2284
Pathway
Warburg effect 2: hormone-dependent cancer in prostate tissue
The Warburg Effect refers to the phenomenon that occurs in most cancer cells where instead of generating energy with a low rate of glycolysis followed by oxidizing pyruvate via the Krebs cycle in the mitochondria, the pyruvate from a high rate of glycolysis undergoes lactic acid fermentation in the cytosol. As the Krebs cycle is an aerobic process, in normal cells lactate production is reserved for anaerobic conditions. However, cancer cells preferentially utilize glucose for lactate production via this “aerobic glycolysis”, even when oxygen is plentiful. The Warburg Effect is thought to be the result of mutations to oncogenes and tumour suppressor genes. It may be an adaptation to low-oxygen environments within tumors, the result of cancer genes shutting down the mitochondria, or a mechanism to aid cell proliferation via increased glycolysis. The Warburg Effect involves numerous pathways, including growth factor stimulation, transcriptional activation, and glycolysis promotion.
A notable alteration in prostate cancer cell is the decreased levels of zincs in the cell which allow for the use of citrate in the TCA cycle. High levels of Sarcosine have also been detected in hormone-dependent prostate cancer.
Metabolic
PW002509
Center
PathwayVisualizationContext2796
5500
4900
#000099
PathwayVisualization2267
2284
Warburg effect 2: hormone-dependent cancer in prostate tissue
The Warburg Effect refers to the phenomenon that occurs in most cancer cells where instead of generating energy with a low rate of glycolysis followed by oxidizing pyruvate via the Krebs cycle in the mitochondria, the pyruvate from a high rate of glycolysis undergoes lactic acid fermentation in the cytosol. As the Krebs cycle is an aerobic process, in normal cells lactate production is reserved for anaerobic conditions. However, cancer cells preferentially utilize glucose for lactate production via this “aerobic glycolysis”, even when oxygen is plentiful. The Warburg Effect is thought to be the result of mutations to oncogenes and tumour suppressor genes. It may be an adaptation to low-oxygen environments within tumors, the result of cancer genes shutting down the mitochondria, or a mechanism to aid cell proliferation via increased glycolysis. The Warburg Effect involves numerous pathways, including growth factor stimulation, transcriptional activation, and glycolysis promotion.
A notable alteration in prostate cancer cell is the decreased levels of zincs in the cell which allow for the use of citrate in the TCA cycle. High levels of Sarcosine have also been detected in hormone-dependent prostate cancer.
Metabolic
1
3785
Tyrosine kinase regulation
InhibitorySubPathway
3023
1134
ProteinComplex
2
3024
471
ProteinComplex
2
5339
Lloyd, S., Arnold, J., & Sreekumar, A. (2015). Metabolomic profiling of hormone-dependent cancers: a bird's eye view. Trends In Endocrinology & Metabolism, 26(9), 477-485. http://dx.doi.org/10.1016/j.tem.2015.07.001
2284
Pathway
6
Myocyte
CL:0000187
5
Hepatocyte
CL:0000182
1
Cell
CL:0000000
7
Epithelial Cell
CL:0000066
8
Beta cell
CL:0000639
10
Glial cell
CL:0000125
2
Platelet
CL:0000233
3
Neuron
CL:0000540
4
Cardiomyocyte
CL:0000746
1
Homo sapiens
9606
Eukaryote
Human
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
3
Escherichia coli
562
Prokaryote
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
2
Bacteria
2
Prokaryote
Bacteria
12
Mus musculus
10090
Eukaryote
Mouse
17
Rattus norvegicus
10116
Eukaryote
Rat
19
Schizosaccharomyces pombe
4896
Eukaryote
38
homo sapiens
9608
Eukaryote
21
Xenopus laevis
8355
Eukaryote
African clawed frog
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
5
Bos taurus
9913
Eukaryote
Cattle
5
Cytoplasm
GO:0005737
1
Cytosol
GO:0005829
25
Golgi apparatus
GO:0005794
6
Lysosome
GO:0005764
3
Mitochondrial Matrix
GO:0005759
11
Extracellular Space
GO:0005615
2
Mitochondrion
GO:0005739
31
Periplasmic Space
GO:0005620
14
Mitochondrial Outer Membrane
GO:0005741
15
Nucleus
GO:0005634
4
Peroxisome
GO:0005777
13
Endoplasmic Reticulum
GO:0005783
7
Endoplasmic Reticulum Membrane
GO:0005789
10
Cell Membrane
GO:0005886
27
Peroxisome Membrane
GO:0005778
34
Plant-Type Vacuole
GO:0000325
19
sarcoplasmic reticulum
GO:0016529
26
Golgi apparatus membrane
GO:0000139
24
Mitochondrial Intermembrane Space
GO:0005758
12
Mitochondrial Inner Membrane
GO:0005743
16
Lysosomal Lumen
GO:0043202
18
Melanosome Membrane
GO:0033162
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
8
Smooth Endoplasmic Reticulum
GO:0005790
17
Nucleoplasm
GO:0005654
9
Muscle
BTO:0000887
141
18
1
Liver
BTO:0000759
72
9
8
Blood Vessel
BTO:0001102
74
11
25
Intestine
BTO:0000648
18
Pancreas
BTO:0000988
7
Nervous System
BTO:0001484
2
Endothelium
BTO:0000393
5
cardiocyte
BTO:0001539
4
Adrenal Medulla
BTO:0000049
71
8
28
Stomach
BTO:0001307
155
26
24
Brain
BTO:0000142
89
16
3
Sympathetic Nervous System
BTO:0001832
50
9
5
1
6
PW_BS000050
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1
1
1
5
PW_BS000026
51
8
1
PW_BS000051
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1
1
1
PW_BS000002
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25
1
1
PW_BS000043
9
6
1
1
PW_BS000009
4
3
1
1
PW_BS000004
60
25
1
PW_BS000060
15
11
1
PW_BS000015
61
25
1
7
PW_BS000061
66
18
5
1
8
PW_BS000066
29
1
1
1
PW_BS000029
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1
1
PW_BS000003
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1
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PW_BS000006
148
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24
PW_BS000148
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24
5
PW_BS000149
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PW_BS000152
153
1
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PW_BS000153
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31
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PW_BS000107
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1
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PW_BS000108
192
8
18
PW_BS000024
193
1
1
18
5
PW_BS000024
200
7
1
10
PW_BS000024
215
6
18
1
PW_BS000024
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PW_BS000008
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PW_BS000016
22
14
1
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PW_BS000022
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PW_BS000013
32
1
15
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5
PW_BS000032
5
4
1
1
PW_BS000005
39
7
1
1
3
PW_BS000039
18
13
1
1
PW_BS000018
10
1
7
1
1
PW_BS000010
49
7
1
1
PW_BS000049
14
10
1
PW_BS000014
58
1
14
1
1
PW_BS000058
59
27
1
1
PW_BS000059
27
15
1
PW_BS000027
46
1
1
4
PW_BS000046
72
5
1
3
PW_BS000072
23
15
1
1
PW_BS000023
31
1
5
1
1
PW_BS000031
91
8
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1
1
PW_BS000091
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1
3
1
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PW_BS000054
89
2
PW_BS000089
7
1
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PW_BS000007
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1
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2
1
PW_BS000097
100
5
2
1
PW_BS000100
104
14
3
1
PW_BS000104
101
5
3
1
PW_BS000101
111
5
12
1
PW_BS000111
112
2
12
1
PW_BS000112
103
3
3
1
PW_BS000103
117
1
3
1
PW_BS000117
118
1
17
1
PW_BS000118
120
3
17
1
PW_BS000120
129
1
5
12
1
PW_BS000129
132
1
12
1
PW_BS000132
133
3
12
1
PW_BS000133
135
5
17
1
PW_BS000135
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
147
1
24
1
PW_BS000147
151
1
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1
PW_BS000151
155
3
24
1
PW_BS000155
161
3
18
1
PW_BS000161
166
1
1
PW_BS000166
173
1
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38
1
PW_BS000173
176
5
38
1
PW_BS000176
178
3
21
1
PW_BS000178
188
1
18
PW_BS000024
160
1
18
1
PW_BS000160
199
14
18
1
PW_BS000024
205
5
6
1
PW_BS000024
206
2
6
1
PW_BS000024
210
13
18
1
PW_BS000024
213
7
18
1
PW_BS000024
211
10
18
PW_BS000024
198
5
18
1
PW_BS000024
216
4
18
1
PW_BS000024
217
15
18
PW_BS000024
218
15
18
1
PW_BS000024
163
2
18
1
PW_BS000163
158
34
24
1
PW_BS000158
47
19
1
4
PW_BS000047
94
3
PW_BS000094
21
5
1
1
4
PW_BS000021
56
26
1
1
PW_BS000056
164
4
PW_BS000164
214
25
18
1
PW_BS000024
42
24
1
1
PW_BS000042
17
12
1
1
PW_BS000017
28
1
16
1
1
PW_BS000028
95
1
7
2
1
PW_BS000095
123
1
7
5
1
PW_BS000123
125
13
5
1
PW_BS000125
141
1
7
19
1
PW_BS000141
157
2
24
1
PW_BS000157
1
1
PW_BS000001
171
1
7
38
1
PW_BS000171
20
4
1
1
1
PW_BS000020
33
18
1
1
PW_BS000033
24
4
10
1
1
PW_BS000024
70
28
5
1
1
PW_BS000070
36
1
20
1
1
PW_BS000036
37
7
21
1
3
PW_BS000037
93
25
20
1
1
PW_BS000093
105
11
3
PW_BS000105
113
6
12
1
PW_BS000113
110
2
3
1
PW_BS000110
126
6
5
1
PW_BS000126
127
1
16
5
1
PW_BS000127
130
13
12
1
PW_BS000130
114
11
12
PW_BS000114
140
10
3
PW_BS000140
159
24
PW_BS000159
180
2
21
1
PW_BS000180
207
6
6
1
PW_BS000024
212
1
7
18
1
PW_BS000024
156
12
24
1
PW_BS000156
177
1
21
1
PW_BS000177
85
24
10
1
1
PW_BS000085
19
3
5
1
3
PW_BS000019
71
11
1
3
PW_BS000071
11
1
8
1
1
PW_BS000011
102
12
3
1
PW_BS000102
124
1
5
1
PW_BS000124
162
12
18
1
PW_BS000162
190
11
18
PW_BS000024
179
12
21
1
PW_BS000179
187
31
18
PW_BS000024
73
10
1
3
PW_BS000073
35
5
19
1
4
PW_BS000035
201
7
5
1
10
PW_BS000024
202
7
11
1
10
PW_BS000024
30
17
1
1
PW_BS000030
136
13
17
1
PW_BS000136
68
2
5
1
2
PW_BS000068
77
D-Glucose
HMDB00122
Glucose is a monosaccharide containing six carbon atoms and an aldehyde group and is therefore referred to as an aldohexose. The glucose molecule can exist in an open-chain (acyclic) and ring (cyclic) form, the latter being the result of an intramolecular reaction between the aldehyde C atom and the C-5 hydroxyl group to form an intramolecular hemiacetal. In water solution both forms are in equilibrium and at pH 7 the cyclic one is the predominant. Glucose is a primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. In animals glucose arises from the breakdown of glycogen in a process known as glycogenolysis. Glucose is synthesized in the liver and kidneys from non-carbohydrate intermediates, such as pyruvate and glycerol, by a process known as gluconeogenesis.
2280-44-6
C00031
5793
4167
GLC
5589
OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O
C6H12O6
InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6?/m1/s1
WQZGKKKJIJFFOK-GASJEMHNSA-N
(3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
180.1559
180.063388116
0.64
5
glucose
0
0
FDB012530
Roferose ST;(+)-Glucose;Anhydrous dextrose;CPC hydrate;Cerelose;Cerelose 2001;Clearsweet 95;Clintose L;Corn sugar;D(+)-Glucose;Dextropur;Dextrose;Dextrosol;Glucodin;Glucolin;Glucose;Goldsugar;Grape sugar;Meritose;Staleydex 111;Staleydex 95M;Tabfine 097(HS);Vadex
PW_C000077
1452
50
1460
26
1461
51
1506
2
1540
43
2193
9
2439
4
2679
60
2721
15
2723
61
3027
66
3114
29
3593
3
5692
6
5896
148
5922
149
5923
152
5954
153
6367
107
6368
108
6869
192
6904
193
7085
200
7244
215
414
Adenosine triphosphate
HMDB00538
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
PW_C000414
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
6430
173
6438
176
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
1083
Glucose 6-phosphate
HMDB01401
Glucose 6 phosphate (alpha-D-glucose 6 phosphate or G6P) is the alpha-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer. Glucose 6 phosphate is an ester of glucose with phosphoric acid, made in the course of glucose metabolism by mammalian and other cells. It is a normal constituent of resting muscle and probably is in constant equilibrium with fructose-6-phosphate. (Stedman, 26th ed). Glucose-6-phosphate is a phosphorylated glucose molecule on carbon 6. When glucose enters a cell, it is immediately phosphorylated to G6P. This is catalyzed with hexokinase enzymes, thus consuming one ATP. A major reason for immediate phosphorylation of the glucose is so that it cannot diffuse out of the cell. The phosphorylation adds a charged group so the G6P cannot easily cross cell membranes. G6P can travel down two metabolic pathways, glycolysis and the pentose phosphate pathway. In addition to the metabolic pathways, G6P can also be stored as glycogen in the liver if blood glucose levels are high. If the body needs energy or carbon skeletons for syntheses, G6P can be isomerized to Fructose-6-phosphate and then phosphorylated to Fructose-1,6-bisphosphate. Note, the molecule now has 2 phosphoryl groups attached. The addition of the 2nd phosphoryl group is an irreversible step, so once this happens G6P will enter glycolysis and be turned into pyruvate (ATP production occurs). If blood glucose levels are high, the body needs a way to store the excess glucose. After being converted to G6P, phosphoglucose mutase (isomerase) can turn the molecule into glucose-1-phosphate. Glucose-1-phosphate can then be combined with uridine triphosphate (UTP) to form UDP-glucose. This reaction is driven by the hydrolysis of pyrophosphate that is released in the reaction. Now, the activated UDP-glucose can add to a growing glycogen molecule with the help of glycogen synthase. This is a very efficient storage mechanism for glucose since it costs the body only 1 ATP to store the 1 glucose molecule and virtually no energy to remove it from storage. It is important to note that glucose-6-phosphate is an allosteric activator of glycogen synthase, which makes sense because when the level of glucose is high the body should store the excess glucose as glycogen. On the other hand, glycogen synthase is inhibited when it is phosphorylated by protein kinase a during times of high stress or low blood glucose levels. -- Wikipedia.
56-73-5
C00092
5958
4170
GLC-6-P
5743
OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O
C6H13O9P
InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1
NBSCHQHZLSJFNQ-GASJEMHNSA-N
{[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
260.1358
260.029718526
-0.92
6
glucose 6-phosphate
0
-2
FDB021818
D(+)-Glucopyranose 6-phosphate;D-Glucose 6-phosphate;D-Glucose-6-dihydrogen phosphate;D-Hexose 6-phosphate;Glucose 6-phosphate;Glucose-6-phosphate;Robison ester;a-D-Glucose 6- phosphate;alpha-D-Glucose 6- phosphate;alpha-D-Glucose 6-phosphate;alpha-D-Hexose 6-phosphate
PW_C001083
1118
8
1804
2
2381
18
3125
29
5898
147
5925
151
6065
158
6871
160
7403
198
1034
Adenosine diphosphate
HMDB01341
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
PW_C001034
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
6433
173
6440
176
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
79
Fructose 6-phosphate
HMDB00124
Fructose 6-phosphate is an important intermediate in the Carbohydrates pathway. The interconversion of glucose-6-phosphate and fructose-6-phosphate, the second step of the Embden-Meyerhof glycolytic pathway, is catalyzed by the enzyme phosphoglucose isomerase (PGI). In gluconeogenesis, fructose-6-phosphate is the immediate precursor of glucose-6-phosphate (wikipedia).
643-13-0
C00085
69507
15946
FRUCTOSE-6P
62713
OCC(=O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O
C6H13O9P
InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h4-7,9-11H,1-2H2,(H2,12,13,14)/t4-,5-,6-/m1/s1
GSXOAOHZAIYLCY-HSUXUTPPSA-N
{[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid
260.1358
260.029718526
-1.05
6
D-fructose 6-phosphate
0
-2
FDB021896
D-Fructose 6-phosphate;D-Fructose 6-phosphorate;D-Fructose 6-phosphoric acid;D-Fructose-6-P;D-Fructose-6-phosphate;FPC;Fru-6-P;Fructose 6-phosphate;Fructose-6-P;Fructose-6-phosphate;Fructose-6P;Neuberg ester
PW_C000079
388
8
1014
3
1785
2
5904
147
5932
151
6465
108
6878
160
833
Fructose 1,6-bisphosphate
HMDB01058
Fructose 1,6-bisphosphate is fructose sugar or fructosephosphate that has been phosphorylated on carbons 1 and 6. The beta-D-form of this compound is very common in cells. The vast majority of glucose and fructose entering a cell is converted to fructose 1,6-bisphosphate at some point. Fructose 1,6-bisphosphate is a key component in the glycolysis metabolic pathway and is produced by phosphorylation of fructose 6-phosphate The enzyme phosphofructokinase uses ATP to transfer a phosphate group to fructose 6-phosphate to form fructose 1, 6-bisphosphate. fructose The enzyme aldolase splits fructose 1, 6-bisphosphate into two sugars that are isomers of each other. These two sugars are dihydroxyacetone phosphate and glyceraldehyde phosphate. Fructose 1,6-bisphosphate is an allosteric activator of pyruvate kinase.
488-69-7
C00354
445557
16905
FRUCTOSE-16-DIPHOSPHATE
393165
O[C@H]1[C@H](O)[C@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O
C6H14O12P2
InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1
RNBGYGVWRKECFJ-ZXXMMSQZSA-N
{[(2S,3S,4S,5R)-2,3,4-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid
340.1157
339.996048936
-1.33
7
fructose 1,6-bisphosphate
0
-4
FDB022397
D-Fructose 1,6-biphosphate;D-Fructose 1,6-bis(dihydrogen phosphate);D-Fructose 1,6-bisphosphate;D-Fructose 1,6-diphosphate;D-Fructose-1,6-bisphosphate;D-Fructose-1,6-diphosphate;Diphosphofructose;Esafosfan;Esafosfina;FDP;Fosfructose;Fructose 1,6-bis;Fructose 1,6-bisphosphate;Fructose 1,6-diphosphate;Harden-Young ester
PW_C000833
1021
8
1790
2
5905
147
5933
151
6880
160
423
Magnesium
HMDB00547
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
PW_C000423
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
1134
Dihydroxyacetone phosphate
HMDB01473
Dihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis.
57-04-5
C00111
668
16108
DIHYDROXY-ACETONE-PHOSPHATE
648
DB04326
OCC(=O)COP(O)(O)=O
C3H7O6P
InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)
GNGACRATGGDKBX-UHFFFAOYSA-N
(3-hydroxy-2-oxopropoxy)phosphonic acid
170.0578
169.998024468
-0.89
3
dihydroxyacetone-phosphate
0
-2
FDB001618
1,3-Dihydroxy-2-Propanone mono(dihydrogen phosphate);1,3-Dihydroxy-2-propanone phosphate;1,3-Dihydroxyacetone 1-phosphate;1-Hydroxy-3-(phosphonooxy)-2-Propanone;1-Hydroxy-3-(phosphonooxy)acetone;DHAP;Di-OH-acetone-P;Dihydroxy-Acetone-P;Dihydroxy-acetone-phosphate;Dihydroxyacetone 3-phosphate;Dihydroxyacetone monophosphate;Dihydroxyacetone phosphate;Dihydroxyacetone-P;Dihydroxyacetone-phosphate;Glycerone phosphate;Glycerone-phosphate;Phosphoric acid ester with 1,3-dihydroxy-2-propanone
PW_C001134
1026
8
1474
2
3305
5
4253
42
5813
108
5908
147
5936
151
6884
160
869
D-Glyceraldehyde 3-phosphate
HMDB01112
Glyceraldehyde 3-phosphate (G3P) or triose phosphate is an aldotriose, an important metabolic intermediate in both glycolysis and gluconeogenesis, and in tryptophan biosynthesis. G3P is formed from Fructose-1,6-bisphosphate, Dihydroxyacetone phosphate (DHAP),and 1,3-bisphosphoglycerate, (1,3BPG), and this is how glycerol (as DHAP) enters the glycolytic and gluconeogenesis pathways.
591-59-3
C00661
729
17138
GAP
709
DB02263
OC(COP(O)(O)=O)C=O
C3H7O6P
InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)
LXJXRIRHZLFYRP-UHFFFAOYSA-N
(2-hydroxy-3-oxopropoxy)phosphonic acid
170.0578
169.998024468
-0.92
3
glyceraldehyde 3 phosphate
0
-2
FDB001619
2-Hydroxy-3-(phosphonooxy)-Propanal;3-Phosphoglyceraldehyde;D-Glyceraldehyde 3-phosphate;D-Glyceraldehyde-3-P;DL-Glyceraldehyde 3-phosphate;GAP;Glyceraldehyde-3-P;Glyceraldehyde-3-phosphate;Glyceraldehyde-P;Glyceraldehyde-phosphate
PW_C000869
1027
8
1781
2
5907
147
5935
151
6883
160
721
NAD
HMDB00902
NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).
53-84-9
C00003
5893
15846
NAD
5682
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
C21H28N7O14P2
InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BAWFJGJZGIEFAR-NNYOXOHSSA-O
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ⁵-pyridin-1-ylium
664.433
664.116946663
-2.59
8
1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ⁵-pyridin-1-ylium
1
-1
FDB022309
3-Carbamoyl-1-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-Carbamoyl-1-beta-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-Carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;CO-I;Codehydrase I;Codehydrogenase I;Coenzyme I;Cozymase;Cozymase I;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;NAD trihydrate;NAD-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3S,2R,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3S,2R,4R,5R)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-P]-NAD;beta-Diphosphopyridine nucleotide;beta-NAD;beta-Nicotinamide adenine dinucleotide;beta-Nicotinamide adenine dinucleotide trihydrate
PW_C000721
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
6396
171
6469
178
6772
117
6890
160
7012
188
7097
163
7174
205
7197
206
7405
198
1441
Phosphoric acid
HMDB02142
Phosphoric acid, also known as orthophosphoric acid or phosphoric(V) acid, is a mineral acid with the chemical formula H3PO4. Alternatively, orthophosphoric acid molecules can combine with themselves to form a variety of compounds referred to as phosphoric acids in a more general way. For a discussion of these, see Phosphoric acids and Phosphates. Appears to exist only as a food additive and produced synthetically. --Wikipedia.
7664-38-2
C00009
1004
26078
979
OP(O)(O)=O
H3O4P
InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)
NBIIXXVUZAFLBC-UHFFFAOYSA-N
phosphoric acid
97.9952
97.976895096
3
phosphoric acid
0
-2
FDB013380
Acide phosphorique (FRENCH);Acido fosforico [Italian];Acidum phosphoricum;Diphosphate tetrasodium;Fosforzuuroplossingen [Dutch];Marphos;NFB;Ortho- phosphoric acid;Orthophosphoric acid;Phosphoric acid (ACD/Name 4.0);Phosphorsaeure;Phosphorsaeureloesungen [German];Sodium Pyrophosphate;Sodium pyrophosphate decahydrate;Sodium pyrophosphate decahydrate BioChemica;Sonac;Tetra-Sodium pyrophosphate;Tetrasodium Pyrophosphate Decahydrate;Tetrasodium pyrophosphate 10-hydrate;White phosphoric acid
PW_C001441
171
8
440
4
483
13
1592
43
1678
2
1902
49
1910
5
4856
3
5913
147
5943
151
6891
160
983
Glyceric acid 1,3-biphosphate
HMDB01270
1,3-Bisphosphogylcerate (1,3BPG), also known as PGAP, is a 3-carbon organic molecule present in most, if not all living creatures. It primarily exists as a metabolic intermediate in glycolysis during respiration. 1,3BPG have been recognized as regulatory signal implicated in the control of metabolism, oxygen affinity of red cells and other cellular functions. 1,3BPG concentration in erythrocytes changes in a number of pathological conditions, such as Inherited Phosphoglycerate kinase deficiency in erythrocytes (involved in the synthesis and breakdown of 1,3 BPG). (PMID 3555887). 1,3-bisphosphoglycerate is the anion form of bisphosphoglyceric acid. It is phosphorylated at the number 1 and 3 carbons. The result of this phosphorylation gives 1,3BPG important biological properties such as the ability to phosphorylate ADP to form the energy storage molecule ATP.(wikipedia).
1981-49-3
C00236
683
DPG
663
OC(COP(O)(O)=O)C(=O)OP(O)(O)=O
C3H8O10P2
InChI=1S/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)
LJQLQCAXBUHEAZ-UHFFFAOYSA-N
{[2-hydroxy-3-(phosphonooxy)propanoyl]oxy}phosphonic acid
266.0371
265.9592695
-1.44
5
1,3-bisphosphoglycerate
0
-4
FDB022524
1,3-Biphosphoglycerate;1,3-Biphosphoglyceric acid;1,3-Bis-phosphoglycerate;1,3-Bisphosphoglycerate;1,3-Diphosphateglycerate;1,3-Diphosphoglycerate;13-DPG;2-Hydroxy-3-(phosphonooxy)-Propanoate;2-Hydroxy-3-(phosphonooxy)-Propanoic acid;2-Hydroxy-3-(phosphonooxy)-Propanoic acid 1-anhydride with phosphorate;2-Hydroxy-3-(phosphonooxy)-Propanoic acid 1-anhydride with phosphoric acid;3-P-Glyceroyl-P;3-Phospho-D-glyceroyl phosphate;3-Phospho-D-glyceroyl-phosphate;3-Phosphoglyceroyl phosphate;3-Phosphoglyceroyl-P;3-Phosphoglyceroyl-phosphate;DPG;Glycerate 1,3-Biphosphate;Glycerate 1,3-bisphosphate;Glycerate 1,3-diphosphate;Glyceric acid 1,3-biphosphate;P-Glyceroyl-P;Phosphoglyceroyl-P
PW_C000983
1041
8
2253
2
5914
147
5944
151
6892
160
1144
NADH
HMDB01487
NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).
58-68-4
C00004
439153
16908
NADH
388299
DB00157
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O14P2
InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BOPGDPNILDQYTO-NNYOXOHSSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid
665.441
665.124771695
-2.35
8
NADH
0
-2
FDB022649
1,4-Dihydronicotinamide adenine dinucleotide;DPNH;Dihydrocodehydrogenase I;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;ENADA;NADH;NADH2;Reduced codehydrogenase I;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;b-DPNH;b-NADH;beta-DPNH;beta-NADH
PW_C001144
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
6398
171
6472
178
6771
117
6893
160
7011
188
7099
163
7172
205
7195
206
644
3-Phosphoglyceric acid
HMDB00807
3-phosphoglyceric acid (3PG) is a 3-carbon molecule that is a metabolic intermediate in both glycolysis and the Calvin cycle. This chemical is often termed PGA when referring to the Calvin cycle. In the Calvin cycle, two glycerate 3-phosphate molecules are reduced to form two molecules of glyceraldehyde 3-phosphate (GALP). (wikipedia).
820-11-1
C00597
724
17050
G3P
704
OC(COP(O)(O)=O)C(O)=O
C3H7O7P
InChI=1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)
OSJPPGNTCRNQQC-UHFFFAOYSA-N
2-hydroxy-3-(phosphonooxy)propanoic acid
186.0572
185.99293909
-0.95
4
phosphoglycerate
0
-3
FDB022255
3-(Dihydrogen phosphate)Glycerate;3-(Dihydrogen phosphate)Glyceric acid;3-Glycerophosphorate;3-Glycerophosphoric acid;3-P-D-Glycerate;3-P-Glycerate;3-PGA;3-Pg;3-Phospho-(R)-glycerate;3-Phospho-D-glycerate;3-Phospho-glycerate;3-Phospho-glyceric acid;3-Phosphoglycerate;3-Phosphoglyceric acid;D-(-)-3-Phosphoglyceric acid;D-Glycerate 3-phosphate;G3P;Glycerate 3-phosphate;Glycerate-3-P;Glyceric acid 3-phosphate;Phosphoglycerate
PW_C000644
2051
8
2257
2
5743
117
5917
147
5948
151
6897
160
1870
2-Phospho-D-glyceric acid
HMDB03391
2-Phospho-D-glycerate or 2PG is an intermediate in gluconeogenesis. It is a glyceric acid which serves as the substrate in the ninth step of glycolysis. 2PG is converted by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. More specifically, 2PG can be generated from Glycerate-3-phosphate via phosphoglycerate mutase or from phosphoenolpyrvate via alpha enolase.
C00631
439278
17835
2-PG
388411
DB01709
OC[C@@H](OP(O)(O)=O)C(O)=O
C3H7O7P
InChI=1S/C3H7O7P/c4-1-2(3(5)6)10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1
GXIURPTVHJPJLF-UWTATZPHSA-N
(2R)-3-hydroxy-2-(phosphonooxy)propanoic acid
186.0572
185.99293909
-0.96
4
(+-)-2-phosphoglycerate
0
-3
FDB001407
(2R)-3-hydroxy-2-(phosphonooxy)propanoate;(2R)-3-hydroxy-2-(phosphonooxy)propanoic acid;2-Phospho-D-glycerate;2-Phospho-D-glyceric acid;3-D-Hydroxy-2-phosphonooxy-propanoate;3-D-Hydroxy-2-phosphonooxy-propanoic acid;D-Glycerate 2-phosphate
PW_C001870
2263
2
5918
147
5949
151
6899
160
180
Phosphoenolpyruvic acid
HMDB00263
Phosphoenolpyruvate (PEP) is an important chemical compound in biochemistry. It has a high energy phosphate bond, and is involved in glycolysis and gluconeogenesis. In glycolysis, PEP is formed by the action of the enzyme enolase on 2-phosphoglycerate. Metabolism of PEP to pyruvate by pyruvate kinase (PK) generates 1 molecule of adenosine triphosphate (ATP) via substrate-level phosphorylation. ATP is one of the major currencies of chemical energy within cells. In gluconeogenesis, PEP is formed from the decarboxylation of oxaloacetate and hydrolysis of 1 guanosine triphosphate molecule. This reaction is catalyzed by the enzyme phosphoenolpyruvate carboxykinase (PEPCK). This reaction is a rate-limiting step in gluconeogenesis. (wikipedia).
138-08-9
C00074
1005
44897
PHOSPHO-ENOL-PYRUVATE
980
DB01819
OC(=O)C(=C)OP(O)(O)=O
C3H5O6P
InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)
DTBNBXWJWCWCIK-UHFFFAOYSA-N
2-(phosphonooxy)prop-2-enoic acid
168.042
167.982374404
-1.10
3
phosphoenolpyruvic acid
0
-3
FDB001451
2-Hydroxy-Acrylic acid dihydrogen phosphate;2-Phosphonooxyprop-2-enoate;2-Phosphonooxyprop-2-enoic acid;P-Enol-pyruvate;PEP;Phosphoenolpyruvate
PW_C000180
419
8
2265
2
2396
4
5919
147
5950
151
6179
108
6901
160
1420
Water
HMDB02111
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
PW_C001420
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
6420
173
6437
176
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
164
Pyruvic acid
HMDB00243
Pyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed.) Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds).
127-17-3
C00022
1060
32816
PYRUVATE
1031
DB00119
CC(=O)C(O)=O
C3H4O3
InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
LCTONWCANYUPML-UHFFFAOYSA-N
2-oxopropanoic acid
88.0621
88.016043994
0.18
1
pyruvic acid
0
-1
FDB008293
2-Oxopropanoate;2-Oxopropanoic acid;2-Oxopropionate;2-Oxopropionic acid;Acetylformate;Acetylformic acid;BTS;Pyroracemate;Pyroracemic acid;Pyruvate;a-Ketopropionate;a-Ketopropionic acid;alpha-Ketopropionate;alpha-Ketopropionic acid
PW_C000164
17
2
20
4
422
8
1181
3
1449
50
1457
26
5365
103
5405
117
5440
118
5444
120
5566
132
5570
133
5893
95
5920
147
5951
151
6022
155
6067
156
6074
161
6126
160
6383
1
6467
178
6510
177
6532
85
457
Potassium
HMDB00586
Potassium is an essential electrolyte. Potassium balance is crucial for regulating the excitability of nerves and muscles and so critical for regulating contractility of cardiac muscle. Although the most important changes seen in the presence of deranged potassium are cardiac, smooth muscle is also affected with increasing muscle weakness, a feature of both hyperkalaemia and hypokalaemia. Physiologically, it exists as an ion in the body. Potassium (K+) is a positively charged electrolyte, cation, which is present throughout the body in both intracellular and extracellular fluids. The majority of body potassium, >90%, are intracellular. It moves freely from intracellular fluid (ICF) to extracellular fluid (ECF) and vice versa when adenosine triphosphate increases the permeability of the cell membrane. It is mainly replaced inside or outside the cells by another cation, sodium (Na+). The movement of potassium into or out of the cells is linked to certain body hormones and also to certain physiological states. Standard laboratory tests measure ECF potassium. Potassium enters the body rapidly during food ingestion. Insulin is produced when a meal is eaten; this causes the temporary movement of potassium from ECF to ICF. Over the ensuing hours, the kidneys excrete the ingested potassium and homeostasis is returned. In the critically ill patient, suffering from hyperkalaemia, this mechanism can be manipulated beneficially by administering high concentration (50%) intravenous glucose. Insulin can be added to the glucose, but glucose alone will stimulate insulin production and cause movement of potassium from ECF to ICF. The stimulation of alpha receptors causes increased movement of potassium from ICF to ECF. A noradrenaline infusion can elevate serum potassium levels. An adrenaline infusion, or elevated adrenaline levels, can lower serum potassium levels. Metabolic acidosis causes a rise in extracellular potassium levels. In this situation, excess of hydrogen ions (H+) are exchanged for intracellular potassium ions, probably as a result of the cellular response to a falling blood pH. Metabolic alkalosis causes the opposite effect, with potassium moving into the cells. (PMID: 17883675).
24203-36-9
C00238
813
29103
K%2b
791
DB01345
[K+]
K
InChI=1S/K/q+1
NPYPAHLBTDXSSS-UHFFFAOYSA-N
potassium(1+) ion
39.0983
38.963706861
0
potassium(1+) ion
1
1
FDB003521
K+;Kalium;Potassium;Potassium (K+);Potassium (ion);Potassium cation;Potassium ion;Potassium ion (K+);Potassium ion (K1+);Potassium ion(+);Potassium ion(1+);Potassium monocation;Potassium(+);Potassium(1+);Potassium(1+) ion;Potassium(I) cation
PW_C000457
573
8
931
19
1926
2
2095
15
3033
66
3161
72
3162
71
3613
51
3614
61
5921
147
5952
151
6902
160
463
Hydrogen carbonate
HMDB00595
Bicarbonate, or hydrogen carbonate, is a simple single carbon molecule that plays surprisingly important roles in diverse biological processes. Among these are photosynthesis, the Krebs cycle, whole-body and cellular pH regulation, and volume regulation. Since bicarbonate is charged it is not permeable to lipid bilayers. Mammalian membranes thus contain bicarbonate transport proteins to facilitate the specific transmembrane movement of HCO3(-). Bicarbonate ion is an anion that consists of one central carbon atom surrounded by three oxygen atoms in a trigonal planar arrangement, with a hydrogen atom attached to one of the oxygens. The bicarbonate ion carries a negative one formal charge and is the conjugate base of carbonic acid, H2CO3. The carbonate radical is an elusive and strong one-electron oxidant. Bicarbonate in equilibrium with carbon dioxide constitutes the main physiological buffer. The bicarbonate-carbon dioxide pair stimulates the oxidation, peroxidation and nitration of several biological targets. The demonstration that the carbonate radical existed as an independent species in aqueous solutions at physiological pH and temperature renewed the interest in the pathophysiological roles of this radical and related species. The carbonate radical has been proposed to be a key mediator of the oxidative damage resulting from peroxynitrite production, xanthine oxidase turnover and superoxide dismutase1 peroxidase activity. The carbonate radical has also been proposed to be responsible for the stimulatory effects of the bicarbonate-carbon dioxide pair on oxidations mediated by hydrogen peroxide/transition metal ions. The ultimate precursor of the carbonate radical anion being bicarbonate, carbon dioxide, peroxymonocarbonate or complexes of transition metal ions with bicarbonate-derived species remains a matter of debate. The carbonate radical mediates some of the pathogenic effects of peroxynitrite. The carbonate radical as the oxidant produced from superoxide dismutase (EC 1.15.1.1, SOD1) peroxidase activity. Peroxymonocarbonate is a biological oxidant, whose existence is in equilibrium with hydrogen peroxide and bicarbonate. (PMID: 17505962, 17215880).
71-52-3
C00288
769
17544
HCO3
749
OC([O-])=O
CHO3
InChI=1S/CH2O3/c2-1(3)4/h(H2,2,3,4)/p-1
BVKZGUZCCUSVTD-UHFFFAOYSA-M
hydrogen carbonate
61.0168
60.992568898
0.97
1
bicarbonate
-1
-1
FDB022134
Bicarbonate;Bicarbonate (HCO3-);Bicarbonate anion;Bicarbonate ion;Bicarbonate ion (HCO31-);Bicarbonate ions;Carbonate;Carbonate (HCO31-);Carbonate ion (HCO31-);Carbonic acid;Hydrocarbonate(1-);Hydrogen carbonate;Hydrogen carbonate (HCO3-);Hydrogen carbonate anion;Hydrogen carbonate ion;Hydrogen carbonate ion (HCO3-);Hydrogencarbonate;Hydrogentrioxocarbonate;Monohydrogen carbonate
PW_C000463
22
4
1687
8
2393
3
2397
2
2613
15
3145
70
5391
103
5445
120
5571
133
6049
155
6110
161
6494
178
1104
Phosphate
HMDB01429
Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.
14265-44-2
C00009
1061
18367
CPD-8587
1032
[O-]P([O-])([O-])=O
O4P
InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3
NBIIXXVUZAFLBC-UHFFFAOYSA-K
phosphate
94.9714
94.95342
0
phosphate
-3
-2
DBMET00532
FDB022617
NFB Orthophosphate;O-Phosphoric acid;Ortho-phosphate;Orthophosphate (PO43-);Orthophosphate(3-);Phosphate;Phosphate (PO43-);Phosphate anion(3-);Phosphate ion (PO43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi
PW_C001104
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
6432
173
6439
176
6487
178
6691
101
6714
117
6842
188
6889
160
7161
205
7189
206
7212
211
7306
198
7389
210
7402
212
7436
163
148
Oxalacetic acid
HMDB00223
Oxaloacetic acid, also known as oxosuccinic acid or oxalacetic acid, is a four-carbon dicarboxylic acid appearing as an intermediate of the citric acid cycle. In vivo, oxaloacetate (the ionized form of oxaloacetic acid) is formed by the oxidation of L-malate, catalyzed by malate dehydrogenase, and reacts with Acetyl-CoA to form citrate, catalyzed by citrate synthase.(wikipedia) A class of ketodicarboxylic acids derived from oxalic acid. Oxaloacetic acid is an intermediate in the citric acid cycle and is converted to aspartic acidD by a transamination reaction.
328-42-7
C00036
970
30744
OXALACETIC_ACID
945
OC(=O)CC(=O)C(O)=O
C4H4O5
InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
KHPXUQMNIQBQEV-UHFFFAOYSA-N
2-oxobutanedioic acid
132.0716
132.005873238
-0.36
2
oxalacetate
0
-2
FDB001479
2-Ketosuccinate;2-Ketosuccinic acid;2-Oxobutanedioate;2-Oxobutanedioic acid;2-Oxosuccinate;2-Oxosuccinic acid;Ketosuccinate;Ketosuccinic acid;OAA;Oxalacetate;Oxaloacetate;Oxaloacetic acid;Oxaloethanoate;Oxaloethanoic acid;Oxosuccinate;Oxosuccinic acid;a-Ketosuccinate;a-Ketosuccinic acid;alpha-Ketosuccinate;alpha-Ketosuccinic acid
PW_C000148
25
4
96
9
111
5
1099
3
1109
42
1113
2
1688
8
5371
103
5448
120
5574
133
6033
155
6088
161
6478
178
20
Biotin
HMDB00030
Biotin is an enzyme co-factor present in minute amounts in every living cell. Biotin is also known as vitamin H or B7 or coenzyme R. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk. Biotin has been recognized as an essential nutrient. Our biotin requirement is fulfilled in part through diet, through endogenous reutilization of biotin and perhaps through capture of biotin generated in the intestinal flora. The utilization of biotin for covalent attachment to carboxylases and its reutilization through the release of carboxylase biotin after proteolytic degradation constitutes the 'biotin cycle'. Biotin deficiency is associated with neurological manifestations, skin rash, hair loss and metabolic disturbances that are thought to relate to the various carboxylase deficiencies (metabolic ketoacidosis with lactic acidosis). It has also been suggested that biotin deficiency is associated with protein malnutrition, and that marginal biotin deficiency in pregnant women may be teratogenic. Biotin acts as a carboxyl carrier in carboxylation reactions. There are four biotin-dependent carboxylases in mammals: those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a Lysine residue in each of these carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. There are four biotin-dependent carboxylases in mammals: those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a Lys residue in each of these carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. Evidence is emerging that biotin participates in processes other than classical carboxylation reactions. Specifically, novel roles for biotin in cell signaling, gene expression, and chromatin structure have been identified in recent years. Human cells accumulate biotin by using both the sodium-dependent multivitamin transporter and monocarboxylate transporter 1. These transporters and other biotin-binding proteins partition biotin to compartments involved in biotin signaling: cytoplasm, mitochondria, and nuclei. The activity of cell signals such as biotinyl-AMP, Sp1 and Sp3, nuclear factor (NF)-kappaB, and receptor tyrosine kinases depends on biotin supply. Consistent with a role for biotin and its catabolites in modulating these cell signals, greater than 2000 biotin-dependent genes have been identified in various human tissues. Many biotin-dependent gene products play roles in signal transduction and localize to the cell nucleus, consistent with a role for biotin in cell signaling. Posttranscriptional events related to ribosomal activity and protein folding may further contribute to effects of biotin on gene expression. Finally, research has shown that biotinidase and holocarboxylase synthetase mediate covalent binding of biotin to histones (DNA-binding proteins), affecting chromatin structure; at least seven biotinylation sites have been identified in human histones. Biotinylation of histones appears to play a role in cell proliferation, gene silencing, and the cellular response to DNA repair. Roles for biotin in cell signaling and chromatin structure are consistent with the notion that biotin has a unique significance in cell biology. (PMID: 15992684, 16011464).
58-85-5
C00120
171548
15956
BIOTIN
149962
DB00121
[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2
C10H16N2O3S
InChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1
YBJHBAHKTGYVGT-ZKWXMUAHSA-N
5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid
244.311
244.088163078
-2.30
3
biotin
0
-1
FDB014510
(+)-Biotin;(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valerate;(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acid;(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valerate;(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valeric acid;-(+)-biotin;1swk;1swn;1swr;5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoate;5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoic acid;Biodermatin;Bioepiderm;Bios II;Bios h;Biotin;Coenzyme R;D(+)-Biotin;D-(+)-Biotin;D-Biotin;D-Biotin factor S;Factor S;Factor S (vitamin);Hexahydro-2-oxo-1H-thieno(3,4-D)imidazole-4-pentanoate;Hexahydro-2-oxo-1H-thieno(3,4-D)imidazole-4-pentanoic acid;Hexahydro-2-oxo-[3aS-(3aa,4b,6aa)]-1H-Thieno[3,4-D]imidazole-4-pentanoate;Hexahydro-2-oxo-[3aS-(3aa,4b,6aa)]-1H-Thieno[3,4-D]imidazole-4-pentanoic acid;Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1H-Thieno[3,4-D]imidazole-4-pentanoate;Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1H-Thieno[3,4-D]imidazole-4-pentanoic acid;Lutavit H2;Meribin;Rovimix H 2;Vitamin B7;Vitamin H;Vitamin-h;cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valerate;cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acid;cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valeric acid;cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valeric acid;delta-(+)-Biotin;delta-Biotin;delta-Biotin factor S
PW_C000020
26
4
135
8
579
15
1699
3
2270
2
5292
101
5298
105
5393
103
5449
120
5546
111
5551
114
5575
133
6051
155
6112
161
6496
178
6925
160
1027
Manganese
HMDB01333
Manganese is an essential trace nutrient in all forms of life. Physiologically, it. exists as an ion in the body. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver.
16397-91-4
C19610
27854
29035
MN%2b3
25916
[Mn++]
Mn
InChI=1S/Mn/q+2
WAEMQWOKJMHJLA-UHFFFAOYSA-N
manganese(2+) ion
54.938
54.938049636
0
manganese(2+) ion
2
2
FDB003636
Manganese
PW_C001027
27
4
473
8
1486
49
1553
43
2271
2
2394
3
2513
14
5394
103
5450
120
5576
133
6052
155
6113
161
6497
178
6926
160
1099
Coenzyme A
HMDB01423
Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate and adenosine triphosphate. Coenzyme A is synthesized in a five-step process from pantothenate and cysteine. In the first step Pantothenate (vitamin B5) is phosphorylated to 4'-phosphopantothenate by the enzyme pantothenate kinase (PanK; CoaA; CoaX)In the second step, a cysteine is added to 4'-phosphopantothenate by the enzyme phosphopantothenoylcysteine synthetase (PPC-DC; CoaB) to form 4'-phospho-N-pantothenoylcysteine (PPC). In the third step, PPC is decarboxylated to 4'-phosphopantetheine by phosphopantothenoylcysteine decarboxylase (CoaC). In the fourth step, 4'-phosphopantetheine is adenylylated to form dephospho-CoA by the enzyme phosphopantetheine adenylyl transferase (CoaD)Finally, dephospho-CoA is phosphorylated using ATP to coenzyme A by the enzyme dephosphocoenzyme A kinase (CoaE). Since coenzyme A is, in chemical terms, a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. CoA assists in transferring fatty acids from the cytoplasm to mitochondria. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group, it is usually referred to as 'CoASH' or 'HSCoA'. Coenzyme A is also the source of the phosphopantetheine group that is added as a prosthetic group to proteins such as acyl carrier protein and formyltetrahydrofolate dehydrogenase Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine, in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production. -- Wikipedia.
85-61-0
C00010
6816
1146900
CO-A
6557
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCS
C21H36N7O16P3S
InChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16?,20-/m1/s1
RGJOEKWQDUBAIZ-DRCCLKDXSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
767.534
767.115208365
-2.22
10
coenzyme A
0
-4
FDB022614
Acetoacetyl coenzyme A sodium salt;CoA;CoA hydrate;CoA-SH;CoASH;Coenzyme A;Coenzyme A hydrate;Coenzyme A-SH;Coenzyme ASH;Coenzymes A;Depot-Zeel;Propionyl CoA;Propionyl Coenzyme A;S-Propanoate;S-Propanoate CoA;S-Propanoate Coenzyme A;S-Propanoic acid;S-Propionate CoA;S-Propionate Coenzyme A;Zeel;[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate
PW_C001099
211
4
386
8
845
3
879
22
892
17
2407
59
2414
2
2459
5
2813
29
2862
31
3342
11
3351
18
4618
10
4629
58
4842
14
4865
54
4879
6
5232
102
5247
104
5280
103
5477
124
5734
108
5777
101
6023
155
6075
161
6384
1
6468
178
6930
160
6961
162
6973
199
7083
188
7108
163
7293
198
7347
210
940
Acetyl-CoA
HMDB01206
The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia). acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.
72-89-9
C00024
444493
15351
ACETYL-COA
392413
CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
C23H38N7O17P3S
InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1
ZSLZBFCDCINBPY-ZSJPKINUSA-N
{[(2R,3S,4R,5R)-2-({[({[(3R)-3-[(2-{[2-(acetylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
809.571
809.125773051
-2.27
9
acetyl-CoA
0
-4
FDB022491
Ac-CoA;Ac-Coenzyme A;Ac-S-CoA;Ac-S-Coenzyme A;Acetyl coenzyme-A;Acetyl-CoA;Acetyl-Coenzyme A;Acetyl-S-CoA;Acetyl-S-Coenzyme A;Acetylcoenzyme-A;S-Acetate CoA;S-Acetate Coenzyme A;S-Acetyl coenzyme A
PW_C000940
213
4
385
8
842
3
2416
2
2446
5
2896
17
3340
11
4840
14
5278
103
5476
124
5733
108
6025
155
6077
161
6386
1
6470
178
6923
160
7106
163
7291
198
1316
Carbon dioxide
HMDB01967
Carbon dioxide is a colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbon dioxide is produced during respiration by all animals, fungi and microorganisms that depend on living and decaying plants for food, either directly or indirectly. It is, therefore, a major component of the carbon cycle. Additionally, carbon dioxide is used by plants during photosynthesis to make sugars which may either be consumed again in respiration or used as the raw material to produce polysaccharides such as starch and cellulose, proteins and the wide variety of other organic compounds required for plant growth and development. When inhaled at concentrations much higher than usual atmospheric levels, it can produce a sour taste in the mouth and a stinging sensation in the nose and throat. These effects result from the gas dissolving in the mucous membranes and saliva, forming a weak solution of carbonic acid. Carbon dioxide is used by the food industry, the oil industry, and the chemical industry. Carbon dioxide is used to produce carbonated soft drinks and soda water. Traditionally, the carbonation in beer and sparkling wine comes about through natural fermentation, but some manufacturers carbonate these drinks artificially.
124-38-9
C00011
280
16526
274
O=C=O
CO2
InChI=1S/CO2/c2-1-3
CURLTUGMZLYLDI-UHFFFAOYSA-N
methanedione
44.0095
43.989829244
0.63
0
carbon dioxide
0
0
DBMET00423
FDB014084
Carbon oxide;Carbon-12 dioxide;Carbonic acid anhydride;Carbonic acid gas;Carbonic anhydride
PW_C001316
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
1060
Thiamine pyrophosphate
HMDB01372
Thiamine pyrophosphate is the active form of thiamine, and it serves as a cofactor for several enzymes involved primarily in carbohydrate catabolism. The enzymes are important in the biosynthesis of a number of cell constituents, including neurotransmitters, and for the production of reducing equivalents used in oxidant stress defenses and in biosyntheses and for synthesis of pentoses used as nucleic acid precursors. The chemical structure of TPP is that of an aromatic methylaminopyrimidine ring, linked via a methylene bridge to a methylthiazolium ring with a pyrophosphate group attached to a hydroxyethyl side chain. In non-enzymatic model studies it has been demonstrated that the thiazolium ring can catalyse reactions which are similar to those of TPP-dependent enzymes but several orders of magnitude slower. Using infrared and NMR spectrophotometry it has been shown that the dissociation of the proton from C2 of the thiazolium ring is necessary for catalysis; the abstraction of the proton leads to the formation of a carbanion (ylid) with the potential for a nucleophilic attack on the carbonyl group of the substrate. In all TPP-dependent enzymes the abstraction of the proton from the C2 atom is the first step in catalysis, which is followed by a nucleophilic attack of this carbanion on the substrate. Subsequent cleavage of a C-C bond releases the first product with formation of a second carbanion (2-greek small letter alpha-carbanion or enamine). The formation of this 2-greek small letter alpha-carbanion is the second feature of TPP catalysis common to all TPP-dependent enzymes. Depending on the enzyme and the substrate(s), the reaction intermediates and products differ. Methyl-branched fatty acids, as phytanic acid, undergo peroxisomal beta-oxidation in which they are shortened by 1 carbon atom. This process includes four steps: activation, 2-hydroxylation, thiamine pyrophosphate dependent cleavage and aldehyde dehydrogenation. In the third step, 2-hydroxy-3-methylacyl-CoA is cleaved in the peroxisomal matrix by 2-hydroxyphytanoyl-CoA lyase (2-HPCL), which uses thiamine pyrophosphate (TPP) as cofactor. The thiamine pyrophosphate dependence of the third step is unique in peroxisomal mammalian enzymology. Human pathology due to a deficient alpha-oxidation is mostly linked to mutations in the gene coding for the second enzyme of the sequence, phytanoyl-CoA hydroxylase (EC 1.14.11.18). (PMID: 12694175, 11899071, 9924800).
154-87-0
C00068
1132
9532
2-(alpha-lactyl)-thpp
1100
CC1=C(CCO[P@](O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N
C12H19N4O7P2S
InChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)/p+1
AYEKOFBPNLCAJY-UHFFFAOYSA-O
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium
425.314
425.044967696
-3.48
4
thiamin pyrophosphate
1
-1
FDB022584
TPP;ThPP;Thaimine pyrophosphate;Thiamin diphosphate;Thiamin pyrophosphate;Thiamin-PPi;Thiamine diphosphate;Thiamine pyrophosphate;Thiamine-PPi;Thiamine-pyrophosphate
PW_C001060
205
4
1075
3
1197
8
1271
5
1736
2
5366
103
6028
155
6080
161
6388
1
6473
178
769
Lipoamide
HMDB00962
Lipoamide is the oxidized form of glutathione. (PMID:8957191). Lipoamide is a trivial name for 6,8-dithiooctanoic amide. It is 6,8-dithiooctanoic acid's functional form where the carboxyl group is attached to protein (or any other amine) by an amide linkage (containing -NH2) to an amino group. Lipoamide forms a thioester bond, oxidizing the disulfide bond, with acetaldehyde (pyruvate after it has been decarboxylated). It then transfers the acetaldehyde group to CoA which can then continue in the TCA cycle. (Wikipedia). Lipoamide is an intermediate in glycolysis/gluconeogenesis, citrate cycle (TCA cycle), alanine, aspartate and pyruvate metabolism, and valine, leucine and isoleucine degradation (KEGG:C00248). It is generated from dihydrolipoamide via the enzyme dihydrolipoamide dehydrogenase (EC:1.8.1.4) and then converted to S-glutaryl-dihydrolipoamide via the enzyme oxoglutarate dehydrogenase (EC:1.2.4.2).
940-69-2
C00248
863
17460
LIPOAMIDE
840
NC(=O)CCCCC1CCSS1
C8H15NOS2
InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)
FCCDDURTIIUXBY-UHFFFAOYSA-N
5-(1,2-dithiolan-3-yl)pentanamide
205.341
205.059505487
-3.31
1
lipoamide
0
0
FDB022340
1,2-Dithiolane-3-pentanamide;5-(1,2-Dithiolan-3-yl)-pentanamide;5-(1,2-Dithiolan-3-yl)pentanamide;5-(1,2-Dithiolan-3-yl)valeramide;5-(Dithiolan-3-yl)valeramide;DL-lipoamide;Dl-6-Thioctic amide;Lipamide;Lipoacin;Lipoamid;Lipoicin;Lipozyme;Lypoaran;Pathoclon;Thioami;Thioctamid;Thioctamide;Thioctic acid amide;Thioctic acid amide (jan);Thiotomin;Ticolin;Vitamin N;alpha-Lipoate;alpha-Lipoic acid;alpha-Lipoic acid amide
PW_C000769
202
4
1073
3
1734
2
4667
8
5367
103
6029
155
6081
161
6389
1
6474
178
964
FAD
HMDB01248
FAD is a condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972).
146-14-5
C00016
643975
16238
FAD
559059
DB03147
CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)CO[P@](O)(=O)O[P@@](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2
C27H33N9O15P2
InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1
VWWQXMAJTJZDQX-UYBVJOGSSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy})phosphinic acid
785.5497
785.157134455
-2.27
9
flavine-adenine dinucleotide
0
-3
FDB022511
1H-Purin-6-amine flavin dinucleotide;1H-Purin-6-amine flavine dinucleotide;Adenine-flavin dinucleotide;Adenine-flavine dinucleotide;Adenine-riboflavin dinuceotide;Adenine-riboflavin dinucleotide;Adenine-riboflavine dinucleotide;FAD;Flamitajin B;Flanin F;Flavin adenine dinucleotide;Flavin adenine dinucleotide oxidized;Flavin-adenine dinucleotide;Flavine adenosine diphosphate;Flavine-adenine dinucleotide;Flavitan;Flaziren;Isoalloxazine-adenine dinucleotide;Riboflavin 5'-adenosine diphosphate;Riboflavin-adenine dinucleotide;Riboflavine-adenine dinucleotide
PW_C000964
99
9
114
5
186
8
192
3
216
4
253
17
628
28
825
18
840
2
1188
14
1489
42
1612
29
1622
49
2133
58
2536
22
3723
26
4602
36
4688
31
4741
13
4758
10
4881
6
5268
103
5285
102
5335
111
5496
126
5511
127
5613
118
6030
155
6054
156
6082
161
6116
162
6390
1
6475
178
6499
179
6666
107
7039
163
7175
205
7321
213
63
Citric acid
HMDB00094
Citric acid (citrate) is a weak acid that is formed in the tricarboxylic acid cycle or that may be introduced with diet. The evaluation of plasma citric acid is scarcely used in the diagnosis of human diseases. On the contrary urinary citrate excretion is a common tool in the differential diagnosis of kidney stones, renal tubular acidosis and it plays also a role in bone diseases. The importance of hypocitraturia should be considered with regard to bone mass, urine crystallization and urolithiasis. (PMID 12957820) The secretory epithelial cells of the prostate gland of humans and other animals posses a unique citrate-related metabolic pathway regulated by testosterone and prolactin. This specialized hormone-regulated metabolic activity is responsible for the major prostate function of the production and secretion of extraordinarily high levels of citrate. The key regulatory enzymes directly associated with citrate production in the prostate cells are mitochondrial aspartate aminotransferase, pyruvate dehydrogenase, and mitochondrial aconitase. testosterone and prolactin are involved in the regulation of the corresponding genes associated with these enzymes. The regulatory regions of these genes contain the necessary response elements that confer the ability of both hormones to control gene transcription. Protein kinase c (PKC) is the signaling pathway for the prolactin regulation of the metabolic genes in prostate cells. testosterone and prolactin regulation of these metabolic genes (which are constitutively expressed in all mammalian cells) is specific for these citrate-producing cells. (PMID 12198595) Citric acid is found in citrus fruits, most concentrated in lemons and limes, where it can comprise as much as 8% of the dry weight of the fruit. Citric acid is a natural preservative and is also used to add an acidic (sour) taste to foods and soft drinks. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability. Intolerance to citric acid in the diet is known to exist. Little information is available as the condition appears to be rare, but like other types of food intolerance it is often described as a "pseudo-allergic" reaction.
77-92-9
C00158
19782904
30769
CIT
305
DB04272
OC(=O)CC(O)(CC(O)=O)C(O)=O
C6H8O7
InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
KRKNYBCHXYNGOX-UHFFFAOYSA-N
2-hydroxypropane-1,2,3-tricarboxylic acid
192.1235
192.02700261
-0.26
4
citric acid
0
-3
FDB012586
2-Hydroxy-1,2,3-propanetricarboxylate;2-Hydroxy-1,2,3-propanetricarboxylic acid;3-Carboxy-3-hydroxypentane-1,5-dioate;3-Carboxy-3-hydroxypentane-1,5-dioic acid;Aciletten;Anhydrous citrate;Anhydrous citric acid;Chemfill;Citraclean;Citrate;Citretten;Citric acid;Citro;E 330;Hydrocerol A;Kyselina citronova;Suby G;Uro-trainer;beta-Hydroxytricarballylate;beta-Hydroxytricarballylic acid
PW_C000063
219
4
2415
2
5372
103
6034
155
6089
161
6479
178
122
L-Lactic acid
HMDB00190
Lactic acid plays a role in several biochemical processes and is produced in the muscles during intense activity. Lactate measurement in the critically ill has been traditionally used to stratify patients with poor outcome. However, plasma lactate levels are the result of a finely tuned interplay of factors that affect the balance between its production and its clearance. When the oxygen supply does not match its consumption, organisms such as man who are forced to produce ATP for their integrity adapt in many different ways up to the point when energy failure occurs. Lactate, being part of the adaptive response, may then be used to assess the severity of the supply/demand imbalance. In such a scenario, the time to intervention becomes relevant: early and effective treatment may allow the cell to revert to a normal state, as long as the oxygen machinery (i.e. mitochondria) is intact. Conversely, once the mitochondria are deranged, energy failure occurs even in the presence of normoxia. The lactate increase in critically ill patients may therefore be viewed as an early marker of a potentially reversible state. (PMID 16356243) A number of studies have demonstrated that malignant transformation is associated with an increase in glycolytic flux and in anaerobic and aerobic cellular lactate excretion. Using quantitative bioluminescence imaging in various primary carcinomas in patients (uterine cervix, head and neck, colorectal region) at first diagnosis of the disease, lactate concentrations in tumors in vivo could be relatively low or extremely high (up to 40 micromol/g) in different individual tumors or within the same lesion. In all tumor entities investigated, high molar concentrations of lactate were correlated with a high incidence of distant metastasis already in an early stage of the disease. Low lactate tumors (< median of approximately 8 micromol/g) were associated with both a longer overall and disease free survival compared to high lactate lesions (lactate > approximately 8 micromol/g). Lactate dehydrogenase was found to be upregulated in most of these tumors compared to surrounding normal tissue. (PMID 15279558).
79-33-4
C00186
107689
422
L-LACTATE
96860
C[C@H](O)C(O)=O
C3H6O3
InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1
JVTAAEKCZFNVCJ-REOHCLBHSA-N
(2S)-2-hydroxypropanoic acid
90.0779
90.031694058
0.79
2
(α)-lactate
0
-1
FDB003294
(+)-Lactate;(+)-Lactic acid;(S)-(+)-2-Hydroxypropanoate;(S)-(+)-2-Hydroxypropanoic acid;(S)-2-Hydroxypropanoate;(S)-2-Hydroxypropanoic acid;(S)-2-Hydroxypropionate;(S)-2-Hydroxypropionic acid;(S)-2-hydroxy-Propanoate;(S)-2-hydroxy-Propanoic acid;(S)-Lactate;(S)-Lactic acid;(alpha)-Lactate;(alpha)-Lactic acid;1-Hydroxyethane 1-carboxylate;1-Hydroxyethane 1-carboxylic acid;1-Hydroxyethanecarboxylate;1-Hydroxyethanecarboxylic acid;2-Hydroxypropanoate;2-Hydroxypropanoic acid;2-Hydroxypropionate;L-(+)- Lactic acid;L-2-Hydroxypropanoate;L-2-Hydroxypropanoic acid;Lactate;Lactic acid;Milk acid;Sarcolactic acid;a-Hydroxypropanoate;a-Hydroxypropanoic acid;a-Hydroxypropionate;a-Hydroxypropionic acid;alpha-Hydroxypropanoate;alpha-Hydroxypropanoic acid;alpha-Hydroxypropionate;alpha-Hydroxypropionic acid
PW_C000122
1717
8
2399
2
5050
15
40034
Hydrogen Ion
HMDB59597
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
hydron
1.0079
1.007825032
0
hydron
1
0
PW_C040034
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
125
Isocitric acid
HMDB00193
The citrate oxidation to isocitrate is catalyzed by the enzyme aconitase. Human prostatic secretion is remarkably rich in citric acid and low aconitase activity will therefore play a significant role in enabling accumulation of high citrate levels (PubMed ID 8115279).
320-77-4
C00311
1198
30887
threo-d(s)-iso-citrate
1161
OC(C(CC(O)=O)C(O)=O)C(O)=O
C6H8O7
InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)
ODBLHEXUDAPZAU-UHFFFAOYSA-N
1-hydroxypropane-1,2,3-tricarboxylic acid
192.1235
192.02700261
-0.56
4
isocitric acid
0
-3
FDB003281
1-Hydroxy-1,2,3-propanetricarboxylate;1-Hydroxy-1,2,3-propanetricarboxylic acid;1-Hydroxypropane-1,2,3-tricarboxylate;1-Hydroxypropane-1,2,3-tricarboxylic acid;1-Hydroxytricarballylate;1-Hydroxytricarballylic acid;3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylate;3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid;3-Carboxy-2,3-dideoxy-Pentarate;3-Carboxy-2,3-dideoxy-Pentaric acid;D-Isocitrate;I-CIT;Isocitrate;Threo-D(S)-iso-citrate;Threo-Ds-isocitrate
PW_C000125
224
4
5064
2
5374
103
6035
155
6091
161
6481
178
40711
4Fe-4S
HMDB61380
33723
S[Fe]12[S]3[Fe]4(S)[S]1[Fe]1(S)[S]2[Fe]3(S)[S]41
Fe4H4S8
InChI=1S/4Fe.4H2S.4S/h;;;;4*1H2;;;;/q4*+1;;;;;;;;/p-4
CFWDOBXUEATMSD-UHFFFAOYSA-J
483.932
483.54763418
0
0
0
PW_C040711
4738
3
4859
8
5051
4
5065
2
5403
110
6060
157
6124
163
6508
180
134
Oxoglutaric acid
HMDB00208
Alpha-ketoglutaric acid is an important biological compound and is a key intermediate in the Krebs cycle. Alpha-ketoglutaric acid occurs naturally within cells. One of its functions is to combine with ammonia to form glutamic acid and then glutamine. Another function is to combine with nitrogen released in the cell, therefore preventing nitrogen overload. (wikipedia).
328-50-7
C00026
51
30915
2-KETOGLUTARATE
50
DB02926
OC(=O)CCC(=O)C(O)=O
C5H6O5
InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)
KPGXRSRHYNQIFN-UHFFFAOYSA-N
2-oxopentanedioic acid
146.0981
146.021523302
-0.44
2
oxoglutarate
0
-2
FDB003361
2-Ketoglutarate;2-Ketoglutaric acid;2-Oxo-1,5-pentanedioate;2-Oxo-1,5-pentanedioic acid;2-Oxoglutarate;2-Oxoglutaric acid;2-Oxopentanedioate;2-Oxopentanedioic acid;Oxoglutarate
PW_C000134
15
2
42
3
141
4
146
8
499
18
673
31
1108
42
1263
5
1447
50
1455
26
1467
54
5375
103
5414
117
5438
118
5564
132
6008
147
6036
155
6069
157
6092
161
6482
178
6530
85
808
Succinyl-CoA
HMDB01022
Succinyl-CoA is an important intermediate in the citric acid cycle, where it is synthesized from α-Ketoglutarate by α-ketoglutarate dehydrogenase (EC 1.2.4.2) through decarboxylation, and is converted into succinate through the hydrolytic release of coenzyme A by succinyl-CoA synthetase (EC 6.2.1.5). Succinyl-CoA may be an end product of peroxisomal beta-oxidation of dicarboxylic fatty acids; the identification of an apparently specific succinyl-CoA thioesterase (ACOT4, EC 3.1.2.3, hydrolyzes succinyl-CoA) in peroxisomes strongly suggests that succinyl-CoA is formed in peroxisomes. Acyl-CoA thioesterases (ACOTs) are a family of enzymes that catalyze the hydrolysis of the CoA esters of various lipids to the free acids and coenzyme A, thereby regulating levels of these compounds. (PMID: 16141203).
604-98-8
C00091
439161
15380
3-METHYLBENZYLSUCCINYL-COA
388307
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O
C25H40N7O19P3S
InChI=1S/C25H40N7O19P3S/c1-25(2,20(38)23(39)28-6-5-14(33)27-7-8-55-16(36)4-3-15(34)35)10-48-54(45,46)51-53(43,44)47-9-13-19(50-52(40,41)42)18(37)24(49-13)32-12-31-17-21(26)29-11-30-22(17)32/h11-13,18-20,24,37-38H,3-10H2,1-2H3,(H,27,33)(H,28,39)(H,34,35)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t13-,18-,19-,20?,24-/m1/s1
VNOYUJKHFWYWIR-FZEDXVDRSA-N
4-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-4-oxobutanoic acid
867.607
867.131252359
-2.35
10
4-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-4-oxobutanoic acid
0
-5
FDB022375
CoA S-(hydrogen succinate);CoA S-succinate;Coenzyme A S-(hydrogen succinate);Coenzyme A S-succinate;S-(Hydrogen butanedioate;S-(Hydrogen butanedioate) CoA;S-(Hydrogen butanedioate) Coenzyme A;S-(Hydrogen butanedioic acid;S-Succinoylcoenzyme A;Suc-co-A;Suc-coa;Succ-CoA;Succ-Coenzyme A;Succ-S-CoA;Succ-S-Coenzyme A;Succ-S-coenzyme-A;Succ-coenzyme-A;Succino-1-yl-coenzyme a;Succinyl CoA;Succinyl coenzyme A;Succinyl-S-CoA;Succinyl-S-Coenzyme A;Succinyl-S-coenzyme-A;Succinylcoenzyme-A
PW_C000808
233
4
1055
3
3669
2
5378
103
6039
155
6097
161
6485
178
7015
160
7361
163
936
Guanosine diphosphate
HMDB01201
Guanosine 5'-(trihydrogen diphosphate). A guanine nucleotide containing two phosphate groups esterified to the sugar moiety. It is an ester of pyrophosphoric acid with the nucleoside guanosine. GDP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase guanine. GDP is the product of GTP dephosphorylation by GTPases, e.g. the G-proteins that are involved in signal transduction.
146-91-8
C00035
8977
17552
GDP-4-DEHYDRO-6-DEOXY-D-MANNOSE
8630
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1
C10H15N5O11P2
InChI=1S/C10H15N5O11P2/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(25-9)1-24-28(22,23)26-27(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1
QGWNDRXFNXRZMB-UUOKFMHZSA-N
[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
443.2005
443.024329371
-2.00
7
GDP
0
-2
FDB022487
5'-GDP;GDP;Guanosine 5'-(trihydrogen pyrophosphate);Guanosine 5'-diphosphate;Guanosine 5'-pyrophosphate;Guanosine mono(trihydrogen diphosphate);Guanosine pyrophosphate;Guanosine-5'-diphosphate;Guanosine-diphosphate;PpG
PW_C000936
83
8
238
4
1762
14
2391
2
4154
73
5007
85
5382
103
6041
155
6101
161
6488
178
174
Succinic acid
HMDB00254
Succinic acid is a dicarboxylic acid. The anion, succinate, is a component of the citric acid cycle capable of donating electrons to the electron transfer chain. Succinate dehydrogenase (SDH) plays an important role in the mitochondria, being both part of the respiratory chain and the Krebs cycle. SDH with a covalently attached FAD prosthetic group, binds enzyme substrates (succinate and fumarate) and physiological regulators (oxaloacetate and ATP). Oxidizing succinate links SDH to the fast-cycling Krebs cycle portion where it participates in the breakdown of acetyl-CoA throughout the whole Krebs cycle. The succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e. g. malate. (PMID 16143825) Mutations in the four genes encoding the subunits of the mitochondrial respiratory chain succinate dehydrogenase are associated with a wide spectrum of clinical presentations (i.e.: Huntington's disease. (PMID 11803021).
110-15-6
C00042
1110
15741
SUC
1078
DB00139
OC(=O)CCC(O)=O
C4H6O4
InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
KDYFGRWQOYBRFD-UHFFFAOYSA-N
butanedioic acid
118.088
118.02660868
0.25
2
succinic acid
0
-2
FDB001931
1,2-Ethanedicarboxylate;1,2-Ethanedicarboxylic acid;1,4-Butanedioate;1,4-Butanedioic acid;Amber acid;Asuccin;Dihydrofumarate;Dihydrofumaric acid;Katasuccin;Succinate;Wormwood acid
PW_C000174
152
3
239
4
502
18
507
8
676
31
1265
5
4255
17
5383
103
6042
155
6102
161
6454
107
6455
108
6489
178
6764
117
6836
166
7362
163
986
Guanosine triphosphate
HMDB01273
Guanosine triphosphate (GTP) is a guanine nucleotide containing three phosphate groups esterified to the sugar moiety. GTP functions as a carrier of phosphates and pyrophosphates involved in channeling chemical energy into specific biosynthetic pathways. GTP activates the signal transducing G proteins which are involved in various cellular processes including proliferation, differentiation, and activation of several intracellular kinase cascades. Proliferation and apoptosis are regulated in part by the hydrolysis of GTP by small GTPases Ras and Rho. Another type of small GTPase, Rab, plays a role in the docking and fusion of vesicles and may also be involved in vesicle formation. In addition to its role in signal transduction, GTP also serves as an energy-rich precursor of mononucleotide units in the enzymatic biosynthesis of DNA and RNA.
86-01-1
C00044
6830
15996
GTP
6569
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1
C10H16N5O14P3
InChI=1S/C10H16N5O14P3/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1
XKMLYUALXHKNFT-UUOKFMHZSA-N
({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
523.1804
522.990659781
-1.70
8
triphosphate, guanosine
0
-3
FDB022527
5'-GTP;GTG;GTP;Guanosine 5'-(tetrahydrogen triphosphate);Guanosine 5'-triphosphate;Guanosine 5'-triphosphorate;Guanosine 5'-triphosphoric acid;Guanosine Triphosphate;Guanosine mono(tetrahydrogen triphosphate) (ester);H4gtp
PW_C000986
81
8
240
4
1939
2
4091
14
4153
73
5006
85
5384
103
6043
155
6103
161
6490
178
846
Coenzyme Q10
HMDB01072
Coenzyme Q10 (ubiquinone) is a naturally occurring compound widely distributed in animal organisms and in humans. The primary compounds involved in the biosynthesis of ubiquinone are 4-hydroxybenzoate and the polyprenyl chain. An essential role of coenzyme Q10 is as an electron carrier in the mitochondrial respiratory chain. Moreover, coenzyme Q10 is one of the most important lipophilic antioxidants, preventing the generation of free radicals as well as oxidative modifications of proteins, lipids, and DNA, it and can also regenerate the other powerful lipophilic antioxidant, alpha-tocopherol. Antioxidant action is a property of the reduced form of coenzyme Q10, ubiquinol (CoQ10H2), and the ubisemiquinone radical (CoQ10H*). Paradoxically, independently of the known antioxidant properties of coenzyme Q10, the ubisemiquinone radical anion (CoQ10-) possesses prooxidative properties. Decreased levels of coenzyme Q10 in humans are observed in many pathologies (e.g. cardiac disorders, neurodegenerative diseases, AIDS, cancer) associated with intensive generation of free radicals and their action on cells and tissues. In these cases, treatment involves pharmaceutical supplementation or increased consumption of coenzyme Q10 with meals as well as treatment with suitable chemical compounds (i.e. folic acid or B-group vitamins) which significantly increase ubiquinone biosynthesis in the organism. Estimation of coenzyme Q10 deficiency and efficiency of its supplementation requires a determination of ubiquinone levels in the organism. Therefore, highly selective and sensitive methods must be applied, such as HPLC with UV or coulometric detection. For a number of years, coenzyme Q (CoQ10 in humans) was known for its key role in mitochondrial bioenergetics; later studies demonstrated its presence in other subcellular fractions and in plasma, and extensively investigated its antioxidant role. These two functions constitute the basis on which research supporting the clinical use of CoQ10 is founded. Also at the inner mitochondrial membrane level, coenzyme Q is recognized as an obligatory co-factor for the function of uncoupling proteins and a modulator of the transition pore. Furthermore, recent data reveal that CoQ10 affects expression of genes involved in human cell signalling, metabolism, and transport and some of the effects of exogenously administered CoQ10 may be due to this property. Coenzyme Q is the only lipid soluble antioxidant synthesized endogenously. In its reduced form, CoQH2, ubiquinol, inhibits protein and DNA oxidation but it is the effect on lipid peroxidation that has been most deeply studied. Ubiquinol inhibits the peroxidation of cell membrane lipids and also that of lipoprotein lipids present in the circulation. Dietary supplementation with CoQ10 results in increased levels of ubiquinol-10 within circulating lipoproteins and increased resistance of human low-density lipoproteins to the initiation of lipid peroxidation. Moreover, CoQ10 has a direct anti-atherogenic effect, which has been demonstrated in apolipoprotein E-deficient mice fed with a high-fat diet. (PMID: 15928598, 17914161).
303-98-0
C11378
5281915
46245
UBIQUINONE-10
4445197
COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O
C59H90O4
InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+
ACTIUHUUMQJHFO-UPTCCGCDSA-N
2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
863.3435
862.683911368
-6.65
0
coenzyme-Q10
0
0
FDB014621
(all-E)-2,3-dimethoxy-5-methyl-6-(3,7,11,15,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaenyl)-2,5-Cyclohexadiene-1,4-dione;(all-E)-2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-2,5-Cyclohexadiene-1,4-dione;2-(3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-p-Benzoquinone;2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl]-5,6-dimethoxy-3-methyl- 2,5-Cyclohexadiene-1,4-dione;4-Ethyl-5-fluoropyrimidine;Aqua Q 10L10;Aqua Q10;Bio-Quinon;Bio-Quinone Q10;CoQ10;Coenzyme Q10;Ensorb;Kaneka Q10;Kudesan;Li-Q-Sorb;Liquid-Q;Neuquinon;Neuquinone;PureSorb Q 40;Q 10AA;Q-Gel;Q-Gel 100;Ubidecarenone;Ubiquinone 10;Ubiquinone 50;Ubiquinone Q10;Ubiquinone-10;Unbiquinone;Unispheres Q 10
PW_C000846
252
17
4251
42
5052
4
5396
102
6053
156
6115
162
6498
179
88
Fumaric acid
HMDB00134
Fumaric acid is a precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase. Fumarate is converted by fumarase to malate. A fumarate is a salt or ester of the organic compound fumaric acid, a dicarboxylic acid. (wikipedia).
110-17-8
C00122
21883788
18012
FUM
10197150
DB04299
OC(=O)\C=C\C(O)=O
C4H4O4
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
VZCYOOQTPOCHFL-OWOJBTEDSA-N
(2E)-but-2-enedioic acid
116.0722
116.010958616
-0.68
2
fumaric acid
0
-2
FDB003291
(2E)-But-2-enedioate;(2E)-But-2-enedioic acid;(E)-2-Butenedioate;(E)-2-Butenedioic acid;2-(E)-Butenedioate;2-(E)-Butenedioic acid;Allomaleate;Allomaleic acid;Boletate;Boletic acid;FC 33;Fumarate;Fumaric acid;Lichenate;Lichenic acid;Sodium fumarate;trans-1,2-Ethylenedicarboxylate;trans-1,2-Ethylenedicarboxylic acid;trans-2-Butenedioate;trans-2-Butenedioic acid;trans-Butenedioate;trans-Butenedioic acid
PW_C000088
102
8
254
17
2004
2
5053
4
5388
102
6047
156
6107
162
6458
107
6459
108
6492
179
6763
117
6837
166
40098
QH(2)
HMDB59661
Qh(2) is part of the Oxidative phosphorylation, Cardiac muscle contraction, Alzheimer's disease, Parkinson's disease, and Huntington's disease pathways. It is a substrate for: Cytochrome b-c1 complex subunit Rieske, mitochondrial.
447920
17976
394877
COC1=C(O)C(C)=C(CC=C(C)C)C(O)=C1OC
C14H20O4
InChI=1S/C14H20O4/c1-8(2)6-7-10-9(3)11(15)13(17-4)14(18-5)12(10)16/h6,15-16H,7H2,1-5H3
TVLSKGDBUQMDPR-UHFFFAOYSA-N
2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)benzene-1,4-diol
252.3062
252.136159128
-2.92
2
2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)benzene-1,4-diol
0
0
PW_C040098
255
17
5054
4
5397
102
6055
156
6117
162
6500
179
932
FADH
HMDB01197
FADH is the reduced form of flavin adenine dinucleotide (FAD). FAD is synthesized from riboflavin and two molecules of ATP. Riboflavin is phosphorylated by ATP to give riboflavin 5-phosphate (FMN). FAD is then formed from FMN by the transfer of an AMP moiety from a second molecule of ATP. FADH is generated in each round of fatty acid oxidation, and the fatty acyl chain is shortened by two carbon atoms as a result of these reactions; because oxidation is on the beta carbon, this series of reactions is called the beta-oxidation pathway. In the citric acid cycle FADH is involved in harvesting of high-energy electrons from carbon fuels; citric acid cycle itself neither generates a large amount of ATP nor includes oxygen as a reactant. Instead, the citric acid cycle removes electrons from acetyl CoA and uses these electrons to form FADH. (Biochemistry. Berg, Jeremy M. Tymoczko, John L. and Stryer, Lubert. New York: W. H. Freeman and Co. 2002.).
1910-41-4
C01352
446013
17877
FADH2
393487
CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=C(N2)C(=O)NC(=O)N1
C27H35N9O15P2
InChI=1S/C27H35N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,32,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H2,33,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1
YPZRHBJKEMOYQH-UYBVJOGSSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy})phosphinic acid
787.5656
787.172784519
-2.47
11
fadh(.)
0
-2
FDB022483
1,5-Dihydro-FAD;1,5-Dihydro-P-5-ester with adenosine;1,5-Dihydro-Riboflavin 5'-(trihydrogen diphosphate) P'->5'-ester with adenosine;Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine;Adenosine 5'-(trihydrogen pyrophosphate), 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine;Adenosine 5'-{3-[D-ribo-5-(7,8-dimethyl-2,4-dioxo-1,2,3,4,5,10-tetrahydrobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] dihydrogen diphosphate};Adenosine 5-(trihydrogen pyrophosphate);Adenosine pyrophosphate 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine;Adenosine pyrophosphate, 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine;Adenosine pyrophosphate, 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine;Benzo[g]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv;Benzo[gr]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv;Dihydro-FAD;Dihydroflavine-adenine dinucleotide;FADH2;FDA;Flavin adenine dinucleotide (reduced);Flavin adenine dinucleotide reduced;Reduced flavine adenine dinucleotide
PW_C000932
256
17
1045
3
1490
42
5055
4
5398
102
6056
156
6118
162
6501
179
40558
2Fe-2S
HMDB61344
S[Fe]1(S)S[Fe](S)(S)S1
Fe2H4S6
InChI=1S/2Fe.4H2S.2S/h;;4*1H2;;/q2*+2;;;;;;/p-4
TUVRTRPESCSNGS-UHFFFAOYSA-J
cyclodiferrathiane-2,2,4,4-tetrathiol
308.112
307.733608534
4
cyclodiferrathiane-2,2,4,4-tetrathiol
0
0
PW_C040558
3742
2
4012
8
4257
17
4389
3
4626
5
4754
31
4829
9
4837
28
5056
4
5497
126
5512
127
7046
160
101
L-Malic acid
HMDB00156
Malic acid is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. Apples contain malic acid, which contributes to the sourness of a green apple. Malic acid can make a wine taste tart, although the amount decreases with increasing fruit ripeness. (wikipedia). In its ionized form malic acid is called malate. Malate is an intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions. In humans, malic acid is both derived from food sources and synthesized in the body through the citric acid cycle or Krebs cycle which takes place in the mitochondria. Malate's importance to the production of energy in the body during both aerobic and anaerobic conditions is well established. Under aerobic conditions, the oxidation of malate to oxaloacetate provides reducing equivalents to the mitochondria through the malate-aspartate redox shuttle. During anaerobic conditions, where a buildup of excess of reducing equivalents inhibits glycolysis, malic acid's simultaneous reduction to succinate and oxidation to oxaloacetate is capable of removing the accumulating reducing equivalents. This allows malic acid to reverse hypoxia's inhibition of glycolysis and energy production. In studies on rats it has been found that only tissue malate is depleted following exhaustive physical activity. Other key metabolites from the citric acid cycle needed for energy production were found to be unchanged. Because of this, a deficiency of malic acid has been hypothesized to be a major cause of physical exhaustion. Notably, the administration of malic acid to rats has been shown to elevate mitochondrial malate and increase mitochondrial respiration and energy production.
97-67-6
C00149
222656
30797
193317
O[C@@H](CC(O)=O)C(O)=O
C4H6O5
InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1
BJEPYKJPYRNKOW-REOHCLBHSA-N
(2S)-2-hydroxybutanedioic acid
134.0874
134.021523302
0.21
3
(-)-malic acid
0
-2
FDB001044
(-)-(S)-Malate;(-)-(S)-Malic acid;(-)-Hydroxysuccinate;(-)-Hydroxysuccinic acid;(-)-L-Malic acid;(-)-Malic acid;(2S)-2-Hydroxybutanedioate;(2S)-2-Hydroxybutanedioic acid;(S)-(-)-Hydroxysuccinate;(S)-(-)-Hydroxysuccinic acid;(S)-Hydroxybutanedioate;(S)-Hydroxybutanedioic acid;(S)-Malic acid;(S)-hydroxy-Butanedioate;(S)-hydroxy-Butanedioic acid;Apple acid;L-(-)-Malic acid;L-Apple acid;L-Hydroxybutanedioate;L-Hydroxybutanedioic acid;L-Hydroxysuccinate;L-Hydroxysuccinic acid;Malic acid;S-(-)-Malate;S-(-)-Malic acid;S-2-Hydroxybutanedioate;S-2-Hydroxybutanedioic acid
PW_C000101
262
4
1098
3
1721
8
2387
2
5387
103
5735
108
6046
155
6106
161
6453
107
6491
178
95
L-Glutamic acid
HMDB00148
Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. (http://en.wikipedia.org/wiki/Glutamic_acid).
56-86-0
C00025
33032
16015
GLT
30572
DB00142
N[C@@H](CCC(O)=O)C(O)=O
C5H9NO4
InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
WHUUTDBJXJRKMK-VKHMYHEASA-N
(2S)-2-aminopentanedioic acid
147.1293
147.053157781
-0.26
3
L-glutamic acid
0
-1
FDB012535
(2S)-2-Aminopentanedioate;(2S)-2-Aminopentanedioic acid;(S)-(+)-Glutamate;(S)-(+)-Glutamic acid;(S)-2-Aminopentanedioate;(S)-2-Aminopentanedioic acid;(S)-Glutamate;(S)-Glutamic acid;1-Amino-propane-1,3-dicarboxylate;1-Amino-propane-1,3-dicarboxylic acid;1-Aminopropane-1,3-dicarboxylate;1-Aminopropane-1,3-dicarboxylic acid;2-Aminoglutarate;2-Aminoglutaric acid;2-Aminopentanedioate;2-Aminopentanedioic acid;Aciglut;Aminoglutarate;Aminoglutaric acid;E;Glt;Glu;Glusate;Glut;Glutacid;Glutamicol;Glutamidex;Glutaminate;Glutaminic acid;Glutaminol;Glutaton;L-(+)-Glutamate;L-(+)-Glutamic acid;L-Glu;L-Glutamate;L-Glutaminate;L-Glutaminic acid;L-a-Aminoglutarate;L-a-Aminoglutaric acid;L-alpha-Aminoglutarate;L-alpha-Aminoglutaric acid;a-Aminoglutarate;a-Aminoglutaric acid;a-Glutamate;a-Glutamic acid;alpha-Aminoglutarate;alpha-Aminoglutaric acid;alpha-Glutamate;alpha-Glutamic acid
PW_C000095
16
2
44
3
65
8
119
1
138
4
164
14
969
9
1105
42
1448
50
1456
26
1462
54
5323
111
5344
113
5415
117
5439
118
5565
132
5631
107
5632
108
5859
105
6006
147
6071
157
6191
94
6531
85
6838
187
6844
188
7092
72
7093
71
7165
205
7182
207
35
Ammonia
HMDB00051
Ammonia is a colorless alkaline gas with a characteristic sharp smell. Ammonia is one of the most abundant nitrogen-containing compounds in the atmosphere. It is an irritant with a characteristic pungent odor, which 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. Ammonia has been shown to be a neurotoxin that 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 is formed in nearly all tissues and organs of the vertebrate organism; it is the most common endogenous neurotoxic compounds. Ammonia can affect the glutamatergic and GABAergic neuronal systems, the two prevailing neuronal systems of the cortical structures. Ammonia is well recognized to be central in the pathogenesis of hepatic encephalopathy and has been of importance to generations dating back to the early Egyptians. 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 explain hyperammonemia and hepatic encephalopathy. The alternative explanation is that hyperammonemia is the result of intestinal breakdown of amino acids, especially glutamine. The intestines have significant glutaminase activity, predominantly located in the enterocytes. On the other hand, this organ has only 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. The excessive formation of ammonia in the brains of Alzheimer's disease patients has 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: there is 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, 12020619).
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
PW_C000035
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
500
L-Glutamine
HMDB00641
Glutamine (Gln) is one of the 20 amino acids encoded by the standard genetic code. Its side chain is an amide; it is formed by replacing a side-chain hydroxyl of glutamic acid with an amine functional group. glutamine is found in foods high in proteins, such as fish, red meat, beans, and dairy products. glutamine is a supplement that is used in weightlifting, bodybuilding, endurance and other sports, as well as by those who suffer from muscular cramps or pain particularly elderly people. The main use of glutamine within the diet of either group is as a means of replenishing the body's stores of amino acids that have been used during exercise or everyday activities. Studies which are looking into problems with excessive consumption of glutamine thus far have proved inconclusive. However, normal supplementation is healthy mainly because glutamine is supposed to be supplemented after prolonged periods of exercise (for example, a workout or exercise in which amino acids are required for use) and replenishes amino acid stores; this being the main reason glutamine is recommended during fasting or for people who suffer from physical trauma, immune deficiencies, or cancer. There is a significant body of evidence that links glutamine-enriched diets with intestinal effects; aiding maintenance of gut barrier function, intestinal cell proliferation and differentiation, as well as generally reducing septic morbidity and the symptoms of Irritable Bowel Syndrome. The reason for such "cleansing" properties is thought to stem from the fact that the intestinal extraction rate of glutamine is higher than that for other amino acids, and is therefore thought to be the most viable option when attempting to alleviate conditions relating to the gastrointestinal tract. These conditions were discovered after comparing plasma concentration within the gut between glutamine-enriched and non glutamine-enriched diets. However, even though glutamine is thought to have "cleansing" properties and effects, it is unknown to what extent glutamine has clinical benefits, due to the varied concentrations of glutamine in varieties of food. It is also known that glutamine has various effects in reducing healing time after operations. Hospital waiting times after abdominal surgery are reduced by providing parenteral nutrition regimens containing amounts of glutamine to patients. Clinical trials have revealed that patients on supplementation regimes containing glutamine have improved nitrogen balances, generation of cysteinyl-leukotrienes from polymorphonuclear neutrophil granulocytes and improved lymphocyte recovery and intestinal permeability (in postoperative patients) - in comparison to those who had no glutamine within their dietary regime; all without any side-effects. (http://en.wikipedia.org/wiki/glutamine).
56-85-9
C00064
5961
18050
GLN
5746
DB00130
N[C@@H](CCC(N)=O)C(O)=O
C5H10N2O3
InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1
ZDXPYRJPNDTMRX-VKHMYHEASA-N
(2S)-2-amino-4-carbamoylbutanoic acid
146.1445
146.069142196
-0.17
3
L-glutamine
0
0
FDB012164
(2S)-2,5-diamino-5-oxopentanoate;(2S)-2,5-diamino-5-oxopentanoic acid;(2S)-2-amino-4-carbamoylbutanoate;(2S)-2-amino-4-carbamoylbutanoic acid;(S)-2,5-Diamino-5-oxopentanoate;(S)-2,5-Diamino-5-oxopentanoic acid;2-Aminoglutaramic acid;Cebrogen;Glavamin;Glumin;Glutamic acid 5-amide;Glutamic acid amide;Glutamine;L-(+)-Glutamine;L-2-Aminoglutaramic acid;L-2-Aminoglutaramidic acid;L-Glutamic acid 5-amide;L-Glutamic acid gamma-amide;L-Glutamid;L-Glutamide;L-Glutamin;L-Glutamine;L-Glutaminsaeure-5-amid;Levoglutamid;Levoglutamida;Levoglutamide;Levoglutamidum;Levoglutamina;Polyglutamine;Stimulina;gamma-Glutamine
PW_C000500
61
8
443
4
2701
2
3021
15
5658
107
5659
108
6068
157
6846
166
6847
3
143
NADP
HMDB00217
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).
53-59-8
C00006
5886
18009
NAD(P)
5675
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O17P3
InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
XJLXINKUBYWONI-NNYOXOHSSA-O
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ⁵-pyridin-1-ylium
744.4129
744.083277073
-2.27
9
nadp(+)
1
-3
FDB021908
Adenine-nicotinamide dinucleotide phosphate;Codehydrase II;Codehydrogenase II;Coenzyme II;Cozymase II;NAD phosphate;NADP;NADP+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;TPN;Triphosphopyridine nucleotide;b-NADP;b-Nicotinamide adenine dinucleotide phosphate;b-TPN;beta-NADP;beta-Nicotinamide adenine dinucleotide phosphate;beta-TPN
PW_C000143
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
146
NADPH
HMDB00221
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).
53-57-6
C00005
22833512
16474
NADPH
17215925
NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O
C21H30N7O17P3
InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m0/s1
ACFIXJIJDZMPPO-NCHANQSKSA-N
{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
745.4209
745.091102105
-2.14
9
[(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
0
-4
FDB021909
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide;2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) P'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) P'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase II;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-P;Dihydrotriphosphopyridine nucleotide reduced;NADP-reduced;NADPH;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced Codehydrase II;Reduced Coenzyme II;Reduced Cozymase II;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;b-NADPH;b-Nicotinamide-adenine-dinucleotide-phosphorate;b-Nicotinamide-adenine-dinucleotide-phosphoric acid;beta-NADPH;beta-Nicotinamide-adenine-dinucleotide-phosphorate;beta-Nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reduced
PW_C000146
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
810
Phosphohydroxypyruvic acid
HMDB01024
Phosphohydroxypyruvic acid is a prduct of both enzyme phosphoglycerate dehydrogenase [EC 1.1.1.95] and phosphoserine transaminase [EC 2.6.1.52] in glycine, serine and threonine metabolism pathway (KEGG).
3913-50-6
C03232
105
30933
3-P-HYDROXYPYRUVATE
103
OC(=O)C(=O)COP(O)(O)=O
C3H5O7P
InChI=1S/C3H5O7P/c4-2(3(5)6)1-10-11(7,8)9/h1H2,(H,5,6)(H2,7,8,9)
LFLUCDOSQPJJBE-UHFFFAOYSA-N
2-oxo-3-(phosphonooxy)propanoic acid
184.0414
183.977289026
-1.14
3
phosphohydroxypyruvate
0
-3
FDB022377
2-Oxo-3-(phosphonooxy)-Propanoate;2-Oxo-3-(phosphonooxy)-Propanoic acid;3-Phosphohydroxypyruvate;3-Phosphohydroxypyruvic acid;3-Phosphonooxypyruvate;3-Phosphonooxypyruvic acid;Phosphohydroxypyruvate;Phosphohydroxypyruvic acid
PW_C000810
3479
2
186
Phosphoserine
HMDB00272
The phosphoric acid ester of serine. As a constituent (residue) of proteins, its side chain can undergo O-linked glycosylation. This might be important in explaining some of the devastating consequences of diabetes. It is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling in eukaryotes. Phosphorylated serine residues are often referred to as phosphoserine. Serine proteases are a common type of protease. Serine, organic compound, one of the 20 amino acids commonly found in animal proteins. Only the L-stereoisomer appears in mammalian protein. It is not essential to the human diet, since it can be synthesized in the body from other metabolites, including glycine. Serine was first obtained from silk protein, a particularly rich source, in 1865. Its name is derived from the Latin for silk, sericum. Serine's structure was established in 1902.
407-41-0
C01005
57689797
15811
3-P-SERINE
62074
DB04522
N[C@@H](COP(O)(O)=O)C(O)=O
C3H8NO6P
InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1
BZQFBWGGLXLEPQ-REOHCLBHSA-N
(2S)-2-amino-3-(phosphonooxy)propanoic acid
185.0725
185.008923505
-0.97
4
phosphoserine
0
-2
FDB021926
3-O-Phosphoserine;Dexfosfoserine;Fosforina;L-3-Phosphoserine;L-O-Phosphoserine;L-O-Serine phosphate;L-Phosphoserine;L-Serine dihydrogen phosphate (ester);L-Serine phosphate;L-Serinephosphorate;L-Serinephosphoric acid;L-Seryl phosphate
PW_C000186
3489
2
1148
Pyridoxal 5'-phosphate
HMDB01491
This is the active form of vitamin B6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (pyridoxamine). -- Pubchem; Pyridoxal-phosphate (PLP, pyridoxal-5'-phosphate) is a cofactor of many enzymatic reactions. It is the active form of vitamin B6 which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine. -- Wikipedia.
54-47-7
C00018
1051
18405
PYRIDOXAL_PHOSPHATE
1022
DB00114
CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O
C8H10NO6P
InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)
NGVDGCNFYWLIFO-UHFFFAOYSA-N
[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid
247.1419
247.024573569
-1.64
3
pyridoxal phosphate
0
-2
FDB021820
Apolon B6;Biosechs;Codecarboxylase;Coenzyme B6;Hairoxal;Hexermin-P;Hi-Pyridoxin;Hiadelon;Himitan;PAL-P;PLP;Phosphopyridoxal;Phosphopyridoxal coenzyme;Pidopidon;Piodel;Pydoxal;Pyridoxal 5'-phosphate;Pyridoxal 5-phosphate;Pyridoxal P;Pyridoxal phosphate;Pyridoxal-P;Pyridoxyl phosphate;Pyromijin;Sechvitan;Vitahexin-P;Vitazechs
PW_C001148
18
2
32
4
45
3
51
8
122
1
401
19
696
20
1110
42
1450
50
1458
26
2120
10
2150
49
5325
111
5416
117
5421
103
5441
118
5455
120
5567
132
5581
133
6533
85
7018
160
7167
205
7216
212
7222
213
120
L-Serine
HMDB00187
Serine is a nonessential amino acid derived from glycine. Like all the amino acid building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. Low-average concentration of serine compared to other amino acids is found in muscle. Serine is highly concentrated in all cell membranes. (http://www.dcnutrition.com/AminoAcids/) L-Serine may be derived from four possible sources: dietary intake; biosynthesis from the glycolytic intermediate 3-phosphoglycerate; from glycine ; and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of l-serine to serine homoeostasis. It is very likely that the predominant source of l-serine will be very different in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxypyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase (3- PGDH; EC 1.1.1.95). Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) and, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine plays a central role in cellular proliferation. L-Serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function. (PMID 12534373).
56-45-1
C00065
5951
17115
SER
5736
DB00133
N[C@@H](CO)C(O)=O
C3H7NO3
InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
MTCFGRXMJLQNBG-REOHCLBHSA-N
(2S)-2-amino-3-hydroxypropanoic acid
105.0926
105.042593095
0.66
3
L-serine
0
0
FDB012739
(-)-Serine;(S)-2-Amino-3-hydroxypropanoate;(S)-2-Amino-3-hydroxypropanoic acid;(S)-2-amino-3-hydroxy-Propanoate;(S)-2-amino-3-hydroxy-Propanoic acid;(S)-Serine;(S)-a-Amino-b-hydroxypropionate;(S)-a-Amino-b-hydroxypropionic acid;(S)-alpha-Amino-beta-hydroxypropionate;(S)-alpha-Amino-beta-hydroxypropionic acid;(S)-b-Amino-3-hydroxypropionate;(S)-b-Amino-3-hydroxypropionic acid;(S)-beta-Amino-3-hydroxypropionate;(S)-beta-Amino-3-hydroxypropionic acid;2-Amino-3-hydroxypropanoate;2-Amino-3-hydroxypropanoic acid;3-Hydroxy-L-Alanine;L-(-)-Serine;L-3-Hydroxy-2-aminopropionate;L-3-Hydroxy-2-aminopropionic acid;L-3-Hydroxy-alanine;L-Ser;Serine;b-Hydroxy-L-alanine;beta-Hydroxy-L-alanine;beta-Hydroxyalanine
PW_C000120
344
8
1810
2
2617
4
5642
107
5643
108
5884
105
6011
147
6907
163
7086
201
7087
202
7090
71
7091
72
7202
160
7438
3
7443
15
7444
166
1221
Tetrahydrofolic acid
HMDB01846
Tetrahydrofolate is a soluble coenzyme (vitamin B9) that is synthesized de novo by plants and microorganisms, and absorbed from the diet by animals. It is composed of three distinct parts: a pterin ring, a p-ABA (p-aminobenzoic acid) and a polyglutamate chain with a number of residues varying between 1 and 8. Only the tetra-reduced form of the molecule serves as a coenzyme for C1 transfer reactions. In biological systems, the C1-units exist under various oxidation states and the different tetrahydrofolate derivatives constitute a family of related molecules named indistinctly under the generic term folate. (PMID 16042593). Folate is important for cells and tissues that rapidly divide. Cancer cells divide rapidly, and drugs that interfere with folate metabolism are used to treat cancer. Methotrexate is a drug often used to treat cancer because it inhibits the production of the active form, tetrahydrofolate. Unfortunately, methotrexate can be toxic, producing side effects such as inflammation in the digestive tract that make it difficult to eat normally. -- Wikipedia; Signs of folic acid deficiency are often subtle. Diarrhea, loss of appetite, and weight loss can occur. Additional signs are weakness, sore tongue, headaches, heart palpitations, irritability, and behavioral disorders. Women with folate deficiency who become pregnant are more likely to give birth to low birth weight and premature infants, and infants with neural tube defects. In adults, anemia is a sign of advanced folate deficiency. In infants and children, folate deficiency can slow growth rate. Some of these symptoms can also result from a variety of medical conditions other than folate deficiency. It is important to have a physician evaluate these symptoms so that appropriate medical care can be given. -- Wikipedia; Folinic acid is a form of folate that can help 'rescue' or reverse the toxic effects of methotrexate. Folinic acid is not the same as folic acid. Folic acid supplements have little established role in cancer chemotherapy. There have been cases of severe adverse effects of accidental substitution of folic acid for folinic acid in patients receiving methotrexate cancer chemotherapy. It is important for anyone receiving methotrexate to follow medical advice on the use of folic or folinic acid supplements. -- Wikipedia. Low concentrations of folate, vitamin B12, or vitamin B6 may increase the level of homocysteine, an amino acid normally found in blood. There is evidence that an elevated homocysteine level is an independent risk factor for heart disease and stroke. The evidence suggests that high levels of homocysteine may damage coronary arteries or make it easier for blood clotting cells called platelets to clump together and form a clot. However, there is currently no evidence available to suggest that lowering homocysteine with vitamins will reduce your risk of heart disease. Clinical intervention trials are needed to determine whether supplementation with folic acid, vitamin B12 or vitamin B6 can lower your risk of developing coronary heart disease. -- Wikipedia.
135-16-0
C00101
13781857
20506
THF
18714427
DB00116
NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)N2)N1
C19H23N7O6
InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11-,12?/m0/s1
MSTNYGQPCMXVAQ-PXYINDEMSA-N
2-{[4-({[(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
445.4292
445.170981503
-3.22
8
2-{[4-({[(6S)-2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
0
-2
FDB022705
(6S)-Tetrahydrofolate;(6S)-Tetrahydrofolic acid;5,6,7,8-Tetrahydrofolate;5,6,7,8-Tetrahydrofolic acid;Tetra-H-folate;Tetrahydrafolate;Tetrahydrofolate;Tetrahydrofolic acid;Tetrahydropteroyl mono-L-glutamate;Tetrahydropteroylglutamate
PW_C001221
448
4
571
8
975
3
1809
2
5307
111
5347
112
5601
135
5786
108
6009
147
7066
188
7151
205
7185
206
78
Glycine
HMDB00123
Glycine is a simple, nonessential amino acid, although experimental animals show reduced growth on low-glycine diets. The average adult ingests 3 to 5 grams of glycine daily. Glycine is involved in the body's production of DNA, phospholipids and collagen, and in release of energy. Glycine levels are effectively measured in plasma in both normal patients and those with inborn errors of glycine metabolism. (http://www.dcnutrition.com/AminoAcids/) Nonketotic hyperglycinaemia (OMIM 606899) is an autosomal recessive condition caused by deficient enzyme activity of the glycine cleavage enzyme system (EC 2.1.1.10). The glycine cleavage enzyme system comprises four proteins: P-, T-, H- and L-proteins (EC 1.4.4.2, EC 2.1.2.10 and EC 1.8.1.4 for P-, T- and L-proteins). Mutations have been described in the GLDC (OMIM 238300), AMT (OMIM 238310), and GCSH (OMIM 238330) genes encoding the P-, T-, and H-proteins respectively. The glycine cleavage system catalyses the oxidative conversion of glycine into carbon dioxide and ammonia, with the remaining one-carbon unit transferred to folate as methylenetetrahydrofolate. It is the main catabolic pathway for glycine and it also contributes to one-carbon metabolism. Patients with a deficiency of this enzyme system have increased glycine in plasma, urine and cerebrospinal fluid (CSF) with an increased CSF: plasma glycine ratio. (PMID 16151895).
56-40-6
C00037
5257127
15428
GLY
730
DB00145
NCC(O)=O
C2H5NO2
InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)
DHMQDGOQFOQNFH-UHFFFAOYSA-N
2-aminoacetic acid
75.0666
75.032028409
0.87
2
glycine
0
0
FDB000484
2-Aminoacetate;2-Aminoacetic acid;Aciport;Amino-Acetate;Amino-Acetic acid;Aminoacetate;Aminoacetic acid;Aminoethanoate;Aminoethanoic acid;Glicoamin;Glycocoll;Glycolixir;Glycosthene;Gyn-Hydralin;Padil
PW_C000078
31
4
179
8
1812
2
1881
27
2829
29
5420
103
5454
120
5580
133
5640
107
5641
108
5863
105
6007
147
7014
160
7439
3
7441
166
7442
15
1178
5,10-Methylene-THF
HMDB01533
5,10-Methylene-THF is an intermediate in glycine, serine and threonine metabolism and one carbon metabolism. 5,10-CH2-THF can also be used as a coenzyme in the biosynthesis of thymidine. More specifically it is the C1-donor in the reactions catalyzed by thymidylate synthase and thymidylate synthase (FAD). It also acts as a coenzyme in the synthesis of serine from glycine via the enzyme serine hydroxymethyl transferase. 5,10-Methylene-THF is a substrate for Methylenetetrahydrofolate reductase. This enzyme converts 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate. This reaction is required for the multistep process that converts the amino acid homocysteine to methionine. The body uses methionine to make proteins and other important compounds. 5,10-CH2-THF is a substrate for many enzymes including Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase (mitochondrial), Aminomethyltransferase (mitochondrial), Serine hydroxymethyltransferase (mitochondrial), Methylenetetrahydrofolate reductase, C-1-tetrahydrofolate synthase (cytoplasmic), Serine hydroxymethyltransferase (cytosolic) and Thymidylate synthase.
3432-99-3
C00143
439175
15636
METHYLENE-THF
388320
[H][C@@]12CN(CN1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)NC(CCC(O)=O)C(O)=O
C20H23N7O6
InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13?/m1/s1
QYNUQALWYRSVHF-PZORYLMUSA-N
2-({4-[(6aR)-3-amino-1-oxo-1H,2H,5H,6H,6aH,7H,8H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid
457.4399
457.170981503
-2.75
6
2-({4-[(6aR)-3-amino-1-oxo-2H,5H,6H,6aH,7H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid
0
-2
FDB022675
(6R)-5,10-methylenetetrahydrofolate;5,10-Methenyltetrahydropteroylglutamate;5,10-Methylene-6-Hydrofolate;5,10-Methylene-6-Hydrofolic acid;5,10-Methylene-THF;5,10-Methylenetetrahydrofolate;5,10-Methylenetetrahydrofolic acid;N5>,N10-methylenetetrahydrofolate
PW_C001178
449
4
956
8
985
3
1811
2
5331
111
5359
112
5785
108
6010
147
6272
35
7065
188
7171
205
7196
206
185
Sarcosine
HMDB00271
Sarcosine is the N-methyl derivative of glycine. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase, while glycine-N-methyl transferase generates sarcosine from glycine. Sarcosine is a natural amino acid found in muscles and other body tissues. In the laboratory it may be synthesized from chloroacetic acid and methylamine. Sarcosine is naturally found in the metabolism of choline to glycine. Sarcosine is sweet to the taste and dissolves in water. It is used in manufacturing biodegradable surfactants and toothpastes as well as in other applications. Sarcosine is ubiquitous in biological materials and is present in such foods as egg yolks, turkey, ham, vegetables, legumes, etc. Sarcosine is formed from dietary intake of choline and from the metabolism of methionine, and is rapidly degraded to glycine. Sarcosine has no known toxicity, as evidenced by the lack of phenotypic manifestations of sarcosinemia, an inborn error of sarcosine metabolism. Sarcosinemia can result from severe folate deficiency because of the folate requirement for the conversion of sarcosine to glycine (Wikipedia). Sarcosine has recently been identified as a biomarker for invasive prostate cancer. It was found to be greatly increased during prostate cancer progression to metastasis and could be detected in urine. Sarcosine levels were also increased in invasive prostate cancer cell lines relative to benign prostate epithelial cells.(PMID: 19212411).
107-97-1
C00213
1088
15611
SARCOSINE
1057
CNCC(O)=O
C3H7NO2
InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6)
FSYKKLYZXJSNPZ-UHFFFAOYSA-N
2-(methylamino)acetic acid
89.0932
89.047678473
0.54
2
sarcosine
0
0
FDB021925
(Methylamino)acetate;(Methylamino)acetic acid;(Methylamino)ethanoate;(Methylamino)ethanoic acid;(methylamino)-Acetate;(methylamino)-Acetic acid;Methylglycine;N-Methyl-Glycine;N-Methylaminoacetate;N-Methylaminoacetic acid;N-Methylglycine;Sarcosin;Sarcosinate;Sarcosine;Sarcosinic acid
PW_C000185
1883
27
2556
3
749
S-Adenosylhomocysteine
HMDB00939
S-Adenosylhomocysteine (AdoHcy) is the immediate precursor of all of the homocysteine produced in the body. The reaction is catalyzed by S-adenosylhomocysteine hydrolase and is reversible with the equilibrium favoring formation of AdoHcy. In vivo, the reaction is driven in the direction of homocysteine formation by the action of the enzyme adenosine deaminase, which converts the second product of the S-adenosylhomocysteine hydrolase reaction, adenosine, to inosine. Except for methyl transfer from betaine and from methylcobalamin in the methionine synthase reaction, AdoHcy is the product of all methylation reactions that involve S-adenosylmethionine (AdoMet) as the methyl donor. Methylation is significant in epigenetic regulation of protein expression via DNA and histone methylation. The inhibition of these AdoMet-mediated processes by AdoHcy is a proven mechanism for metabolic alteration. Because the conversion of AdoHcy to homocysteine is reversible, with the equilibrium favoring the formation of AdoHcy, increases in plasma homocysteine are accompanied by an elevation of AdoHcy in most cases. Disturbances in the transmethylation pathway indicated by abnormal S-adenosylmethionine, S-adenosylhomocysteine or their ratio have been reported in many neurodegenerative diseases, such as dementia, depression or Parkinson's disease. (PMID: 18065573, 17892439).
979-92-0
C00021
25246222
16680
ADENOSYL-HOMO-CYS
388301
N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12)C(O)=O
C14H20N6O5S
InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1
ZJUKTBDSGOFHSH-WFMPWKQPSA-N
(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid
384.411
384.12158847
-1.97
5
S-adenosyl-L-homocysteine
0
0
DBMET00514
FDB022327
(S)-5'-(S)-(3-Amino-3-carboxypropyl)-5'-thioadenosine;2-S-Adenosyl-L-homocysteine;5'-Deoxy-S-adenosyl-L-homocysteine;5'-S-(3-Amino-3-carboxypropyl)-5'-thio-L-Adenosine;Adenosyl-L-homocysteine;Adenosyl-homo-CYS;Adenosylhomo-CYS;Adenosylhomocysteine;Adohcy;Formycinylhomocysteine;L-5'-S-(3-Amino-3-carboxypropyl)-5'-thior-Adenosine;L-S-Adenosyl-Homocysteine;L-S-Adenosylhomocysteine;S-(5'-Adenosyl)-L-homocysteine;S-(5'-Deoxyadenosin-5'-yl)-L-homocysteine;S-(5'-Deoxyadenosine-5')-L-homocysteine;S-Adenosyl-L-homocysteine;S-Adenosyl-homocysteine;SAH
PW_C000749
520
8
575
18
635
30
705
20
1221
3
1882
27
2067
2
4683
10
5025
50
5607
136
7137
163
921
S-Adenosylmethionine
HMDB01185
Physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in treatment of chronic liver disease. (From Merck, 11th ed).
S-Adenosylmethionine is only found in individuals that have used or taken this drug. It is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in treatment of chronic liver disease. (From Merck, 11th ed)S-Adenosylmethionine (SAMe) is a natural substance present in the cells of the body. It is a direct metabolite of the essential amino acid L-methionine. SAMe plays a crucial biochemical role in the body by donating a one-carbon methyl group in a process called transmethylation. SAMe, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine and other molecules.
29908-03-0
C00019
24762165
15414
S-ADENOSYLMETHIONINE
31983
DB00118
C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12
C15H23N6O5S
InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1
MEFKEPWMEQBLKI-AIRLBKTGSA-O
[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium
399.445
399.145063566
-2.56
5
SAMe
1
1
FDB022473
(3S)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine;2-S-Adenosyl-L-methionine;5'-Deoxyadenosine-5'-L-methionine disulfate ditosylate;Active methionine;Ademetionine;Adenosylmethionine;AdoMet;Donamet;L-S-Adenosylmethionine;S-(5'-Adenosyl)-L-methionine;S-(5'-Deoxyadenosin-5'-yl)-L-methionine;S-Adenosyl methionine;S-Adenosyl-L-Methionine Disulfate Tosylate;S-Adenosyl-L-methionine;S-Adenosyl-methionine;S-Adenosylmethionine;5'-Deoxyadenosine-5'-L-methionine disulphate ditosylate;S-Adenosyl-L-Methionine Disulphate Tosylate
PW_C000921
519
8
633
30
704
20
1220
3
1880
27
2066
2
4681
10
5023
50
5604
135
7136
163
1005
Zinc (II) ion
HMDB01303
Zinc is an essential element, necessary for sustaining all life.Physiologically, it exists as an ion in the body. It is estimated that 3000 of the hundreds of thousands of proteins in the human body contain zinc prosthetic groups. In addition, there are over a dozen types of cells in the human body that secrete zinc ions, and the roles of these secreted zinc signals in medicine and health are now being actively studied. Intriguingly, brain cells in the mammalian forebrain are one type of cell that secretes zinc, along with its other neuronal messenger substances. Cells in the salivary gland, prostate, immune system and intestine are other types that secrete zinc. Obtaining a sufficient zinc intake during pregnancy and in young children is a problem, especially among those who cannot afford a good and varied diet. Brain development is stunted by zinc deficiency in utero and in youth. Zinc is an activator of certain enzymes, such as carbonic anhydrase. Carbonic anhydrase is important in the transport of carbon dioxide in vertebrate blood. Even though zinc is an essential requirement for a healthy body, too much zinc can be harmful. Excessive absorption of zinc can also suppress copper and iron absorption. The free zinc ion in solution is highly toxic to plants, invertebrates, and even vertebrate fish. The Free Ion Activity Model (FIAM) is well-established in the literature, and shows that just micromolar amounts of the free ion kills some organisms.
23713-49-7
C00038
32051
29105
ZN%2b2
29723
DB01593
[Zn++]
Zn
InChI=1S/Zn/q+2
PTFCDOFLOPIGGS-UHFFFAOYSA-N
zinc(2+) ion
65.409
63.929146578
0
zinc(2+) ion
2
2
FDB003729
Zinc;Zinc ion
PW_C001005
13
2
38
4
118
8
271
16
529
15
2957
51
3044
68
3120
29
3147
70
5410
117
5425
103
5434
118
5459
120
5560
132
5585
133
5598
135
7449
166
207
Hexokinase-2
P52789
HMDBP00213
HK2
2p13
Z46358
1
2.7.1.1
2217
2
751
Glucose-6-phosphate isomerase
P06744
Besides it's role as a glycolytic enzyme, mammalian GPI can function as a tumor-secreted cytokine and an angiogenic factor (AMF) that stimulates endothelial cell motility. GPI is also a neurotrophic factor (Neuroleukin) for spinal and sensory neurons.
HMDBP00806
GPI
19q13.1
AH002710
1
5.3.1.9
1805
2
5955
147
706
6-phosphofructokinase, liver type
P17858
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
HMDBP00758
PFKL
21q22.3
BC006422
1
2.7.1.11
1022
8
1793
2
918
Fructose-bisphosphate aldolase B
P05062
HMDBP00980
ALDOB
9q21.3-q22.2
M15657
1
4.1.2.13
2880
8
5048
2
5958
147
659
Glyceraldehyde-3-phosphate dehydrogenase
P04406
Has both glyceraldehyde-3-phosphate dehydrogenase and nitrosylase activities, thereby playing a role in glycolysis and nuclear functions, respectively. Participates in nuclear events including transcription, RNA transport, DNA replication and apoptosis. Nuclear functions are probably due to the nitrosylase activity that mediates cysteine S-nitrosylation of nuclear target proteins such as SIRT1, HDAC2 and PRKDC. Modulates the organization and assembly of the cytoskeleton. Facilitates the CHP1-dependent microtubule and membrane associations through its ability to stimulate the binding of CHP1 to microtubules (By similarity). Glyceraldehyde-3-phosphate dehydrogenase is a key enzyme in glycolysis that catalyzes the first step of the pathway by converting D-glyceraldehyde 3-phosphate (G3P) into 3-phospho-D-glyceroyl phosphate. Component of the GAIT (gamma interferon-activated inhibitor of translation) complex which mediates interferon-gamma-induced transcript-selective translation inhibition in inflammation processes. Upon interferon-gamma treatment assembles into the GAIT complex which binds to stem loop-containing GAIT elements in the 3'-UTR of diverse inflammatory mRNAs (such as ceruplasmin) and suppresses their translation.
HMDBP00695
GAPDH
12p13
BC013310
1
1.2.1.12; 2.6.99.-
1042
8
2254
2
5959
147
1417
Phosphoglycerate kinase 1
P00558
In addition to its role as a glycolytic enzyme, it seems that PGK-1 acts as a polymerase alpha cofactor protein (primer recognition protein).
HMDBP01528
PGK1
Xq13.3
AB062432
1
2.7.2.3
4107
23
5049
2
5960
147
261
Phosphoglycerate mutase 2
P15259
Interconversion of 3- and 2-phosphoglycerate with 2,3-bisphosphoglycerate as the primer of the reaction. Can also catalyze the reaction of EC 5.4.2.4 (synthase) and EC 3.1.3.13 (phosphatase), but with a reduced activity.
HMDBP00267
PGAM2
7p13-p12
BC001904
1
3.1.3.13; 5.4.2.11; 5.4.2.4
2264
2
1021
Alpha-enolase
P06733
Multifunctional enzyme that, as well as its role in glycolysis, plays a part in various processes such as growth control, hypoxia tolerance and allergic responses. May also function in the intravascular and pericellular fibrinolytic system due to its ability to serve as a receptor and activator of plasminogen on the cell surface of several cell-types such as leukocytes and neurons. Stimulates immunoglobulin production.
MBP1 binds to the myc promoter and acts as a transcriptional repressor. May be a tumor suppressor.
HMDBP01087
ENO1
1p36.2
AL833741
1
4.2.1.11
2266
2
5962
147
712
Pyruvate kinase isozymes R/L
P30613
Plays a key role in glycolysis (By similarity).
HMDBP00765
PKLR
1q21
S60712
1
2.7.1.40
1719
8
2267
2
5966
147
19
Pyruvate carboxylase, mitochondrial
P11498
Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second. Catalyzes in a tissue specific manner, the initial reactions of glucose (liver, kidney) and lipid (adipose tissue, liver, brain) synthesis from pyruvate.
HMDBP00019
PC
11q13.4-q13.5
K02282
1
6.4.1.1
28
4
1689
8
2395
3
2398
2
44
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial
P08559
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
HMDBP00046
PDHA1
Xp22.1
M29155
1
1.2.4.1
206
4
1780
3
6391
1
12
Pyruvate dehydrogenase E1 component subunit beta, mitochondrial
P11177
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
HMDBP00012
PDHB
3p21.1-p14.2
M34479
1
1.2.4.1
207
4
1727
3
6392
1
53
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial
P10515
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
HMDBP00055
DLAT
11q23.1
AP000907
1
2.3.1.12
214
4
1787
8
6393
1
52
Dihydrolipoyl dehydrogenase, mitochondrial
P09622
Lipoamide dehydrogenase is a component of the glycine cleavage system as well as of the alpha-ketoacid dehydrogenase complexes. Involved in the hyperactivation of spermatazoa during capacitation and in the spermatazoal acrosome reaction.
HMDBP00054
DLD
7q31-q32
L13757
1
1.8.1.4
217
4
1080
3
4670
8
6394
1
41
Citrate synthase, mitochondrial
O75390
HMDBP00043
CS
12q13.2
AF047042
1
2.3.3.1
220
4
836
L-lactate dehydrogenase A-like 6A
Q6ZMR3
Displays an lactate dehydrogenase activity. Significantly increases the transcriptional activity of JUN, when overexpressed.
HMDBP00893
LDHAL6A
11p15.1
AY581313
1
1.1.1.27
720
8
2400
2
688
Aconitate hydratase, mitochondrial
Q99798
Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
HMDBP00725
ACO2
22q13.2
U87932
1
4.2.1.3
223
4
4739
3
842
Isocitrate dehydrogenase [NAD] subunit alpha, mitochondrial
P50213
HMDBP00899
IDH3A
15q25.1-q25.2
CH471136
1
1.1.1.41
228
4
840
Isocitrate dehydrogenase [NAD] subunit beta, mitochondrial
O43837
HMDBP00897
IDH3B
20p13
BC001960
1
1.1.1.41
229
4
843
Isocitrate dehydrogenase [NAD] subunit gamma, mitochondrial
P51553
HMDBP00900
IDH3G
Xq28
BC001902
1
1.1.1.41
230
4
430
2-oxoglutarate dehydrogenase, mitochondrial
Q02218
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
HMDBP00439
OGDH
7p14-p13
BC014617
1
1.2.4.2
234
4
1076
3
4668
8
882
Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial
P36957
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of 3 enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
HMDBP00939
DLST
14q24.3
AC006530
1
2.3.1.61
235
4
1079
3
4669
8
832
Succinyl-CoA ligase [ADP/GDP-forming] subunit alpha, mitochondrial
P53597
Catalyzes the ATP- or GTP-dependent ligation of succinate and CoA to form succinyl-CoA. The nature of the beta subunit determines the nucleotide specificity (By similarity).
HMDBP00889
SUCLG1
2p11.2
Z68204
1
6.2.1.4; 6.2.1.5
241
4
834
Succinyl-CoA ligase [GDP-forming] subunit beta, mitochondrial
Q96I99
Catalyzes the GTP-dependent ligation of succinate and CoA to form succinyl-CoA (By similarity).
HMDBP00891
SUCLG2
3p14.1
AC114401
1
6.2.1.4
242
4
145
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial
P31040
Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). Can act as a tumor suppressor.
HMDBP00150
SDHA
5p15
AK291311
1
1.3.5.1
257
17
5057
4
188
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial
P21912
Iron-sulfur protein (IP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
HMDBP00193
SDHB
1p36.1-p35
U17248
1
1.3.5.1
258
17
5058
4
116
Succinate dehydrogenase cytochrome b560 subunit, mitochondrial
Q99643
Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
HMDBP00121
SDHC
1q23.3
AK294305
1
259
17
5059
4
174
Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial
O14521
Membrane-anchoring subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q) (By similarity).
HMDBP00179
SDHD
11q23
BC022350
1
260
17
5060
4
806
Fumarate hydratase, mitochondrial
P07954
Also acts as a tumor suppressor.
HMDBP00861
FH
1q42.1
U59309
1
4.2.1.2
263
4
805
Malate dehydrogenase, cytoplasmic
P40925
HMDBP00860
MDH1
2p13.3
AK312331
1
1.1.1.37; 1.1.1.96
1722
8
2390
2
5061
4
658
Glutamate dehydrogenase 1, mitochondrial
P00367
Mitochondrial glutamate dehydrogenase that converts L-glutamate into alpha-ketoglutarate. Plays a key role in glutamine anaplerosis by producing alpha-ketoglutarate, an important intermediate in the tricarboxylic acid cycle. May be involved in learning and memory reactions by increasing the turnover of the excitatory neurotransmitter glutamate (By similarity).
HMDBP00694
GLUD1
10q23.3
X66306
1
1.4.1.3
144
4
1470
54
4875
3
639
Glutaminase liver isoform, mitochondrial
Q9UI32
Plays an important role in the regulation of glutamine catabolism. Promotes mitochondrial respiration and increases ATP generation in cells by catalyzing the synthesis of glutamate and alpha-ketoglutarate. Increases cellular anti-oxidant function via NADH and glutathione production. May play a role in preventing tumor proliferation.
HMDBP00675
GLS2
12q13
CH471054
1
3.5.1.2
137
8
445
4
4132
3
689
Cytoplasmic aconitate hydratase
P21399
Iron sensor. Binds a 4Fe-4S cluster and functions as aconitase when cellular iron levels are high. Functions as mRNA binding protein that regulates uptake, sequestration and utilization of iron when cellular iron levels are low. Binds to iron-responsive elements (IRES) in target mRNA species when iron levels are low. Binding of a 4Fe-4S cluster precludes RNA binding.
Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
HMDBP00726
ACO1
9p21.1
BC018103
1
4.2.1.3
5066
2
841
Isocitrate dehydrogenase [NADP] cytoplasmic
O75874
HMDBP00898
IDH1
2q33.3
BX537411
1
1.1.1.42
5067
2
2449
Solute carrier family 2, facilitated glucose transporter member 2
P11168
Facilitative glucose transporter. This isoform likely mediates the bidirectional transfer of glucose across the plasma membrane of hepatocytes and is responsible for uptake of glucose by the beta cells; may comprise part of the glucose-sensing mechanism of the beta cell. May also participate with the Na(+)/glucose cotransporter in the transcellular transport of glucose in the small intestine and kidney.
HMDBP05474
SLC2A2
3q26.1-q26.2
CH471052
1
5479
Mitochondrial pyruvate carrier 1
Q9Y5U8
Mediates the uptake of pyruvate into mitochondria.
HMDBP11834
MPC1
6q27
AF151887
1
1045
Monocarboxylate transporter 1
P53985
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
HMDBP01111
SLC16A1
1p12
L31801
1
1700
Neutral amino acid transporter B(0)
Q15758
Has a broad substrate specificity, a preference for zwitterionic amino acids, and a sodium-dependence. It accepts as substrates all neutral amino acids, including glutamine, asparagine, and branched-chain and aromatic amino acids, and excludes methylated amino acids, anionic amino acids, and cationic amino acids. Act as a cell surface receptor for feline endogenous virus RD114, baboon M7 endogenous virus and type D simian retroviruses
HMDBP01955
SLC1A5
19q13.3
GQ919058
1
5711
Mitochondrial citrate transport protein
Q6LAP8
X96924
1
2429
17
710
Pyruvate kinase PKM
P14618
Glycolytic enzyme that catalyzes the transfer of a phosphoryl group from phosphoenolpyruvate (PEP) to ADP, generating ATP. Stimulates POU5F1-mediated transcriptional activation. Plays a general role in caspase independent cell death of tumor cells. The ratio betwween the highly active tetrameric form and nearly inactive dimeric form determines whether glucose carbons are channeled to biosynthetic processes or used for glycolytic ATP production. The transition between the 2 forms contributes to the control of glycolysis and is important for tumor cell proliferation and survival.
HMDBP00763
PKM
15q22
AK300800
1
2.7.1.40
5068
2
865
D-3-phosphoglycerate dehydrogenase
O43175
HMDBP00922
PHGDH
1p12
BC011262
1
1.1.1.95
3480
2
796
Phosphoserine aminotransferase
Q9Y617
Catalyzes the reversible conversion of 3-phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4-phosphonooxybutanoate to phosphohydroxythreonine (By similarity).
HMDBP00851
PSAT1
9q21.2
AY131232
1
2.6.1.52
3490
2
830
Phosphoserine phosphatase
P78330
Catalyzes the last step in the biosynthesis of serine from carbohydrates. The reaction mechanism proceeds via the formation of a phosphoryl-enzyme intermediates.
HMDBP00887
PSPH
7p11.2
BX537439
1
3.1.3.3
3491
2
739
Serine hydroxymethyltransferase, cytosolic
P34896
Interconversion of serine and glycine.
HMDBP00794
SHMT1
17p11.2
L23928
1
2.1.2.1
644
8
1813
2
395
Glycine N-methyltransferase
Q14749
Catalyzes the methylation of glycine by using S-adenosylmethionine (AdoMet) to form N-methylglycine (sarcosine) with the concomitant production of S-adenosylhomocysteine (AdoHcy). Possible crucial role in the regulation of tissue concentration of AdoMet and of metabolism of methionine.
HMDBP00403
GNMT
6p12
BC032627
1
2.1.1.20
3472
2
5579
Zinc transporter ZIP1
Q9NY26
Mediates zinc uptake. May function as a major endogenous zinc uptake transporter in many cells of the body. Responsible for the rapid uptake and accumulation of physiologically effective zinc in prostate cells.
HMDBP11934
SLC39A1
1q21
AJ271671
1
5580
Zinc transporter ZIP2
Q9NP94
Mediates zinc uptake. Zinc uptake may be mediated by a Zn(2+)-HCO(3)(-) symport mechanism and can function in the presence of albumin. May also transport other divalent cations. May be important in contact inhibition of normal epithelial cells and loss of its expression may play a role in tumorigenesis.
HMDBP11935
SLC39A2
14q11.2
AK314974
1
5581
Zinc transporter ZIP3
Q9BRY0
Acts as a zinc-influx transporter (Potential).
HMDBP11936
SLC39A3
19p13.3
AK002044
1
5582
Zinc transporter ZIP4
Q6P5W5
Plays an important role in cellular zinc homeostasis as a zinc transporter. Regulated in response to zinc availability (By similarity).
HMDBP11937
SLC39A4
8q24.3
BC062625
1
5583
Zinc transporter ZIP5
Q6ZMH5
May play a role in polarized cells by carrying out serosal-to-mucosal zinc transport. Seems to play a central role in controlling organismal zinc status (By similarity).
HMDBP11938
SLC39A5
12q13.3
AK313188
1
5586
Zinc transporter ZIP8
Q9C0K1
Acts as a zinc-influx transporter.
HMDBP11941
SLC39A8
4q22-q24
AF193052
1
5588
Zinc transporter ZIP10
Q9ULF5
May act as a zinc-influx transporter.
HMDBP11943
SLC39A10
2q32.3
CH471063
1
3906
Zinc transporter ZIP14
Q15043
May mediate cellular uptake of nontransferrin-bound iron (By similarity). Broad-scope metal ion transporter with a preference for zinc uptake.
HMDBP08690
SLC39A14
8p21.3
CH471080
1
2356
L-lactate dehydrogenase A chain
P00338
HMDBP03579
LDHA
11p15.4
CR541714
1
1.1.1.27
4308
Probable 2-oxoglutarate dehydrogenase E1 component DHKTD1, mitochondrial
Q96HY7
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3) (By similarity).
HMDBP09099
DHTKD1
10p14
AC073160
1
1.2.4.2
5151
3
916
Fructose-bisphosphate aldolase A
P04075
Plays a key role in glycolysis and gluconeogenesis. In addition, may also function as scaffolding protein (By similarity).
HMDBP00978
ALDOA
16p11.2
BC010660
1
4.1.2.13
1028
8
1791
2
5957
147
578
Hexokinase-2
1
PW_P000578
619
207
1
495
Glucose-6-phosphate isomerase
1
PW_P000495
519
751
2
285
6-phosphofructokinase, liver type
1
PW_P000285
304
706
4
128
423
1
723
Fructose-bisphosphate aldolase B
1
PW_P000723
817
918
291
Glyceraldehyde-3-phosphate dehydrogenase
1
PW_P000291
310
659
4
969
Phosphoglycerate kinase 1
1
PW_P000969
1095
1417
1
588
Phosphoglycerate mutase 2
1
PW_P000588
632
261
1
589
Alpha-enolase
1
PW_P000589
633
1021
1
279
423
1
471
Pyruvate kinase PKLR
1
PW_P000471
494
712
4
225
423
1
226
457
1
5
Pyruvate carboxylase, mitochondrial
1
PW_P000005
6
19
4
5
20
1
6
1027
4
8
4
61
Pyruvate dehydrogenase complex
1
PW_P000061
68
44
60
69
12
60
70
53
60
71
52
24
34
1060
1
35
769
1
36
964
24
236
4
57
Citrate synthase, mitochondrial
1
PW_P000057
60
41
2
218
7
210
L-lactate dehydrogenase
1
PW_P000210
228
2356
1
58
Aconitate hydratase, mitochondrial
1
PW_P000058
61
688
1
460
40711
1
221
4
59
Isocitrate dehydrogenase
1
PW_P000059
62
842
2
63
840
1
64
843
1
30
423
4
225
4
60
Oxoglutarate dehydrogenase complex
1
PW_P000060
65
4308
1
66
882
1
67
52
2
31
1060
1
32
769
1
33
964
2
232
4
62
Succinyl-CoA ligase
1
PW_P000062
72
832
1
73
834
1
237
4
64
Succinate dehydrogenase
1
PW_P000064
75
145
1
76
188
1
77
116
1
78
174
1
38
964
1
423
40558
1
243
17
66
Fumarate hydratase, mitochondrial
1
PW_P000066
80
806
4
261
4
473
Malate dehydrogenase, cytoplasmic
1
PW_P000473
496
805
1
32
Glutamate dehydrogenase 1, mitochondrial
1
PW_P000032
33
658
6
125
4
36
Glutaminase liver isoform, mitochondrial
1
PW_P000036
37
639
1
131
13
1132
Cytoplasmic aconitate hydratase
1
PW_P001132
1294
689
1
469
40711
1
1133
Isocitrate dehydrogenase [NADP] cytoplasmic
1
PW_P001133
1295
841
2
470
423
1
398
Solute carrier family 2, facilitated glucose transporter member 2
1
PW_P000398
420
2449
1
303
Mitochondrial pyruvate carrier
1
PW_P000303
322
5479
1
1097
17
1130
Monocarboxylate transporter
1
PW_P001130
1292
1045
1
748
Neutral amino acid transporter B(0)
1
PW_P000748
843
1700
1
618
Mitochondrial citrate transport protein
1
PW_P000618
662
5711
2430
17
1134
Pyruvate kinase PKM
1
PW_P001134
1296
710
2
846
D-3-phosphoglycerate dehydrogenase
1
PW_P000846
971
865
1
847
Phosphoserine aminotransferase
1
PW_P000847
972
796
1
355
1148
1
848
Phosphoserine phosphatase
1
PW_P000848
973
830
1
356
423
1
193
Serine hydroxymethyltransferase, cytosolic
1
PW_P000193
211
739
4
88
1148
1
844
Glycine N-methyltransferase
1
PW_P000844
969
395
1
4784
Zinc Transporter
1
PW_P004784
11977
5579
11978
5580
11979
5581
11980
5582
11981
5583
11982
5586
11983
5588
11984
3906
287
Fructose-bisphosphate aldolase A
1
PW_P000287
306
916
4
1231
false
PW_R001231
Right
4695
77
1
Compound
4696
414
1
Compound
4697
1083
1
Compound
4698
1034
1
Compound
936
578
2.7.1.1
1057
false
PW_R001057
Both
4081
79
1
Compound
4082
1083
1
Compound
713
495
5.3.1.9
805
false
PW_R000805
Right
3266
79
1
Compound
3267
414
1
Compound
3268
833
1
Compound
3269
1034
1
Compound
342
285
2.7.1.11
807
false
PW_R000807
Both
3274
833
1
Compound
3275
1134
1
Compound
3276
869
1
Compound
344
287
4.1.2.13
1315
723
4.1.2.13
812
false
PW_R000812
Both
3290
869
1
Compound
3291
721
1
Compound
3292
1441
1
Compound
3293
983
1
Compound
3294
1144
1
Compound
349
291
1241
false
PW_R001241
Right
4756
983
1
Compound
4757
1034
1
Compound
4758
644
1
Compound
4759
414
1
Compound
953
969
2.7.2.3
1246
false
PW_R001246
Both
4780
644
1
Compound
4781
1870
1
Compound
958
588
243
false
PW_R000243
Both
1044
1870
1
Compound
1045
180
1
Compound
1046
1420
1
Compound
960
589
4.2.1.11
365
false
PW_R000365
Both
1513
414
1
Compound
1514
164
1
Compound
1515
1034
1
Compound
1516
180
1
Compound
659
471
2.7.1.40
4
false
PW_R000004
Right
15
414
1
Compound
16
164
1
Compound
17
463
1
Compound
18
1034
1
Compound
19
1104
1
Compound
20
148
1
Compound
4
5
6.4.1.1
594
false
PW_R000594
Right
2500
164
1
Compound
2501
1099
1
Compound
2502
721
1
Compound
2503
940
1
Compound
2504
1316
1
Compound
2505
1144
1
Compound
69
61
1.2.4.1
590
false
PW_R000590
Right
2476
940
1
Compound
2477
1420
1
Compound
2478
148
1
Compound
2479
63
1
Compound
2480
1099
1
Compound
62
57
2.3.3.1
374
false
PW_R000374
Both
1549
122
1
Compound
1550
721
1
Compound
1551
164
1
Compound
1552
1144
1
Compound
1553
40034
1
Compound
658
210
1.1.1.27
88
false
PW_R000088
Right
348
63
1
Compound
349
125
1
Compound
2237
58
4.2.1.3
2241
1132
4.2.1.3
332
false
PW_R000332
Right
1380
125
1
Compound
1381
721
1
Compound
1382
134
1
Compound
1383
1316
1
Compound
1384
1144
1
Compound
1385
40034
1
Compound
70
59
1.1.1.41
592
false
PW_R000592
Right
2487
134
1
Compound
2488
721
1
Compound
2489
1099
1
Compound
2490
808
1
Compound
2491
1144
1
Compound
2492
40034
1
Compound
2493
1316
1
Compound
67
60
1.2.4.2
593
false
PW_R000593
Both
2494
808
1
Compound
2495
1104
1
Compound
2496
936
1
Compound
2497
174
1
Compound
2498
1099
1
Compound
2499
986
1
Compound
68
62
233
false
PW_R000233
Both
1010
174
1
Compound
1011
846
1
Compound
2512
964
1
Compound
1012
88
1
Compound
1013
1006
1
Compound
2513
932
1
Compound
75
64
1.3.5.1
269
false
PW_R000269
Both
1145
101
1
Compound
1146
88
1
Compound
1147
1420
1
Compound
78
66
4.2.1.2
390
false
PW_R000390
Both
1605
101
1
Compound
1606
721
1
Compound
1607
148
1
Compound
1608
1144
1
Compound
1609
40034
1
Compound
79
473
38
false
PW_R000038
Right
136
95
1
Compound
137
1420
1
Compound
138
721
1
Compound
139
134
1
Compound
140
35
1
Compound
141
1144
1
Compound
38
32
1.4.1.3
43
false
PW_R000043
Right
162
500
1
Compound
163
1420
1
Compound
164
95
1
Compound
165
35
1
Compound
43
36
3.5.1.2
2338
false
PW_R002338
Right
9042
125
1
Compound
9043
143
1
Compound
9044
134
1
Compound
9045
146
1
Compound
9046
1316
1
Compound
2242
1133
1.1.1.42
1785
false
PW_R001785
Both
6682
644
1
Compound
6683
721
1
Compound
6684
810
1
Compound
6685
1144
1
Compound
1522
846
1.1.1.95
1787
false
PW_R001787
Both
6688
810
1
Compound
6689
95
1
Compound
6690
186
1
Compound
6691
134
1
Compound
1523
847
2.6.1.52
1788
false
PW_R001788
Right
6692
186
1
Compound
6693
1420
1
Compound
6694
120
1
Compound
6695
1104
1
Compound
1524
848
3.1.3.3
1791
false
PW_R001791
Both
6705
120
1
Compound
6706
1221
1
Compound
6707
78
1
Compound
6708
1178
1
Compound
6709
1420
1
Compound
1527
193
2.1.2.1
1781
false
PW_R001781
Both
6670
185
1
Compound
6671
749
1
Compound
6672
921
1
Compound
6673
78
1
Compound
1520
844
2.1.1.20
279
PW_T000279
318
77
1
Compound
15
2
Both
227
398
2014-03-19T21:44:31-06:00
2014-03-19T21:44:31-06:00
14
1
PW_T000001
1
164
1
Compound
2
4
Right
6
303
2013-07-08T16:38:23-06:00
2013-07-08T16:38:23-06:00
17
280
PW_T000280
319
122
1
Compound
2
15
Right
228
1130
2014-03-20T00:32:24-06:00
2014-03-20T00:32:24-06:00
14
281
PW_T000281
320
500
1
Compound
2
4
Right
139
PW_T000139
161
500
1
Compound
15
8
Right
101
748
2013-09-05T02:17:20-06:00
2013-09-05T02:17:20-06:00
14
72
PW_T000072
82
63
1
Compound
2
4
Left
36
618
2013-08-16T13:09:33-06:00
2013-08-16T13:09:33-06:00
17
568
PW_T000568
714
1005
1
Compound
15
166
Right
476
4784
2016-03-29T16:46:57-06:00
2016-03-29T16:46:57-06:00
14
82239
77
2
81
false
675
765
10
200
190
82240
414
2
42
false
850
1015
10
50
30
82241
1083
2
81
false
675
1240
10
200
190
82242
1034
2
43
false
855
1175
10
50
30
82243
79
2
81
false
675
1640
10
200
190
82244
414
2
42
false
660
1860
10
50
30
82245
833
2
81
false
675
2090
10
200
190
82246
1034
2
43
false
660
2020
10
50
30
82247
423
2
9
false
790
1915
10
100
25
82248
1134
2
81
true
700
2460
10
200
190
82249
869
2
81
false
675
2510
10
200
190
82250
721
2
59
false
851
2715
10
50
30
82251
1441
2
46
true
629
2538
10
44
43
82252
983
2
81
false
677
2935
10
200
190
82253
1144
2
60
false
867
2875
10
50
30
82254
1034
2
43
false
862
3140
10
50
30
82255
644
2
3
false
727
3345
10
100
120
82256
414
2
42
false
862
3300
10
50
30
82257
1870
2
3
false
727
3665
10
100
110
82258
180
2
81
false
677
4010
10
200
190
82259
1420
2
49
false
837
3925
10
78
78
82260
423
2
9
false
792
3885
10
100
25
82261
414
2
42
false
1162
4010
10
50
30
82262
164
2
81
false
1277
4010
10
200
190
82263
1034
2
43
false
937
4010
10
50
30
82264
423
2
9
false
1082
4135
10
100
25
82265
457
2
9
false
962
4135
10
100
25
82266
414
4
42
false
2047
3692
10
50
30
82267
164
4
3
false
1832
4055
10
100
100
82268
463
4
47
false
1898
3748
10
78
78
82269
1034
4
43
false
2267
3692
10
50
30
82270
1104
4
46
false
2295
3855
10
44
43
82271
148
4
3
false
2467
3736
10
100
110
82272
20
4
9
false
2072
3812
10
100
25
82273
1027
4
9
false
2192
3812
10
100
25
82274
1099
4
85
false
1967
4175
10
50
30
82275
721
4
59
false
1972
4005
10
50
30
82276
940
4
81
false
2322
4013
10
200
190
82277
1316
4
52
false
2208
4169
10
78
78
82278
1144
4
60
false
2212
4006
10
50
30
82279
1060
4
9
false
2052
4020
10
100
35
82280
769
4
9
false
2007
4140
10
100
25
82281
964
4
9
false
2127
4140
10
100
25
82282
1420
4
49
false
2527
4203
10
78
78
82283
63
4
3
false
2867
4058
10
100
100
82284
1099
4
85
false
2772
3978
10
50
30
82285
122
2
3
false
1329
4530
19
100
100
82286
721
2
59
false
1219
4380
10
50
30
82287
1144
2
60
false
1255
4240
10
50
30
82288
40034
2
55
true
1183
4176
10
78
78
82289
125
4
3
false
3297
4058
10
100
100
82290
40711
4
9
false
3082
4133
10
100
25
82291
721
4
59
false
3442
4008
10
50
30
82292
134
4
3
false
3847
4054
10
100
110
82293
1316
4
52
false
3728
4185
10
78
78
82294
1144
4
60
false
3722
4007
10
50
30
82295
40034
4
55
true
3953
4248
10
78
78
82296
423
4
9
false
3562
4168
10
100
25
82297
721
4
59
false
3777
3939
10
50
30
82298
1099
4
85
false
3997
3944
10
50
30
82299
808
4
81
false
3798
3394
10
200
190
82300
1144
4
60
false
3768
3689
10
50
30
82301
40034
4
55
true
4069
3585
10
78
78
82302
1316
4
52
false
3962
3655
10
78
78
82303
1060
4
9
false
3774
3866
10
100
35
82304
769
4
9
false
3929
3771
10
100
25
82305
964
4
9
false
3759
3776
10
100
25
82306
1104
4
46
false
3726
3574
10
44
43
82307
936
4
53
false
3718
3360
10
50
30
82308
174
4
3
false
3378
3438
10
100
100
82309
1099
4
85
false
3488
3583
10
50
30
82310
986
4
54
false
3498
3363
10
50
30
82311
846
4
139
false
3263
3373
10
50
30
82312
964
4
137
false
3368
3333
10
50
30
82313
88
4
3
false
2888
3438
10
100
100
82314
40098
4
140
false
3043
3373
10
50
30
82315
932
4
138
false
2948
3328
10
50
30
82316
964
4
9
true
2888
3338
10
100
25
82317
40558
4
9
true
3028
3328
10
100
25
82318
101
4
3
false
2468
3438
10
100
100
82319
1420
4
49
false
2803
3348
10
78
78
82320
721
4
59
false
2398
3548
10
50
30
82321
1144
4
60
false
2394
3691
10
50
30
82322
40034
4
55
true
2370
3752
10
78
78
82323
95
4
3
false
3846
4364
10
100
110
82324
1420
4
49
false
3971
4319
10
78
78
82325
721
4
59
true
3856
4424
10
50
30
82326
35
4
63
false
3965
4150
10
78
78
82327
1144
4
60
true
3822
4204
10
50
30
82328
500
4
3
false
3406
4368
10
100
100
82329
1420
4
49
false
3526
4288
10
78
78
82330
35
4
63
false
3742
4297
10
78
78
82349
63
2
3
false
2867
4683
10
100
100
82350
125
2
3
false
2432
4683
10
100
100
82351
40711
2
9
false
2652
4753
10
100
25
82352
143
2
61
false
2327
4793
10
50
30
82353
134
2
3
false
1882
4681
10
100
110
82354
146
2
62
false
2067
4796
10
50
30
82355
1316
2
52
false
1978
4802
10
78
78
82356
423
2
9
false
2177
4688
10
100
25
82357
77
15
3
false
720
355
10
100
100
82358
122
15
3
false
1329
5115
10
100
100
82359
500
8
3
false
3406
4683
10
100
100
82360
500
15
3
false
3406
5098
10
100
100
82361
721
59
false
862
3455
10
50
30
82362
810
3
false
1287
3347
10
100
110
82363
1144
60
false
1177
3462
10
50
30
82364
95
156
false
1137
3222
10
100
110
82365
186
3
false
1287
2677
10
100
100
82366
134
156
false
1137
2822
10
100
110
82367
1148
9
false
1192
3067
10
100
35
82368
1420
49
false
1149
2593
10
78
78
82369
120
3
false
1286
2182
10
100
100
82370
1104
46
false
1166
2310
10
44
43
82371
423
9
false
1187
2472
10
100
25
82372
1221
156
false
1341
2032
10
100
110
82373
78
81
false
1981
2140
10
200
190
82374
1178
3
false
1836
2040
10
100
110
82375
1420
49
false
1842
2340
10
78
78
82376
1148
9
false
1606
2184
10
100
35
82377
185
81
false
2871
2142
10
200
190
82378
749
3
false
2661
2032
10
100
110
82379
921
156
false
2276
2035
10
100
110
82380
1005
15
81
false
4648
2135
10
200
190
82381
1005
166
81
false
3858
2135
10
200
190
38966
207
2
2
false
700
1077
8
150
70
38967
751
2
6
false
695
1495
8
160
80
38968
706
2
6
false
695
1915
8
160
80
38969
918
2
8
false
705
2350
8
140
85
38970
659
2
8
false
706
2770
8
140
85
38971
1417
2
2
false
702
3200
8
150
70
38972
261
2
6
false
697
3522
8
160
80
38973
1021
2
6
false
697
3830
8
160
80
38974
712
2
8
false
1002
4065
8
140
85
38975
19
4
8
false
2112
3747
8
140
85
38976
44
4
135
false
2032
4025
8
175
155
38977
12
4
2
true
2012
4085
8
150
70
38978
53
4
2
true
2007
4175
8
150
70
38979
52
4
2
true
2032
4265
8
150
70
38980
41
4
2
false
2617
4073
8
150
70
38981
836
2
8
false
1309
4285
8
140
85
38982
688
4
2
false
3057
4073
8
150
70
38983
842
4
6
false
3522
4038
8
160
80
38984
840
4
97
false
3477
4108
8
150
70
38985
843
4
98
false
3592
4108
8
150
70
38986
430
4
135
false
3809
3751
8
175
155
38987
882
4
2
true
3929
3752
8
150
70
38988
52
4
2
true
3929
3751
8
150
70
38989
832
4
105
false
3553
3476
8
150
70
38990
834
4
100
false
3553
3431
8
150
70
38991
145
4
107
false
3088
3418
8
150
70
38992
188
4
106
false
3118
3433
8
150
70
38993
116
4
105
false
3088
3438
8
150
70
38994
174
4
100
false
3103
3453
8
150
70
38995
806
4
8
false
2653
3448
8
140
85
38996
805
4
2
false
2443
3604
8
150
70
38997
658
4
17
false
3806
4229
8
180
85
38998
639
4
2
false
3601
4383
8
150
70
39006
689
2
2
false
2627
4698
8
150
70
39007
841
2
6
false
2147
4693
8
160
80
39008
2449
76
false
700
560
8
150
70
39009
5479
76
false
1632
4070
8
150
70
39010
1045
76
false
1304
4885
8
150
70
39011
1700
76
false
3381
4878
8
150
70
39012
5711
76
false
2842
4473
8
150
70
39013
710
2
113
false
992
3710
8
160
80
39014
865
2
false
967
3367
8
150
70
39015
796
2
false
1262
3042
8
150
70
39016
830
2
false
1262
2452
8
150
70
39017
739
8
false
1586
2194
8
140
85
39018
395
2
false
2451
2200
8
150
70
39019
5579
76
false
4313
2005
8
150
70
39020
5580
76
false
4308
2060
8
150
70
39021
5581
76
false
4313
2125
8
150
70
39022
5582
76
false
4308
2180
8
150
70
39023
5583
76
false
4313
2245
8
150
70
39024
5586
76
false
4308
2300
8
150
70
39025
5588
76
false
4308
2360
8
150
70
39026
3906
76
false
4308
2195
8
150
70
31727
578
2267
2
38287
38966
31728
495
2267
2
38288
38967
31729
285
2267
2
38289
38968
4457
82247
118015
Cofactor
31730
723
2267
2
38290
38969
31731
291
2267
2
38291
38970
31732
969
2267
2
38292
38971
31733
588
2267
2
38293
38972
31734
589
2267
2
38294
38973
4458
82260
118033
Cofactor
31735
471
2267
2
38295
38974
4459
82264
118038
Cofactor
4460
82265
118039
Cofactor
31736
5
2267
4
38296
38975
4461
82272
118046
Cofactor
4462
82273
118047
Cofactor
31737
61
2267
4
38297
38976
38298
38977
38299
38978
38300
38979
4463
82279
118054
Cofactor
4464
82280
118055
Cofactor
4465
82281
118056
Cofactor
31738
57
2267
4
38301
38980
31739
210
2267
2
38302
38981
31740
58
2267
4
38303
38982
4466
82290
118069
Cofactor
31741
59
2267
4
38304
38983
38305
38984
38306
38985
4467
82296
118076
Cofactor
31742
60
2267
4
38307
38986
38308
38987
38309
38988
4468
82303
118084
Cofactor
4469
82304
118085
Cofactor
4470
82305
118086
Cofactor
31743
62
2267
4
38310
38989
38311
38990
31744
64
2267
4
38312
38991
38313
38992
38314
38993
38315
38994
4471
82316
118099
Cofactor
4472
82317
118100
Cofactor
31745
66
2267
4
38316
38995
31746
473
2267
4
38317
38996
31747
32
2267
4
38318
38997
31748
36
2267
4
38319
38998
31756
1132
2267
2
38327
39006
4475
82351
118149
Cofactor
31757
1133
2267
2
38328
39007
4476
82356
118155
Cofactor
31758
398
2267
38329
39008
31759
303
2267
38330
39009
31760
1130
2267
38331
39010
31761
748
2267
38332
39011
31762
618
2267
38333
39012
31763
1134
2267
2
38334
39013
31764
846
2267
38335
39014
31765
847
2267
38336
39015
4477
82367
118178
Cofactor
31766
848
2267
38337
39016
4478
82371
118183
Cofactor
31767
193
2267
38338
39017
4479
82376
118189
Cofactor
31768
844
2267
38339
39018
31769
4784
2267
38340
39019
38341
39020
38342
39021
38343
39022
38344
39023
38345
39024
38346
39025
38347
39026
118005
M775 955 C775 985 775 1047.5 775 1077.5
5
false
18
118006
M850 1030 C815 1030 775 1047 775 1077
5
false
18
118007
M775 1240 C775 1210 775 1177 775 1147
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118008
M855 1190 C827 1190 775 1177 775 1147
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118009
M775 1640 C775 1610 775 1605 775 1575
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118010
M775 1430 C775 1460 775 1465 775 1495
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118011
M775 1830 C775 1860 775 1885 775 1915
5
false
18
118012
M710 1875 C740 1875 775 1885 775 1915
5
false
18
118013
M775 2090 C775 2060 775 2025 775 1995
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118014
M710 2035 C737 2035 775 2025 775 1995
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118015
M795 1965 L795 2015 L845 1965 z
10
true
18
118016
M775 2280 C775 2310 775 2320 775 2350
5
false
18
false
false
118017
M800 2460 C800 2430 775 2465 775 2435
5
true
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118018
M775 2510 C775 2480 775 2465 775 2435
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118019
M775 2700 C775 2730 776 2740 776 2770
5
false
18
false
false
118020
M851 2730 C820 2730 776 2740 776 2770
5
false
18
false
false
118021
M651 2581.5 C651 2611.5 776 2740 776 2770
5
true
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118022
M777 2935 C777 2905 776 2885 776 2855
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118023
M867 2890 C843 2890 776 2885 776 2855
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118024
M777 3125 C777 3155 777 3170 777 3200
5
false
18
118025
M862 3155 C827 3155 777 3170 777 3200
5
false
18
118026
M777 3345 C777 3315 777 3300 777 3270
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118027
M862 3315 C833 3315 777 3300 777 3270
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118028
M777 3465 C777 3495 777 3492 777 3522
5
false
18
false
false
118029
M777 3665 C777 3635 777 3632 777 3602
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118030
M777 3775 C777 3805 777 3800 777 3830
5
false
18
false
false
118031
M777 4010 C777 3980 777 3940 777 3910
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118032
M837 3964 C804 3964 777 3940 777 3910
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118033
M907 4000 L907 4050 L957 4000 z
10
true
18
118034
M1187 4040 C1187 4068 1172 4105 1142 4105
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118035
M1277 4105 C1247 4105 1172 4105 1142 4105
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118036
M962 4040 C962 4068 972 4105 1002 4105
5
false
18
false
false
118037
M877 4105 C907 4105 972 4105 1002 4105
5
false
18
false
false
118038
M982 4120 L982 4170 L1032 4120 z
10
true
18
118039
M982 4120 L982 4170 L1032 4120 z
10
true
18
118040
M2072 3722 C2070 3752 2082 3787 2112 3787
5
false
18
118041
M1882 4055 C1882 4000 1992 3788 2112 3787
5
false
18
118042
M1976 3787 C2010 3787 2082 3787 2112 3787
5
false
18
118043
M2292 3722 C2290 3751 2282 3787 2252 3787
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118044
M2317 3855 C2317 3823 2300 3787 2252 3787
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118045
M2467 3791 C2412 3791 2312 3787 2252 3787
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118046
M2157 4132 L2157 4182 L2207 4132 z
10
true
18
118047
M2157 4132 L2157 4182 L2207 4132 z
10
true
18
118048
M1932 4105 C1979 4105 1963 4105 2037 4105
5
false
18
118049
M1992 4175 C1992 4142 2007 4105 2037 4105
5
false
18
118050
M1997 4035 C1997 4066 2007 4105 2037 4105
5
false
18
118051
M2322 4108 C2292 4108 2237 4105 2207 4105
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118052
M2247 4169 C2247 4135 2237 4105 2207 4105
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118053
M2237 4036 C2237 4069 2237 4105 2207 4105
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118054
M2157 4180 L2157 4230 L2207 4180 z
10
true
18
118055
M2157 4180 L2157 4230 L2207 4180 z
10
true
18
118056
M2157 4180 L2157 4230 L2207 4180 z
10
true
18
118057
M2522 4108 C2577 4108 2557 4108 2617 4108
5
false
18
118058
M2566 4203 C2566 4164 2587 4108 2617 4108
5
false
18
118059
M2517 3846 C2517 3895 2587 4108 2617 4108
5
false
18
118060
M2867 4108 C2837 4108 2797 4108 2767 4108
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118061
M2797 4008 C2797 4055 2797 4108 2767 4108
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118062
M1379 4530 C1379 4500 1379 4400 1379 4370
149
false
10
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118063
M1269 4395 C1315 4395 1379 4400 1379 4370
149
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118064
M1377 4200 C1377 4230 1379 4255 1379 4285
149
false
18
false
false
118065
M1305 4255 C1353 4255 1379 4255 1379 4285
149
false
18
false
false
118066
M1222 4254 C1222 4284 1379 4255 1379 4285
149
true
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118067
M2967 4108 C2997 4108 3027 4108 3057 4108
5
false
18
118068
M3297 4108 C3267 4108 3237 4108 3207 4108
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118069
M150 650 L150 700 L200 650 z
10
true
18
118070
M3397 4108 C3427 4108 3522 4108 3552 4108
5
false
18
118071
M3467 4038 C3467 4072 3522 4108 3552 4108
5
false
18
118072
M3847 4109 C3817 4109 3697 4108 3667 4108
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118073
M3767 4185 C3767 4124 3737 4108 3667 4108
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118074
M3747 4037 C3747 4065 3697 4108 3667 4108
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118075
M3953 4287 C3923 4287 3772 4143 3742 4143
5
true
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118076
M3802 4223 L3802 4273 L3852 4223 z
10
true
18
118077
M3897 4054 C3897 4024 3899 3936 3899 3906
5
false
18
118078
M3827 3954 C3858 3954 3899 3936 3899 3906
5
false
18
118079
M3997 3959 C3963 3959 3899 3936 3899 3906
5
false
18
118080
M3898 3584 C3898 3614 3899 3728 3899 3758
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118081
M3818 3704 C3866 3704 3899 3728 3899 3758
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118082
M4108 3663 C4108 3693 3899 3728 3899 3758
5
true
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118083
M3962 3694 C3924 3694 3899 3728 3899 3758
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118084
M4079.5 3902 L4079.5 3952 L4129.5 3902 z
10
true
18
118085
M4079.5 3902 L4079.5 3952 L4129.5 3902 z
10
true
18
118086
M4079.5 3902 L4079.5 3952 L4129.5 3902 z
10
true
18
118087
M3798 3489 C3768 3489 3716 3489 3686 3489
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118088
M3748 3574 C3748 3535 3719 3490 3689 3490
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118089
M3743 3390 C3743 3424 3720 3489 3690 3489
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118090
M3478 3488 C3508 3488 3538 3488 3568 3488
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118091
M3513 3583 C3513 3541 3536 3488 3566 3488
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118092
M3523 3393 C3523 3427 3542 3488 3572 3488
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118093
M3378 3488 C3348 3488 3283 3488 3253 3488
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118094
M3288 3403 C3288 3439 3283 3488 3253 3488
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118095
M3393 3363 C3393 3451 3340 3488 3253 3488
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118096
M2988 3488 C3018 3488 3073 3488 3103 3488
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118097
M3068 3403 C3068 3446 3073 3488 3103 3488
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118098
M2973 3358 C2973 3423 3030 3488 3103 3488
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118099
M3148 3563 L3148 3613 L3198 3563 z
10
true
18
118100
M3148 3563 L3148 3613 L3198 3563 z
10
true
18
118101
M2568 3488 C2598 3488 2623 3488 2653 3488
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118102
M2888 3488 C2858 3488 2823 3488 2793 3488
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118103
M2842 3426 C2842 3460 2823 3488 2793 3488
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118104
M2518 3538 C2518 3568 2518 3574.5 2518 3604.5
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118105
M2448 3563 C2485 3563 2518 3574 2518 3604
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118106
M2517 3736 C2517 3706 2518 3704.5 2518 3674.5
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118107
M2444 3706 C2471 3706 2518 3704 2518 3674
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118108
M2409 3752 C2409 3722 2518 3704.5 2518 3674.5
5
true
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118109
M3896 4364 C3896 4334 3896 4344 3896 4314
5
false
18
118110
M3971 4358 C3938 4358 3896 4344 3896 4314
5
false
18
118111
M3881 4424 C3881 4394 3896 4342 3896 4312
5
true
18
118112
M3897 4164 C3897 4194 3896 4199 3896 4229
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118113
M3965 4189 C3929 4189 3896 4199 3896 4229
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118114
M3847 4234 C3847 4264 3896 4199 3896 4229
5
true
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118115
M3506 4418 C3536 4418 3571 4418 3601 4418
5
false
18
118116
M3565 4366 C3565 4399 3571 4418 3601 4418
5
false
18
118117
M3846 4419 C3816 4419 3781 4418 3751 4418
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118118
M3781 4375 C3781 4406 3781 4418 3751 4418
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118147
M2867 4733 C2837 4733 2807 4733 2777 4733
5
false
18
118148
M2532 4733 C2562 4733 2597 4733 2627 4733
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118149
M2792 4888 L2792 4938 L2842 4888 z
10
true
18
118150
M2432 4733 C2402 4733 2337 4733 2307 4733
5
false
18
118151
M2352 4793 C2352 4764 2337 4733 2307 4733
5
false
18
118152
M1982 4736 C2012 4736 2117 4733 2147 4733
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118153
M2092 4796 C2092 4763 2117 4733 2147 4733
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118154
M2017 4802 C2044 4751 2117 4733 2147 4733
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
118155
M2357 4848 L2357 4898 L2407 4848 z
10
true
18
118156
M775 470 C775 500 775 530 775 560
83
false
18
118157
M775 765 C775 735 775 660 775 630
83
false
18
true
M 87.5 347.0096189432334 L 95 360 L 102.5 347.0096189432334
false
118158
M1477 4105 C1507 4105 1602 4105 1632 4105
83
false
18
false
false
118159
M1832 4105 C1802 4105 1812 4105 1782 4105
83
false
18
false
false
118160
M1379 4630 C1379 4660 1379 4855 1379 4885
83
false
18
118161
M1379 5115 C1379 5085 1379 4985 1379 4955
83
false
18
true
M 1326.5 4292.009618943233 L 1334 4305 L 1341.5 4292.009618943233
false
118162
M3456 4683 C3456 4653 3432 4546 3456 4563
83
true
18
118163
M3456 4468 C3456 4498 3456 4641 3456 4683
83
false
18
true
M 3463.5 4000.9903810567666 L 3456 3988 L 3448.5 4000.9903810567666
false
118164
M3456 5098 C3456 5068 3456 4978 3456 4948
83
false
18
118165
M3456 4783 C3456 4813 3456 4848 3456 4878
83
false
18
true
M 3463.5 4230.990381056767 L 3456 4218 L 3448.5 4230.990381056767
false
118166
M2917 4683 C2917 4653 2917 4573 2917 4543
83
false
18
true
M 2909.5 3865.0096189432334 L 2917 3878 L 2924.5 3865.0096189432334
false
118167
M2917 4158 C2917 4188 2917 4443 2917 4473
83
false
18
true
M 2924.5 3670.9903810567666 L 2917 3658 L 2909.5 3670.9903810567666
false
118168
M1072 3725 C1072 3695 1082 4376 1082 4346
148
true
18
118169
M1072 4065 C1072 3972 1072 3898 1072 3790
148
false
18
false
true
M 1057 3560 L 1072 3560 L 1087 3560
118170
M827 3405 C857 3405 937 3402 967 3402
5
false
18
true
M 761.9468550441649 2728.261556296296 L 747 2727 L 753.3808877211858 2740.575134323078
false
118171
M912 3470 C915 3405 937 3402 967 3402
5
false
18
true
M 761.9468550441649 2728.261556296296 L 747 2727 L 753.3808877211858 2740.575134323078
false
118172
M1287 3402 C1257 3402 1147 3402 1117 3402
5
false
18
true
M 761.9468550441649 2728.261556296296 L 747 2727 L 753.3808877211858 2740.575134323078
false
118173
M1177 3477 C1174 3402 1147 3402 1117 3402
5
false
18
true
M 761.9468550441649 2728.261556296296 L 747 2727 L 753.3808877211858 2740.575134323078
false
118174
M1337 3347 C1337 3317 1337 3142 1337 3112
5
false
18
true
M 761.9468550441649 2599.261556296296 L 747 2598 L 753.3808877211858 2611.575134323078
false
118175
M1187 3222 C1337 3219 1337 3142 1337 3112
5
false
18
true
M 761.9468550441649 2599.261556296296 L 747 2598 L 753.3808877211858 2611.575134323078
false
118176
M1337 2777 C1337 2807 1337 3012 1337 3042
5
false
18
true
M 761.9468550441649 2599.261556296296 L 747 2598 L 753.3808877211858 2611.575134323078
false
118177
M1187 2932 C1336 2941 1337 3012 1337 3042
5
false
18
true
M 761.9468550441649 2599.261556296296 L 747 2598 L 753.3808877211858 2611.575134323078
false
118178
M1222 3172 L1222 3222 L1272 3172 z
10
true
18
118179
M1337 2677 C1337 2647 1337 2552 1337 2522
5
false
18
118180
M1188 2593 C1330 2588 1337 2552 1337 2522
5
false
18
118181
M1336 2282 C1336 2312 1337 2422 1337 2452
5
false
18
true
M 915.9468550441649 2083.261556296296 L 901 2082 L 907.3808877211858 2095.575134323078
false
118182
M1188 2353 C1335 2355 1337 2422 1337 2452
5
false
18
true
M 915.9468550441649 2083.261556296296 L 901 2082 L 907.3808877211858 2095.575134323078
false
118183
M1227.5 2512 L1227.5 2562 L1277.5 2512 z
10
true
18
118184
M1386 2232 C1416 2232 1556 2234 1586 2234
5
false
18
true
M 915.9468550441649 1560.261556296296 L 901 1559 L 907.3808877211858 1572.5751343230784
false
118185
M1441 2087 C1445 2211 1556 2234 1586 2234
5
false
18
true
M 915.9468550441649 1560.261556296296 L 901 1559 L 907.3808877211858 1572.5751343230784
false
118186
M1981 2235 C1951 2235 1756 2234 1726 2234
5
false
18
true
M 915.9468550441649 1560.261556296296 L 901 1559 L 907.3808877211858 1572.5751343230784
false
118187
M1836 2095 C1831 2238 1756 2234 1726 2234
5
false
18
true
M 915.9468550441649 1560.261556296296 L 901 1559 L 907.3808877211858 1572.5751343230784
false
118188
M1842 2379 C1841 2235 1756 2234 1726 2234
5
false
18
true
M 915.9468550441649 1560.261556296296 L 901 1559 L 907.3808877211858 1572.5751343230784
false
118189
M1476 2109.5 L1476 2159.5 L1526 2109.5 z
10
true
18
118190
M2871 2237 C2841 2237 2631 2235 2601 2235
5
false
18
true
M 1645.9468550441647 1263.261556296296 L 1631 1262 L 1637.380887721186 1275.5751343230784
false
118191
M2661 2087 C2659 2232 2631 2235 2601 2235
5
false
18
true
M 1645.9468550441647 1263.261556296296 L 1631 1262 L 1637.380887721186 1275.5751343230784
false
118192
M2376 2090 C2377 2237 2421 2235 2451 2235
5
false
18
true
M 1645.9468550441647 1263.261556296296 L 1631 1262 L 1637.380887721186 1275.5751343230784
false
118193
M2181 2235 C2211 2235 2421 2235 2451 2235
5
false
18
true
M 1645.9468550441647 1263.261556296296 L 1631 1262 L 1637.380887721186 1275.5751343230784
false
118194
M4648 2230 C4618 2230 4488 2230 4458 2230
83
false
18
118195
M4058 2230 C4088 2230 4278 2230 4308 2230
83
false
18
true
M 3863.9468550441647 1423.261556296296 L 3849 1422 L 3855.380887721186 1435.5751343230784
false
24227
2267
1231
2
93408
82239
118005
Left
93409
82240
118006
Left
93410
82241
118007
Right
93411
82242
118008
Right
24004
936
31727
24228
2267
1057
2
93412
82243
118009
Left
93413
82241
118010
Right
24005
713
31728
24229
2267
805
2
93414
82243
118011
Left
93415
82244
118012
Left
93416
82245
118013
Right
93417
82246
118014
Right
24006
342
31729
24230
2267
807
2
93418
82245
118016
Left
93419
82248
118017
Right
93420
82249
118018
Right
24007
1315
31730
24231
2267
812
2
93421
82249
118019
Left
93422
82250
118020
Left
93423
82251
118021
Left
93424
82252
118022
Right
93425
82253
118023
Right
24008
349
31731
24232
2267
1241
2
93426
82252
118024
Left
93427
82254
118025
Left
93428
82255
118026
Right
93429
82256
118027
Right
24009
953
31732
24233
2267
1246
2
93430
82255
118028
Left
93431
82257
118029
Right
24010
958
31733
24234
2267
243
2
93432
82257
118030
Left
93433
82258
118031
Right
93434
82259
118032
Right
24011
960
31734
24235
2267
365
2
93435
82261
118034
Left
93436
82262
118035
Left
93437
82263
118036
Right
93438
82258
118037
Right
24012
659
31735
24236
2267
4
4
93439
82266
118040
Left
93440
82267
118041
Left
93441
82268
118042
Left
93442
82269
118043
Right
93443
82270
118044
Right
93444
82271
118045
Right
24013
4
31736
24237
2267
594
4
93445
82267
118048
Left
93446
82274
118049
Left
93447
82275
118050
Left
93448
82276
118051
Right
93449
82277
118052
Right
93450
82278
118053
Right
24014
69
31737
24238
2267
590
4
93451
82276
118057
Left
93452
82282
118058
Left
93453
82271
118059
Left
93454
82283
118060
Right
93455
82284
118061
Right
24015
62
31738
24239
2267
374
2
93456
82285
118062
Left
93457
82286
118063
Left
93458
82262
118064
Right
93459
82287
118065
Right
93460
82288
118066
Right
24016
658
31739
24240
2267
88
4
93461
82283
118067
Left
93462
82289
118068
Right
24017
2237
31740
24241
2267
332
4
93463
82289
118070
Left
93464
82291
118071
Left
93465
82292
118072
Right
93466
82293
118073
Right
93467
82294
118074
Right
93468
82295
118075
Right
24018
70
31741
24242
2267
592
4
93469
82292
118077
Left
93470
82297
118078
Left
93471
82298
118079
Left
93472
82299
118080
Right
93473
82300
118081
Right
93474
82301
118082
Right
93475
82302
118083
Right
24019
67
31742
24243
2267
593
4
93476
82299
118087
Left
93477
82306
118088
Left
93478
82307
118089
Left
93479
82308
118090
Right
93480
82309
118091
Right
93481
82310
118092
Right
24020
68
31743
24244
2267
233
4
93482
82308
118093
Left
93483
82311
118094
Left
93484
82312
118095
Left
93485
82313
118096
Right
93486
82314
118097
Right
93487
82315
118098
Right
24021
75
31744
24245
2267
269
4
93488
82318
118101
Left
93489
82313
118102
Right
93490
82319
118103
Right
24022
78
31745
24246
2267
390
4
93491
82318
118104
Left
93492
82320
118105
Left
93493
82271
118106
Right
93494
82321
118107
Right
93495
82322
118108
Right
24023
79
31746
24247
2267
38
4
93496
82323
118109
Left
93497
82324
118110
Left
93498
82325
118111
Left
93499
82292
118112
Right
93500
82326
118113
Right
93501
82327
118114
Right
24024
38
31747
24248
2267
43
4
93502
82328
118115
Left
93503
82329
118116
Left
93504
82323
118117
Right
93505
82330
118118
Right
24025
43
31748
24256
2267
88
2
93532
82349
118147
Left
93533
82350
118148
Right
24033
2241
31756
24257
2267
2338
2
93534
82350
118150
Left
93535
82352
118151
Left
93536
82353
118152
Right
93537
82354
118153
Right
93538
82355
118154
Right
24034
2242
31757
24258
2267
1785
93539
82255
118170
Left
93540
82361
118171
Left
93541
82362
118172
Right
93542
82363
118173
Right
24035
1522
31764
24259
2267
1787
93543
82362
118174
Left
93544
82364
118175
Left
93545
82365
118176
Right
93546
82366
118177
Right
24036
1523
31765
24260
2267
1788
93547
82365
118179
Left
93548
82368
118180
Left
93549
82369
118181
Right
93550
82370
118182
Right
24037
1524
31766
24261
2267
1791
93551
82369
118184
Left
93552
82372
118185
Left
93553
82373
118186
Right
93554
82374
118187
Right
93555
82375
118188
Right
24038
1527
31767
24262
2267
1781
93556
82377
118190
Left
93557
82378
118191
Left
93558
82379
118192
Right
93559
82373
118193
Right
24039
1520
31768
1080
279
2267
2615
82357
118156
Left
2616
82239
118157
Right
794
31758
227
1081
1
2267
2617
82262
118158
Left
2618
82267
118159
Right
795
31759
6
1082
280
2267
2619
82285
118160
Left
2620
82358
118161
Right
796
31760
228
1083
281
2267
2621
82359
118162
Left
2622
82328
118163
Right
1084
139
2267
2623
82360
118164
Left
2624
82359
118165
Right
797
31761
101
1085
72
2267
2625
82349
118166
Left
2626
82283
118167
Right
798
31762
36
1086
568
2267
2627
82380
118194
Left
2628
82381
118195
Right
799
31769
476
3321
3785
2267
14
true
1007
4276
16
750
31763
118168
Left
751
31735
118169
Right
1569
13
3020
2645
1.6
1.6
0
2
1
490
240
1570
1217
4468
0.8
0.8
0
13
51
400
274
1571
2710
2045
1.3
1.3
0
2
51
400
274
1572
3692
2038
1.3
1.3
0
2
52
400
274
1573
507
665
1.3
1.3
0
2
51
400
274
4423
M2915 3227 C3019 3227 3046 3308 3046 3352 C3046 3522 3313 3527 3313 3357 C3313 3306 3333 3230 3413 3230 C3572 3230 3787 3230 3953 3230 C4076 3230 4161 3337 4161 3420 C4161 3722 4161 4087 4161 4378 C4161 4478 4060 4514 3980 4514 C3435 4514 2432 4509 1877 4509 C1787 4509 1692 4448 1692 4348 C1692 4058 1692 3659 1692 3372 C1692 3300 1787 3227 1862 3227 C2173 3227 2640 3227 2916 3227
84
false
6
2469.0
1287.0
4424
M1600 3235 C1600 3185 1650 3135 1700 3135 C2449 3135 3423 3135 4172 3135 C4222 3135 4272 3185 4272 3235 C4272 3623 4272 4127 4272 4515 C4272 4565 4222 4615 4172 4615 C3423 4615 2449 4615 1700 4615 C1650 4615 1600 4565 1600 4515 C1600 4127 1600 3623 1600 3235
84
true
6
2672.0
1480.0
4425
M169 701 C169 651 219 601 269 601 C1490 601 3077 601 4298 601 C4348 601 4398 651 4398 701 C4398 1947 4398 3568 4398 4814 C4398 4864 4348 4914 4298 4914 C3077 4914 1490 4914 269 4914 C219 4914 169 4864 169 4814 C169 3568 169 1947 169 701
1
true
6
4229.0
4313.0
2059
15
Lactate shuttle
1060
4875
20
1.0
1.0
160
15
2061
15
Citric Acid Cycle
3050
3680
20
2.5
2.5
160
15
2062
15
Inner Mitochondrial Membrane
2045
3185
20
1.0
1.0
160
15
2063
15
Outer Mitochondrial Membrane
2040
3090
20
1.0
1.0
160
15
2064
15
Mitochondrion
3465
2730
20
1.0
1.0
160
15
2065
15
Cytosol
1245
955
20
1.0
1.0
160
15
2066
15
Glycolysis
205
1420
20
2.8
2.8
160
15
2067
15
Phosphoenolpyruvic acid
314
4033
20
1.9
1.9
160
15
2068
15
Pyruvic acid
1223
3878
20
1.9
1.9
160
15
2069
15
L-Lactic acid
1208
4636
20
1.9
1.9
160
15
2070
15
2-Phospho-D-glyceric acid
380
3644
20
1.9
1.9
160
15
2071
15
3-Phosphoglyceric acid
375
3326
20
1.9
1.9
160
15
2072
15
Glyceric acid 1,3-biphosphate
330
2944
20
1.9
1.9
160
15
2073
15
D-Glyceraldehyde 3-phosphate
340
2529
20
1.9
1.9
160
15
2074
15
Fructose 6-phosphate
287
1634
20
2.2
2.2
160
15
2075
15
Fructose 1,6-bisphosphate
327
2133
20
1.9
1.9
160
15
2076
15
Pyruvate kinase PKLR
890
4146
20
1.9
1.9
160
15
2077
15
L-lactate dehydrogenase
1221
4372
20
1.9
1.9
160
15
2078
15
Pyruvate kinase PKM
911
3589
20
1.9
1.9
160
15
748
3635
2836
1544
3083
4321
4664
4
#FFEBEB
4
2777
1581