1820
Pathway
Allantoin Degradation (Anaerobic)
Allantoin can be degraded in anaerobic conditions. The first step involves allantoin being degraded by an allantoinase resulting in an allantoate. This compound in turn is metabolized by reacting with water and 2 hydrogen ions through an allantoate amidohydrolase resulting in the release of a carbon dioxide, ammonium and an S-ureidoglycine. The latter compund is further degrades through a S-ureidoglycine aminohydrolase resulting in the release of an ammonium and an S-ureidoglycolate.
S-ureidoglycolate can be metabolized into oxalurate by two different reactions. The first reactions involves a NAD driven ureidoglycolate dehydrogenase resulting in the release of a hydrogen ion , an NADH and a oxalurate. On the other hand S-ureidoglycolate can react with NADP resulting in the release of an NADPH, a hydroge ion and an oxalurate.
It is hypothesized that oxalurate can interact with a phosphate and release a a carbamoyl phosphate and an oxamate.
The carbamoyl phosphate can be further degraded by reacting with an ADP, and a hydrogen ion through a carbamate kinase resulting in the release of an ammonium , ATP and carbon dioxide
Metabolic
PW002050
Center
PathwayVisualizationContext2338
1400
2402
#000099
PathwayVisualization1804
1820
Allantoin Degradation (Anaerobic)
Allantoin can be degraded in anaerobic conditions. The first step involves allantoin being degraded by an allantoinase resulting in an allantoate. This compound in turn is metabolized by reacting with water and 2 hydrogen ions through an allantoate amidohydrolase resulting in the release of a carbon dioxide, ammonium and an S-ureidoglycine. The latter compund is further degrades through a S-ureidoglycine aminohydrolase resulting in the release of an ammonium and an S-ureidoglycolate.
S-ureidoglycolate can be metabolized into oxalurate by two different reactions. The first reactions involves a NAD driven ureidoglycolate dehydrogenase resulting in the release of a hydrogen ion , an NADH and a oxalurate. On the other hand S-ureidoglycolate can react with NADP resulting in the release of an NADPH, a hydroge ion and an oxalurate.
It is hypothesized that oxalurate can interact with a phosphate and release a a carbamoyl phosphate and an oxamate.
The carbamoyl phosphate can be further degraded by reacting with an ADP, and a hydrogen ion through a carbamate kinase resulting in the release of an ammonium , ATP and carbon dioxide
Metabolic
3
3804
10601204
Cusa E, Obradors N, Baldoma L, Badia J, Aguilar J: Genetic analysis of a chromosomal region containing genes required for assimilation of allantoin nitrogen and linked glyoxylate metabolism in Escherichia coli. J Bacteriol. 1999 Dec;181(24):7479-84.
1820
Pathway
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
12
Astrocyte
CL:0000127
2
Platelet
CL:0000233
8
Beta cell
CL:0000639
3
Escherichia coli
562
Prokaryote
23
Pseudomonas aeruginosa
287
Prokaryote
1
Homo sapiens
9606
Eukaryote
Human
2
Bacteria
2
Prokaryote
Bacteria
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
19
Schizosaccharomyces pombe
4896
Eukaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
21
Xenopus laevis
8355
Eukaryote
African clawed frog
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
25
Escherichia coli (strain K12)
83333
Prokaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
202
Spathaspora passalidarum
340170
Eukaryote
Spathaspora passalidarum
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
11
Extracellular Space
GO:0005615
31
Periplasmic Space
GO:0005620
1
Cytosol
GO:0005829
5
Cytoplasm
GO:0005737
6
Lysosome
GO:0005764
4
Peroxisome
GO:0005777
3
Mitochondrial Matrix
GO:0005759
2
Mitochondrion
GO:0005739
10
Cell Membrane
GO:0005886
16
Lysosomal Lumen
GO:0043202
7
Endoplasmic Reticulum Membrane
GO:0005789
18
Melanosome Membrane
GO:0033162
13
Endoplasmic Reticulum
GO:0005783
25
Golgi Apparatus
GO:0005794
14
Mitochondrial Outer Membrane
GO:0005741
12
Mitochondrial Inner Membrane
GO:0005743
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
15
Nucleus
GO:0005634
35
Chloroplast
GO:0009507
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
40
Periplasm
GO:0042597
24
Mitochondrial Intermembrane Space
GO:0005758
32
Inner Membrane
GO:0070258
19
Sarcoplasmic Reticulum
GO:0016529
27
Peroxisome Membrane
GO:0005778
1
Liver
BTO:0000759
72
9
4
Adrenal Medulla
BTO:0000049
71
8
25
Intestine
BTO:0000648
28
Stomach
BTO:0001307
155
26
7
Nervous System
BTO:0001484
8
Blood Vessel
BTO:0001102
74
11
11
Heart
BTO:0000562
73
10
6
Kidney
BTO:0000671
71
8
24
Brain
BTO:0000142
89
16
5
cardiocyte
BTO:0001539
2
Endothelium
BTO:0000393
18
Pancreas
BTO:0000988
105
11
3
PW_BS000105
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31
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PW_BS000107
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1
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PW_BS000108
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31
23
PW_BS000024
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1
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PW_BS000024
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11
23
PW_BS000024
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PW_BS000024
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PW_BS000024
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PW_BS000024
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PW_BS000024
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PW_BS000170
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PW_BS000024
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PW_BS000162
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PW_BS000115
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PW_BS000028
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PW_BS000028
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16
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PW_BS000028
341
4
1
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PW_BS000028
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18
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PW_BS000028
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PW_BS000028
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14
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25
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PW_BS000028
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25
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PW_BS000028
356
25
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PW_BS000028
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4
10
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PW_BS000028
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3
60
1
PW_BS000028
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383
7
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12
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390
7
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391
12
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10
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11
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18
17
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5
17
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PW_BS000115
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1
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PW_BS000115
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1
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PW_BS000115
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PW_BS000115
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4
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PW_BS000115
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14
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25
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25
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PW_BS000115
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10
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12
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PW_BS000115
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40970
(S)-(+)-allantoin
Allantoin, also known as glyoxyldiureide or 5-ureidohydantoin, belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms. Allantoin exists as a solid, slightly soluble (in water), and a very weakly acidic compound (based on its pKa). Allantoin has been detected in most biofluids, including urine, blood, cerebrospinal fluid, and saliva. Within the cell, allantoin is primarily located in the cytoplasm. Allantoin exists in all living organisms, ranging from bacteria to humans. Allantoin can be converted into allantoin; which is catalyzed by the enzyme outer membrane pore protein N. Outside of the human body, allantoin can be found in a number of food items such as pepper (c. chinense), mamey sapote, tartary buckwheat, and black elderberry. This makes allantoin a potential biomarker for the consumption of these food products. Allantoin is a potentially toxic compound.
15678
NC(=O)NC1NC(=O)NC1=O
C4H6N4O3
InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)
POJWUDADGALRAB-UHFFFAOYSA-N
158.1154
158.043990078
S-allantoin;Allantoin
PW_C040970
Saltoin
5745
105
5746
107
5747
108
42423
318
42424
315
42633
320
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
18.0153
18.010564686
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
941
Allantoic acid
HMDB0001209
Allantoic acid is the END product of Allantoicase [EC:3.5.3.4], an enzyme involved in uric acid degradation (Purine metabolism). Although it is commonly accepted that allantoicase is lost in mammals, it has been identified in mice and humans. (PMID 11852104). A crystalline, transparent, colorless substance found in the allantoic liquid of the fetal calf; -- formerly called allantoic acid and amniotic acid.
99-16-1
C00499
203
30837
ALLANTOATE
198
NC(=O)NC(NC(N)=O)C(O)=O
C4H8N4O4
InChI=1S/C4H8N4O4/c5-3(11)7-1(2(9)10)8-4(6)12/h1H,(H,9,10)(H3,5,7,11)(H3,6,8,12)
NUCLJNSWZCHRKL-UHFFFAOYSA-N
176.1307
176.054554764
FDB012646
Allantoate;Allantoic acid;Diureidoacetate;Diureidoacetic acid;Bis[(aminocarbonyl)amino]acetic acid;Bis[(aminocarbonyl)amino]acetate;2,2-bis(carbamoylamino)acetate
PW_C000941
Allanto
5748
108
12465
226
12467
151
12468
249
42625
315
40034
Hydrogen Ion
HMDB0059597
Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])
C00080
1038
15378
1010
[H+]
H
InChI=1S/p+1
GPRLSGONYQIRFK-UHFFFAOYSA-N
1.0079
1.007825032
H+;H(+);Hydrogen cation;Hydron;Proton
PW_C040034
H+
215
4
670
8
753
15
788
31
848
3
1116
2
1463
26
1464
54
2231
49
2780
17
4250
22
4254
42
4547
10
4576
18
4694
70
5241
103
5327
111
5353
112
5626
108
5639
107
5699
100
5720
105
5742
117
5963
147
6037
155
6070
157
6093
161
6130
159
6232
166
6483
178
6601
152
6692
101
6843
188
6910
187
7100
163
7168
205
7191
206
7453
219
7454
220
7472
222
7525
213
7532
210
7558
212
7572
160
7590
170
8195
225
8218
151
8243
226
8413
162
8420
224
9139
195
9155
249
11915
164
12015
281
12181
285
12246
286
12266
287
12521
227
13257
223
13325
294
15330
308
42329
315
42354
318
42401
322
42405
312
42454
320
76912
293
77136
133
77210
134
77372
331
77804
114
77955
132
77990
327
77991
347
78379
345
79929
130
80019
368
80387
310
80388
304
80722
119
93823
124
94823
383
110550
388
112855
94
113280
390
115537
398
115539
118
115856
336
116205
109
119973
406
120193
407
120549
122
120593
409
121170
424
121171
425
122569
418
122615
384
122687
125
122758
120
123183
135
123218
137
123742
459
123743
460
125141
454
125188
121
125273
136
125359
479
125550
481
125730
483
125736
297
125809
299
126517
495
126717
489
126766
480
126823
300
126902
501
127213
208
128308
506
128361
391
128430
395
140692
882
140693
883
140699
167
140707
168
140715
14
140742
788
140743
597
140760
185
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
44.0095
43.989829244
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
22608
Ammonium
HMDB0041827
Ammonium is an important source of nitrogen for many plant species, especially those growing on hypoxic soils. However, it is also toxic to most crop species and is rarely applied as a sole nitrogen source. The ammonium (more obscurely: aminium) cation is a positively charged polyatomic cation with the chemical formula NH4+. It is formed by the protonation of ammonia (NH3). Ammonium is also a general name for positively charged or protonated substituted amines and quaternary ammonium cations (NR4+), where one or more hydrogen atoms are replaced by organic radical groups (indicated by R).
14798-03-9
C01342
16741146
28938
218
[NH4+]
H4N
InChI=1S/H3N/h1H3/p+1
QGZKDVFQNNGYKY-UHFFFAOYSA-O
18.0385
18.034374133
Ammonium ion;Ammonia ion;Ammonium;Ammonium chloride;Ammonium(1+);Azanium;Nh4+;[nh4]+;[nh4](+);Nh4(+)
PW_C022608
Ammon
5751
108
5892
95
5969
100
6226
166
8273
151
8367
225
11909
170
12470
249
42627
315
116281
109
40764
S-ureidoglycine
(2S)-Ureidoglycine belongs to the class of organic compounds known as n-carbamoyl-alpha amino acids. N-carbamoyl-alpha amino acids are compounds containing an alpha amino acid which bears an carbamoyl group at its terminal nitrogen atom (2S)-Ureidoglycine is soluble (in water) and a moderately acidic compound (based on its pKa).
59947
N[C@@H](NC(N)=O)C(O)=O
C3H7N3O3
InChI=1S/C3H7N3O3/c4-1(2(7)8)6-3(5)9/h1H,4H2,(H,7,8)(H3,5,6,9)/t1-/m0/s1
VTFWFHCECSOPSX-SFOWXEAESA-N
133.106
133.048741105
PW_C040764
Sug
5752
108
12469
249
42628
315
795
(S)-Ureidoglycolic acid
HMDB0001005
(S)-Ureidoglycolic acid, also known as (S)-ureidoglycolate, belongs to the class of organic compounds known as n-carbamoyl-alpha amino acids. N-carbamoyl-alpha amino acids are compounds containing an alpha amino acid which bears an carbamoyl group at its terminal nitrogen atom (S)-Ureidoglycolic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, (S)-ureidoglycolic acid is primarily located in the cytoplasm (S)-Ureidoglycolic acid exists in all living organisms, ranging from bacteria to humans (S)-Ureidoglycolic acid participates in a number of enzymatic reactions. In particular, Ammonium and (S)-ureidoglycolic acid can be biosynthesized from S-ureidoglycine through its interaction with the enzyme S-ureidoglycine aminohydrolase. Furthermore, (S)-Ureidoglycolic acid can be converted into urea and glyoxylic acid; which is mediated by the enzyme ureidoglycolate lyase. Furthermore, Ammonium and (S)-ureidoglycolic acid can be biosynthesized from S-ureidoglycine through the action of the enzyme S-ureidoglycine aminohydrolase. Finally, (S)-Ureidoglycolic acid can be converted into oxalureate through its interaction with the enzyme ureidoglycolate dehydrogenase. (S)-Ureidoglycolic acid is a substrate of enzyme ureidoglycolate dehydrogenase [EC 1.1.1.154] in purine metabolism pathway (KEGG).
7424-03-5
C00603
439269
15412
CPD-1091
388403
NC(=O)N[C@@H](O)C(O)=O
C3H6N2O4
InChI=1S/C3H6N2O4/c4-3(9)5-1(6)2(7)8/h1,6H,(H,7,8)(H3,4,5,9)/t1-/m0/s1
NWZYYCVIOKVTII-SFOWXEAESA-N
134.0907
134.03275669
FDB022364
(-)-ureidoglycolate;(-)-ureidoglycolic acid;(s)-ureidoglycolate;(s)-ureidoglycolic acid;(s)-[(aminocarbonyl)amino]hydroxy-acetic acid;S-(-)-ureidoglycolic acid;Ureidoglycolate
PW_C000795
Ureidog
5754
108
12472
249
42629
315
721
NAD
HMDB0000902
NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).
53-84-9
C00003
5893
15846
NAD
5682
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H27N7O14P2
InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BAWFJGJZGIEFAR-NNYOXOHSSA-N
663.4251
663.109121631
FDB022309
3-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nad
PW_C000721
NAD
140
4
150
3
353
8
651
10
1114
2
1134
43
1273
5
1466
54
2229
49
2779
17
2835
29
3107
9
4807
18
4813
18
4819
28
4902
6
4960
31
5167
95
5238
103
5334
111
5360
112
5469
123
5482
125
5590
135
5610
118
5696
100
5738
108
5827
141
5912
147
5942
151
6024
155
6072
157
6076
161
6385
1
6469
178
6772
117
6890
160
7012
188
7097
163
7174
205
7197
206
7405
198
7459
222
8241
226
8359
225
9085
224
11819
216
12322
249
13006
298
13018
300
13256
223
42404
322
42619
315
77104
132
77120
133
77209
134
77370
331
77650
336
77667
334
77702
332
77709
130
77915
113
77983
347
78406
356
80006
368
80690
119
93825
124
110552
388
112750
166
112853
94
119929
122
119952
406
120171
407
120834
419
120984
408
121159
425
121242
126
121259
429
121817
383
122614
384
122742
120
123130
447
123141
136
123419
455
123549
374
123731
460
123812
443
123829
464
124370
398
125187
121
125319
297
125342
479
125530
481
125806
299
125825
490
125924
482
126515
495
126765
480
126885
501
127278
507
127383
502
128089
390
128360
391
128428
395
140757
185
1144
NADH
HMDB0001487
NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).
58-68-4
C00004
439153
16908
NADH
388299
DB00157
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O14P2
InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BOPGDPNILDQYTO-NNYOXOHSSA-N
665.441
665.124771695
FDB022649
1,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotide
PW_C001144
NADH
143
4
153
3
490
8
648
10
1115
2
1275
5
1469
54
2230
49
2781
17
2836
29
3109
9
4806
18
4812
18
4821
28
4904
6
4959
31
5169
95
5240
103
5332
111
5358
112
5466
123
5479
125
5593
135
5698
100
5737
108
5829
141
5915
147
5945
151
6027
155
6079
161
6387
1
6472
178
6771
117
6893
160
7011
188
7099
163
7172
205
7195
206
7462
222
8244
226
8360
225
9086
224
11809
198
11821
216
12320
249
13003
298
13015
300
13255
223
42403
322
42618
315
77107
132
77123
133
77208
134
77371
331
77651
336
77668
334
77700
332
77707
130
77917
113
77986
347
80009
368
80691
119
93822
124
110549
388
112854
94
115838
118
119955
406
120172
407
120378
122
120986
408
121162
425
121244
126
121693
429
121818
383
122616
384
122745
120
123127
447
123138
136
123551
374
123734
460
123814
443
124242
464
124371
398
125189
121
125345
479
125531
481
125762
297
125808
299
125926
482
126516
495
126767
480
126888
501
127385
502
128090
390
128362
391
128429
395
140759
185
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
743.405
743.075452041
FDB021908
Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acid
PW_C000143
NADP
183
8
191
3
768
5
780
10
824
18
839
2
1611
29
1617
49
4685
31
4796
14
4801
14
5308
111
5790
108
6017
147
6132
159
6273
35
6778
117
7069
188
7105
163
7152
205
7206
160
7317
213
7346
210
7562
212
7589
170
8197
225
8220
151
8419
224
11811
198
11897
211
12008
222
12152
164
12249
286
12597
226
12650
249
42344
315
43745
322
76913
293
77164
132
77384
331
77396
332
77461
130
77515
115
77624
336
77814
334
77870
112
80713
119
113165
94
120106
407
120429
405
120450
122
120604
408
120618
123
121142
125
121277
429
121401
124
121485
383
123063
376
123084
135
123229
374
123243
447
123713
136
123848
464
123960
118
124043
398
125473
481
125694
297
125743
482
126215
299
126528
495
127010
206
127225
502
127570
388
128100
390
140709
168
146
NADPH
HMDB0000221
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).
53-57-6
C00005
22833512
16474
NADPH
17215925
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H30N7O17P3
InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
ACFIXJIJDZMPPO-NNYOXOHSSA-N
745.4209
745.091102105
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
43000
Oxalureate
Oxaluric acid, also known as monooxalylurea or oxalurate, belongs to the class of organic compounds known as n-carbamoyl-alpha amino acids. N-carbamoyl-alpha amino acids are compounds containing an alpha amino acid which bears an carbamoyl group at its terminal nitrogen atom. Oxaluric acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Oxaluric acid may be a unique E.coli metabolite. Outside of the human body, oxaluric acid can be found in cocoa bean. This makes oxaluric acid a potential biomarker for the consumption of this food product.
456
16582
OC(=N)N=C(O)C(O)=O
C3H4N2O4
InChI=1S/C3H4N2O4/c4-3(9)5-1(6)2(7)8/h(H,7,8)(H3,4,5,6,9)
UWBHMRBRLOJJAA-UHFFFAOYSA-N
132.0749
132.017106626
((aminocarbonyl)amino)oxo-acetate;((aminocarbonyl)amino)oxo-acetic acid;Carbamoylamino(oxo)acetate;Carbamoylamino(oxo)acetic acid;Carbamoyloxamate;Carbamoyloxamic acid;Carbamyl oxamate;Carbamyl oxamic acid;Monooxalylurea;Onooxalylurea;Oxal;Oxalurate;Oxalureate;Oxalureic acid;Oxaluric acid;Ureido(oxo)acetate;Ureido(oxo)acetic acid;[(aminocarbonyl)amino]oxo-acetate;[(aminocarbonyl)amino]oxo-acetic acid
PW_C043000
Oxalu
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
97.9952
97.976895096
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
43228
Oxamate
Oxamate, also known as oxalic monoamide or oxamic acid, 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. Oxamate is soluble (in water) and a moderately acidic compound (based on its pKa). Oxamate may be a unique E.coli metabolite.
974
18058
NC(=O)C(O)=O
C2H3NO3
InChI=1S/C2H3NO3/c3-1(4)2(5)6/h(H2,3,4)(H,5,6)
SOWBFZRMHSNYGE-UHFFFAOYSA-N
89.0501
89.011292967
(aminocarbonyl)-formate;(aminocarbonyl)-formic acid;(aminocarbonyl)-oxamate;2-oxo-glycine;Amino(oxo)acetate;Amino(oxo)acetic acid;Amino-glyoxylate;Amino-glyoxylic acid;Aminooxo-acetate;Aminooxo-acetic acid;Carbamoyl-formate;Carbamoyl-formic acid;Iodoxamate meglumine (usan);Iodoxamic acid meglumine (usan);Oa (van);Oxalamate;Oxalamic acid;Oxalate monoamide;Oxalic acid monoamide;Oxalic monoamide;Oxamate;Oxamic acid;Oxamidate;Oxamidic acid
PW_C043228
Oxa
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
141.0199
140.982708755
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
427.2011
427.029414749
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
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
507.181
506.995745159
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
6795
Allantoinase
P77671
Involved in allantoinase activity. Catalyzes the conversion of allantoin (5- ureidohydantoin) to allantoic acid by hydrolytic cleavage of the five-member hydantoin ring.
allB
b0512
AP009048
3
3.5.2.5
5749
108
6774
Allantoate amidohydrolase
P77425
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amidines. Involved in the anaerobic utilization of allantoin. Converts allantoate to (S)-ureidoglycolate and ammonia.
allC
b0516
AP009048
3
3.5.3.-
5753
108
7544
conserved protein
P75713
ylbA
b0515
3
3.5.3.26
5755
108
8883
101
6785
Ureidoglycolate dehydrogenase
P77555
Involved in oxidoreductase activity. Involved in the anaerobic utilization of allantoin.
allD
b0517
AP009048
3
1.1.1.350
8884
101
7719
putative carbonate kinase
P37306
ybcF
3
2.7.2.2
8529
101
1588
Allantoinase
3
PW_P001588
1873
6795
4
1589
Allantoate amidohydrolase
3
PW_P001589
1874
6774
2
1590
S-ureidoglycine aminohydrolase
3
PW_P001590
1875
7544
4022
ureidoglycolate dehydrogenase
3
PW_P004022
11021
6785
2
4024
predicted carbamate kinase
3
PW_P004024
11023
7719
2985
false
PW_R002985
Right
11837
40970
1
Compound
false
11838
1420
1
Compound
false
11839
941
1
Compound
false
11840
40034
1
Compound
false
2951
1588
3.5.2.5
2986
false
PW_R002986
Right
11841
941
1
Compound
false
11842
1420
1
Compound
false
11843
40034
2
Compound
false
11844
1316
1
Compound
false
11845
22608
1
Compound
false
11846
40764
1
Compound
false
2952
1589
3.5.3.-
2987
false
PW_R002987
Right
11847
40764
1
Compound
false
11848
1420
1
Compound
false
11849
22608
1
Compound
false
11850
795
1
Compound
false
2953
1590
3.5.3.26
5989
PW_R005989
Right
24465
795
1
Compound
false
24466
143
1
Compound
false
24467
40034
1
Compound
false
24468
146
1
Compound
false
24469
43000
1
Compound
false
5990
PW_R005990
Right
24470
43000
1
Compound
false
24471
1104
1
Compound
false
24472
43228
1
Compound
false
24473
862
1
Compound
false
5991
false
PW_R005991
Right
24474
862
1
Compound
false
24475
1034
1
Compound
false
24476
40034
2
Compound
false
24477
22608
1
Compound
false
24478
414
1
Compound
false
24479
1316
1
Compound
false
5951
4024
2.7.2.2
5987
false
PW_R005987
Right
24456
795
1
Compound
false
24457
721
1
Compound
false
24458
40034
1
Compound
false
24459
1144
1
Compound
false
24460
43000
1
Compound
false
5949
4022
1.1.1.350
70491
40970
3
false
300
396
10
regular
100
110
70492
1420
49
false
415
492
10
regular
78
78
70493
941
3
false
755
401
10
regular
100
100
70494
40034
55
false
660
497
10
regular
78
78
70495
1420
49
false
871
495
10
regular
78
78
70496
40034
55
false
871
328
10
regular
78
78
70497
1316
52
false
1161
334
10
regular
78
78
70498
22608
3
false
1160
497
10
regular
100
100
70499
40764
3
false
1265
402
10
regular
100
100
70500
1420
49
false
1396
334
10
regular
78
78
70501
22608
3
false
1680
307
10
regular
100
100
70502
795
3
false
1800
392
10
regular
100
120
70507
721
59
false
1755
557
10
regular
50
30
70508
40034
55
false
1714
758
10
regular
78
78
70509
1144
60
false
1892
787
10
regular
50
30
70514
143
61
false
1995
547
10
regular
50
30
70515
40034
55
false
1969
778
10
regular
78
78
70516
146
62
false
1987
707
10
regular
50
30
70517
43000
3
false
1802
902
10
regular
100
100
70518
1104
46
false
1713
1005
10
regular
44
43
70519
43228
3
false
1501
1002
10
regular
100
100
70520
862
3
false
1369
896
10
regular
100
110
70521
1034
43
false
1279
1001
10
regular
50
30
70522
40034
55
false
1255
828
10
regular
78
78
70523
22608
3
false
819
902
10
regular
100
100
70524
414
42
false
984
990
10
regular
50
30
70525
1316
52
false
960
837
10
regular
78
78
32349
6795
8
false
509
411
8
subunit
regular
140
85
32350
6774
6
false
975
412
8
subunit
regular
160
80
32351
7544
101
2
false
1505
417
8
subunit
regular
150
70
32353
6785
101
6
false
1772
647
8
subunit
regular
160
80
32355
7719
101
2
false
1069
914
8
subunit
regular
150
70
27213
1588
1804
32030
32349
27214
1589
1804
32031
32350
27215
1590
1804
32032
32351
27217
4022
1804
32034
32353
27219
4024
1804
32036
32355
100212
M400.33333333333337 451.66666666666663 C456.33333333333337 450.66666666666663 467.33333333333337 451.66666666666663 509.33333333333337 451.66666666666663
5
false
18
100213
M454.33333333333337 492.66666666666663 C454.33333333333337 458.66666666666663 474.33333333333337 450.66666666666663 509.33333333333337 451.66666666666663
5
false
18
100214
M755.3333333333334 451.66666666666663 C722.3333333333334 451.66666666666663 682.3333333333334 451.66666666666663 649.3333333333334 451.66666666666663
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
100215
M699.3333333333334 497.66666666666663 C700.3333333333334 456.66666666666663 686.3333333333334 451.66666666666663 649.3333333333334 451.66666666666663
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
100216
M855.3333333333334 451.66666666666663 C885.3333333333334 451.66666666666663 945.3333333333334 452.66666666666663 975.3333333333334 452.66666666666663
5
false
18
100217
M910.3333333333334 495.66666666666663 C913.3333333333334 448.66666666666663 945.3333333333334 452.66666666666663 975.3333333333334 452.66666666666663
5
false
18
100218
M910.3333333333334 406.66666666666663 C908.3333333333334 434.66666666666663 909.3333333333334 452.66666666666663 975.3333333333334 452.66666666666663
5
false
18
100219
M1200.3333333333333 412.66666666666663 C1200.3333333333333 456.66666666666663 1176.3333333333333 451.66666666666663 1135.3333333333333 452.66666666666663
5
false
18
true
M 25.946855044164835 264.9282229629627 L 11 263.6666666666667 L 17.380887721185843 277.241800989745
false
100220
M1210.3333333333333 497.66666666666663 C1210.3333333333333 463.66666666666663 1193.3333333333333 452.66666666666663 1135.3333333333333 452.66666666666663
5
false
18
true
M 25.946855044164835 264.9282229629627 L 11 263.6666666666667 L 17.380887721185843 277.241800989745
false
100221
M1265.3333333333333 452.66666666666663 C1235.3333333333333 452.66666666666663 1165.3333333333333 452.66666666666663 1135.3333333333333 452.66666666666663
5
false
18
true
M 25.946855044164835 264.9282229629627 L 11 263.6666666666667 L 17.380887721185843 277.241800989745
false
100222
M1365.3333333333333 452.66666666666663 C1395.3333333333333 452.66666666666663 1475.3333333333333 452.66666666666663 1505.3333333333333 452.66666666666663
5
false
18
100223
M1435.3333333333333 412.66666666666663 C1434.3333333333333 454.66666666666663 1475.3333333333333 452.66666666666663 1505.3333333333333 452.66666666666663
5
false
18
100224
M1730.3333333333333 407.66666666666663 C1729.3333333333333 446.66666666666663 1685.3333333333333 452.66666666666663 1655.3333333333333 452.66666666666663
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
100225
M1800.3333333333333 452.66666666666663 C1770.3333333333333 452.66666666666663 1685.3333333333333 452.66666666666663 1655.3333333333333 452.66666666666663
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
100239
M1900 452 C1982 452 2040.5 451 2099.5 450 C2099.5 550 2101.5 609 2101.5 686
5
false
18
100240
M2049.3333333333335 562.6666666666666 C2100.3333333333335 562.6666666666666 2101.8333333333335 615.6666666666666 2101.8333333333335 645.6666666666666
5
false
18
100241
M2047.3333333333333 817.6666666666666 C2091.3333333333335 817.6666666666666 2101.8333333333335 777.6666666666666 2098.8333333333335 694.6666666666666
5
false
18
true
M 153.6135217108315 531.5948896296294 L 138.66666666666666 530.3333333333334 L 145.0475543878525 543.9084676564117
false
100242
M2041.3333333333333 722.6666666666666 C2072.3333333333335 727.6666666666666 2103.8333333333335 712.6666666666666 2101.8333333333335 666.6666666666666
5
false
18
true
M 153.6135217108315 531.5948896296294 L 138.66666666666666 530.3333333333334 L 145.0475543878525 543.9084676564117
false
100243
M1902 952 C1970 951 1996.5 951 2101.5 950 C2102.5 902 2101.5 683 2101.5 583
5
false
18
true
M 153.6135217108315 531.5948896296294 L 138.66666666666666 530.3333333333334 L 145.0475543878525 543.9084676564117
false
100244
M1802.3333333333333 952.6666666666666 C1752.3333333333333 953.6666666666666 1531.3333333333333 951.6666666666666 1469.3333333333333 951.6666666666666
5
false
18
100245
M1735.3333333333333 1005.6666666666666 C1735.3333333333333 967.6666666666666 1693.3333333333333 950.1666666666666 1635.3333333333333 952.1666666666666
5
false
18
100246
M1551.3333333333333 1002.6666666666666 C1551.3333333333333 960.6666666666666 1602.3333333333333 952.1666666666666 1636.3333333333333 952.1666666666666
5
false
18
true
M 153.6135217108315 664.9282229629626 L 138.66666666666666 663.6666666666666 L 145.0475543878525 677.241800989745
false
100247
M1469.3333333333333 951.6666666666666 C1534.3333333333333 951.6666666666666 1705.3333333333333 952.6666666666666 1802.3333333333333 952.6666666666666
5
false
18
true
M 153.6135217108315 664.9282229629626 L 138.66666666666666 663.6666666666666 L 145.0475543878525 677.241800989745
false
100248
M1369.3333333333333 951.6666666666666 C1339.3333333333333 951.6666666666666 1249.3333333333333 949.6666666666666 1219.3333333333333 949.6666666666666
5
false
18
100249
M1304.3333333333333 1001.6666666666666 C1302.3333333333333 958.6666666666666 1249.3333333333333 949.6666666666666 1219.3333333333333 949.6666666666666
5
false
18
100250
M1294.3333333333333 906.6666666666666 C1290.3333333333333 947.6666666666666 1249.3333333333333 949.6666666666666 1219.3333333333333 949.6666666666666
5
false
18
100251
M927.3333333333334 949.6666666666666 C983.3333333333334 949.6666666666666 1039.3333333333333 949.6666666666666 1069.3333333333333 949.6666666666666
5
false
18
true
M 153.6135217108315 664.9282229629626 L 138.66666666666666 663.6666666666666 L 145.0475543878525 677.241800989745
false
100252
M1009.3333333333334 990.6666666666666 C1009.3333333333334 966.6666666666666 1039.3333333333333 949.6666666666666 1069.3333333333333 949.6666666666666
5
false
18
true
M 153.6135217108315 664.9282229629626 L 138.66666666666666 663.6666666666666 L 145.0475543878525 677.241800989745
false
100253
M999.3333333333334 915.6666666666666 C1001.3333333333334 946.6666666666666 1039.3333333333333 949.6666666666666 1069.3333333333333 949.6666666666666
5
false
18
true
M 153.6135217108315 664.9282229629626 L 138.66666666666666 663.6666666666666 L 145.0475543878525 677.241800989745
false
3660308
M1850.3333333333333 512.6666666666666 C1850.3333333333333 542.6666666666666 1852.3333333333333 617.6666666666666 1852.3333333333333 647.6666666666666
5
false
18
3660309
M1805.3333333333333 572.6666666666666 C1835.3333333333333 574.6666666666666 1851.3333333333333 580.6666666666666 1852.3333333333333 647.6666666666666
5
false
18
3660310
M1792.3333333333333 797.6666666666666 C1843.3333333333333 797.6666666666666 1853.3333333333333 792.6666666666666 1852.3333333333333 727.6666666666666
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3660311
M1892.3333333333333 802.6666666666666 C1848.3333333333333 801.6666666666666 1852.3333333333333 757.6666666666666 1852.3333333333333 727.6666666666666
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3660312
M1852.3333333333333 902.6666666666666 C1852.3333333333333 872.6666666666666 1852.3333333333333 757.6666666666666 1852.3333333333333 727.6666666666666
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
20510
1804
2985
79680
70491
100212
Left
79681
70492
100213
Left
79682
70493
100214
Right
79683
70494
100215
Right
20685
2951
27213
20511
1804
2986
79684
70493
100216
Left
79685
70495
100217
Left
79686
70496
100218
Left
79687
70497
100219
Right
79688
70498
100220
Right
79689
70499
100221
Right
20686
2952
27214
20512
1804
2987
79690
70499
100222
Left
79691
70500
100223
Left
79692
70501
100224
Right
79693
70502
100225
Right
20687
2953
27215
20516
1804
5989
79707
70502
100239
Left
79708
70514
100240
Left
79709
70515
100241
Right
79710
70516
100242
Right
79711
70517
100243
Right
20517
1804
5990
79712
70517
100244
Left
79713
70518
100245
Left
79714
70519
100246
Right
79715
70520
100247
Right
20518
1804
5991
79716
70520
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