321
Pathway
Gemcitabine Action Pathway
Gemcitabine is a cytidine analogue used in the treatment of certain cancers. Gemcitabine enters the cell via sodium nucleoside co-transporters (SLC29A1, SLC28A1, and SLC28A3), where it acts through multiple mechanisms to produce a cytotoxic effect. Gemcitabine is phosphorylated into gemcitabine monophosphate by deoxycytidine kinase, which is then subsequently phosphorylated into the diphosphate and triphosphate nucleotides by UMP-CMP kinase and nucleoside diphosphate kinase respectively. Gemcitabine diphosphate inhibits ribonucleoside-diphosphate reductase, a crucial enzyme in the conversion of ribonucleotides into deoxyribonucleotides for DNA synthesis. Gemcitabine triphosphate on the other hand can be incorporated into DNA, causing chain termination. Furthermore, gemcitabine monophosphate can be deaminated into difluoro-deoxyuridine monophosphate, which inhibits thymidylate synthase, an enzyme involved in the production of dTTP for DNA synthesis.
Drug Action
PW000247
Top
PathwayVisualizationContext263
1380
2100
#000099
PathwayVisualization167
321
Gemcitabine Pathway
Gemcitabine is a cytidine analogue used in the treatment of certain cancers. Gemcitabine enters the cell via sodium nucleoside co-transporters (SLC29A1, SLC28A1, and SLC28A3), where it acts through multiple mechanisms to produce a cytotoxic effect. Gemcitabine is phosphorylated into gemcitabine monophosphate by deoxycytidine kinase, which is then subsequently phosphorylated into the diphosphate and triphosphate nucleotides by UMP-CMP kinase and nucleoside diphosphate kinase respectively. Gemcitabine diphosphate inhibits ribonucleoside-diphosphate reductase, a crucial enzyme in the conversion of ribonucleotides into deoxyribonucleotides for DNA synthesis. Gemcitabine triphosphate on the other hand can be incorporated into DNA, causing chain termination. Furthermore, gemcitabine monophosphate can be deaminated into difluoro-deoxyuridine monophosphate, which inhibits thymidylate synthase, an enzyme involved in the production of dTTP for DNA synthesis.
Drug
1
741
Difluorodeoxyuridine monophosphate inhibition of
InhibitorySubPathway
1221
40657
Compound
8
1222
705
ProteinComplex
8
742
Gemcitabine Di- and Triphosphate inhibit Ribonucleoside-diphosphate reductase
InhibitorySubPathway
1223
40483
Compound
8
1224
40485
Compound
8
1225
491
ProteinComplex
8
1226
1057
ProteinComplex
8
743
Gemcitabine Triphosphate inhibits CTP synthase 1
InhibitorySubPathway
1227
40485
Compound
8
1228
693
ProteinComplex
8
744
Incorporation into DNA and RNA
SubPathway
1229
40485
Compound
23
1474
8893876
Plunkett W, Huang P, Searcy CE, Gandhi V: Gemcitabine: preclinical pharmacology and mechanisms of action. Semin Oncol. 1996 Oct;23(5 Suppl 10):3-15.
321
Pathway
1475
19514966
Wong A, Soo RA, Yong WP, Innocenti F: Clinical pharmacology and pharmacogenetics of gemcitabine. Drug Metab Rev. 2009;41(2):77-88. doi: 10.1080/03602530902741828.
321
Pathway
1
Cell
CL:0000000
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
5
Hepatocyte
CL:0000182
2
Platelet
CL:0000233
8
Beta cell
CL:0000639
1
Homo sapiens
9606
Eukaryote
Human
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
2
Bacteria
2
Prokaryote
Bacteria
3
Escherichia coli
562
Prokaryote
19
Schizosaccharomyces pombe
4896
Eukaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
21
Xenopus laevis
8355
Eukaryote
African clawed frog
25
Escherichia coli (strain K12)
83333
Prokaryote
23
Pseudomonas aeruginosa
287
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
11
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GO:0005615
5
Cytoplasm
GO:0005737
15
Nucleus
GO:0005634
2
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GO:0005739
7
Endoplasmic Reticulum Membrane
GO:0005789
1
Cytosol
GO:0005829
3
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GO:0005759
14
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GO:0005741
4
Peroxisome
GO:0005777
10
Cell Membrane
GO:0005886
13
Endoplasmic Reticulum
GO:0005783
27
Peroxisome Membrane
GO:0005778
19
sarcoplasmic reticulum
GO:0016529
31
Periplasmic Space
GO:0005620
35
Chloroplast
GO:0009507
12
Mitochondrial Inner Membrane
GO:0005743
32
Inner Membrane
GO:0070258
25
Golgi apparatus
GO:0005794
26
Golgi apparatus membrane
GO:0000139
6
Lysosome
GO:0005764
16
Lysosomal Lumen
GO:0043202
18
Melanosome Membrane
GO:0033162
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
8
Blood Vessel
BTO:0001102
74
11
1
Liver
BTO:0000759
72
9
25
Intestine
BTO:0000648
2
Endothelium
BTO:0000393
7
Nervous System
BTO:0001484
18
Pancreas
BTO:0000988
5
cardiocyte
BTO:0001539
4
Adrenal Medulla
BTO:0000049
71
8
28
Stomach
BTO:0001307
155
26
11
Heart
BTO:0000562
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10
41
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8951
Gemcitabine
HMDB0014584
Gemcitabine is a nucleoside analog used as chemotherapy. It is marketed as Gemzar by Eli Lilly and Company. As with fluorouracil and other analogues of pyrimidines, the drug replaces one of the building blocks of nucleic acids, in this case cytidine, during DNA replication. The process arrests tumor growth, as new nucleosides cannot be attached to the 'faulty' nucleoside, resulting in apoptosis (cellular 'suicide').
95058-81-4
C07650
60750
175901
54753
DB00441
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)C1(F)F
C9H11F2N3O4
InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7-/m1/s1
SDUQYLNIPVEERB-QPPQHZFASA-N
4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
263.1981
263.071762265
-1.07
3
gemcitabine
0
0
2',2'-difluorodeoxycytidine;2'-deoxy-2',2'-difluorocytidine;4-amino-1-((2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidin-2(1h)-one;Gemcitabina;Gemcitabinum
PW_C008951
Gemcitb
3336
41
4309
15
4310
8
40476
Gemcitabine Monophosphate
HMDB0061262
Gemcitabine monophosphate belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Gemcitabine monophosphate is soluble (in water) and a moderately acidic compound (based on its pKa).
503015
439295
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)C1(F)F
C9H12F2N3O7P
InChI=1S/C9H12F2N3O7P/c10-9(11)6(15)4(3-20-22(17,18)19)21-7(9)14-2-1-5(12)13-8(14)16/h1-2,4,6-7,15H,3H2,(H2,12,13,16)(H2,17,18,19)/t4-,6-,7-/m1/s1
KNTREFQOVSMROS-QPPQHZFASA-N
{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
343.178
343.038092675
-1.37
4
[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxyphosphonic acid
0
-2
DBMET01145
PW_C040476
GcbMP
3337
41
4081
7
4313
23
40657
Difluorodeoxyuridine monophosphate
HMDB0061204
{[(2R,3R)-4,4-difluoro-3-hydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. {[(2R,3R)-4,4-difluoro-3-hydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid is soluble (in water) and a moderately acidic compound (based on its pKa).
O[C@@H]1[C@@H](COP(O)(O)=O)OC(N2C=CC(=O)NC2=O)C1(F)F
C9H11F2N2O8P
InChI=1S/C9H11F2N2O8P/c10-9(11)6(15)4(3-20-22(17,18)19)21-7(9)13-2-1-5(14)12-8(13)16/h1-2,4,6-7,15H,3H2,(H,12,14,16)(H2,17,18,19)/t4-,6-,7?/m1/s1
APSMIPKDENVCML-WETFRILZSA-N
{[(2R,3R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
344.1628
344.02210826
-1.47
4
[(2R,3R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxyphosphonic acid
0
-2
DBMET00694
PW_C040657
Difluor
4082
7
4314
8
40483
Gemcitabine diphosphate
HMDB0060639
Gemcitabine diphosphate belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O. Gemcitabine diphosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Gemcitabine diphosphate has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, gemcitabine diphosphate is primarily located in the cytoplasm. In humans, gemcitabine diphosphate is involved in the gemcitabine action pathway and the gemcitabine metabolism pathway. Gemcitabine diphosphate is a metabolite of gemcitabine. Gemcitabine is a nucleoside analog used as chemotherapy. It is marketed as Gemzar by Eli Lilly and Company. (Wikipedia)
6420157
4925716
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)C1(F)F
C9H13F2N3O10P2
InChI=1S/C9H13F2N3O10P2/c10-9(11)6(15)4(3-22-26(20,21)24-25(17,18)19)23-7(9)14-2-1-5(12)13-8(14)16/h1-2,4,6-7,15H,3H2,(H,20,21)(H2,12,13,16)(H2,17,18,19)/t4-,6-,7-/m1/s1
FRQISCZGNNXEMD-QPPQHZFASA-N
[({[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
423.158
423.004423085
-1.48
5
{[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
0
-2
DBMET00858
PW_C040483
GD
3370
7
4317
8
40485
Gemcitabine triphosphate
HMDB0060638
Gemcitabine triphosphate, also known as 2,2-df-ctp, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Gemcitabine triphosphate is soluble (in water) and an extremely strong acidic compound (based on its pKa). Gemcitabine triphosphate has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, gemcitabine triphosphate is primarily located in the cytoplasm. In humans, gemcitabine triphosphate is involved in the gemcitabine action pathway and the gemcitabine metabolism pathway. Gemcitabine triphosphate is a metabolite of gemcitabine. Gemcitabine is a nucleoside analog used as chemotherapy. It is marketed as Gemzar by Eli Lilly and Company. (Wikipedia)
130659
115568
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)C1(F)F
C9H14F2N3O13P3
InChI=1S/C9H14F2N3O13P3/c10-9(11)6(15)4(25-7(9)14-2-1-5(12)13-8(14)16)3-24-29(20,21)27-30(22,23)26-28(17,18)19/h1-2,4,6-7,15H,3H2,(H,20,21)(H,22,23)(H2,12,13,16)(H2,17,18,19)/t4-,6-,7-/m1/s1
YMOXEIOKAJSRQX-QPPQHZFASA-N
({[({[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
503.1379
502.970753495
-1.47
6
({[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
0
-3
DBMET00859
2'2'-difluorodeoxycytidine 5'-triphosphate;2'2'-difluorodeoxycytidine 5'-triphosphoric acid;Gemcitabine triphosphoric acid
PW_C040485
GcbTP
3346
41
3372
7
4319
8
4323
23
8133
Fe3+
HMDB0012943
Fe3+, also known as ferric ion or fe(iii), belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. Fe3+ exists in all living organisms, ranging from bacteria to humans. 2,3-Dihydroxybenzoylserine and fe3+ can be biosynthesized from ferric enterobactin through its interaction with the enzyme enterochelin esterase. Outside of the human body, fe3+ can be found in a number of food items such as bamboo shoots, catjang pea, chickpea, and orange bell pepper. This makes fe3+ a potential biomarker for the consumption of these food products. The major activity of supplemental iron is in the prevention and treatment of iron deficiency anemia. Iron has putative immune-enhancing, anticarcinogenic and cognition-enhancing activities.
20074-52-6
C14819
29936
29034
CPD-10134
27815
[Fe+3]
Fe
InChI=1S/Fe/q+3
VTLYFUHAOXGGBS-UHFFFAOYSA-N
iron(3+) ion
55.845
55.934942133
0
iron(3+) ion
3
3
C14819
Fe(iii);Ferric ion;Iron(3+);Fe (iii) ion;Fe(3+);Ferric iron;Iron, ion (fe(3+))
PW_C008133
Fe3+
1230
3
1296
8
1420
49
1997
2
7042
163
11841
160
12675
151
77431
111
77450
331
78599
112
78721
132
120949
407
121013
122
121127
383
121593
124
123515
119
123578
135
123696
398
124151
118
125890
481
127351
206
127559
388
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
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
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
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
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
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
HCHKCACWOHOZIP-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
1902
Equilibrative nucleoside transporter 1
Q99808
Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). It is sensitive (ES) to low concentrations of the inhibitor nitrobenzylmercaptopurine riboside (NBMPR) and is sodium-independent. It has a higher affinity for adenosine. Inhibited by dipyridamole and dilazep (anticancer chemotherapeutics drugs)
HMDBP02365
SLC29A1
6p21.1
BC008954
1
1639
Sodium/nucleoside cotransporter 1
O00337
Sodium-dependent and pyrimidine-selective. Exhibits the transport characteristics of the nucleoside transport system cit or N2 subtype (N2/cit) (selective for pyrimidine nucleosides and adenosine). It also transports the antiviral pyrimidine nucleoside analogs 3'-azido-3'-deoxythymidine (AZT) and 2',3'-dideoxycytidine (ddC). It may be involved in the intestinal absorption and renal handling of pyrimidine nucleoside analogs used to treat acquired immunodeficiency syndrome (AIDS). It has the following selective inhibition: adenosine, thymidine, cytidine, uridine >> guanosine, inosine.
HMDBP01844
SLC28A1
15q25.3
U62967
1
8485
14
2371
Solute carrier family 28 member 3
Q9HAS3
Sodium-dependent, pyrimidine- and purine-selective. Involved in the homeostasis of endogenous nucleosides. Exhibits the transport characteristics of the nucleoside transport system cib or N3 subtype (N3/cib) (with marked transport of both thymidine and inosine). Employs a 2:1 sodium/nucleoside ratio. Also able to transport gemcitabine, 3'-azido-3'-deoxythymidine (AZT), ribavirin and 3-deazauridine
HMDBP03808
SLC28A3
9q22.2
AK292849
1
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
104
Ribonucleoside-diphosphate reductase large subunit
P23921
Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides.
HMDBP00108
RRM1
11p15.5
X59543
1
1.17.4.1
1798
8
4712
2
136738
166
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
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
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
6
5'(3')-deoxyribonucleotidase, cytosolic type
Q8TCD5
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
HMDBP00006
NT5C
AK000419
1
3.1.3.-
4111
8
4541
31
7
Deoxycytidine kinase
P27707
Required for the phosphorylation of the deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA). Has broad substrate specificity, and does not display selectivity based on the chirality of the substrate. It is also an essential enzyme for the phosphorylation of numerous nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
HMDBP00007
DCK
4q13.3-q21.1
BC103764
1
2.7.1.74
3338
41
4102
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
3
UMP-CMP kinase
P30085
Catalyzes specific phosphoryl transfer from ATP to UMP and CMP.
HMDBP00003
CMPK1
1p32
AL513322
1
2.7.4.14; 2.7.4.6
1528
2
3347
41
3371
7
4105
23
4318
8
136733
166
105
Nucleoside diphosphate kinase A
P15531
Major role in the synthesis of nucleoside triphosphates other than ATP. Possesses nucleoside-diphosphate kinase, serine/threonine-specific protein kinase, geranyl and farnesyl pyrophosphate kinase, histidine protein kinase and 3'-5' exonuclease activities. Involved in cell proliferation, differentiation and development, signal transduction, G protein-coupled receptor endocytosis, and gene expression. Required for neural development including neural patterning and cell fate determination.
HMDBP00109
NME1
17q21.3
X17620
1
2.7.4.6
729
26
3374
7
3557
2
4108
23
4320
8
4765
31
4775
91
835
Equilibrative nucleoside transporter 1
1
PW_P000835
960
1902
1
1055
Sodium/nucleoside cotransporter 1
1
PW_P001055
1200
1639
1
832
Solute carrier family 28 member 3
1
PW_P000832
957
2371
1
705
Thymidylate synthase
1
PW_P000705
798
2411
1
491
Ribonucleoside-diphosphate reductase 1
1
PW_P000491
514
104
1
515
107
1
238
8133
2
1057
Ribonucleoside-diphosphate reductase 2
1
PW_P001057
1202
104
1
1203
2631
1
425
8133
2
693
CTP synthase 1
1
PW_P000693
785
640
1
968
5'(3')-deoxyribonucleotidase, cytosolic type
1
PW_P000968
1094
6
2
411
423
1
819
Deoxycytidine kinase
1
PW_P000819
943
7
2
702
Deoxycytidylate deaminase
1
PW_P000702
795
2
1
314
9795
1
416
UMP-CMP kinase
1
PW_P000416
438
3
1
407
423
1
1526
2
206
Nucleoside diphosphate kinase A
1
PW_P000206
224
105
6
93
423
1
2202
false
PW_R002202
Right
7786
40476
1
Compound
false
8066
1034
1
Compound
true
7787
8951
1
Compound
false
8067
414
1
Compound
true
2051
968
3.1.3.-
1731
false
PW_R001731
Right
6546
8951
1
Compound
false
8062
414
1
Compound
true
6547
40476
1
Compound
false
8063
1034
1
Compound
true
1459
819
2.7.1.74
2077
false
PW_R002077
Right
7393
40476
1
Compound
false
8064
1420
1
Compound
true
7394
40657
1
Compound
false
8065
35
1
Compound
true
1955
702
3.5.4.12
1735
false
PW_R001735
Right
6556
40476
1
Compound
false
8057
414
1
Compound
true
6557
40483
1
Compound
false
8058
1034
1
Compound
true
1469
416
1737
false
PW_R001737
Right
6560
40483
1
Compound
false
8068
414
1
Compound
true
6561
40485
1
Compound
false
8069
1034
1
Compound
true
1478
206
2.7.4.6
223
PW_T000223
260
8951
1
Compound
15
8
Right
181
835
2013-09-19T15:23:51-06:00
2013-09-19T15:23:51-06:00
14
182
1055
2013-09-19T15:23:51-06:00
2013-09-19T15:23:51-06:00
14
183
832
2013-09-19T15:23:51-06:00
2013-09-19T15:23:51-06:00
14
8835
8951
15
157
false
45
235
10
regular
200
190
8836
8951
8
157
false
565
235
10
regular
200
190
8838
40476
23
157
false
1155
235
10
regular
200
190
8839
40657
8
157
false
1755
230
10
regular
200
200
8844
40483
8
157
false
1155
635
10
regular
200
190
8849
40485
8
157
false
1155
1045
10
regular
200
190
8851
8133
8
9
false
1725
1050
10
regular
100
25
8852
8133
8
9
false
1720
885
10
regular
100
25
8853
40485
23
3
true
0
0
10
regular
100
110
9482
1034
31
43
false
1235
150
10
regular
50
30
9483
414
31
42
false
640
145
10
regular
50
30
9484
423
31
9
false
912
120
10
regular
100
25
9485
414
23
42
false
790
235
10
regular
50
30
9486
1034
23
43
false
1080
235
10
regular
50
30
9489
1420
8
49
false
1370
170
10
regular
78
78
9490
35
8
63
false
1661
173
10
regular
78
78
9491
9795
8
9
false
1502
290
10
regular
100
25
9497
414
23
42
false
1345
440
10
regular
50
30
9498
1034
23
43
false
1345
590
10
regular
50
30
9499
423
23
9
false
1145
485
10
regular
100
25
9501
414
8
42
false
1345
840
10
regular
50
30
9502
1034
8
43
false
1345
1000
10
regular
50
30
9503
423
8
9
false
1140
900
10
regular
100
25
4808
1902
76
false
325
170
8
subunit
regular
150
70
4809
1639
14
76
false
325
295
8
subunit
regular
150
70
4810
2371
76
false
325
420
8
subunit
regular
150
70
4814
2411
8
6
false
1775
515
8
subunit
regular
160
80
4821
104
8
2
false
1695
775
8
subunit
regular
150
70
4822
107
8
2
false
1695
830
8
subunit
regular
150
70
4823
104
8
2
false
1700
940
8
subunit
regular
150
70
4824
2631
8
2
false
1700
995
8
subunit
regular
150
70
4825
640
8
2
false
895
1105
8
subunit
regular
150
70
5254
6
31
6
false
887
120
8
subunit
regular
160
80
5255
7
23
6
false
882
290
8
subunit
regular
160
80
5256
2
8
17
false
1462
290
8
subunit
regular
180
85
5260
3
23
2
false
1180
495
8
subunit
regular
150
70
5262
105
8
17
false
1165
895
8
subunit
regular
180
85
3983
835
167
4781
4808
3984
1055
167
4782
4809
3985
832
167
4783
4810
3989
705
167
8
4787
4814
3996
491
167
8
4794
4821
4795
4822
1703
8851
13756
Cofactor
3997
1057
167
8
4796
4823
4797
4824
1704
8852
13758
Cofactor
3998
693
167
8
4798
4825
4282
968
167
31
5226
5254
1859
9484
14963
Cofactor
4283
819
167
23
5227
5255
4284
702
167
8
5228
5256
1860
9491
14975
Cofactor
4287
416
167
23
5232
5260
1864
9499
14988
Cofactor
4289
206
167
8
5234
5262
1865
9503
14996
Cofactor
13720
M245 330 C275 330 295 330 325 330
83
false
18
13721
M565 330 C535 330 505 330 475 330
83
false
18
true
M 542.0096189432334 337.5 L 555 330 L 542.0096189432334 322.5
false
13722
M475 455 C495 455 545 330 565 330
83
false
18
true
M 542.0096189432334 337.5 L 555 330 L 542.0096189432334 322.5
false
13723
M475 205 C495 205 545 329 565 330
83
false
18
true
M 541.6512944095607 336.8419338684158 L 555 330 L 542.4003586637191 321.86064878524815
false
13724
M245 330 C265 330 305 455 325 455
83
false
18
13727
M245 330 C265 329 306 206 325 205
83
false
18
13735
M11 12 C34 28 74 55 98 72
5
true
18
13736
M1855 430 C1855 449 1855 497 1855 515
148
false
18
false
true
M 1840 515 L 1855 515 L 1870 515
13754
M11 12 C34 28 74 55 98 72
5
true
18
13755
M11 12 C34 28 74 55 98 72
5
true
18
13756
M150 150 L150 200 L200 150 z
10
true
18
13757
M1355 1140 C1374 1140 1480 933 1539 932 C1591 931 1697 1002 1717 1002
148
false
18
false
true
M 1493 1187 L 1493 1172 L 1493 1157
13758
M150 150 L150 200 L200 150 z
10
true
18
13759
M1355 730 C1374 730 1479 933 1539 932 C1591 931 1693 837 1712 837
148
false
18
false
true
M 1530.2116175031585 1042.9792674399876 L 1531 1028 L 1531.7883824968415 1013.0207325600123
13760
M11 12 C34 28 74 55 98 72
5
true
18
13761
M1045 1140 C1065 1140 1135 1140 1155 1140
148
false
18
false
true
M 1050 1125 L 1050 1140 L 1050 1155
13762
M1155 1140 C1099 1141 1000 643 1000 625
83
false
18
false
false
true
M 1017.5 487.9903810567666 L 1010 475 L 1002.5 487.9903810567666
false
14959
M665 235 C665 215 857 160 887 160
5
false
18
true
M 677.9903810567666 227.5 L 665 235 L 677.9903810567666 242.5
false
14960
M690 160 C720 160 857 160 887 160
5
false
18
true
M 837.9903810567666 132.5 L 825 140 L 837.9903810567666 147.5
false
14961
M1255 235 C1255 215 1077 160 1047 160
5
false
18
false
false
14962
M1235 165 C1205 165 1077 160 1047 160
5
false
18
false
false
14963
M987.5 400 L987.5 450 L1037.5 400 z
10
true
18
14964
M765 330 C795 330 852 330 882 330
5
false
18
14965
M815 265 C815 284 852 330 882 330
5
false
18
14966
M1155 330 C1125 330 1072 330 1042 330
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14967
M1105 265 C1104 285 1072 330 1042 330
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14971
M1355 330 C1385 330 1432 330 1462 330
5
false
18
14972
M1409 248 C1409 268 1432 330 1462 330
5
false
18
false
false
14973
M1755 330 C1725 330 1672 330 1642 330
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14974
M1700 251 C1699 271 1672 330 1642 330
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14975
M1582.5 400 L1582.5 450 L1632.5 400 z
10
true
18
14984
M1255 425 C1255 443 1255 483 1255 495
5
false
18
14985
M1345 455 C1327 454 1255 474 1255 495
5
false
18
14986
M1255 635 C1254 613 1256 589 1255 565
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14987
M1345 605 C1315 605 1255 586 1255 565
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14988
M150 150 L150 200 L200 150 z
10
true
18
14992
M1255 825 C1255 843 1256 879 1255 895
5
false
18
14993
M1345 1015 C1320 1015 1255 999 1255 980
5
false
18
true
M 1327.0096189432334 1022.5 L 1340 1015 L 1327.0096189432334 1007.5
false
14994
M1255 1045 C1255 1026 1255 998 1255 980
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
14995
M1345 855 C1315 855 1255 877 1255 895
5
false
18
false
false
14996
M150 150 L150 200 L200 150 z
10
true
18
2853
167
2202
8
8907
8838
14959
Left
8908
9482
14960
Left
8909
8836
14961
Right
8910
9483
14962
Right
2856
2051
4282
2854
167
1731
23
8911
8836
14964
Left
8912
9485
14965
Left
8913
8838
14966
Right
8914
9486
14967
Right
2857
1459
4283
2855
167
2077
8
8915
8838
14971
Left
8916
9489
14972
Left
8917
8839
14973
Right
8918
9490
14974
Right
2858
1955
4284
2857
167
1735
23
8919
8838
14984
Left
8920
9497
14985
Left
8921
8844
14986
Right
8922
9498
14987
Right
2859
1469
4287
2859
167
1737
8
8924
8844
14992
Left
8925
9501
14993
Left
8926
8849
14994
Right
8927
9502
14995
Right
2860
1478
4289
353
223
167
791
8835
13720
Left
792
8836
13721
Right
230
3983
181
231
3984
182
232
3985
183
825
741
167
14
true
0
0
16
regular
781
8839
13735
Left
483
3989
13736
Right
826
742
167
14
true
0
0
16
regular
782
8844
13754
Left
783
8849
13755
Left
484
3996
13757
Right
485
3997
13759
Right
827
743
167
14
true
65
65
16
regular
784
8849
13760
Left
486
3998
13761
Right
828
744
167
217
false
925
555
16
regular
785
8853
13762
Left
109
13722
110
13723
111
13724
112
13727
591
87
745
210
2.2
2.2
0
2
14
327
267
598
M398 167 C398 117 448 67 498 67 C931 67 1493 67 1926 67 C1976 67 2026 117 2026 167 C2026 481 2026 890 2026 1204 C2026 1254 1976 1304 1926 1304 C1493 1304 931 1304 498 1304 C448 1304 398 1254 398 1204 C398 890 398 481 398 167
1
true
6
1628.0
1237.0