5'-ump;Ump;Uridine 5'-monophosphate;Uridine 5'-phosphate;Uridine 5'-phosphorate;Uridine 5'-phosphoric acid;Uridine mono(dihydrogen phosphate);Uridine monophosphate;Uridine phosphate;Uridine-5'-monophosphate;Uridylic acid;5'uridylic acid;Pu;Uridine 5'-(dihydrogen phosphate);Uridylate
PW_C000194
U-5-P
1527
2
1591
43
78257
132
78271
356
121367
124
121382
419
123926
118
123941
455
126040
299
126055
490
127492
388
127507
507
201
Uridine 5'-diphosphate
HMDB0000295
Uridine 5'-diphosphate is a uracil nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety. UDP is an important extracellular pyrimidine signaling molecule that mediates diverse biological effects via P1 and P2 purinergic receptors, such as the uptake of thymidine and proliferation of gliomas. (PMID: 14558596). UDP induces intracellular Ca(2+) responses and oscillations in HeLa cells, due to the activation of P2Ys (G-protein coupled ATP receptors). (PMID: 1257952).
58-98-0
C00015
6031
17659
UDP
5809
DB03435
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O
C9H14N2O12P2
InChI=1S/C9H14N2O12P2/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
XCCTYIAWTASOJW-XVFCMESISA-N
[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
404.1612
404.002196946
-1.66
6
UDP
0
-2
FDB007509
5'-udp;Udp;Uridine 5'-diphosphate;Uridine 5'-pyrophosphate;Uridine 5'-pyrophosphorate;Uridine 5'-pyrophosphoric acid;Uridine diphosphate;Uridine pyrophosphate;Uridine 5'-diphosphoric acid;Uridine diphosphoric acid
PW_C000201
UDP
410
8
1517
2
1545
43
2197
49
2352
9
3115
29
4463
18
4518
10
4846
36
4946
92
5178
95
5527
130
5834
141
7057
160
7246
213
7248
214
7287
210
8433
151
11913
164
12615
225
77304
111
77360
331
77924
336
78255
132
78264
356
120315
122
121252
429
121365
124
121375
419
122101
383
122378
125
122970
135
123822
464
123924
118
123934
455
124652
398
124932
136
125643
297
126038
299
126048
490
126257
495
127490
388
127500
507
127820
390
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
192
Uridine triphosphate
HMDB0000285
Uridine 5'-(tetrahydrogen triphosphate). A uracil nucleotide containing three phosphate groups esterified to the sugar moiety. Uridine triphosphate has the role of a source of energy or an activator of substrates in metabolic reactions, like that of adenosine triphosphate, but more specific. When Uridine triphosphate activates a substrate, UDP-substrate is usually formed and inorganic phosphate is released. (Wikipedia).
63-39-8
C00075
6133
15713
UTP
5903
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O
C9H15N2O15P3
InChI=1S/C9H15N2O15P3/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
PGAVKCOVUIYSFO-XVFCMESISA-N
({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
484.1411
483.968527356
-1.76
7
uridine 5'-triphosphoric acid
0
-3
FDB021929
5'-utp;Utp;Uridine 5'-triphosphate;Uridine mono(tetrahydrogen triphosphate);Uridine triphosphate;Uteplex;H4utp;Uridine 5'-triphosphoric acid
PW_C000192
UTP
393
8
1514
2
3123
29
5979
147
6175
108
7270
160
42712
315
77299
111
77932
336
78252
132
120310
122
121262
429
121362
124
122965
135
123832
464
123921
118
125639
297
126035
299
127271
205
127487
388
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
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
1918
3'-AMP
HMDB0003540
3-AMP, also known as 3'-adenylic acid or AMP 3'-phosphate, belongs to the class of organic compounds known as ribonucleoside 3'-phosphates. These are ribonucleosides that contain a phosphate group attached to the C-3 carbon of the ribose or deoxyribose moiety. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives. 3-AMP exists as a solid, slightly soluble (in water), and an extremely strong acidic compound (based on its pKa). 3-AMP has been primarily detected in saliva. 3-AMP exists in all living organisms, ranging from bacteria to humans. In humans, 3-AMP is involved in the tryptophan metabolism pathway, the pyrimidine metabolism pathway, congenital bile acid synthesis defect type II pathway, and congenital bile acid synthesis defect type III pathway. 3-AMP is also involved in several metabolic disorders, some of which include Beta ureidopropionase deficiency, dihydropyrimidinase deficiency, 27-hydroxylase deficiency, and the mngie (mitochondrial neurogastrointestinal encephalopathy) pathway. 3-AMP is adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2-, 3-, or 5-position.
84-21-9
C01367
41211
28931
37610
NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](OP(O)(O)=O)[C@H]3O)C2=NC=N1
C10H14N5O7P
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(17)7(4(1-16)21-10)22-23(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
LNQVTSROQXJCDD-KQYNXXCUSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid
347.2212
347.063084339
-2.00
5
adenosine-3'-phosphate
0
-2
FDB023193
3'-adenosine monophosphate;3'-adenylic acid;Amp 3'-phosphate;Adenosine 3'-monophosphate;Adenosine 3'-phosphate;Adenosine-3'-monophosphate;Adenosine-3'-monophosphoric acid;Adenosine-3'-phosphate;Synadenylic acid;Yeast adenylic acid;3'-adenosine monophosphoric acid;3'-adenylate;Adenosine 3'-monophosphoric acid;Adenosine 3'-phosphoric acid;Amp 3'-phosphoric acid;Synadenylate
PW_C001918
3'-AMP
2715
2
2816
29
77636
336
78732
132
121668
429
121740
124
124222
464
124291
118
126371
299
127626
388
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
57
Cytidine triphosphate
HMDB0000082
Cytidine 5'-(tetrahydrogen triphosphate) or CTP is a cytosine nucleotide containing three phosphate groups esterified to a ribose moiety at the 5' position. CTP is integral to the synthesis or mRNA, rRNA and tRNA through RNA polymerases. Cytidine triphosphate (CTP) is also critical to the synthesis of phosphatidylcholine via the enzyme CTP: phosphocholine cytidyltransferase. This reaction is the rate-limiting step in the synthesis of phosphatidylcholine.
65-47-4
C00063
6176
17677
CTP
5941
DB02431
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C9H16N3O14P3
InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
PCDQPRRSZKQHHS-XVFCMESISA-N
({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
483.1563
482.984511771
-1.64
7
CTP
0
-3
FDB012833
5'-(tetrahydrogen triphosphate) cytidine;5'-ctp;Ctp;Cytidine 3'-triphosphate;Cytidine 5'-(tetrahydrogen triphosphate);Cytidine 5'-triphosphate;Cytidine 5'-triphosphoric acid;Cytidine 5-prime-triphosphate;Cytidine triphosphate;Cytidine mono;Cytidine mono(tetrahydrogen triphosphate) (ester);Cytidine-5'-triphosphate;Deoxycytosine triphosphate;H4ctp
PW_C000057
CTP
427
23
1150
8
2718
2
5766
101
5800
108
7077
188
7593
160
9137
195
9142
213
12194
164
12510
288
15285
151
15317
249
15342
22
15374
18
34759
17
42650
315
77315
128
78448
111
78733
132
79949
134
79957
130
79964
329
80416
170
94784
384
94812
125
94817
382
98677
223
110633
391
113268
395
113273
389
115525
136
115530
399
120328
410
120854
122
121340
121
122212
124
122983
444
123434
135
124764
118
125654
485
125840
297
126374
299
127292
205
127935
388
790
dCTP
HMDB0000998
dCTP, also known as deoxy-ctp, belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside triphosphates. These are pyrimidine nucleotides with a triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. dCTP is soluble (in water) and an extremely strong acidic compound (based on its pKa). dCTP has been primarily detected in blood. Within the cell, dCTP is primarily located in the cytoplasm, mitochondria and nucleus. dCTP exists in all living organisms, ranging from bacteria to humans. dCTP participates in a number of enzymatic reactions. In particular, dCTP can be biosynthesized from dCDP through its interaction with the enzyme nucleoside diphosphate kinase. In addition, dCTP can be biosynthesized from cytidine triphosphate through its interaction with the enzyme ribonucleoside-triphosphate reductase. In humans, dCTP is involved in the pyrimidine metabolism pathway. dCTP is also involved in several metabolic disorders, some of which include the mngie (mitochondrial neurogastrointestinal encephalopathy) pathway, Beta ureidopropionase deficiency, UMP synthase deficiency (orotic aciduria), and dihydropyrimidinase deficiency. Deoxycytidine triphosphate (dCTP) is a cytidine nucleotide triphosphate that is used whenever DNA is synthesized, such as in the polymerase chain reaction. e.g.:.
2056-98-6
C00458
65091
16311
DCTP
58601
NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1
C9H16N3O13P3
InChI=1S/C9H16N3O13P3/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(23-8)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,13H,3-4H2,(H,18,19)(H,20,21)(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
RGWHQCVHVJXOKC-SHYZEUOFSA-N
({[({[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
467.1569
466.989597149
-1.60
6
dCTP
0
-3
FDB022359
2'-deoxycytidine-5'-triphosphate;Deoxy-ctp;Deoxycytidine-triphosphate;Dctp;2'-deoxycytidine 5'-triphosphate;Deoxycytidine 5'-triphosphate;Deoxycytidine triphosphate;2'-deoxycytidine 5'-triphosphoric acid;Deoxycytidine 5'-triphosphoric acid;Deoxycytidine triphosphoric acid
PW_C000790
dCTP
2719
2
12753
151
78734
132
122213
124
124765
118
126375
299
127936
388
1189
CDP
HMDB0001546
CDP, also known as 5'-cdp, belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. CDP is soluble (in water) and a moderately acidic compound (based on its pKa). CDP has been primarily detected in blood. Within the cell, CDP is primarily located in the mitochondria, nucleus and cytoplasm. In humans, CDP is involved in the pyrimidine metabolism pathway. CDP is also involved in several metabolic disorders, some of which include dihydropyrimidinase deficiency, UMP synthase deficiency (orotic aciduria), the mngie (mitochondrial neurogastrointestinal encephalopathy) pathway, and Beta ureidopropionase deficiency. Cytidine 5\'-(trihydrogen diphosphate). A cytosine nucleotide containing two phosphate groups esterified to the sugar moiety. Synonyms: CRPP; cytidine pyrophosphate.
63-38-7
C00112
6132
17239
CDP
5902
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C9H15N3O11P2
InChI=1S/C9H15N3O11P2/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
ZWIADYZPOWUWEW-XVFCMESISA-N
[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
403.1764
403.018181361
-1.60
6
CDP
0
-2
FDB022683
Cdp;Cytidine-5'-diphosphate;Cytidine-diphosphate;5'-cdp;Cytidine 5'-diphosphate;Cytidine 5'-diphosphoric acid;Cytidine 5'-pyrophosphate;Cytidine diphosphate;Cytidine, 5'-(trihydrogen pyrophosphate);Cytidine 5'-pyrophosphoric acid;Cytidine diphosphoric acid;Cytidine, 5'-(trihydrogen pyrophosphoric acid);Cytidine-5'-diphosphoric acid
PW_C001189
CDP
2733
2
9140
195
9143
213
78735
132
122215
124
124767
118
126377
299
127939
388
64
Cytidine monophosphate
HMDB0000095
Cytidine monophosphate, also known as 5'-cytidylic acid and abbreviated CMP, is a nucleotide. It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine. Cytidine monophosphate (CMP) is derived from cytidine triphosphate (CTP) with subsequent loss of two phosphates. The synthesis of the pyrimidines CTP and UTP occurs in the cytoplasm and starts with the formation of carbamoyl phosphate from glutamine and CO2. Next, aspartate undergoes a condensation reaction with carbamoyl-phosphate to form orotic acid. In a subsequent cyclization reaction, the enzyme Aspartate carbamoyltransferase forms N-carbamoyl-aspartate which is converted into dihydroorotic acid by Dihydroorotase. The latter is converted to orotate by Dihydroorotate oxidase. Orotate is covalently linked with a phosphorylated ribosyl unit with Orotate phosphoribosyltransferase (aka "PRPP transferase") catalyzing reaction, yielding orotidine monophosphate (OMP). Orotidine-5-phosphate is decarboxylated by Orotidine-5'-phosphate decarboxylase to form uridine monophosphate (UMP). UMP is phosphorylated by two kinases to uridine triphosphate (UTP) via two sequential reactions with ATP. CTP is subsequently formed by amination of UTP by the catalytic activity of CTP synthetase. Cytosine monophosphate (CMP) and uridine monophosphate (UMP) have been prescribed for the treatment of neuromuscular affections in humans. Patients treated with CMP/UMP recover from altered neurological functions. Additionally, the administration of CMP/UMP appears to favour the entry of glucose in the muscle and CMP/UMP may be important in maintaining the level of hepatic glycogen constant during exercise. [PMID:18663991].
63-37-6
C00055
6131
17361
CMP
5901
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
C9H14N3O8P
InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
IERHLVCPSMICTF-XVFCMESISA-N
{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
323.1965
323.051850951
-1.30
5
cytidine monophosphate
0
-2
FDB011882
5'-cmp;5-cytidylate;5-cytidylic acid;Cmp;Cytidine 5'-monophosphate;Cytidine 5'-monophosphorate;Cytidine 5'-monophosphoric acid;Cytidine 5'-phosphate;Cytidine 5'-phosphorate;Cytidine 5'-phosphoric acid;Cytidine mono(dihydrogen phosphate);Cytidine monophosphate;Cytidylate;Cytidylic acid;Cytidine-5'-monophosphate;Pc;Cytidine-5'-monophosphoric acid
PW_C000064
CMP
1151
8
2512
14
2734
2
3386
18
4972
56
5768
101
5802
108
7079
188
7595
160
9147
249
9151
224
9257
195
12196
164
12210
151
15274
285
15336
308
15373
49
34815
17
42652
315
78449
111
78488
115
78573
130
78736
132
79953
134
79969
331
80421
170
94791
384
94821
383
98680
223
110637
391
113277
390
115535
398
120855
122
121346
121
122216
124
122487
405
122605
125
123435
135
124768
118
125053
376
125177
136
125841
297
126378
299
126641
478
126752
300
127293
205
127940
388
128217
209
128346
395
61
Cytidine
HMDB0000089
Cytidine is a nucleoside that is composed of the base cytosine linked to the five-carbon sugar D-ribose. Cytidine is a pyrimidine that besides being incorporated into nucleic acids, can serve as a substrate for the salvage pathway of pyrimidine nucleotide synthesis. It is a precursor of cytidine triphosphate (CTP) needed in the phosphatidylcholine (PC) and phosphatidylethanolamine (PE) biosynthetic pathways. These variations probably reflect the species differences in cytidine deaminase, the enzyme that converts cytidine to uridine in the body. The transport of cytidine into the brain's extracellular fluid, and then into neurons and glia, are essential prerequisites for cytidine to be utilized in the brain. An efficient mechanism mediating the brain uptake of circulating cytidine has not yet been demonstrated. The biosynthesis of PC, the most abundant phosphatide in the brain, via the Kennedy pathway requires phosphocholine and cytidine triphosphate (CTP), a cytidine nucleotide involved in the rate-limiting step. The enzyme that converts CTP to endogenous CDP-choline (CTP:phosphocholine cytidylyltransferase) is unsaturated at physiological brain CTP levels. APOBEC is a family of enzymes that has been discovered with the ability to deaminate cytidines on RNA or DNA. The human apolipoprotein B mRNA-editing enzyme, catalytic polypeptide-like 3G protein (APOBEC3G, or hA3G), provides cells with an intracellular antiretroviral activity that is associated with the hypermutation of viral DNA through cytidine deamination. Indeed, hA3G belongs to a family of vertebrate proteins that contains one or two copies of a signature sequence motif unique to cytidine deaminases (CTDAs) (PMID: 16769123, 15780864, 16720547).
65-46-3
C00475
6175
17562
CYTIDINE
5940
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
C9H13N3O5
InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7-,8-/m1/s1
UHDGCWIWMRVCDJ-XVFCMESISA-N
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
243.2166
243.085520541
-0.74
4
cytidine
0
0
FDB021809
1-(b-d-ribofuranosyl)-2-oxo-4-amino-1,2-dihydro-1,3-diazine;1-(b-delta-ribofuranosyl)-2-oxo-4-amino-1,2-dihydro-1,3-diazine;1-b-d-ribofuranosylcytosine;1-b-d-ribosyl-cytosine;1-beta-d-ribofuranosyl-cytosine;1-beta-d-ribofuranosylcytosine;1-beta-delta-ribofuranosyl-cytosine;1-beta-delta-ribofuranosylcytosine;1-beta-delta-ribosyl-cytosine;1beta-d-ribofuranosylcytosine;1beta-ribofuranosylcytosine;1beta-delta-ribofuranosylcytosine;4-amino-1-b-d-ribofuranosyl-2(1h)-pyrimidinone;4-amino-1-beta-delta-ribofuranosyl-2(1h)-pyrimidinone;Cytidine;Cytosine riboside;Cytosine-1b-d-ribofuranoside;Cytosine-1b-delta-ribofuranoside;Cytosine-1beta-d-ribofuranoside;Cytosine-1beta-delta-ribofuranoside;4-amino-1-beta-d-ribofuranosyl-2(1h)-pyrimidinone;4-amino-1-beta-d-ribofuranosylpyrimidin-2(1h)-one;4-amino-1beta-d-ribofuranosyl-2(1h)-pyrimidinone;Cyd;Cytidin;Zytidin;1-β-d-ribofuranosylcytosine;1b-d-ribofuranosylcytosine;1β-d-ribofuranosylcytosine;4-amino-1-β-d-ribofuranosyl-2(1h)-pyrimidinone;4-amino-1-b-d-ribofuranosylpyrimidin-2(1h)-one;4-amino-1-β-d-ribofuranosylpyrimidin-2(1h)-one;4-amino-1b-d-ribofuranosyl-2(1h)-pyrimidinone;4-amino-1β-d-ribofuranosyl-2(1h)-pyrimidinone;Cytosine-1β-d-ribofuranoside
PW_C000061
Cytdin
2735
2
6678
108
6679
107
43668
318
43669
315
78737
132
122217
124
124769
118
126379
299
127941
388
202
Uridine
HMDB0000296
Uridine, also known as beta-uridine or 1-beta-D-ribofuranosylpyrimidine-2,4(1H,3H)-dione, is a member of the class of compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. More specifically, uridine is a nucleoside consisting of uracil and D-ribose and a component of RNA. Uridine is soluble (in water) and a very weakly acidic compound (based on its pKa). Uridine can be synthesized from uracil. It is one of the five standard nucleosides which make up nucleic acids; the others being adenosine, thymidine, cytidine, and guanosine. The five nucleosides are commonly abbreviated to their one-letter codes U, A, T, C, and G respectively. Uridine is also a parent compound for other transformation products, including but not limited to, nikkomycin Z, 3'-(enolpyruvyl)uridine 5'-monophosphate and 5-aminomethyl-2-thiouridine. Uridine can be found in most biofluids, including urine, breast milk, cerebrospinal fluid (CSF), and blood. Within the cell, uridine is primarily located in the mitochondria, in the nucleus, and in the lysosome. It can also be found in the extracellular space. As an essential nucleoside, uridine exists in all living species, ranging from bacteria to humans. In humans, uridine is involved in several metabolic disorders, some of which include dhydropyrimidinase deficiency, MNGIE (mitochondrial neurogastrointestinal encephalopathy), and beta-ureidopropionase deficiency. Uridine is a nucleoside consisting of uracil and D-ribose and is a component of RNA. Uridine plays a role in the glycolysis pathway of galactose. In humans there is no catabolic process to metabolize galactose. Therefore, galactose is converted to glucose and metabolized via the normal glucose metabolism pathways. More specifically, consumed galactose is converted into galactose 1-phosphate (Gal-1-P). This molecule is a substrate for the enzyme galactose-1-phosphate uridyl transferase which transfers a UDP molecule to the galactose molecule. The end result is UDP-galactose and glucose-1-phosphate. This process is continued to allow the proper glycolysis of galactose. Uridine is found in many foods (anything containing RNA) but is destroyed in the liver and gastrointestinal tract, and so no food, when consumed, has ever been reliably shown to elevate blood uridine levels. On the other hand, consumption of RNA-rich foods may lead to high levels of purines (adenine and guanosine) in blood. High levels of purines are known to increase uric acid production and may aggravate or lead to conditions such as gout.
58-96-8
C00299
6029
16704
URIDINE
5807
DB02745
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O
C9H12N2O6
InChI=1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1
DRTQHJPVMGBUCF-XVFCMESISA-N
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
244.2014
244.069536126
-0.26
4
uridine
0
0
FDB007411
1-b-d-ribofuranosyl-2,4(1h,3h)-pyrimidinedione;1-b-d-ribofuranosyluracil;1-beta-delta-ribofuranosyl-2,4(1h,3h)-pyrimidinedione;1-beta-delta-ribofuranosyluracil;Uridin;B-d-ribofuranoside 2,4(1h,3h)-pyrimidinedione-1;B-uridine;Beta-uridine;Beta-delta-ribofuranoside 2,4(1h,3h)-pyrimidinedione-1;1-beta-d-ribofuranosylpyrimidine-2,4(1h,3h)-dione;1-beta-d-ribofuranosyluracil;U;Urd;1-b-d-ribofuranosylpyrimidine-2,4(1h,3h)-dione;1-β-d-ribofuranosylpyrimidine-2,4(1h,3h)-dione;1-β-d-ribofuranosyluracil;β-uridine
PW_C000202
Uridine
2738
2
6677
108
6823
107
43667
315
43771
318
78738
132
122218
124
124770
118
126381
299
127942
388
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
204
Uracil
HMDB0000300
Uracil is a common naturally occurring pyrimidine found in RNA, it base pairs with adenine and is replaced by thymine in DNA. Methylation of uracil produces thymine. Uracil's use in the body is to help carry out the synthesis of many enzymes necessary for cell function through bonding with riboses and phosphates. Uracil serves as allosteric regulator and coenzyme for many important biochemical reactions. UDP and UTP regulate CPSase II activity in animals. UDP-glucose regulates the conversion of glucose to galactose in the liver and other tissues in the process of carbohydrate metabolism. Uracil is also involved in the biosynthesis of polysaccharides and the transportation of sugars containing aldehydes.
66-22-8
C00106
1174
17568
URACIL
1141
DB03419
O=C1NC=CC(=O)N1
C4H4N2O2
InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
ISAKRJDGNUQOIC-UHFFFAOYSA-N
1,2,3,4-tetrahydropyrimidine-2,4-dione
112.0868
112.027277382
-0.63
2
uracil
0
0
FDB006426
2,4-dihydroxypyrimidine;2,4-dioxopyrimidine;2,4-pyrimidinediol;2,4-pyrimidinedione;Hybar x;Pirod;Pyrod;Uracil;Sq-8493sid51088798;Sq-6201sq-7726sid70371;Bms-205603-01uracil
PW_C000204
Uracil
538
8
2741
2
77589
111
78739
132
120451
122
122220
124
123085
135
124772
118
125695
297
126383
299
127189
205
127943
388
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
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
53
Dihydrouracil
HMDB0000076
Dihydrouracil is an intermediate breakdown product of uracil. Dihydropyrimidine dehydrogenase (DHP) catalyzes the reduction of uracil into 5,6-dihydrouracil then dihydropyrimidinase hydrolyzes 5,6-dihydrouracil into N-carbamyl-beta-alanine. Finally, beta-ureidopropionase catalyzes the conversion of N-carbamyl-beta-alanine into beta-alanine. When present at abnormally high levels, dihydrouracil can be toxic although the mechanism of toxicity is not clear. In particular, patients with dihydropyrimidinase deficiency exhibit highly increased concentrations of 5,6-dihydrouracil and 5,6-dihydrothymine, and moderately increased concentrations of uracil and thymine can be detected in urine. Dihydropyrimidinase deficiency is a disorder that can cause neurological and gastrointestinal problems in some affected individuals (OMIM: 222748). The neurological abnormalities that occur most often in people with dihydropyrimidinase deficiency are intellectual disability, seizures, weak muscle tone (hypotonia), an abnormally small head size (microcephaly), and autistic behaviours that affect communication and social interaction. Gastrointestinal problems that occur in dihydropyrimidinase deficiency include backflow of acidic stomach contents into the esophagus (gastroesophageal reflux) and recurrent episodes of vomiting. The direct measurement of the activity of DHP in patients has been hampered by the fact that the enzyme is expressed almost exclusively in liver tissue.
504-07-4
C00429
649
15901
DI-H-URACIL
629
DB01849
O=C1CCNC(=O)N1
C4H6N2O2
InChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)
OIVLITBTBDPEFK-UHFFFAOYSA-N
1,3-diazinane-2,4-dione
114.1026
114.042927446
-0.64
2
dihydrouracil
0
0
FDB021890
5,6-dihydro-2,4(1h,3h)-pyrimidinedione;5,6-dihydro-2,4-dihydroxypyrimidine;5,6-dihydrouracil;Dihydro-2,4(1h,3h)-pyrimidinedione;Dihydro-pyrimidine-2,4-dione;Dihydrouracil;Dihydrouracile;Hydrouracil;2,4-dioxotetrahydropyrimidine
PW_C000053
DUC
536
8
2743
2
77587
111
78740
132
120448
122
122222
124
123082
135
124774
118
125692
297
126385
299
127187
205
127945
388
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
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
18
Ureidopropionic acid
HMDB0000026
Ureidopropionic acid is an intermediate in the metabolism of uracil. More specifically it is a breakdown product of dihydrouracil and is produced by the enzyme dihydropyrimidase. It is further decomposed to beta-alanine via the enzyme beta-ureidopropionase. Ureidopropionic acid is essentially a urea derivative of beta-alanine. High levels of Ureidopropionic acid are found in individuals with beta-ureidopropionase (UP) deficiency [PMID: 11675655]. Enzyme deficiencies in pyrimidine metabolism are associated with a risk for severe toxicity against the antineoplastic agent 5-fluorouracil.
462-88-4
C02642
111
18261
3-UREIDO-PROPIONATE
109
NC(=O)NCCC(O)=O
C4H8N2O3
InChI=1S/C4H8N2O3/c5-4(9)6-2-1-3(7)8/h1-2H2,(H,7,8)(H3,5,6,9)
JSJWCHRYRHKBBW-UHFFFAOYSA-N
3-(carbamoylamino)propanoic acid
132.1179
132.053492132
-0.40
3
ureidopropionic acid
0
-1
FDB021879
3-(carbamoylamino)propanoate;3-(carbamoylamino)propanoic acid;3-ureido-propionate;3-ureidopropanoate;3-ureidopropanoic acid;3-ureidopropionate;3-ureidopropionic acid;Carbamoyl-b-ala-oh;Carbamoyl-beta-ala-oh;N-(aminocarbonyl)-'b-alanine;N-(aminocarbonyl)-b-alanine;N-(aminocarbonyl)-beta-alanine;N-carbamoyl-b-alanine;N-carbamoyl-beta-alanine;N-carbamyl-b-alanine;N-carbamyl-beta-alanine;Ureidopropionate;Ureidopropionic acid;Beta-ureidopropionate;Beta-ureidopropionic acid;3-[(aminocarbonyl)amino]propanoic acid;Ureidopropanoic acid;3-[(aminocarbonyl)amino]propanoate;N-carbamoyl-β-alanine;B-ureidopropionate;B-ureidopropionic acid;β-ureidopropionate;β-ureidopropionic acid;N-(aminocarbonyl)-β-alanine;Ureidopropanoate
PW_C000018
Ureidop
534
8
2745
2
77585
111
78741
132
120446
122
122224
124
123080
135
124776
118
125690
297
126387
299
127185
205
127947
388
40
β-Alanine
HMDB0000056
beta-Alanine is the only naturally occurring beta-amino acid - an amino acid in which the amino group is at the beta-position from the carboxylate group. It is formed in vivo by the degradation of dihydrouracil and carnosine. It is a component of the naturally occurring peptides carnosine and anserine and also of pantothenic acid (vitamin B-5), which itself is a component of coenzyme A. Under normal conditions, beta-alanine is metabolized into acetic acid. beta-Alanine can undergo a transanimation reaction with pyruvate to form malonate-semialdehyde and L-alanine. The malonate semialdehyde can then be converted into malonate via malonate-semialdehyde dehydrogenase. Malonate is then converted into malonyl-CoA and enter fatty acid biosynthesis. Since neuronal uptake and neuronal receptor sensitivity to beta-alanine have been demonstrated, beta-alanine may act as a false transmitter replacing gamma-aminobutyric acid. When present in sufficiently high levels, beta-alanine can act as a neurotoxin, a mitochondrial toxin, and a metabotoxin. A neurotoxin is a compound that damages the brain or nerve tissue. A mitochondrial toxin is a compound that damages mitochondria and reduces cellular respiration as well as oxidative phosphorylation. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of beta-alanine are associated with at least three inborn errors of metabolism, including GABA-transaminase deficiency, hyper-beta-alaninemia, and methylmalonate semialdehyde dehydrogenase deficiency. beta-Alanine is a central nervous system (CNS) depressant and is an inhibitor of GABA transaminase. The associated inhibition of GABA transaminase and displacement of GABA from CNS binding sites can also lead to GABAuria (high levels of GABA in the urine) and convulsions. In addition to its neurotoxicity, beta-alanine reduces cellular levels of taurine, which are required for normal respiratory chain function. Cellular taurine depletion is known to reduce respiratory function and elevate mitochondrial superoxide generation, which damages mitochondria and increases oxidative stress (PMID: 27023909). Individuals suffering from mitochondrial defects or mitochondrial toxicity typically develop neurotoxicity, hypotonia, respiratory distress, and cardiac failure. beta-Alanine is a biomarker for the consumption of meat, especially red meat.
107-95-9
C00099
239
16958
B-ALANINE
234
DB03107
NCCC(O)=O
C3H7NO2
InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)
UCMIRNVEIXFBKS-UHFFFAOYSA-N
3-aminopropanoic acid
89.0932
89.047678473
0.74
2
β alanine
0
0
FDB002253
2-carboxyethylamine;3-amino-propanoate;3-amino-propanoic acid;3-aminopropanoate;3-aminopropanoic acid;3-aminopropionate;3-aminopropionic acid;Abufene;B-alanine;Omega-aminopropionate;Omega-aminopropionic acid;B-aminopropanoate;B-aminopropanoic acid;B-aminopropionate;B-aminopropionic acid;Beta alanine;Beta-alanine;Beta-aminopropanoate;Beta-aminopropanoic acid;Beta-aminopropionate;Beta-aminopropionic acid;β-alanine
PW_C000040
b-Ala
41
3
49
8
527
15
2320
4
2747
2
5794
108
7071
188
12680
289
12687
290
42645
315
77522
112
77527
111
77578
114
78159
132
78633
133
120083
407
120439
409
120445
122
121056
124
122260
406
122830
119
123073
137
123079
135
123620
118
124813
120
125454
481
125683
483
125689
297
126389
299
126424
479
126992
206
127178
208
127184
205
127950
388
127992
501
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
962
dCDP
HMDB0001245
dCDP is a substrate for Uridine-cytidine kinase 1, Nucleoside diphosphate kinase (mitochondrial), Nucleoside diphosphate kinase homolog 5, Ribonucleoside-diphosphate reductase large subunit, Nucleoside diphosphate kinase A, Nucleoside diphosphate kinase 7, Ribonucleoside-diphosphate reductase M2 chain, Nucleoside diphosphate kinase B, Nucleoside diphosphate kinase 3, Nucleoside diphosphate kinase 6 and UMP-CMP kinase.
800-73-7
C00705
150855
28846
DCDP
132961
NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O1
C9H15N3O10P2
InChI=1S/C9H15N3O10P2/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(21-8)4-20-24(18,19)22-23(15,16)17/h1-2,5-6,8,13H,3-4H2,(H,18,19)(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
FTDHDKPUHBLBTL-SHYZEUOFSA-N
[({[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
387.177
387.023266739
-1.53
5
dCDP
0
-2
FDB022510
2'-deoxy-cytidine 5'-pyrophosphate;2'-deoxy-cytidine pyrophosphate;2'-deoxycytidine 5'-diphosphate;2'-deoxycytidine diphosphate;2'-deoxycytidine-5'-diphosphate;4-amino-1-[2-deoxy-5-o-[hydroxy(phosphonooxy)phosphinyl]-beta-d-erythro-pentofuranosyl]-2(1h)-pyrimidinone;4-amino-1-[2-deoxy-5-o-[hydroxy(phosphonooxy)phosphinyl]-beta-delta-erythro-pentofuranosyl]-2(1h)-pyrimidinone;D-1beta-ribofuranosylcytosine diphosphate;Deoxy-cdp;Deoxycytidine 5'-diphosphate;Deoxycytidine diphosphate;Dcdp;Delta-1beta-ribofuranosylcytosine diphosphate;2'-deoxycytidine 5'-diphosphoric acid;2'-deoxycytidine diphosphoric acid;D-1b-ribofuranosylcytosine diphosphate;D-1b-ribofuranosylcytosine diphosphoric acid;D-1beta-ribofuranosylcytosine diphosphoric acid;D-1β-ribofuranosylcytosine diphosphate;D-1β-ribofuranosylcytosine diphosphoric acid;Deoxycytidine diphosphoric acid
PW_C000962
dCDP
2749
2
12752
151
78742
132
122227
124
124779
118
126391
299
127952
388
544
Fe2+
HMDB0000692
Iron is a chemical element with the symbol Fe and atomic number 26. Iron makes up 5% of the Earth's crust and is second in abundance to aluminium among the metals and fourth in abundance among the elements. Physiologically, it. exists as an ion in the body. Iron (as Fe2+, ferrous ion) is a necessary trace element used by all known living organisms. Iron-containing enzymes, usually containing heme prosthetic groups, participate in catalysis of oxidation reactions in biology, and in transport of a number of soluble gases. Iron is an essential constituent of hemoglobin, cytochrome, and other components of respiratory enzyme systems. Its chief functions are in the transport of oxygen to tissue (hemoglobin) and in cellular oxidation mechanisms. Inorganic iron involved in redox reactions is also found in the iron-sulfur clusters of many enzymes, such as nitrogenase (involved in the synthesis of ammonia from nitrogen and hydrogen) and hydrogenase. A class of non-heme iron proteins is responsible for a wide range of functions such as ribonucleotide reductase (reduces ribose to deoxyribose; DNA biosynthesis) and purple acid phosphatase (hydrolysis of phosphate esters). When the body is fighting a bacterial infection, the body sequesters iron inside of cells (mostly stored in the storage molecule ferritin) so that it cannot be used by bacteria. Depletion of iron stores may result in iron-deficiency anemia. Iron is used to build up the blood in anemia. Humans experience iron toxicity above 20 milligrams of iron for every kilogram of weight, and 60 milligrams per kilogram is a lethal dose. Over-consumption of iron, often the result of children eating large quantities of ferrous sulfate tablets intended for adult consumption, is the most common toxicological cause of death in children under six. The DRI lists the Tolerable Upper Intake Level (UL) for adults as 45 mg/day. For children under fourteen years old the UL is 40 mg/day. Iron is a metal extracted from iron ore, and is almost never found in the free elemental state.
15438-31-0
C14818
27284
29033
Ferric-Hydroxamate-Complexes
25394
DB01592
[Fe++]
Fe
InChI=1S/Fe/q+2
CWYNVVGOOAEACU-UHFFFAOYSA-N
lambda2-iron(2+) ion
55.845
55.934942133
0
lambda2-iron(2+) ion
2
2
FDB016251
Armco iron;Carbonyl iron;Fe;Ferrovac e;Hematite;Infed;Loha;Limonite;Magnetite;Malleable iron;Metopirone;Metyrapone;Pzho;Pzh2m;Remko;Suy-b 2;Taconite;Venofer;Wrought iron;Fe (ii) ion;Fe(ii);Fe2+;Fe(2+);Ferrous ion;Iron ion(2+)
PW_C000544
Fe2+
398
19
641
3
678
31
692
20
709
8
1777
2
7041
163
7052
160
12060
225
12143
151
77179
132
77740
112
77751
129
77760
341
77782
111
120544
407
120557
414
120570
122
121765
124
123178
119
123191
450
123204
135
124316
118
126143
299
126185
481
127650
388
140710
49
140716
18
937
dCMP
HMDB0001202
Deoxycytidine (dihydrogen phosphate). A deoxycytosine nucleotide containing one phosphate group esterified to the deoxyribose moiety in the 2'-,3'- or 5- positions. Deficiency of the enzyme Deoxycytidine kinase (EC 2.7.1.74) is associated with resistance to antiviral and anticancer chemotherapeutic agents, whereas increased enzyme activity is associated with increased activation of these compounds to cytotoxic nucleoside triphosphate derivatives. (OMIM 125450).
1032-65-1
C00239
13945
15918
DCMP
13343
NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1
C9H14N3O7P
InChI=1S/C9H14N3O7P/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(19-8)4-18-20(15,16)17/h1-2,5-6,8,13H,3-4H2,(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
NCMVOABPESMRCP-SHYZEUOFSA-N
{[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
307.1971
307.056936329
-1.45
4
dCMP
0
-2
FDB022488
2'-deoxycytidine 5'-monophosphate;2'-deoxycytidine-3'-monophosphate;2'-deoxycytidine-5'-monophosphate;2'-deoxycytidine-5'-monophosphorate;2'-deoxycytidine-5'-monophosphoric acid;2'-deoxycytidine-5'-phosphate;C;Deoxycytidine monophosphate;Deoxycytidine-phosphate;Deoxycytidylate;Deoxycytidylic acid;Dcmp;2'-deoxycytosine 5'-monophosphate;2'-deoxycytidine 5'-monophosphoric acid;2'-deoxycytosine 5'-monophosphoric acid;Deoxycytidine monophosphoric acid
PW_C000937
dCMP
2752
2
12750
151
78743
132
122228
124
124780
118
126392
299
127953
388
8
Deoxycytidine
HMDB0000014
One of the principal nucleosides of DNA composed of cytosine and deoxyribose. A nucleoside consists of only a pentose sugar linked to a purine or pyrimidine base, without a phosphate group. When N1 is linked to the C1 of deoxyribose, deoxynucleosides and nucleotides are formed from cytosine and deoxyribose; deoxycytidine monophosphate (dCMP), deoxycytidine diphosphate (dCDP), deoxycytidine triphosphate (dCTP). CTP is the source of the cytidine in RNA (ribonucleic acid) and deoxycytidine triphosphate (dCTP) is the source of the deoxycytidine in DNA (deoxyribonucleic acid).
951-77-9
C00881
13711
15698
DEOXYCYTIDINE
13117
NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](CO)O1
C9H13N3O4
InChI=1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/m0/s1
CKTSBUTUHBMZGZ-SHYZEUOFSA-N
4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
227.2172
227.090605919
-1.16
3
2'-deoxycytidine
0
0
FDB021871
1-(2-deoxy-b-d-ribofuranosyl)cytosine;1-(2-deoxy-beta-d-erythro-pentofuranosyl)-cytosine;1-(2-deoxy-beta-d-ribofuranosyl)cytosine;1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-cytosine;1-(2-deoxy-beta-delta-ribofuranosyl)cytosine;2'-deoxycytidine;2-deoxy-cytidine;4-amino-1-(2-deoxy-b-d-erythro-pentofuranosyl)-2(1h)-pyrimidinone;4-amino-1-(2-deoxy-beta-d-erythro-pentofuranosyl)-2(1h)-pyrimidinone;4-amino-1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-2(1h)-pyrimidinone;Cytosine deoxyribonucleoside;Cytosine deoxyriboside;Deoxy-cytidine;Deoxyribose cytidine;Desoxycytidine;4-amino-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1h)-one;Dc;Dcyd;Deoxycytidine
PW_C000008
DC
2753
2
6743
107
6744
108
12749
151
12763
294
43714
315
43716
318
78744
132
122229
124
124781
118
126393
299
127954
388
7
Deoxyuridine
HMDB0000012
2'-Deoxyuridine is a naturally occurring nucleoside. It is similar in chemical structure to uridine, but without the 2'-hydroxyl group. It is considered to be an antimetabolite that is converted to deoxyuridine triphosphate during DNA synthesis. Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemia due to vitamin B12 and folate deficiencies.
951-78-0
C00526
13712
16450
DEOXYURIDINE
13118
OC[C@H]1O[C@H](C[C@@H]1O)N1C=CC(=O)NC1=O
C9H12N2O5
InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1
MXHRCPNRJAMMIM-SHYZEUOFSA-N
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
228.202
228.074621504
-0.40
3
2'-deoxyuridine
0
0
FDB021870
1-(2-deoxy-d-erythro-pentofuranosyl)uracil;1-(2-deoxy-beta-d-erythro-pentofuranosyl)-2,4(1h,3h)-pyrimidinedione;1-(2-deoxy-beta-d-ribofuranosyl)-2,4(1h,3h)-pyrimidinedione;1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-2,4(1h,3h)-pyrimidinedione;1-(2-deoxy-beta-delta-ribofuranosyl)-2,4(1h,3h)-pyrimidinedione;1-(2-deoxy-delta-erythro-pentofuranosyl)uracil;2'-deoxyuridine;2'-desoxyuridine;Deoxyribose uracil;Desoxyuridine;Uracil deoxyriboside;Uracil desoxyuridine;2-deoxyuridine;Deoxyuridine;Du
PW_C000007
Du
2755
2
6745
107
6746
108
12751
151
43715
315
43717
318
78745
132
122231
124
124783
118
126395
299
127956
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
1087
dUMP
HMDB0001409
dUMP is formed by the reduction of ribonucleotides to deoxyribonucleotides by ribonucleoside diphosphate reductase [EC 1.17.4.1]. dUMP by the action of by thymidylate synthetase [EC 2.1.1.45] produces dTMP (5,10-Methylene-5,6,7,8-tetrahydrofolate is a cofactor for the reaction). The nuclear form of uracil-DNA glycosylase (UNG2), that its major role is to remove misincorporated dUMP residues (cells deficient in removal of misincorporated dUMP accumulate uracil residues). (PMID 11554311).
964-26-1
C00365
65063
17622
DUMP
58574
DB03800
O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=CC(=O)NC1=O
C9H13N2O8P
InChI=1S/C9H13N2O8P/c12-5-3-8(11-2-1-7(13)10-9(11)14)19-6(5)4-18-20(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
JSRLJPSBLDHEIO-SHYZEUOFSA-N
{[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
308.1819
308.040951914
-1.59
4
2'-deoxyuridylic acid
0
-2
FDB022604
2'-deoxy-5'-uridylate;2'-deoxy-5'-uridylic acid;2'-deoxyuridine 5'-monophosphate;2'-deoxyuridine 5'-phosphate;2'-deoxyuridylate;2'-deoxyuridylic acid;Deoxy-ump;Deoxyuridine 5'-monophosphate;Deoxyuridine 5'-phosphate;Deoxyuridine monophosphate;Deoxyuridylate;Deoxyuridylic acid;2'-deoxyuridine 5'-monophosphoric acid;2'-deoxyuridine 5'-phosphoric acid;Deoxyuridine 5'-phosphoric acid;Deoxyuridine monophosphoric acid
PW_C001087
dUMP
2758
2
12755
151
78746
132
122233
124
124786
118
126397
299
127958
388
9795
Zinc
HMDB0015532
Zinc is an essential element, necessary for sustaining all life. It is a trace element in the diet, forming an essential part of many enzymes, and playing an important role in protein synthesis and in cell division. 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 cell types 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. Zinc deficiency is associated with anemia, short stature, hypogonadism, impaired wound healing, and geophagia. 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 kill some organisms.
7440-66-6
23994
27363
22430
DB01593
[Zn++]
Zn
InChI=1S/Zn/q+2
PTFCDOFLOPIGGS-UHFFFAOYSA-N
zinc(2+) ion
65.409
63.929146578
0
zinc(2+) ion
2
2
30zn;Cinc;Zincum;Zink;Zn;Zn(ii);Zn2+
PW_C009795
Zinc
57
8
1711
2
1904
3
2137
17
2154
49
3610
29
4083
7
4469
18
4543
14
4999
31
6689
107
6690
101
6699
108
7020
160
11758
115
12229
151
12633
65
42397
315
42399
318
77030
253
78023
132
78328
112
78811
111
120119
124
120898
122
122308
407
122852
118
123469
135
124860
119
125486
299
126474
481
127023
388
127317
205
128043
206
1178
5,10-Methylene-THF
HMDB0001533
5,10-Methylene-THF is an intermediate in glycine, serine and threonine metabolism and one carbon metabolism. 5,10-CH2-THF can also be used as a coenzyme in the biosynthesis of thymidine. More specifically it is the C1-donor in the reactions catalyzed by thymidylate synthase and thymidylate synthase (FAD). It also acts as a coenzyme in the synthesis of serine from glycine via the enzyme serine hydroxymethyl transferase. 5,10-Methylene-THF is a substrate for Methylenetetrahydrofolate reductase. This enzyme converts 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate. This reaction is required for the multistep process that converts the amino acid homocysteine to methionine. The body uses methionine to make proteins and other important compounds. 5,10-CH2-THF is a substrate for many enzymes including Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase (mitochondrial), Aminomethyltransferase (mitochondrial), Serine hydroxymethyltransferase (mitochondrial), Methylenetetrahydrofolate reductase, C-1-tetrahydrofolate synthase (cytoplasmic), Serine hydroxymethyltransferase (cytosolic) and Thymidylate synthase.
3432-99-3
C00143
439175
15636
METHYLENE-THF
388320
[H][C@@]12CN(CN1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)NC(CCC(O)=O)C(O)=O
C20H23N7O6
InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13?/m1/s1
QYNUQALWYRSVHF-PZORYLMUSA-N
2-({4-[(6aR)-1-hydroxy-3-imino-3H,4H,5H,6H,6aH,7H,8H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid
457.4399
457.170981503
-2.75
7
2-({4-[(6aR)-1-hydroxy-3-imino-4H,5H,6H,6aH,7H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid
0
-1
FDB022675
(6r)-5,10-methylenetetrahydrofolate;5,10-methenyltetrahydropteroylglutamate;5,10-methylene-6-hydrofolate;5,10-methylene-6-hydrofolic acid;5,10-methylene-thf;5,10-methylenetetrahydrofolate;5,10-methylenetetrahydrofolic acid;N5>,n10-methylenetetrahydrofolate;(6r)-5,10-methylenetetrahydrofolic acid
PW_C001178
5XM-THF
449
4
956
8
985
3
1811
2
5331
111
5359
112
5785
108
6010
147
6272
35
7065
188
7171
205
7196
206
7582
163
42639
315
77339
133
78119
132
120355
406
120683
122
120704
407
122167
124
123004
120
123293
135
123309
119
124719
118
125676
479
125761
297
125779
481
126325
299
127171
501
127887
388
950
5-Thymidylic acid
HMDB0001227
5-Thymidylic acid is a thymine nucleotide. Also known as thymidine monophosphate, and abbreviated TMP, is a nucleotide that is found in DNA. It is an ester of phosphoric acid with the nucleoside thymidine. TMP consists of a phosphate group, esterified to the the pentose sugar deoxyribose moiety, and the nucleobase thymine. In mammalian cells, thymidine deprivation induces chromosome aberrations such as chromatid breaks, chromatid interchanges, and chromosome fragmentation. (PMID 3888175).
365-07-1
C00364
9700
17013
TMP
9319
DB01643
CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O
C10H15N2O8P
InChI=1S/C10H15N2O8P/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(20-8)4-19-21(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1
GYOZYWVXFNDGLU-XLPZGREQSA-N
{[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid
322.2085
322.056601978
-1.68
4
thymidylate
0
-2
FDB022499
2'-deoxythymidine 5'-monophosphate;5'-tmp;5'-thymidylate;5'-thymidylic acid;5'-dtmp;5-methyl-dump;Deoxy tmp;Deoxyribosylthymine monophosphate;Deoxythymidine 5'-monophosphate;Deoxythymidine 5'-phosphate;Deoxythymidine monophosphate;Deoxythymidylate;Deoxythymidylic acid;Deoxythymydilate;Deoxythymydilic acid;Thymidine 5'-monophosphate;Thymidine 5'-phosphate;Thymidine 5'-phosphorate;Thymidine 5'-phosphoric acid;Thymidine 5'mp;Thymidine mononucleotide;Thymidine monophosphate;Thymidine phosphate;Thymidine-5'-monophosphorate;Thymidine-5'-monophosphoric acid;Thymidylate;Thymidylic acid;Dtmp;(dt)1;Ribothymidine 5'-monophosphate;Thymidine 5'-(dihydrogen phosphate);Thymidine-5'-phosphate;Tmp;5-thymidylate;Deoxyribosylthymine monophosphoric acid;Ribothymidine 5'-monophosphoric acid;Thymidine 5'-(dihydrogen phosphoric acid);Thymidine monophosphoric acid;Thymidine-5'-monophosphate;Thymidine-5'-phosphoric acid
PW_C000950
5TMA
2764
2
12756
151
12764
294
78747
132
122236
124
124789
118
126399
299
127962
388
831
Dihydrofolic acid
HMDB0001056
Dihydrofolic acid is a folic acid derivative acted upon by dihydrofolate reductase to produce tetrahydrofolic acid. It interacts with bacteria during cell division. It can be targeted with drug analogs to prevent nucleic acid synthesis. Dihydrofolic acid is also known by the name Dihydrofolate - more commonly Vitamin B9.
4033-27-6
C00415
98792
15633
DIHYDROFOLATE
89228
NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=N2)N1
C19H21N7O6
InChI=1S/C19H21N7O6/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/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1
OZRNSSUDZOLUSN-LBPRGKRZSA-N
(2S)-2-[(4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
443.4133
443.155331439
-3.50
7
dihydrofolic acid
0
-2
FDB022395
7,8-dihydro-l-folic acid;7,8-dihydrofolate;7,8-dihydrofolic acid;7,8-dihydropteroylglutamate;Dihydrofolate;H2pteglu;H2pteglu1;L-n-[p-[[(2-amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-glutamic acid;N-(4-(((2-amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-l-glutamic acid;N-(4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoyl)-l-glutamic acid;N-(7,8-dihydropteroyl)-l-glutamic acid;N-[4-[[(2-amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-l-glutamic acid;N-[4-[[(2-amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-l-glutamic acid;Vitamin b9
PW_C000831
FAH2
943
8
2765
2
5309
111
7153
205
78748
132
120667
122
122237
124
123281
135
124790
118
125750
297
126400
299
127963
388
987
dTDP
HMDB0001274
dTDP, also known as deoxy-tdp, belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside diphosphates. These are pyrimidine nucleotides with a diphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. dTDP is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, dTDP is primarily located in the mitochondria, nucleus and cytoplasm. dTDP exists in all living organisms, ranging from bacteria to humans. dTDP participates in a number of enzymatic reactions. In particular, dTDP can be converted into thymidine 5'-triphosphate; which is mediated by the enzyme nucleoside diphosphate kinase. Furthermore, dTDP and undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate can be biosynthesized from undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate and TDP-fuc4nac; which is mediated by the enzyme 4-acetamido-4,6-dideoxy-D-galactose transferase. Finally, dTDP and undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate can be biosynthesized from undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate and TDP-fuc4nac through its interaction with the enzyme 4-acetamido-4,6-dideoxy-D-galactose transferase. In humans, dTDP is involved in the pyrimidine metabolism pathway. dTDP is also involved in several metabolic disorders, some of which include Beta ureidopropionase deficiency, UMP synthase deficiency (orotic aciduria), dihydropyrimidinase deficiency, and the mngie (mitochondrial neurogastrointestinal encephalopathy) pathway. Is an intermediate in the Thymidylate kinase (EC 2.7.4.9; ATP:dTMP phosphotransferase) catalyzes the phosphorylation of dTMP (to form dTDP) in the dTTP synthesis pathway for DNA synthesis. (OMIM 188345 )
491-97-4
C00363
164628
18075
TDP
144320
CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O2)C(=O)NC1=O
C10H16N2O11P2
InChI=1S/C10H16N2O11P2/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(22-8)4-21-25(19,20)23-24(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,19,20)(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1
UJLXYODCHAELLY-XLPZGREQSA-N
{[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}phosphonic acid
402.1884
402.022932388
-1.76
5
dTDP
0
-2
FDB022528
Deoxy-tdp;Deoxythymidine 5'-diphosphate;Tdp;Thymidine 5'-diphosphate;Thymidine 5'-pyrophosphate;Dtdp;2'-deoxyribosylthymine 5'-(trihydrogen diphosphate);Thymidine-5'- diphosphate;2'-deoxyribosylthymine 5'-(trihydrogen diphosphoric acid)
PW_C000987
dTDP
2770
2
12759
151
78749
132
122239
124
124792
118
126402
299
127965
388
1035
Thymidine 5'-triphosphate
HMDB0001342
"Thymidine 5-triphosphate, also known as TTP or DTHD5'ppp, belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside triphosphates. These are pyrimidine nucleotides with a triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. Thymidine 5-triphosphate is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Within the cell, thymidine 5-triphosphate is primarily located in the mitochondria, nucleus and cytoplasm. Thymidine 5-triphosphate exists in all living organisms, ranging from bacteria to humans. In humans, thymidine 5-triphosphate is involved in the pyrimidine metabolism pathway. Thymidine 5-triphosphate is also involved in several metabolic disorders, some of which include Beta ureidopropionase deficiency, the mngie (mitochondrial neurogastrointestinal encephalopathy) pathway, UMP synthase deficiency (orotic aciduria), and dihydropyrimidinase deficiency. Outside of the human body, thymidine 5-triphosphate can be found in a number of food items such as nopal, saskatoon berry, grass pea, and sourdock. This makes thymidine 5-triphosphate a potential biomarker for the consumption of these food products. Thymidine 5-triphosphate or TTP is one of the four nucleoside triphosphates that make up DNA. It can be used by DNA ligase to create overlapping ""sticky ends"" so that protruding ends of opened microbial plasmids maybe closed up."
365-08-2
C00459
64968
18077
TTP
58493
CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)NC1=O
C10H17N2O14P3
InChI=1S/C10H17N2O14P3/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(24-8)4-23-28(19,20)26-29(21,22)25-27(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,19,20)(H,21,22)(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1
NHVNXKFIZYSCEB-XLPZGREQSA-N
{[hydroxy({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphoryl]oxy}phosphonic acid
482.1683
481.989262798
-1.70
6
dTTP
0
-3
FDB022565
2'-deoxythymidine 5'-triphosphate;2'-deoxythymidine triphosphate;5'-ttp;5-methyl-dutp;Deoxy-ttp;Deoxythymidine 5'-triphosphate;Deoxythymidine triphosphate;Ttp;Thymidine 5'-triphosphate;Thymidine mono(tetrahydrogen triphosphate);Thymidine triphosphate;Dttp;Dthd5'ppp;Pppdt;Thymidine-5'-triphosphate;2'-deoxythymidine triphosphoric acid
PW_C001035
Tm5TP
2771
2
12760
151
78750
132
122240
124
124793
118
126403
299
127966
388
187
Thymidine
HMDB0000273
Thymidine is non-toxic and is a naturally occurring compound that exists in all living organisms and DNA viruses. 25% of DNA is composed of thymidine. RNA does not have thymidine and has uridine instead. Thymidine is a chemical compound which is a pyrimidine nucleoside. Thymidine is the DNA base T, which pairs with adenosine in double stranded DNA.
50-89-5
C00214
5789
17748
THYMIDINE
5585
DB04485
CC1=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)NC1=O
C10H14N2O5
InChI=1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/m0/s1
IQFYYKKMVGJFEH-XLPZGREQSA-N
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
242.2286
242.090271568
-0.56
3
thymidine
0
0
FDB012757
1-(2-deoxy-b-d-erythro-pentofuranosyl)-5-methyl-2,4(1h,3h)-pyrimidinedione;1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-5-methyl-2,4(1h,3h)-pyrimidinedione;1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione;2'-deoxy-5-methyl-uridine;2'-deoxythymidine;5-methyl-2'-deoxyuridine;5-methyldeoxyuridine;Dt;Dthyd;Deoxyribothymidine;Deoxythymidine;Thymidin;Thymidine;Thymine 2-desoxyriboside;Thymine deoxyriboside;Thymine-1 2-deoxy-b-d-ribofuranoside;Thymine-1 2-deoxy-beta-delta-ribofuranoside;1-(2-deoxy-beta-d-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1h,3h)-dione;2'-deoxy-5-methyluridine;2'-thymidine;Dthd;T;Thymine 2'-deoxyriboside;1-(2-deoxy-b-d-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1h,3h)-dione;1-(2-deoxy-β-d-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1h,3h)-dione
PW_C000187
T
2773
2
6752
107
6753
108
12758
151
12765
294
43725
318
43726
315
78751
132
122241
124
124794
118
126404
299
127967
388
179
Thymine
HMDB0000262
One of the pyrimidine bases of living matter. Derivation: Hydrolysis of deoxyribonucleic acid, from methylcyanoacetylurea by catalytic reduction. Use: Biochemical research. (Hawley's Condensed Chemical Dictionary). Thymine is a pyrimidine nucleobase. As the name implies, thymine may be derived by methylation of uracil at the 5th carbon. Thymine is found in the nucleic acid DNA. In RNA thymine is replaced with uracil in most cases. In DNA, thymine binds to adenine via two hydrogen bonds to assist in stabilizing the nucleic acid structures.
65-71-4
C00178
1135
17821
THYMINE
1103
DB03462
CC1=CNC(=O)NC1=O
C5H6N2O2
InChI=1S/C5H6N2O2/c1-3-2-6-5(9)7-4(3)8/h2H,1H3,(H2,6,7,8,9)
RWQNBRDOKXIBIV-UHFFFAOYSA-N
5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
126.1133
126.042927446
-1.07
2
thymine
0
0
FDB021922
2,4-dihydroxy-5-methylpyrimidine;4-hydroxy-5-methylpyrimidin-2(1h)-one;5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione;5-methyl-2,4(1h,3h)-pyrimidinedione;5-methyl-2,4-dihydroxypyrimidine;5-methylpyrimidine-2,4-dione;5-methyluracil;Thymine
PW_C000179
Thymine
2782
2
78752
132
122242
124
124795
118
126405
299
127968
388
56
Dihydrothymine
HMDB0000079
Dihydrothymine is an intermediate breakdown product of thymine. Dihydropyrimidine dehydrogenase catalyzes the reduction of thymine into 5,6-dihydrothymine then dihydropyrimidinase hydrolyzes 5,6-dihydrothymine into N-carbamyl-beta-alanine. Finally, beta-ureidopropionase catalyzes the conversion of N-carbamyl-beta-alanine to beta-alanine. When present at abnormally high levels, dihydrothymine can be toxic, although the mechanism of toxicity is not clear. In particular, patients with dihydropyrimidinase deficiency exhibit highly increased concentrations of 5,6-dihydrouracil and 5,6-dihydrothymine, and moderately increased concentrations of uracil and thymine can be detected in urine. Dihydropyrimidinase deficiency is a disorder that can cause neurological and gastrointestinal problems in some affected individuals. The most common neurological abnormalities that occur are intellectual disability, seizures, weak muscle tone (hypotonia), abnormally small head size (microcephaly), and autistic behaviours that affect communication and social interaction. Gastrointestinal problems that occur in dihydropyrimidinase deficiency include backflow of acidic stomach contents into the esophagus (gastroesophageal reflux) and recurrent episodes of vomiting.
696-04-8
C00906
93556
27468
DIHYDRO-THYMINE
84456
CC1CNC(=O)NC1=O
C5H8N2O2
InChI=1S/C5H8N2O2/c1-3-2-6-5(9)7-4(3)8/h3H,2H2,1H3,(H2,6,7,8,9)
NBAKTGXDIBVZOO-UHFFFAOYSA-N
5-methyl-1,3-diazinane-2,4-dione
128.1292
128.05857751
-0.84
2
dihydrothymine
0
0
FDB021892
5,6-dihydro-5-methyluracil;5,6-dihydrothymine;5-methyl-5,6-dihydrouracil;5-methyl-hydrouracil;5-methyldihydropyrimidine-2,4(1h,3h)-dione;Dihydro-5-methyl-2,4(1h,3h)-pyrimidinedione;Dihydrothymine
PW_C000056
DHThy
2783
2
78753
132
122243
124
124796
118
126406
299
127969
388
1363
Ureidoisobutyric acid
HMDB0002031
Beta-ureidoisobutyrate (betaUIB) is increased in the urine of patients with beta-ureidopropionase deficiency [EC 3.5.1.6] (PMID: 12271438). Ureidoisobutyric acid can be used to predict patient's individual phenotypes of enzyme deficiencies in pyrimidine metabolism when associated with a risk for severe toxicity against the antineoplastic agent 5-fluorouracil (PMID: 12798197).
2905-86-4
C05100
160663
1670
3-UREIDO-ISOBUTYRATE
141172
CC(CNC(N)=O)C(O)=O
C5H10N2O3
InChI=1S/C5H10N2O3/c1-3(4(8)9)2-7-5(6)10/h3H,2H2,1H3,(H,8,9)(H3,6,7,10)
PHENTZNALBMCQD-UHFFFAOYSA-N
3-(carbamoylamino)-2-methylpropanoic acid
146.1445
146.069142196
-0.50
3
β-ureidoisobutyric acid
0
-1
FDB022808
3-carbamoylamino-2-methylpropanoate;3-carbamoylamino-2-methylpropanoic acid;3-ureidoisobutyrate;3-ureidoisobutyric acid;Dl-beta-ureidoisobutyrate;Dl-beta-ureidoisobutyric acid;N-carbamyl-amino isobutyrate;N-carbamyl-b-aminoisobutyric acid;N-carbamyl-beta-aminoisobutyric acid;Beta-uba;Beta-ureidoisobutyrate;Beta-ureidoisobutyric acid;3-((aminocarbonyl)amino)-2-methylpropanoic acid;3-((aminocarbonyl)amino)-2-methylpropanoate;B-uba;β-uba;B-ureidoisobutyrate;B-ureidoisobutyric acid;β-ureidoisobutyrate;β-ureidoisobutyric acid
PW_C001363
UrisoBa
2784
2
78754
132
122244
124
124797
118
126407
299
127970
388
927
Deoxyuridine triphosphate
HMDB0001191
Deoxyuridine triphosphate (dUTP) is a deoxynucleotide triphosphate (dNTP) that is chemically similar to uridine triphosphate (UTP) except that it has a deoxyribose sugar instead of a ribose sugar. DNA synthesis requires the availability of deoxynucleotide triphosphates (dTTP, dATP, dGTP, dCTP), whereas RNA synthesis requires the availability of nucleotide triphosphates (NTPs) such as TTP, ATP, GTP, and UTP. The conversion of nucleotide triphosphates (NTPs) into dNTPs can only be done in the diphosphate form. Typically, an NTP has one phosphate removed to become an NDP. This is then converted into a dNDP by an enzyme called ribonucleotide reductase and followed by the re-addition of phosphate to give a dNTP. dUTP is a substrate for several enzymes, including inosine triphosphate pyrophosphatase, deoxyuridine 5'-triphosphate nucleotidohydrolase (mitochondrial), uridine-cytidine kinase 1, nucleoside diphosphate kinase 3, nucleoside diphosphate kinase B, nucleoside diphosphate kinase 6, nucleoside diphosphate kinase (mitochondrial), nucleoside diphosphate kinase homolog 5, nucleoside diphosphate kinase A, and nucleoside diphosphate kinase 7. While UTP is routinely incorporated into RNA, dUTP is not normally incorporated into DNA. Instead, if dUTP is misincorporated into DNA, it can cause DNA damage. Therefore, dUTP can be considered as a teratogen or a mutagen. The extent of DNA damage caused by dUTP is highly dependent on the levels of the dUTP pyrophosphatase (dUTPase) and uracil-DNA glycosylase (UDG), which limits the intracellular accumulation of dUTP. Additionally, loss of viability following thymidylate synthase (TS) inhibition occurs as a consequence of the accumulation of dUTP in some cell lines and subsequent misincorporation of uracil into DNA (PMID: 11487279).
1173-82-6
C00460
65070
17625
DUTP
58580
O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O
C9H15N2O14P3
InChI=1S/C9H15N2O14P3/c12-5-3-8(11-2-1-7(13)10-9(11)14)23-6(5)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,18,19)(H,20,21)(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
AHCYMLUZIRLXAA-SHYZEUOFSA-N
({[({[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
468.1417
467.973612734
-1.73
6
dUTP
0
-3
FDB022478
2'-deoxyuridine 5'-triphosphate;2'-deoxyuridine-5'-triphosphorate;2'-deoxyuridine-5'-triphosphoric acid;2'-deoxyuridine-5'-triphosphoric acid = dutp;Deoxy-utp;Deoxyuridine triphosphate;Deoxyuridine-5'-triphosphate;Dutp;2'-deoxyuridine 5'-triphosphoric acid
PW_C000927
dUTP
2785
2
78755
132
122245
124
124798
118
126408
299
127972
388
792
dUDP
HMDB0001000
dUDP is a derivative of nucleic acid UTP, 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 UTP has been removed, most likely by hydrolysis (Wikipedia).
4208-67-7
C01346
145729
28850
DUDP
128553
O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O
C9H14N2O11P2
InChI=1S/C9H14N2O11P2/c12-5-3-8(11-2-1-7(13)10-9(11)14)21-6(5)4-20-24(18,19)22-23(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,18,19)(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
QHWZTVCCBMIIKE-SHYZEUOFSA-N
[({[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
388.1618
388.007282324
-1.68
5
dUDP
0
-2
FDB022361
2'-deoxyuridine-5'-diphosphate;Deoxyuridine-diphosphate;Dudp;2'-deoxyuridine 5'-diphosphate;2'-deoxyuridine 5'-diphosphoric acid
PW_C000792
dUDP
2788
2
78756
132
122247
124
124800
118
126410
299
127974
388
1993
3-Aminoisobutanoic acid
HMDB0003911
beta-aminoisobutyric acid is the product from the conversion of N-carbamyl-beta-aminoisobutyric acid by the enzyme Beta-ureidopropionase (EC 3.5.1.6), the last step in pyrimidine degradation. Beta-ureidopropionase deficiency is an inborn error of pyrimidine degradation associated with neurological abnormalities (OMIM 606673).
144-90-1
C05145
64956
27389
3-AMINO-ISOBUTYRATE
58481
CC(CN)C(O)=O
C4H9NO2
InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)
QCHPKSFMDHPSNR-UHFFFAOYSA-N
3-amino-2-methylpropanoic acid
103.1198
103.063328537
0.55
2
(+)-β-aminoisobutyric acid
0
0
FDB023248
(+/-)-3-amino-2-methylpropanoate;(+/-)-3-amino-2-methylpropanoic acid;(+/-)-3-aminoisobutyric acid;(+/-)-b-aminoisobutyric acid;(+/-)-beta-aminoisobutyric acid;2-methyl-b-alanine;2-methyl-beta-alanine;3-amino-2-methylpropanoate;3-amino-2-methylpropanoic acid;3-amino-isobutanoate;3-amino-isobutanoic acid;3-aminoisobutanoate;3-aminoisobutanoic acid;3-aminoisobutyrate;3-aminoisobutyric acid;Dl-2-methyl-b-alanine;Dl-2-methyl-beta-alanine;Dl-3-amino-2-methylpropionic acid;Dl-beta-aminoisobutyric acid;Dl-3-aminoisobutyric acid;A-methyl-b-alanine;Alpha-methyl-beta-alanine;B-aminoisobutyric acid;Beta-aminoisobutyric acid;2-(aminomethyl)propionic acid;Baib;2-(aminomethyl)propionate;2-methyl-β-alanine;α-methyl-β-alanine;B-aminoisobutyrate;Beta-aminoisobutyrate;β-aminoisobutyrate;β-aminoisobutyric acid;Dl-b-aminoisobutyrate;Dl-b-aminoisobutyric acid;Dl-beta-aminoisobutyrate;Dl-β-aminoisobutyrate;Dl-β-aminoisobutyric acid
PW_C001993
AmnIsoB
2797
2
78757
132
122248
124
124801
118
126411
299
127975
388
52
quinol
Compound
PW_EC000052
17594
ChEBI
quinol
53
thioredoxin disulfide
Compound
PW_EC000053
18191
ChEBI
TD
54
thioredoxin
Compound
PW_EC000054
15033
ChEBI
Thiored
27
Thioredoxin disulfide
ProteinComplex
PW_EC000027
18191
ChEBI
TD
28
Thioredoxin
ProteinComplex
PW_EC000028
15033
ChEBI
Thiored
2335
CAD protein
P27708
This protein is a "fusion" protein encoding four enzymatic activities of the pyrimidine pathway (GATase, CPSase, ATCase and DHOase).
HMDBP03298
CAD
2p22-p21
BC065510
1
6.3.5.5; 2.1.3.2; 3.5.2.3
91
8
2703
2
142085
26
179
Dihydroorotate dehydrogenase (quinone), mitochondrial
Q02127
Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
HMDBP00184
DHODH
16q22
M94065
1
1.3.5.2
2709
2
142089
961
142092
55
5726
Uridine monophosphate synthetase isoform A
A8K5J1
UMPS
1
2711
2
82
Soluble calcium-activated nucleotidase 1
Q8WVQ1
Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
HMDBP00085
CANT1
17q25.3
BC065038
1
3.6.1.6
1593
43
2712
2
139660
23
2633
UMP-CMP kinase 2, mitochondrial
Q5EBM0
May participate in dUTP and dCTP synthesis in mitochondria. Is able to phosphorylate dUMP, dCMP, CMP, UMP and monophosphates of the pyrimidine nucleoside analogs ddC, dFdC, araC, BVDU and FdUrd with ATP as phosphate donor. Efficacy is highest for dUMP followed by dCMP; CMP and UMP are poor substrates. May be involved in mtDNA depletion caused by long term treatment with ddC or other pyrimidine analogs.
HMDBP07409
CMPK2
2p25.2
BC132821
1
2.7.4.14; 2.7.4.6
2713
2
142996
1076
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
542
GTP:AMP phosphotransferase, mitochondrial
Q9UIJ7
HMDBP00573
AK3
9p24.1
AL353151
1
2.7.4.10
2716
2
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
640
CTP synthase 1
P17812
Catalyzes the ATP-dependent amination of UTP to CTP with either L-glutamine or ammonia as the source of nitrogen.
HMDBP00676
CTPS1
1p34.1
AL391730
1
6.3.4.2
2720
2
4322
8
143000
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
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
2480
Uridine phosphorylase 2
O95045
Catalyzes the reversible phosphorylytic cleavage of uridine and deoxyuridine to uracil and ribose- or deoxyribose-1-phosphate. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis. Shows substrate specificity and accept uridine, deoxyuridine, and thymidine as well as the two pyrimidine nucleoside analogs 5-fluorouridine and 5-fluoro-2(')-deoxyuridine as substrates.
HMDBP06424
UPP2
2q24.1
BC033529
1
2.4.2.3
2742
2
136721
166
139664
23
142984
1076
690
Dihydropyrimidine dehydrogenase [NADP(+)]
Q12882
Involved in pyrimidine base degradation. Catalyzes the reduction of uracil and thymine. Also involved the degradation of the chemotherapeutic drug 5-fluorouracil.
HMDBP00727
DPYD
1p22
BT006740
1
1.3.1.2
540
8
2744
2
140506
1
515
Dihydropyrimidinase
Q14117
Catalyzes the second step of the reductive pyrimidine degradation, the reversible hydrolytic ring opening of dihydropyrimidines. Can catalyze the ring opening of 5,6-dihydrouracil to N-carbamyl-alanine and of 5,6-dihydrothymine to N-carbamyl-amino isobutyrate.
HMDBP00543
DPYS
8q22
D78011
1
3.5.2.2
537
8
2746
2
140507
1
516
Beta-ureidopropionase
Q9UBR1
Converts N-carbamyl-beta-aminoisobutyric acid and N-carbamyl-beta-alanine to, respectively, beta-aminoisobutyric acid and beta-alanine, ammonia and carbon dioxide.
HMDBP00544
UPB1
22q11.2
AF169555
1
3.5.1.6
535
8
2748
2
140508
1
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
2631
Ribonucleoside-diphosphate reductase subunit M2 B
Q7LG56
Plays a pivotal role in cell survival by repairing damaged DNA in a p53/TP53-dependent manner. Supplies deoxyribonucleotides for DNA repair in cells arrested at G1 or G2. Contains an iron-tyrosyl free radical center required for catalysis. Forms an active ribonucleotide reductase (RNR) complex with RRM1 which is expressed both in resting and proliferating cells in response to DNA damage.
HMDBP07407
RRM2B
8q23.1
AP001328
1
1.17.4.1
2751
2
4321
8
142995
1076
2634
Uridine-cytidine kinase-like 1
Q9NWZ5
May contribute to UTP accumulation needed for blast transformation and proliferation.
HMDBP07410
UCKL1
20q13.33
AK000524
1
2.7.1.48
2754
2
136724
27
136747
166
142997
1076
2457
Cytidine deaminase
P32320
This enzyme scavenge exogenous and endogenous cytidine and 2'-deoxycytidine for UMP synthesis.
HMDBP05584
CDA
1p36.2-p35
AL391357
1
3.5.4.5
2756
2
3355
29
4603
36
136066
8
142992
1076
143517
26
2374
Thymidine phosphorylase
P19971
May have a role in maintaining the integrity of the blood vessels. Has growth promoting activity on endothelial cells, angiogenic activity in vivo and chemotactic activity on endothelial cells in vitro.
Catalyzes the reversible phosphorolysis of thymidine. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
HMDBP03818
TYMP
22q13.33
U62317
1
2.4.2.4
2757
2
4595
8
136729
166
139665
23
2
Deoxycytidylate deaminase
P32321
Supplies the nucleotide substrate for thymidylate synthetase.
HMDBP00002
DCTD
4q35.1
CH471056
1
3.5.4.12
2759
2
4084
7
4315
8
142989
1076
143516
26
2372
Thymidine kinase, cytosolic
P04183
HMDBP03814
TK1
17q23.2-q25.3
K02581
1
2.7.1.21
2761
2
136732
166
138904
8
139666
23
142985
1076
2411
Thymidylate synthase
P04818
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
HMDBP04363
TYMS
18p11.32
X02308
1
2.1.1.45
2766
2
4316
8
139446
4
139659
23
142986
1076
423
Deoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrial
P33316
This enzyme is involved in nucleotide metabolism: it produces dUMP, the immediate precursor of thymidine nucleotides and it decreases the intracellular concentration of dUTP so that uracil cannot be incorporated into DNA.
HMDBP00432
DUT
15q21.1
BC033645
1
3.6.1.23
2786
2
136744
3
14
CAD protein
1
PW_P000014
15
2335
6
11
1005
6
88
8
689
Dihydroorotate dehydrogenase (quinone), mitochondrial
1
PW_P000689
781
179
1
311
1170
1
690
Uridine monophosphate synthetase isoform A
1
PW_P000690
782
5726
1
432
Soluble calcium-activated nucleotidase 1
1
PW_P000432
455
82
1
205
353
1
1586
43
691
UMP-CMP kinase 2, mitochondrial
1
PW_P000691
783
2633
1
457
Nucleoside diphosphate kinase 6
1
PW_P000457
480
110
1
217
423
1
692
GTP:AMP phosphotransferase AK3, mitochondrial
1
PW_P000692
784
542
1
507
Inosine triphosphate pyrophosphatase
1
PW_P000507
531
422
2
244
423
2
693
CTP synthase 1
1
PW_P000693
785
640
1
496
Cytosolic purine 5'-nucleotidase
1
PW_P000496
520
2368
4
241
423
4
501
Guanine deaminase
1
PW_P000501
525
654
2
243
1005
1
697
Uridine phosphorylase 2
1
PW_P000697
789
2480
1
155
Dihydropyrimidine dehydrogenase [NADP(+)]
1
PW_P000155
173
690
2
69
964
2
70
1170
2
154
Dihydropyrimidinase
1
PW_P000154
172
515
4
68
1005
8
153
Beta-ureidopropionase
1
PW_P000153
171
516
1
67
1005
1
533
8
698
Ribonucleoside-diphosphate reductase large subunit
1
PW_P000698
790
107
1
791
2631
1
312
544
2
699
Uridine-cytidine kinase-like 1
1
PW_P000699
792
2634
1
700
Cytidine deaminase
1
PW_P000700
793
2457
1
313
964
1
701
Thymidine phosphorylase
1
PW_P000701
794
2374
1
702
Deoxycytidylate deaminase
1
PW_P000702
795
2
1
314
9795
1
704
Thymidine kinase, cytosolic
1
PW_P000704
797
2372
1
705
Thymidylate synthase
1
PW_P000705
798
2411
1
706
Deoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrial
1
PW_P000706
799
423
1
315
423
1
1487
false
PW_R001487
Right
5639
500
1
Compound
false
5640
414
2
Compound
true
5641
1420
1
Compound
true
5642
463
1
Compound
true
5643
862
1
Compound
false
5644
1034
2
Compound
true
5645
1104
1
Compound
true
1208
14
1488
false
PW_R001488
Right
5646
862
1
Compound
false
5647
662
1
Compound
false
1209
14
1489
false
PW_R001489
Right
5648
662
1
Compound
false
5649
1852
1
Compound
false
1210
14
1490
false
PW_R001490
Right
5650
1852
1
Compound
false
5651
1860
1
Compound
true
5652
151
1
Compound
false
5653
52
1
ElementCollection
true
1211
689
1.3.5.2
1491
false
PW_R001491
Both
5654
151
1
Compound
false
5655
190
1
Compound
false
5656
144
1
Compound
false
1212
690
1492
false
PW_R001492
Right
5657
144
1
Compound
false
5658
194
1
Compound
false
1213
690
1493
false
PW_R001493
Right
5659
201
1
Compound
false
5660
1420
1
Compound
true
5661
194
1
Compound
false
5662
1104
1
Compound
true
1214
432
3.6.1.6
1494
false
PW_R001494
Right
5663
194
1
Compound
false
5664
414
1
Compound
true
5665
201
1
Compound
false
5666
1034
1
Compound
true
1215
691
1496
false
PW_R001496
Both
5671
192
1
Compound
false
5672
1034
1
Compound
true
5673
201
1
Compound
false
5674
414
1
Compound
true
1217
457
2.7.4.6
251
false
PW_R000251
Right
1075
192
1
Compound
false
1076
1420
1
Compound
true
1077
201
1
Compound
false
1078
1441
1
Compound
true
1218
432
3.6.1.6
1497
false
PW_R001497
Right
5675
201
1
Compound
false
5676
1034
1
Compound
true
5677
192
1
Compound
false
5678
1918
1
Compound
true
1219
692
2.7.4.10
1498
false
PW_R001498
Right
5679
192
1
Compound
false
5680
1420
1
Compound
true
5681
194
1
Compound
false
5682
170
1
Compound
true
1220
507
3.6.1.19
1499
false
PW_R001499
Right
5684
192
1
Compound
false
5685
414
1
Compound
true
5686
57
1
Compound
false
5687
1034
1
Compound
true
5688
1104
1
Compound
true
5689
790
1
Compound
true
1221
693
6.3.4.2
1502
false
PW_R001502
Right
5698
57
1
Compound
false
5699
1420
1
Compound
true
5700
1189
1
Compound
false
5701
1104
1
Compound
true
1224
432
3.6.1.6
1503
false
PW_R001503
Both
5702
57
1
Compound
false
5703
1034
1
Compound
true
5704
1189
1
Compound
false
5705
414
1
Compound
true
1225
457
2.7.4.6
1504
false
PW_R001504
Right
5706
1189
1
Compound
false
5707
1420
1
Compound
true
5708
64
1
Compound
false
5709
1104
1
Compound
true
1226
432
3.6.1.6
1505
false
PW_R001505
Both
5710
1189
1
Compound
false
5711
1034
1
Compound
true
5712
64
1
Compound
false
5713
414
1
Compound
true
1227
691
63
false
PW_R000063
Right
241
64
1
Compound
false
242
1420
1
Compound
true
243
61
1
Compound
false
244
1441
1
Compound
true
1229
496
3.1.3.5
1507
false
PW_R001507
Right
5717
61
1
Compound
false
5718
1420
1
Compound
true
5719
202
1
Compound
false
5720
35
1
Compound
true
1230
501
3.5.4.3
1508
false
PW_R001508
Right
5721
194
1
Compound
false
5722
1420
1
Compound
true
5723
202
1
Compound
false
5724
1104
1
Compound
true
1231
496
3.1.3.5
1509
false
PW_R001509
Right
5725
202
1
Compound
false
5726
1104
1
Compound
true
5727
204
1
Compound
false
5728
1146
1
Compound
true
1232
697
2.4.2.3
1510
false
PW_R001510
Right
5729
204
1
Compound
false
5730
143
1
Compound
true
5731
53
1
Compound
false
5732
146
1
Compound
true
1233
155
1.3.1.2
1511
false
PW_R001511
Right
5733
53
1
Compound
false
5734
1420
1
Compound
true
5735
18
1
Compound
false
1234
154
3.5.2.2
1512
false
PW_R001512
Right
5736
18
1
Compound
false
5737
1420
1
Compound
true
5738
40
1
Compound
false
5739
35
1
Compound
true
5740
1316
1
Compound
true
1235
153
3.5.1.6
1513
false
PW_R001513
Right
5741
1189
1
Compound
false
5742
53
1
ElementCollection
true
5743
1420
1
Compound
true
5744
962
1
Compound
false
5745
54
1
ElementCollection
true
1236
698
1.17.4.1
1514
false
PW_R001514
Right
5746
962
1
Compound
false
5747
414
1
Compound
true
5748
790
1
Compound
false
5749
1034
1
Compound
true
1237
457
2.7.4.6
1515
false
PW_R001515
Right
5750
937
1
Compound
false
5751
414
1
Compound
true
5752
962
1
Compound
false
5753
1034
1
Compound
true
1238
691
1516
false
PW_R001516
Right
5754
937
1
Compound
false
5755
1420
1
Compound
true
5756
8
1
Compound
false
5757
1104
1
Compound
true
1239
496
3.1.3.5
1517
false
PW_R001517
Right
5758
8
1
Compound
false
5759
414
1
Compound
true
5760
937
1
Compound
false
5761
1034
1
Compound
true
1240
699
2.7.1.48
1518
false
PW_R001518
Right
5762
8
1
Compound
false
5763
1420
1
Compound
true
5764
7
1
Compound
false
5765
35
1
Compound
true
1241
700
3.5.4.5
1519
false
PW_R001519
Right
5766
7
1
Compound
false
5767
1104
1
Compound
true
5768
204
1
Compound
false
5769
1042
1
Compound
true
1242
701
2.4.2.4
1520
false
PW_R001520
Right
5770
937
1
Compound
false
5771
1420
1
Compound
true
5772
1087
1
Compound
false
5773
35
1
Compound
true
1243
702
3.5.4.12
1521
false
PW_R001521
Right
5774
7
1
Compound
false
5775
414
1
Compound
true
5776
1087
1
Compound
false
5777
1034
1
Compound
true
1244
704
2.7.1.21
1523
false
PW_R001523
Right
5784
1087
1
Compound
false
5785
1178
1
Compound
true
5786
950
1
Compound
false
5787
831
1
Compound
true
1246
705
2.1.1.45
1524
false
PW_R001524
Both
5788
950
1
Compound
false
5789
414
1
Compound
true
5790
987
1
Compound
false
5791
1034
1
Compound
true
1248
705
2.1.1.45
1525
false
PW_R001525
Right
5792
987
1
Compound
false
5793
1420
1
Compound
true
5794
950
1
Compound
false
5795
1104
1
Compound
true
1249
432
3.6.1.6
1526
false
PW_R001526
Both
5796
987
1
Compound
false
5797
414
1
Compound
true
5798
1035
1
Compound
false
5799
1034
1
Compound
true
1250
457
2.7.4.6
1527
false
PW_R001527
Right
5800
1035
1
Compound
false
5801
1420
1
Compound
true
5802
987
1
Compound
false
5803
1104
1
Compound
true
1251
432
3.6.1.6
1528
false
PW_R001528
Right
5804
950
1
Compound
false
5805
1420
1
Compound
true
5806
187
1
Compound
false
5807
1104
1
Compound
true
1252
496
3.1.3.5
1529
false
PW_R001529
Right
5808
187
1
Compound
false
5809
414
1
Compound
true
5810
950
1
Compound
false
5811
1034
1
Compound
true
1254
704
2.7.1.21
1530
false
PW_R001530
Right
5812
187
1
Compound
false
5813
1104
1
Compound
true
5814
179
1
Compound
false
5815
1042
1
Compound
true
1261
701
2.4.2.4
1531
false
PW_R001531
Right
5816
179
1
Compound
false
5817
143
1
Compound
true
5818
56
1
Compound
false
5819
146
1
Compound
true
1262
155
1.3.1.2
1534
false
PW_R001534
Right
5828
927
1
Compound
false
5829
1420
1
Compound
true
5830
1087
1
Compound
false
5831
1104
1
Compound
true
1265
706
3.6.1.23
1535
false
PW_R001535
Right
5832
927
1
Compound
false
5833
1034
1
Compound
true
5834
792
1
Compound
false
5835
414
1
Compound
true
1266
457
2.7.4.6
1536
false
PW_R001536
Both
5836
1087
1
Compound
false
5837
414
1
Compound
true
5838
792
1
Compound
false
5839
1034
1
Compound
true
1267
705
2.1.1.45
1537
false
PW_R001537
Right
5840
201
1
Compound
false
5841
27
1
ElementCollection
true
5842
1420
1
Compound
true
5843
792
1
Compound
false
5844
28
1
ElementCollection
true
1268
698
1.17.4.1
1540
false
PW_R001540
Right
5852
202
1
Compound
false
5853
414
1
Compound
true
5854
194
1
Compound
false
5855
1034
1
Compound
true
1271
699
2.7.1.48
182
false
PW_R000182
Right
807
1363
1
Compound
false
808
1420
1
Compound
true
809
1993
1
Compound
false
810
1316
1
Compound
true
811
35
1
Compound
true
1274
153
3.5.1.6
1532
false
PW_R001532
Right
5820
56
1
Compound
false
5821
1420
1
Compound
true
5822
1363
1
Compound
false
1263
154
3.5.2.2
5301
500
2
81
false
920
355
10
regular
200
190
5302
414
2
42
false
815
485
10
regular
50
30
5303
1420
2
49
false
765
535
10
regular
78
78
5304
463
2
47
false
760
315
10
regular
78
78
5305
862
2
81
false
230
355
10
regular
200
190
5306
1034
2
43
false
495
488
10
regular
50
30
5307
1104
2
46
false
503
351
10
regular
44
43
5308
1005
2
9
false
635
405
10
regular
100
25
5313
662
2
81
false
230
745
10
regular
200
190
5314
1005
2
9
false
280
600
20
regular
100
25
5317
1852
2
81
false
695
745
10
regular
200
190
5318
1005
2
9
false
510
790
10
regular
100
25
5319
1860
2
3
false
855
630
10
regular
100
100
5320
151
2
81
false
1145
745
10
regular
200
190
5321
1170
2
9
false
960
780
10
regular
100
35
5322
190
2
81
false
1255
510
10
regular
200
190
5323
144
2
81
false
1650
745
10
regular
200
190
5324
194
2
81
false
1650
1305
10
regular
200
190
5325
201
2
81
false
1120
1305
10
regular
200
190
5326
1420
2
49
false
1325
1264
10
regular
78
78
5327
1104
2
46
false
1568
1275
10
regular
44
43
5328
353
2
9
false
1430
1349
10
regular
100
25
5329
414
2
42
false
1585
1545
10
regular
50
30
5330
1034
2
43
false
1330
1554
10
regular
50
30
5331
192
2
81
false
580
1303
10
regular
200
190
5335
1034
2
43
false
805
1448
10
regular
50
30
5336
414
2
42
false
1040
1444
10
regular
50
30
5337
423
2
9
false
895
1355
10
regular
100
25
5338
1420
2
49
false
790
1193
10
regular
78
78
5339
1441
2
46
false
1038
1229
10
regular
44
43
5340
353
2
9
false
892
1268
10
regular
100
25
5341
1034
2
43
false
1030
1579
10
regular
50
30
5342
1918
2
44
false
805
1588
10
regular
50
30
5343
1420
2
49
false
940
968
10
regular
78
78
5344
170
2
45
false
1378
910
10
regular
63
43
5345
423
2
9
false
1122
1053
10
regular
100
25
5347
414
2
42
false
715
1598
10
regular
50
30
5348
57
2
81
false
579
1838
10
regular
200
190
5349
1034
2
43
false
764
1738
10
regular
50
30
5350
1104
2
46
false
737
1771
10
regular
44
43
5351
790
2
81
false
367
1723
10
regular
200
190
5378
1420
2
49
false
799
1798
10
regular
78
78
5379
1189
2
81
false
1159
1836
10
regular
200
190
5380
1104
2
46
false
1077
1819
10
regular
44
43
5381
353
2
9
false
924
1883
10
regular
100
25
5382
1034
2
43
false
819
2068
10
regular
50
30
5383
414
2
42
false
1084
2071
10
regular
50
30
5384
423
2
9
false
929
1978
10
regular
100
25
5385
1420
2
49
false
1374
1796
10
regular
78
78
5386
64
2
81
false
1709
1834
10
regular
200
190
5387
1104
2
46
false
1637
1817
10
regular
44
43
5388
353
2
9
false
1479
1881
10
regular
100
25
5389
1034
2
43
false
1364
2071
10
regular
50
30
5390
414
2
42
false
1659
2074
10
regular
50
30
5394
1420
2
49
false
1929
1799
10
regular
78
78
5395
61
2
81
false
2264
1832
10
regular
200
190
5396
1441
2
46
false
2197
1830
10
regular
44
43
5397
423
2
9
false
2024
1879
10
regular
100
25
5398
1420
2
49
false
2419
1747
10
regular
78
78
5399
202
2
81
false
2262
1302
10
regular
200
190
5400
35
2
63
false
2418
1553
10
regular
78
78
5401
1005
2
9
false
2309
1647
19
regular
100
25
5402
1420
2
49
false
1870
1275
10
regular
78
78
5403
1104
2
46
false
2170
1292
10
regular
44
43
5404
423
2
9
false
2001
1355
10
regular
100
25
5405
1104
2
46
false
2236
1250
10
regular
44
43
5406
204
2
81
false
2259
782
10
regular
200
190
5407
1146
2
81
false
2084
982
10
regular
200
190
5408
143
2
61
false
2479
787
10
regular
50
30
5409
53
2
81
false
2809
777
10
regular
200
190
5410
146
2
62
false
2734
787
10
regular
50
30
5411
964
2
9
false
2529
827
10
regular
100
25
5412
1170
2
9
false
2634
822
10
regular
100
35
5413
1420
2
49
false
3019
727
10
regular
78
78
5414
18
2
81
false
3304
777
10
regular
200
190
5415
1005
2
9
false
3134
827
10
regular
100
25
5416
1420
2
49
false
3259
972
10
regular
78
78
5417
40
2
81
false
3305
1269
10
regular
200
190
5418
35
2
63
false
3261
1165
10
regular
78
78
5419
1316
2
52
false
3464
1165
10
regular
78
78
5420
1005
2
9
false
3357
1061
19
regular
100
25
5421
1420
2
49
false
1144
2101
10
regular
78
78
5422
962
2
81
false
1159
2431
10
regular
200
190
5423
544
2
9
false
1209
2208
20
regular
100
25
5424
414
2
42
false
1154
2651
10
regular
50
30
5425
790
2
81
false
1159
2901
10
regular
200
190
5426
1034
2
43
false
1154
2826
10
regular
50
30
5427
423
2
9
false
1209
2711
19
regular
100
25
5428
937
2
81
false
1744
2431
10
regular
200
190
5429
414
2
42
false
1664
2436
10
regular
50
30
5430
1034
2
43
false
1394
2436
10
regular
50
30
5431
1420
2
49
false
1954
2401
10
regular
78
78
5432
8
2
81
false
2254
2429
10
regular
200
190
5433
1104
2
46
false
2212
2437
10
regular
44
43
5434
423
2
9
false
2054
2481
10
regular
100
25
5435
414
2
42
false
2204
2659
10
regular
50
30
5436
1034
2
43
false
1944
2661
10
regular
50
30
5437
1420
2
49
false
2459
2384
10
regular
78
78
5438
7
2
81
false
2734
2427
10
regular
200
190
5439
35
2
63
false
2655
2383
10
regular
78
78
5440
964
2
9
false
2544
2479
10
regular
100
25
5441
1104
2
46
false
2698
1925
10
regular
44
43
5442
1042
2
81
false
2734
1217
10
regular
200
190
5443
1420
2
49
false
1694
2641
10
regular
78
78
5444
1087
2
81
false
1742
2916
10
regular
200
190
5445
35
2
63
false
1688
2827
10
regular
78
78
5446
9795
2
9
false
1799
2731
20
regular
100
25
5447
414
2
42
false
2459
2687
10
regular
50
30
5448
1034
2
43
false
2187
2701
10
regular
50
30
5457
1178
2
81
false
1532
3026
10
regular
200
190
5458
950
2
81
false
1742
3366
10
regular
200
190
5459
831
2
81
false
1532
3241
10
regular
200
190
5465
414
2
42
false
1577
3516
10
regular
50
30
5466
987
2
81
false
1112
3366
10
regular
200
190
5467
1034
2
43
false
1342
3516
10
regular
50
30
5468
1420
2
49
false
1317
3631
10
regular
78
78
5469
1104
2
46
false
1600
3641
10
regular
44
43
5470
353
2
9
false
1442
3546
10
regular
100
25
5471
414
2
42
false
1032
3371
10
regular
50
30
5472
1035
2
81
false
537
3366
10
regular
200
190
5473
1034
2
43
false
777
3371
10
regular
50
30
5474
423
2
9
false
872
3411
10
regular
100
25
5475
1420
2
49
false
757
3596
10
regular
78
78
5476
1104
2
46
false
1030
3596
10
regular
44
43
5477
353
2
9
false
879
3571
10
regular
100
25
5478
1420
2
49
false
1992
3586
10
regular
78
78
5479
187
2
81
false
1746
3896
10
regular
200
190
5480
1104
2
46
false
2014
3779
10
regular
44
43
5481
423
2
9
false
1892
3671
19
regular
100
25
5486
414
2
42
false
1676
3786
10
regular
50
30
5487
1034
2
43
false
1672
3611
10
regular
50
30
5517
1104
2
46
false
1979
3901
10
regular
44
43
5518
179
2
81
false
2331
3895
10
regular
200
190
5519
1042
2
81
false
2181
4090
10
regular
200
190
5520
143
2
61
false
2531
3870
10
regular
50
30
5521
56
2
81
false
2861
3895
10
regular
200
190
5522
146
2
62
false
2806
3880
10
regular
50
30
5523
964
2
9
false
2651
3925
10
regular
100
25
5524
1170
2
9
false
2651
3945
10
regular
100
35
5529
1363
2
81
false
3402
3895
10
regular
200
190
5533
927
2
81
false
2387
2915
10
regular
200
190
5534
1420
2
49
false
2287
3070
10
regular
78
78
5535
1104
2
46
false
2050
3061
10
regular
44
43
5536
423
2
9
false
2152
2960
10
regular
100
25
5537
1034
2
43
false
2372
3140
10
regular
50
30
5538
792
2
81
false
2387
3380
10
regular
200
190
5539
414
2
42
false
2377
3280
10
regular
50
30
5540
423
2
9
false
2442
3185
19
regular
100
25
5542
414
2
42
false
1977
3241
10
regular
50
30
5543
1034
2
43
false
2307
3240
10
regular
50
30
5544
201
2
81
false
2977
3380
10
regular
200
190
5545
1420
2
49
false
2882
3525
10
regular
78
78
5546
544
2
9
false
2737
3425
10
regular
100
25
5556
414
2
42
false
2152
1572
10
regular
50
30
5557
1034
2
43
false
1890
1565
10
regular
50
30
5569
1420
2
49
false
3557
3810
10
regular
78
78
5570
1993
2
81
false
3403
3430
10
regular
200
190
5571
1316
2
52
false
3374
3636
10
regular
78
78
5572
35
2
63
false
3557
3636
10
regular
78
78
5573
1005
2
9
false
3452
3737
19
regular
100
25
3180341
1420
2
49
false
3067
3837
10
regular
78
78
3180342
1005
2
9
false
3186
3938
10
regular
100
25
141
52
37
2
false
1070
630
12
regular
100
90
142
53
37
2
false
1334
2111
12
regular
100
90
143
54
37
2
false
1334
2321
12
regular
100
90
144
27
37
2
false
2857
3280
12
regular
100
90
145
28
37
2
false
2602
3285
12
regular
100
90
2190
2335
2
17
false
585
410
8
subunit
regular
180
85
2196
2335
2
17
false
240
605
8
subunit
regular
180
85
2198
2335
2
17
false
470
800
8
subunit
regular
180
85
2199
179
2
2
false
940
805
8
subunit
regular
150
70
2200
5726
2
2
false
1455
805
8
subunit
regular
150
70
2201
5726
2
2
false
1675
1035
8
subunit
regular
150
70
2202
82
2
2
false
1405
1364
8
subunit
regular
150
70
2203
2633
2
2
false
1415
1450
8
subunit
regular
150
70
2205
110
2
2
false
872
1363
8
subunit
regular
150
70
2206
82
2
2
false
872
1283
8
subunit
regular
150
70
2207
542
2
2
false
882
1499
8
subunit
regular
150
70
2208
422
2
6
false
1087
1063
8
subunit
regular
160
80
2209
640
2
2
false
605
1643
8
subunit
regular
150
70
2221
82
2
2
false
899
1898
8
subunit
regular
150
70
2222
110
2
2
false
904
1988
8
subunit
regular
150
70
2223
82
2
2
false
1459
1896
8
subunit
regular
150
70
2224
2633
2
2
false
1459
1986
8
subunit
regular
150
70
2226
2368
2
8
false
2004
1889
8
subunit
regular
140
85
2227
654
2
2
false
2289
1652
8
subunit
regular
150
70
2228
2368
2
8
false
1976
1360
8
subunit
regular
140
85
2231
2480
2
2
false
2288
1149
8
subunit
regular
150
70
2232
690
2
2
false
2550
840
8
subunit
regular
150
70
2233
515
2
8
false
3114
832
8
subunit
regular
140
85
2234
516
2
2
false
3328
1074
8
subunit
regular
150
70
2235
107
2
113
false
1179
2233
8
none
regular
160
80
2236
2631
2
6
false
1179
2213
8
protein
regular
160
80
2237
110
2
2
false
1184
2721
8
subunit
regular
150
70
2238
2633
2
2
false
1469
2491
8
subunit
regular
150
70
2239
2368
2
8
false
2039
2486
8
subunit
regular
140
85
2240
2634
2
2
false
2034
2574
8
subunit
regular
150
70
2241
2457
2
8
false
2524
2484
8
subunit
regular
140
85
2242
2374
2
6
false
2755
1752
8
subunit
regular
160
80
2243
2
2
17
false
1754
2731
8
subunit
regular
180
85
2244
2372
2
8
false
2280
2732
8
subunit
regular
140
85
2250
2411
2
6
false
1762
3201
8
subunit
regular
160
80
2259
2411
2
2
false
1407
3426
8
subunit
regular
150
70
2260
82
2
2
false
1422
3561
8
subunit
regular
150
70
2261
110
2
2
false
852
3426
8
subunit
regular
150
70
2264
82
2
2
false
854
3511
8
subunit
regular
150
70
2265
2368
2
8
false
1862
3671
8
subunit
regular
140
85
2267
2372
2
2
false
1696
3678
8
subunit
regular
150
70
2287
2374
2
6
false
2061
3953
8
subunit
regular
160
80
2288
690
2
6
false
2616
3950
8
subunit
regular
160
80
2291
423
2
2
false
2127
2975
8
subunit
regular
150
70
2292
110
2
2
false
2412
3195
8
subunit
regular
150
70
2295
2411
2
2
false
2102
3221
8
subunit
regular
150
70
2296
107
2
113
false
2707
3455
8
none
regular
160
80
2297
2631
2
6
false
2707
3435
8
protein
regular
160
80
2301
2634
2
2
false
1971
1457
8
subunit
regular
150
70
2308
516
2
2
false
3427
3742
8
subunit
regular
150
70
1230599
515
2
8
false
3161
3948
8
subunit
regular
140
85
1957
14
105
2
2183
2190
894
5308
8047
Cofactor
1960
14
105
2
2189
2196
895
5314
8054
Cofactor
1962
14
105
2
2191
2198
896
5318
8059
Cofactor
1963
689
105
2
2192
2199
897
5321
8063
Cofactor
1964
690
105
2
2193
2200
1965
690
105
2
2194
2201
1966
432
105
2
2195
2202
898
5328
8074
Cofactor
1967
691
105
2
2196
2203
1969
457
105
2
2198
2205
900
5337
8088
Cofactor
1970
432
105
2
2199
2206
901
5340
8093
Cofactor
1971
692
105
2
2200
2207
1972
507
105
2
2201
2208
902
5345
8102
Cofactor
1973
693
105
2
2202
2209
1984
432
105
2
2214
2221
905
5381
8150
Cofactor
1985
457
105
2
2215
2222
906
5384
8155
Cofactor
1986
432
105
2
2216
2223
907
5388
8160
Cofactor
1987
691
105
2
2217
2224
1989
496
105
2
2219
2226
909
5397
8173
Cofactor
1990
501
105
2
2220
2227
910
5401
8178
Cofactor
1991
496
105
2
2221
2228
911
5404
8183
Cofactor
1994
697
105
2
2224
2231
1995
155
105
2
2225
2232
912
5411
8194
Cofactor
913
5412
8195
Cofactor
1996
154
105
2
2226
2233
914
5415
8199
Cofactor
1997
153
105
2
2227
2234
915
5420
8205
Cofactor
1998
698
105
2
2228
2235
2229
2236
916
5423
8209
Cofactor
1999
457
105
2
2230
2237
917
5427
8216
Cofactor
2000
691
105
2
2231
2238
2001
496
105
2
2232
2239
918
5434
8225
Cofactor
2002
699
105
2
2233
2240
2003
700
105
2
2234
2241
919
5440
8234
Cofactor
2004
701
105
2
2235
2242
2005
702
105
2
2236
2243
920
5446
8243
Cofactor
2006
704
105
2
2237
2244
2012
705
105
2
2243
2250
2018
705
105
2
2252
2259
2019
432
105
2
2253
2260
923
5470
8283
Cofactor
2020
457
105
2
2254
2261
924
5474
8288
Cofactor
2023
432
105
2
2257
2264
925
5477
8295
Cofactor
2024
496
105
2
2258
2265
926
5481
8300
Cofactor
2026
704
105
2
2260
2267
2041
701
105
2
2280
2287
2042
155
105
2
2281
2288
932
5523
8368
Cofactor
933
5524
8369
Cofactor
2045
706
105
2
2284
2291
936
5536
8384
Cofactor
2046
457
105
2
2285
2292
937
5540
8389
Cofactor
2049
705
105
2
2288
2295
2050
698
105
2
2289
2296
2290
2297
939
5546
8400
Cofactor
2054
699
105
2
2294
2301
2060
153
105
2
2301
2308
941
5573
8449
Cofactor
968400
154
105
2
1224186
1230599
50631
3180342
4354233
Cofactor
8040
M920 450 C890 450 795 450 765 450
5
false
18
8041
M840 485 C839 462 795 450 765 450
5
false
18
8042
M804 535 C805 497 795 450 765 450
5
false
18
8043
M799 393 C796 432 782 452 765 450
5
false
18
8044
M430 450 C460 450 555 450 585 450
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8045
M520 488 C520 460 555 450 585 450
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8046
M525 394 C528 428 555 450 585 450
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8047
M375 505 L375 555 L425 505 z
10
true
18
8052
M330 545 C330 575 330 575 330 605
5
false
18
8053
M330 745 C330 715 330 720 330 690
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8054
M485 915 L485 965 L535 915 z
10
true
18
8057
M430 840 C460 840 440 840 470 840
5
false
18
8058
M695 840 C665 840 680 840 650 840
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8059
M630 1150 L630 1200 L680 1150 z
10
true
18
8060
M895 840 C925 840 910 840 940 840
5
false
18
8061
M905 730 C903 773 911 839 940 840
5
false
18
8062
M1145 840 C1115 840 1120 840 1090 840
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8063
M200 450 L200 500 L250 450 z
10
true
18
8064
M1120 730 C1121 780 1120 840 1090 840
5
false
18
8065
M1345 840 C1375 840 1425 840 1455 840
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8066
M1355 700 C1356 778 1425 840 1455 840
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8067
M1650 840 C1620 840 1635 840 1605 840
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8069
M1750 1305 C1750 1275 1750 1135 1750 1105
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8070
M1320 1400 C1362 1399 1370 1398 1405 1399
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8071
M1364 1342 C1358 1368 1374 1384 1405 1399
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8072
M1650 1400 C1602 1399 1585 1400 1555 1399
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8074
M200 450 L200 500 L250 450 z
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8075
M1649 1483 C1619 1483 1595 1485 1565 1485
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8076
M1610 1545 C1598 1512 1595 1485 1565 1485
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8077
M1323 1485 C1353 1485 1385 1485 1415 1485
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M1355 1554 C1354 1526 1385 1485 1415 1485
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8088
M200 450 L200 500 L250 450 z
10
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8089
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8090
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8091
M1118 1317 C1088 1317 1052 1318 1022 1318
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8092
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8093
M200 450 L200 500 L250 450 z
10
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M1123 1492 C1103 1518 1057 1534 1027 1534
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8095
M1055 1579 C1056 1553 1058 1534 1032 1534
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8096
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M1750 1305 C1751 1169 1484 1101 1249 1103
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M1409.5 910 C1407 850.5 1375 840 1345 840
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M200 450 L200 500 L250 450 z
10
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8103
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M715 1613 C696 1611 679 1619 680 1643
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8147
M838 1876 C833 1904 869 1933 899 1933
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false
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8148
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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false
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8150
M200 450 L200 500 L250 450 z
10
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M773 2026 C803 2026 874 2023 904 2023
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M844 2068 C838 2038 874 2023 904 2023
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M200 450 L200 500 L250 450 z
10
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8156
M1359 1931 C1389 1931 1429 1931 1459 1931
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8158
M1709 1929 C1679 1929 1639 1931 1609 1931
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8159
M1659 1860 C1660 1904 1639 1931 1609 1931
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8160
M200 450 L200 500 L250 450 z
10
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8161
M1354 2022 C1384 2022 1429 2021 1459 2021
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8162
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M1716 2019 C1686 2019 1639 2021 1609 2021
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
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M1909 1929 C1939 1929 1974 1929 2004 1929
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8170
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8171
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8172
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M2034 1999 L2034 2049 L2084 1999 z
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M2364 1832 C2364 1802 2364 1752 2364 1722
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8175
M2419 1786 C2383 1785 2364 1752 2364 1722
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8176
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M2384 1807 L2384 1857 L2434 1807 z
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M1850 1400 C1880 1400 1946 1400 1976 1400
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8181
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M2076 1475 L2076 1525 L2126 1475 z
10
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M2362 1302 C2362 1272 2363 1249 2363 1219
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8191
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8192
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M200 450 L200 500 L250 450 z
10
true
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8195
M200 450 L200 500 L250 450 z
10
true
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8196
M3009 872 C3039 872 3084 872 3114 872
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8197
M3058 805 C3063 841 3084 872 3114 872
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M3074 1137 L3074 1187 L3124 1137 z
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8201
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8202
M3405 1269 C3405 1239 3403 1174 3403 1144
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false
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M3339 1204 C3375 1204 3403 1174 3403 1144
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M3464 1204 C3413 1202 3403 1174 3403 1144
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M1153 630 L1153 680 L1203 630 z
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M1259 2213 C1256 2145 1241 2141 1222 2140
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8208
M1259 2431 C1259 2401 1259 2323 1259 2293
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false
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8209
M1169 2163.5 L1169 2213.5 L1219 2163.5 z
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8210
M1334 2166 C1296 2163 1259 2183 1259 2213
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8211
M1334 2371 C1274 2370 1259 2323 1259 2293
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false
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8212
M1259 2621 C1259 2651 1259 2691 1259 2721
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false
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8213
M1204 2666 C1246 2669 1259 2691 1259 2721
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8214
M1259 2901 C1259 2871 1259 2821 1259 2791
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false
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8215
M1204 2841 C1223 2842 1259 2821 1259 2791
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8216
M1279 2756 L1279 2806 L1329 2756 z
10
true
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8217
M1744 2526 C1714 2526 1649 2526 1619 2526
5
false
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8218
M1689 2466 C1687 2511 1649 2526 1619 2526
5
false
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8219
M1359 2526 C1389 2526 1439 2526 1469 2526
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false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8220
M1419 2466 C1423 2504 1439 2526 1469 2526
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false
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8221
M1944 2526 C1974 2526 2009 2526 2039 2526
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false
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8222
M1993 2479 C1992 2515 2009 2526 2039 2526
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false
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8223
M2254 2524 C2224 2524 2209 2526 2179 2526
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false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8224
M2234 2480 C2234 2518 2209 2526 2179 2526
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false
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true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8225
M2059 2596 L2059 2646 L2109 2596 z
10
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8226
M2253 2609 C2225 2610 2204 2609 2184 2609
5
false
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8227
M2229 2659 C2226 2632 2213 2614 2184 2609
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false
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8228
M1941 2608 C1980 2610 1992 2606 2034 2609
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false
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8229
M1969 2661 C1971 2627 1997 2605 2034 2609
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8230
M2454 2524 C2484 2524 2494 2524 2524 2524
5
false
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8231
M2498 2462 C2496 2490 2500 2524 2524 2524
5
false
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8232
M2734 2522 C2704 2522 2694 2524 2664 2524
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false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
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M2694 2461 C2693 2498 2698 2524 2664 2524
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false
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
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M2609 2639 L2609 2689 L2659 2639 z
10
true
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8235
M2834 2427 C2834 2397 2835 1862 2835 1832
5
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8236
M2742 1946.5 C2787 1945.5 2836 1926 2835 1832
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false
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8237
M2413 968 C2613 1214 2832 1524 2835 1752
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false
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8238
M2834 1407 C2834 1437 2835 1722 2835 1752
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8239
M1844 2621 C1844 2651 1844 2701 1844 2731
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false
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8240
M1772 2680 C1816 2681 1844 2701 1844 2731
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8241
M1842 2916 C1842 2886 1844 2846 1844 2816
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false
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M1766 2866 C1810 2864 1844 2846 1844 2816
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8243
M1864 2756 L1864 2806 L1914 2756 z
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8245
M2484 2717 C2483 2750 2450 2772 2420 2772
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8246
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8260
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8261
M1732 3121 C1771 3125 1842 3127 1842 3201
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8262
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8275
M1742 3461 C1712 3461 1587 3461 1557 3461
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8276
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8279
M1305 3553 C1326 3569 1392 3596 1422 3596
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8280
M1356 3631 C1369 3604 1392 3596 1422 3596
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8281
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false
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M1622 3641 C1616 3617 1602 3596 1572 3596
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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8283
M200 450 L200 500 L250 450 z
10
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8284
M1112 3461 C1082 3461 1032 3461 1002 3461
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
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18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8287
M802 3401 C810 3437 822 3461 852 3461
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8288
M1037 3531 L1037 3581 L1087 3531 z
10
true
18
8291
M735 3548 C765 3548 824 3546 854 3546
5
false
18
8292
M796 3596 C796 3567 824 3546 854 3546
5
false
18
8293
M1116 3545 C1086 3545 1034 3546 1004 3546
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8294
M1052 3596 C1049 3570 1034 3546 1004 3546
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8295
M200 450 L200 500 L250 450 z
10
true
18
8296
M1931 3556 C1931 3586 1932 3641 1932 3671
5
false
18
8297
M1992 3625 C1946 3622 1932 3641 1932 3671
5
false
18
8298
M1932 3893 C1932 3863 1932 3786 1932 3756
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8299
M2014 3800.5 C1962 3797.5 1932 3786 1932 3756
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8300
M1862 3691 L1862 3741 L1912 3691 z
10
true
18
8306
M1771 3895 C1771 3865 1771 3778 1771 3748
5
false
18
8307
M1726 3801 C1750 3800 1771 3778 1771 3748
5
false
18
8308
M1769 3560 C1769 3590 1771 3648 1771 3678
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8309
M1722 3626 C1749 3626 1771 3648 1771 3678
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8360
M1946 3991 C1976 3991 2031 3991 2061 3993
5
false
18
8361
M2001 3944 C2001 3974 2031 3993 2061 3993
5
false
18
false
false
8362
M2331 3990 C2301 3991 2255 3991 2221 3993
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8363
M2281 4090 C2281 4042 2251 3993 2221 3993
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8364
M2531 3990 C2561 3990 2586 3990 2616 3990
5
false
18
8365
M2556 3900 C2555 3946 2586 3990 2616 3990
5
false
18
8366
M2861 3990 C2831 3990 2806 3990 2776 3990
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8367
M2831 3910 C2833 3953 2806 3990 2776 3990
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8368
M2656 4105 L2656 4155 L2706 4105 z
10
true
18
8369
M2656 4105 L2656 4155 L2706 4105 z
10
true
18
8380
M2387 3010 C2357 3010 2307 3010 2277 3010
5
false
18
8381
M2326 3070 C2324 3039 2307 3010 2277 3010
5
false
18
8382
M1942 3011 C1972 3011 2097 3010 2127 3010
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8383
M2072 3061 C2074 3025 2097 3010 2127 3010
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8384
M2072 3065 L2072 3115 L2122 3065 z
10
true
18
8385
M2487 3105 C2487 3135 2487 3165 2487 3195
5
false
18
8386
M2422 3155 C2456 3151 2487 3165 2487 3195
5
false
18
8387
M2487 3380 C2487 3350 2487 3295 2487 3265
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8388
M2427 3295 C2459 3298 2487 3295 2487 3265
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8389
M200 450 L200 500 L250 450 z
10
true
18
8393
M1944 3091 C2081 3117 2075 3192 2102 3256
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8394
M2027 3256 C2057 3256 2072 3256 2102 3256
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8395
M2387 3475 C2293 3456 2274 3308 2252 3256
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8396
M2307 3255 C2277 3255 2282 3256 2252 3256
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8397
M2977 3475 C2947 3475 2897 3475 2867 3475
5
false
18
8398
M2921 3525 C2923 3491 2897 3475 2867 3475
5
false
18
8399
M2587 3475 C2617 3475 2677 3475 2707 3475
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8400
M2712 3525 L2712 3575 L2762 3525 z
10
true
18
8401
M2907 3390 C2899 3433 2897 3475 2867 3475
5
false
18
8402
M2652 3385 C2645 3435 2677 3475 2707 3475
5
false
18
8414
M2264 1490 C2234 1490 2151 1492 2121 1492
5
false
18
8415
M2177 1572 C2177 1546 2151 1492 2121 1492
5
false
18
8416
M1844 1492 C1874 1492 1941 1492 1971 1492
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8417
M1915 1565 C1917 1538 1941 1492 1971 1492
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8420
M712 1499 C748 1652 964 1703 994 1703
5
false
18
true
M 516.9422803323257 1105.3821377039737 L 530 1098 L 517.0780213802866 1090.3827519042852
false
true
M 1021.0096189432334 1420.5 L 1034 1413 L 1021.0096189432334 1405.5
false
8421
M776 1834 C877 1704 964 1703 994 1703
5
false
18
false
false
true
M 723.9903810567666 1531.5 L 711 1539 L 723.9903810567666 1546.5
false
8422
M1144 1703 C1229 1703 1220 1588 1220 1495
5
false
18
true
M 1184.056882052697 1398.0001078526518 L 1184 1413 L 1197.0187286799787 1405.5493152289807
false
true
M 1196.9903810567666 1405.5 L 1184 1413 L 1196.9903810567666 1420.5
false
8423
M1144 1703 C1174 1703 1275 1745 1259 1836
5
false
18
true
M 1108.172993398856 1398.0881512527374 L 1094 1403 L 1105.340282494104 1412.8182479574473
false
8424
M1160 2996 C1036 2995 983 2996 914 2996
5
false
18
true
M 834.055535331241 2789.8695818047045 L 824 2801 L 838.6669925774909 2804.143139947859
false
true
M 1097.5456202022485 2704.3599296560055 L 1110 2696 L 1096.5328986451725 2689.3941555347706
false
8425
M638 3366 C638 3236 635 3065 636 2996 C675 2996 699 2996 764 2996
5
false
18
true
M 580.6811278348205 3052.906715071085 L 588 3066 L 595.6796812848388 3053.115028313446
false
true
M 661.0096189432334 2808.5 L 674 2801 L 661.0096189432334 2793.5
false
8426
M3405 1459 C3405 1487 3404 1554 3405 1584
5
false
18
true
M 3277.0096189432334 1126.5 L 3290 1119 L 3277.0096189432334 1111.5
false
8427
M1120 450 C1150 450 1185 450 1215 450
5
false
18
true
M 992.0096189432334 342.5 L 1005 335 L 992.0096189432334 327.5
false
true
M 907.9903810567666 327.5 L 895 335 L 907.9903810567666 342.5
false
8431
M330 355 C330 330 330 311 330 295
5
false
18
true
M 300.4307192981926 260.7128843404944 L 305 275 L 315.08836475703464 263.89932900546
false
8435
M1455 605 C1485 605 1540 605 1570 605
5
false
18
true
M 1352.9903810567666 467.5 L 1340 475 L 1352.9903810567666 482.5
false
8444
M3502 3895 C3502 3865 3502 3842 3502 3812
5
false
18
8445
M3557 3849 C3521 3845 3502 3842 3502 3812
5
false
18
8446
M3503 3620 C3503 3650 3502 3712 3502 3742
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8447
M3452 3675 C3494 3675 3502 3712 3502 3742
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8448
M3557 3675 C3511 3675 3502 3712 3502 3742
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
8449
M200 450 L200 500 L250 450 z
10
true
18
8450
M3503 3430 C3504 3360 3502 3389 3503 3320
5
false
18
true
M 3160.0096189432334 2947.5 L 3173 2940 L 3160.0096189432334 2932.5
false
true
M 3075.9903810567666 2932.5 L 3063 2940 L 3075.9903810567666 2947.5
false
18649
M1334 2166 C1305 2164 1258 2180 1259 2213
5
false
18
4354230
M3061 3990 C3091 3990 3131 3988 3161 3988
5
false
18
4354231
M3106 3915 C3105 3965 3131 3988 3161 3988
5
false
18
4354232
M3402 3990 C3372 3990 3331 3988 3301 3988
5
false
18
true
M 2663.9468550441647 3802.261556296296 L 2649 3801 L 2655.380887721186 3814.575134323078
false
4354233
M3176.5 3858 L3176.5 3908 L3226.5 3858 z
10
true
18
1680
105
1487
2
5867
5301
8040
Left
5868
5302
8041
Left
5869
5303
8042
Left
5870
5304
8043
Left
5871
5305
8044
Right
5872
5306
8045
Right
5873
5307
8046
Right
1613
1208
1957
1681
105
1488
2
5874
5305
8052
Left
5875
5313
8053
Right
1614
1209
1960
1682
105
1489
2
5876
5313
8057
Left
5877
5317
8058
Right
1615
1210
1962
1683
105
1490
2
5878
5317
8060
Left
5879
5319
8061
Left
5880
5320
8062
Right
149
141
8064
Right
1616
1211
1963
1684
105
1491
2
5881
5320
8065
Left
5882
5322
8066
Left
5883
5323
8067
Right
1617
1212
1964
1685
105
1492
2
5884
5323
8068
Left
5885
5324
8069
Right
1618
1213
1965
1686
105
1493
2
5886
5325
8070
Left
5887
5326
8071
Left
5888
5324
8072
Right
5889
5327
8073
Right
1619
1214
1966
1687
105
1494
2
5890
5324
8075
Left
5891
5329
8076
Left
5892
5325
8077
Right
5893
5330
8078
Right
1620
1215
1967
1689
105
1496
2
5898
5331
8084
Left
5899
5335
8085
Left
5900
5325
8086
Right
5901
5336
8087
Right
1622
1217
1969
1690
105
251
2
5902
5331
8089
Left
5903
5338
8090
Left
5904
5325
8091
Right
5905
5339
8092
Right
1623
1218
1970
1691
105
1497
2
5906
5325
8094
Left
5907
5341
8095
Left
5908
5331
8096
Right
5909
5342
8097
Right
1624
1219
1971
1692
105
1498
2
5910
5331
8098
Left
5911
5343
8099
Left
5912
5324
8100
Right
5913
5344
8101
Right
1625
1220
1972
1693
105
1499
2
5914
5331
8103
Left
5916
5347
8105
Left
5917
5348
8106
Right
5918
5349
8107
Right
5919
5350
8108
Right
5920
5351
8109
Right
1626
1221
1973
1696
105
1502
2
5929
5348
8146
Left
5930
5378
8147
Left
5931
5379
8148
Right
5932
5380
8149
Right
1629
1224
1984
1697
105
1503
2
5933
5348
8151
Left
5934
5382
8152
Left
5935
5379
8153
Right
5936
5383
8154
Right
1630
1225
1985
1698
105
1504
2
5937
5379
8156
Left
5938
5385
8157
Left
5939
5386
8158
Right
5940
5387
8159
Right
1631
1226
1986
1699
105
1505
2
5941
5379
8161
Left
5942
5389
8162
Left
5943
5386
8163
Right
5944
5390
8164
Right
1632
1227
1987
1701
105
63
2
5948
5386
8169
Left
5949
5394
8170
Left
5950
5395
8171
Right
5951
5396
8172
Right
1634
1229
1989
1702
105
1507
2
5952
5395
8174
Left
5953
5398
8175
Left
5954
5399
8176
Right
5955
5400
8177
Right
1635
1230
1990
1703
105
1508
2
5956
5324
8179
Left
5957
5402
8180
Left
5958
5399
8181
Right
5959
5403
8182
Right
1636
1231
1991
1704
105
1509
2
5960
5399
8186
Left
5961
5405
8187
Left
5962
5406
8188
Right
5963
5407
8189
Right
1637
1232
1994
1705
105
1510
2
5964
5406
8190
Left
5965
5408
8191
Left
5966
5409
8192
Right
5967
5410
8193
Right
1638
1233
1995
1706
105
1511
2
5968
5409
8196
Left
5969
5413
8197
Left
5970
5414
8198
Right
1639
1234
1996
1707
105
1512
2
5971
5414
8200
Left
5972
5416
8201
Left
5973
5417
8202
Right
5974
5418
8203
Right
5975
5419
8204
Right
1640
1235
1997
1708
105
1513
2
5976
5379
8206
Left
5977
5421
8207
Left
5978
5422
8208
Right
150
142
8210
Left
151
143
8211
Right
1641
1236
1998
1709
105
1514
2
5979
5422
8212
Left
5980
5424
8213
Left
5981
5425
8214
Right
5982
5426
8215
Right
1642
1237
1999
1710
105
1515
2
5983
5428
8217
Left
5984
5429
8218
Left
5985
5422
8219
Right
5986
5430
8220
Right
1643
1238
2000
1711
105
1516
2
5987
5428
8221
Left
5988
5431
8222
Left
5989
5432
8223
Right
5990
5433
8224
Right
1644
1239
2001
1712
105
1517
2
5991
5432
8226
Left
5992
5435
8227
Left
5993
5428
8228
Right
5994
5436
8229
Right
1645
1240
2002
1713
105
1518
2
5995
5432
8230
Left
5996
5437
8231
Left
5997
5438
8232
Right
5998
5439
8233
Right
1646
1241
2003
1714
105
1519
2
5999
5438
8235
Left
6000
5441
8236
Left
6001
5406
8237
Right
6002
5442
8238
Right
1647
1242
2004
1715
105
1520
2
6003
5428
8239
Left
6004
5443
8240
Left
6005
5444
8241
Right
6006
5445
8242
Right
1648
1243
2005
1716
105
1521
2
6007
5438
8244
Left
6008
5447
8245
Left
6009
5444
8246
Right
6010
5448
8247
Right
1649
1244
2006
1718
105
1523
2
6017
5444
8260
Left
6018
5457
8261
Left
6019
5458
8262
Right
6020
5459
8263
Right
1651
1246
2012
1722
105
1524
2
6029
5458
8275
Left
6030
5465
8276
Left
6031
5466
8277
Right
6032
5467
8278
Right
1655
1248
2018
1723
105
1525
2
6033
5466
8279
Left
6034
5468
8280
Left
6035
5458
8281
Right
6036
5469
8282
Right
1656
1249
2019
1724
105
1526
2
6037
5466
8284
Left
6038
5471
8285
Left
6039
5472
8286
Right
6040
5473
8287
Right
1657
1250
2020
1725
105
1527
2
6041
5472
8291
Left
6042
5475
8292
Left
6043
5466
8293
Right
6044
5476
8294
Right
1658
1251
2023
1726
105
1528
2
6045
5458
8296
Left
6046
5478
8297
Left
6047
5479
8298
Right
6048
5480
8299
Right
1659
1252
2024
1728
105
1529
2
6054
5479
8306
Left
6055
5486
8307
Left
6056
5458
8308
Right
6057
5487
8309
Right
1661
1254
2026
1739
105
1530
2
6097
5479
8360
Left
6098
5517
8361
Left
6099
5518
8362
Right
6100
5519
8363
Right
1672
1261
2041
1740
105
1531
2
6101
5518
8364
Left
6102
5520
8365
Left
6103
5521
8366
Right
6104
5522
8367
Right
1673
1262
2042
1743
105
1534
2
6113
5533
8380
Left
6114
5534
8381
Left
6115
5444
8382
Right
6116
5535
8383
Right
1676
1265
2045
1744
105
1535
2
6117
5533
8385
Left
6118
5537
8386
Left
6119
5538
8387
Right
6120
5539
8388
Right
1677
1266
2046
1745
105
1536
2
6121
5444
8393
Left
6122
5542
8394
Left
6123
5538
8395
Right
6124
5543
8396
Right
1678
1267
2049
1746
105
1537
2
6125
5544
8397
Left
6126
5545
8398
Left
6127
5538
8399
Right
152
144
8401
Left
153
145
8402
Right
1679
1268
2050
1749
105
1540
2
6135
5399
8414
Left
6136
5556
8415
Left
6137
5324
8416
Right
6138
5557
8417
Right
1682
1271
2054
1754
105
182
2
6152
5529
8444
Left
6153
5569
8445
Left
6154
5570
8446
Right
6155
5571
8447
Right
6156
5572
8448
Right
1687
1274
2060
932268
105
1532
2
3788023
5521
4354230
Left
3788024
3180341
4354231
Left
3788025
5529
4354232
Right
885372
1263
968400
362
328
105
217
false
994
1668
16
regular
340
5331
8420
Left
341
5348
8421
Left
342
5325
8422
Left
343
5379
8423
Left
363
335
105
217
false
764
2961
16
regular
344
5425
8424
Left
345
5472
8425
Left
364
329
105
14
false
3330
1584
16
regular
346
5417
8426
Left
368
340
105
14
false
1215
415
16
regular
347
5301
8427
Left
369
343
105
14
false
255
225
16
regular
348
5305
8431
Right
370
344
105
14
false
1570
570
16
regular
349
5322
8435
Left
371
345
105
14
false
3428
3250
16
regular
350
5570
8450
Right
255
18649
276
13
785
730
0.9
0.9
0
2
1
490
240
277
13
1340
1420
0.6
0.6
0
2
1
490
240
278
13
800
1470
0.6
0.6
0
2
1
490
240
279
13
1385
1945
0.6
0.6
0
2
1
490
240
281
13
1405
2455
0.6
0.6
0
2
1
490
240
285
13
2055
2940
0.6
0.6
0
2
1
490
240
187434
2846
1745
2.5
2.5
0
3
14
327
267
479747
3470
2053
2.2
2.2
60
2
3
280
360
329
M127 226 C127 176 177 126 227 126 C1272 126 2631 126 3676 126 C3726 126 3776 176 3776 226 C3776 1453 3776 3048 3776 4275 C3776 4325 3726 4375 3676 4375 C2631 4375 1272 4375 227 4375 C177 4375 127 4325 127 4275 C127 3048 127 1453 127 226
1
true
6
3649.0
4249.0
650
235
Intracellular Space
1085
160
20
1.6
1.6
200
15
651
235
Mitochondria
905
880
20
1.0
1.0
200
15
652
235
Extracellular Space
1080
25
20
1.3
1.3
200
15