773
Pathway
TCA Cycle (Ubiquinol-9)
The citric acid cycle (also named tricarboxylic acid (TCA) cycle or the Krebs cycle), is a collection of 9 enzyme-catalyzed chemical reactions that occur in all living cells undergoing aerobic respiration. The citric acid cycle itself was officially identified in 1937 by Hans Adolf Krebs, who received the Nobel Prize for this discovery in 1953. In eukaryotes, the citric acid cycle occurs in the mitochondria. In prokaryotes, the TCA cycle occurs in the cytoplasm. The TCA cycle starts with acetyl-CoA, which is the “fuel†for the entire cycle. This important molecule comes from the breakdown of glycogen (a stored form of glucose), fats, and many amino acids. At beginning, acetyl-CoA first transfers its 2-carbon acetyl group to the 4-carbon acceptor compound called oxaloacetate to form the 6-carbon compound (citrate) for which the cycle is named. The resulting citrate will have numbers of chemical transformations, whereby it loses one carboxyl group (leading to the 5-carbon compound called alpha-ketoglutarate) and then a second carboxyl group (leading to the 4-carbon compound called succinate). Succinate molecule is further oxidized to fumarate, then malate and finally oxaloacetate. The regeneration of the 4-carbon oxaloacetate, allows the TCA cycle to continue. Oxidation step generates energy that is transferring energy-rich electrons for NAD+ to form NADH in TCA cycle. Each acetyl group will generate 3 NADH in TCA cycle.
Metabolic
PW001009
Center
PathwayVisualizationContext1296
2535
2257
#000099
PathwayVisualization757
773
TCA Cycle (Ubiquinol-9)
The citric acid cycle (also named tricarboxylic acid (TCA) cycle or the Krebs cycle), is a collection of 9 enzyme-catalyzed chemical reactions that occur in all living cells undergoing aerobic respiration. The citric acid cycle itself was officially identified in 1937 by Hans Adolf Krebs, who received the Nobel Prize for this discovery in 1953. In eukaryotes, the citric acid cycle occurs in the mitochondria. In prokaryotes, the TCA cycle occurs in the cytoplasm. The TCA cycle starts with acetyl-CoA, which is the “fuel†for the entire cycle. This important molecule comes from the breakdown of glycogen (a stored form of glucose), fats, and many amino acids. At beginning, acetyl-CoA first transfers its 2-carbon acetyl group to the 4-carbon acceptor compound called oxaloacetate to form the 6-carbon compound (citrate) for which the cycle is named. The resulting citrate will have numbers of chemical transformations, whereby it loses one carboxyl group (leading to the 5-carbon compound called alpha-ketoglutarate) and then a second carboxyl group (leading to the 4-carbon compound called succinate). Succinate molecule is further oxidized to fumarate, then malate and finally oxaloacetate. The regeneration of the 4-carbon oxaloacetate, allows the TCA cycle to continue. Oxidation step generates energy that is transferring energy-rich electrons for NAD+ to form NADH in TCA cycle. Each acetyl group will generate 3 NADH in TCA cycle.
Metabolic
3
111203
551
SubPathway
110815
148
Compound
117
111204
549
SubPathway
110816
940
Compound
117
111205
556
SubPathway
110817
174
Compound
117
2375
13152052
SWIM HE, KRAMPITZ LO: Acetic acid oxidation by Escherichia coli; evidence for the occurrence of a tricarboxylic acid cycle. J Bacteriol. 1954 Apr;67(4):419-25.
773
Pathway
2376
3889909
Walsh K, Koshland DE Jr: Characterization of rate-controlling steps in vivo by use of an adjustable expression vector. Proc Natl Acad Sci U S A. 1985 Jun;82(11):3577-81.
773
Pathway
2377
3332995
Walsh K, Schena M, Flint AJ, Koshland DE Jr: Compensatory regulation in metabolic pathways--responses to increases and decreases in citrate synthase levels. Biochem Soc Symp. 1987;54:183-95.
773
Pathway
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
6
Myocyte
CL:0000187
2
Platelet
CL:0000233
8
Beta cell
CL:0000639
1
Homo sapiens
9606
Eukaryote
Human
3
Escherichia coli
562
Prokaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
21
Xenopus laevis
8355
Eukaryote
African clawed frog
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
12
Mus musculus
10090
Eukaryote
Mouse
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
2
Bacteria
2
Prokaryote
Bacteria
19
Schizosaccharomyces pombe
4896
Eukaryote
25
Escherichia coli (strain K12)
83333
Prokaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
23
Pseudomonas aeruginosa
287
Prokaryote
29
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
559292
Eukaryote
Baker's yeast
143
Klebsiella pneumoniae
573
Prokaryote
Klebsiella
3
Mitochondrial Matrix
GO:0005759
1
Cytosol
GO:0005829
5
Cytoplasm
GO:0005737
6
Lysosome
GO:0005764
4
Peroxisome
GO:0005777
2
Mitochondrion
GO:0005739
10
Cell Membrane
GO:0005886
11
Extracellular Space
GO:0005615
16
Lysosomal Lumen
GO:0043202
7
Endoplasmic Reticulum Membrane
GO:0005789
18
Melanosome Membrane
GO:0033162
13
Endoplasmic Reticulum
GO:0005783
25
Golgi apparatus
GO:0005794
14
Mitochondrial Outer Membrane
GO:0005741
12
Mitochondrial Inner Membrane
GO:0005743
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
15
Nucleus
GO:0005634
31
Periplasmic Space
GO:0005620
35
Chloroplast
GO:0009507
36
Membrane
GO:0016020
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
40
Periplasm
GO:0042597
19
sarcoplasmic reticulum
GO:0016529
24
Mitochondrial Intermembrane Space
GO:0005758
27
Peroxisome Membrane
GO:0005778
8
Smooth Endoplasmic Reticulum
GO:0005790
32
Inner Membrane
GO:0070258
39
Mitochondrial membrane
GO:0031966
1
Liver
BTO:0000759
72
9
4
Adrenal Medulla
BTO:0000049
71
8
25
Intestine
BTO:0000648
28
Stomach
BTO:0001307
155
26
7
Nervous System
BTO:0001484
8
Blood Vessel
BTO:0001102
74
11
11
Heart
BTO:0000562
73
10
5
cardiocyte
BTO:0001539
9
Muscle
BTO:0000887
141
18
24
Brain
BTO:0000142
89
16
2
Endothelium
BTO:0000393
18
Pancreas
BTO:0000988
4
3
1
1
PW_BS000004
103
3
3
1
PW_BS000103
155
3
24
1
PW_BS000155
161
3
18
1
PW_BS000161
178
3
21
1
PW_BS000178
222
3
4
1
PW_BS000024
117
1
3
1
PW_BS000117
133
3
12
1
PW_BS000133
368
3
60
1
PW_BS000028
406
3
5
1
PW_BS000115
120
3
17
1
PW_BS000120
479
3
10
1
PW_BS000115
501
3
6
1
PW_BS000115
8
5
1
1
PW_BS000008
9
6
1
1
PW_BS000009
5
4
1
1
PW_BS000005
3
2
1
1
PW_BS000003
14
10
1
PW_BS000014
13
1
2
1
PW_BS000013
15
11
1
PW_BS000015
28
1
16
1
1
PW_BS000028
10
1
7
1
1
PW_BS000010
20
4
1
1
1
PW_BS000020
33
18
1
1
PW_BS000033
18
13
1
1
PW_BS000018
2
1
1
1
PW_BS000002
31
1
5
1
1
PW_BS000031
49
7
1
1
PW_BS000049
54
1
3
1
5
PW_BS000054
43
25
1
1
PW_BS000043
24
4
10
1
1
PW_BS000024
22
14
1
1
PW_BS000022
60
25
1
PW_BS000060
46
1
1
4
PW_BS000046
17
12
1
1
PW_BS000017
29
1
1
1
PW_BS000029
70
28
5
1
1
PW_BS000070
72
5
1
3
PW_BS000072
61
25
1
7
PW_BS000061
36
1
20
1
1
PW_BS000036
37
7
21
1
3
PW_BS000037
93
25
20
1
1
PW_BS000093
27
15
1
PW_BS000027
7
1
1
PW_BS000007
97
1
5
2
1
PW_BS000097
100
5
2
1
PW_BS000100
94
3
PW_BS000094
105
11
3
PW_BS000105
111
5
12
1
PW_BS000111
113
6
12
1
PW_BS000113
112
2
12
1
PW_BS000112
110
2
3
1
PW_BS000110
123
1
7
5
1
PW_BS000123
125
13
5
1
PW_BS000125
126
6
5
1
PW_BS000126
127
1
16
5
1
PW_BS000127
130
13
12
1
PW_BS000130
114
11
12
PW_BS000114
129
1
5
12
1
PW_BS000129
135
5
17
1
PW_BS000135
118
1
17
1
PW_BS000118
108
1
3
PW_BS000108
6
1
3
1
PW_BS000006
140
10
3
PW_BS000140
101
5
3
1
PW_BS000101
143
1
5
19
1
PW_BS000143
146
5
19
1
PW_BS000146
107
31
3
PW_BS000107
95
1
7
2
1
PW_BS000095
147
1
24
1
PW_BS000147
151
1
4
1
PW_BS000151
157
2
24
1
PW_BS000157
163
2
18
1
PW_BS000163
159
24
PW_BS000159
1
1
PW_BS000001
166
1
1
PW_BS000166
180
2
21
1
PW_BS000180
152
8
4
PW_BS000152
188
1
18
PW_BS000024
160
1
18
1
PW_BS000160
205
5
6
1
PW_BS000024
207
6
6
1
PW_BS000024
206
2
6
1
PW_BS000024
211
10
18
PW_BS000024
213
7
18
1
PW_BS000024
214
25
18
1
PW_BS000024
215
6
18
1
PW_BS000024
198
5
18
1
PW_BS000024
216
4
18
1
PW_BS000024
210
13
18
1
PW_BS000024
212
1
7
18
1
PW_BS000024
224
2
4
1
PW_BS000024
190
11
18
PW_BS000024
170
18
PW_BS000170
225
35
4
1
PW_BS000024
226
4
4
1
PW_BS000024
162
12
18
1
PW_BS000162
26
1
1
1
5
PW_BS000026
277
1
2
18
PW_BS000024
164
4
PW_BS000164
281
1
25
1
PW_BS000024
285
10
4
1
PW_BS000024
286
36
4
1
PW_BS000024
287
53
4
1
PW_BS000024
249
13
4
1
PW_BS000024
227
34
4
1
PW_BS000024
65
11
1
PW_BS000065
290
5
49
1
PW_BS000024
291
6
49
1
PW_BS000024
292
4
49
1
PW_BS000024
298
1
7
10
1
PW_BS000024
300
13
10
1
PW_BS000024
301
6
10
1
PW_BS000024
302
1
16
10
1
PW_BS000024
223
12
4
1
PW_BS000024
294
11
4
1
PW_BS000024
308
10
1
1
PW_BS000024
315
1
23
PW_BS000024
318
31
23
PW_BS000024
322
1
23
1
PW_BS000024
293
4
1
PW_BS000024
253
5
4
1
PW_BS000024
132
1
12
1
PW_BS000132
134
12
12
1
PW_BS000134
331
7
12
1
PW_BS000028
332
1
7
12
1
PW_BS000028
333
1
2
12
PW_BS000028
115
10
12
PW_BS000115
334
4
12
1
PW_BS000028
336
1
12
1
PW_BS000028
337
1
16
12
1
PW_BS000028
341
4
1
12
1
PW_BS000028
343
18
12
1
PW_BS000028
347
1
3
12
5
PW_BS000028
329
14
12
1
PW_BS000028
352
25
12
PW_BS000028
353
25
12
7
PW_BS000028
356
25
12
1
PW_BS000028
360
4
10
12
1
PW_BS000028
370
2
60
1
PW_BS000028
228
36
1
PW_BS000024
119
2
17
1
PW_BS000119
383
7
5
1
PW_BS000100
384
12
5
1
PW_BS000100
390
7
6
1
PW_BS000112
391
12
6
1
PW_BS000112
398
7
17
1
PW_BS000113
232
40
3
PW_BS000024
122
5
5
1
PW_BS000122
407
2
5
1
PW_BS000115
408
4
5
1
PW_BS000115
124
1
5
1
PW_BS000124
412
1
2
5
PW_BS000115
405
10
5
PW_BS000115
409
11
5
PW_BS000115
415
18
5
1
PW_BS000115
414
1
5
5
1
PW_BS000115
425
1
3
5
5
PW_BS000115
429
1
5
1
PW_BS000115
121
12
17
1
PW_BS000121
419
25
5
1
PW_BS000115
434
4
10
5
1
PW_BS000115
382
14
5
1
PW_BS000100
436
25
5
PW_BS000115
374
4
17
1
PW_BS000053
443
6
17
1
PW_BS000115
446
1
2
17
PW_BS000115
376
10
17
PW_BS000053
137
11
17
PW_BS000137
447
1
7
17
1
PW_BS000115
136
13
17
1
PW_BS000136
448
1
16
17
1
PW_BS000115
451
18
17
1
PW_BS000115
450
1
5
17
1
PW_BS000115
460
1
3
17
5
PW_BS000115
464
1
17
1
PW_BS000115
455
25
17
1
PW_BS000115
469
4
10
17
1
PW_BS000115
399
14
17
1
PW_BS000113
471
25
17
PW_BS000115
472
25
17
7
PW_BS000115
297
5
10
1
PW_BS000024
481
2
10
1
PW_BS000115
482
4
10
1
PW_BS000115
299
1
10
1
PW_BS000024
483
11
10
PW_BS000115
478
10
10
PW_BS000115
487
18
10
1
PW_BS000115
490
25
10
1
PW_BS000115
495
7
10
1
PW_BS000115
484
14
10
1
PW_BS000115
480
12
10
1
PW_BS000115
502
4
6
1
PW_BS000115
388
1
6
1
PW_BS000112
208
11
6
PW_BS000024
209
10
6
PW_BS000024
504
18
6
1
PW_BS000115
507
25
6
1
PW_BS000115
515
4
10
6
1
PW_BS000115
389
14
6
1
PW_BS000112
395
13
6
1
PW_BS000113
513
1
7
6
1
PW_BS000115
35
5
19
1
4
PW_BS000035
42
24
1
1
PW_BS000042
50
9
5
1
6
PW_BS000050
85
24
10
1
1
PW_BS000085
220
1
4
PW_BS000024
289
2
49
1
PW_BS000024
345
24
12
1
PW_BS000028
346
9
5
12
6
PW_BS000028
327
1
1
12
5
PW_BS000028
418
24
5
1
PW_BS000115
423
9
5
5
6
PW_BS000115
424
1
1
5
5
PW_BS000115
454
24
17
1
PW_BS000115
458
9
5
17
6
PW_BS000115
459
1
1
17
5
PW_BS000115
489
24
10
1
PW_BS000115
506
24
6
1
PW_BS000115
141
1
7
19
1
PW_BS000141
59
27
1
1
PW_BS000059
11
1
8
1
1
PW_BS000011
58
1
14
1
1
PW_BS000058
102
12
3
1
PW_BS000102
104
14
3
1
PW_BS000104
199
14
18
1
PW_BS000024
195
13
18
PW_BS000024
350
1
14
12
1
PW_BS000028
335
27
12
1
PW_BS000028
288
14
4
1
PW_BS000024
433
1
14
5
1
PW_BS000115
422
27
5
1
PW_BS000115
468
1
14
17
1
PW_BS000115
375
27
17
1
PW_BS000053
491
27
10
1
PW_BS000115
508
27
6
1
PW_BS000115
47
19
1
4
PW_BS000047
23
15
1
1
PW_BS000023
91
8
5
1
1
PW_BS000091
217
15
18
PW_BS000024
218
15
18
1
PW_BS000024
313
23
PW_BS000024
128
15
12
1
PW_BS000128
351
15
12
PW_BS000028
109
32
3
PW_BS000109
410
15
5
1
PW_BS000115
435
15
5
PW_BS000115
444
15
17
1
PW_BS000115
470
15
17
PW_BS000115
485
15
10
1
PW_BS000115
499
15
10
PW_BS000115
516
15
6
1
PW_BS000115
517
15
6
PW_BS000115
241
5
29
PW_BS000024
257
15
29
1
PW_BS000024
304
1
2
PW_BS000024
16
2
1
2
PW_BS000016
32
1
15
1
5
PW_BS000032
39
7
1
1
3
PW_BS000039
66
18
5
1
8
PW_BS000066
51
8
1
PW_BS000051
89
2
PW_BS000089
184
1
2
1
PW_BS000024
219
31
4
PW_BS000024
156
12
24
1
PW_BS000156
179
12
21
1
PW_BS000179
358
39
12
PW_BS000028
369
12
60
1
PW_BS000028
189
32
18
PW_BS000024
317
32
23
PW_BS000024
187
31
18
PW_BS000024
312
5
23
1
PW_BS000024
320
11
23
PW_BS000024
310
31
2
PW_BS000024
730
32
143
PW_BS000512
731
5
143
1
PW_BS000512
51
cis-Aconitic acid
HMDB0000072
cis-Aconitic acid is an intermediate in the tricarboxylic acid cycle produced by the dehydration of citric acid. The enzyme aconitase (aconitate hydratase; EC 4.2.1.3) catalyses the stereo-specific isomerization of citrate to isocitrate via cis-aconitate in the tricarboxylic acid cycle.
585-84-2
C00417
643757
32805
CIS-ACONITATE
558863
OC(=O)C\C(=C\C(O)=O)C(O)=O
C6H6O6
InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1-
GTZCVFVGUGFEME-IWQZZHSRSA-N
(1Z)-prop-1-ene-1,2,3-tricarboxylic acid
174.1082
174.016437924
-1.41
3
cis-aconitic acid
0
-3
FDB008306
(1z)-1-propene-1,2,3-tricarboxylate;(1z)-1-propene-1,2,3-tricarboxylic acid;(z)-1-propene-1,2,3-tricarboxylate;(z)-1-propene-1,2,3-tricarboxylic acid;(z)-aconitate;(z)-aconitic acid;1-propene-1,2,3-tricarboxylate;1-propene-1,2,3-tricarboxylic acid;1-cis-2,3-propenetricarboxylate;1-cis-2,3-propenetricarboxylic acid;Cis-1-propene-1,2,3-tricarboxylate;Cis-1-propene-1,2,3-tricarboxylic acid;Cis-aconate;Cis-aconic acid;Cis-aconitate;Cis-aconitic acid;Cis-oxaloacetate;Cis-oxaloacetic acid
PW_C000051
Aconiti
222
4
5401
103
6058
155
6122
161
6506
178
7491
222
11745
117
77159
133
80038
368
120007
406
122783
120
125385
479
126927
501
1420
Water
HMDB0002111
Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71% of Earth's surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the body's solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the sun's energy to split off water's hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the sun's energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia).
7732-18-5
C00001
962
15377
937
O
H2O
InChI=1S/H2O/h1H2
XLYOFNOQVPJJNP-UHFFFAOYSA-N
water
18.0153
18.010564686
1
water
0
0
FDB013390
Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;Wasser
PW_C001420
H2O
55
8
94
9
109
5
139
4
151
3
162
14
481
13
526
15
624
28
652
10
691
20
770
33
823
18
838
2
1094
31
1377
49
1465
54
1590
43
2018
24
2532
22
2678
60
2727
46
2778
17
2805
29
3143
70
3164
72
3634
61
4598
36
4727
37
4941
93
5030
27
5156
7
5195
97
5214
100
5227
94
5236
103
5297
105
5319
111
5343
113
5355
112
5402
110
5470
123
5483
125
5492
126
5507
127
5534
130
5537
114
5541
129
5591
135
5608
118
5622
108
5691
6
5759
140
5778
101
5841
143
5853
146
5877
107
5890
95
5910
147
5940
151
6032
155
6059
157
6087
161
6123
163
6133
159
6215
1
6218
166
6477
178
6507
180
6600
152
6713
117
6840
188
6888
160
7162
205
7181
207
7193
206
7211
211
7228
213
7238
214
7243
215
7295
198
7350
216
7388
210
7401
212
7467
222
7492
224
7500
190
7588
170
8201
225
8237
226
8414
162
9265
26
11850
277
11922
164
12011
281
12213
285
12250
286
12264
287
12327
249
12520
227
12632
65
12693
290
12705
291
12715
292
13007
298
13019
300
13025
301
13037
302
13261
223
13327
294
15340
308
42327
315
42695
318
43691
322
76914
293
77019
253
77102
132
77131
133
77215
134
77378
331
77397
332
77471
333
77516
115
77536
334
77628
336
77722
337
77759
341
77816
343
77982
347
78071
329
78235
352
78242
353
78270
356
79113
360
80014
368
80039
370
80591
228
80656
119
93830
383
94794
384
110557
390
110639
391
115844
398
119879
232
119915
122
119963
406
120008
407
120046
408
120113
124
120365
412
120430
405
120438
409
120606
415
120794
414
121158
425
121240
429
121351
121
121381
419
121607
434
122118
382
122384
436
122753
120
122797
374
122804
443
123012
446
123064
376
123072
137
123131
447
123142
136
123162
448
123231
451
123384
450
123730
460
123810
464
123940
455
124165
469
124670
399
124938
471
124945
472
125305
297
125353
479
125386
481
125424
482
125480
299
125682
483
125707
478
125745
487
126054
490
126238
495
126273
484
126764
480
126896
501
126963
502
127017
388
127177
208
127199
209
127227
504
127506
507
127576
515
127836
389
128082
395
128176
513
1246
D-threo-Isocitric acid
HMDB0001874
D-Threo-isocitric acid, also known as isocitrate, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. D-Threo-isocitric acid is soluble (in water) and a weakly acidic compound (based on its pKa). D-Threo-isocitric acid has been primarily detected in blood. Within the cell, D-threo-isocitric acid is primarily located in the mitochondria and peroxisome. D-Threo-isocitric acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, D-threo-isocitric acid can be found in a number of food items such as fruits, rubus (blackberry, raspberry), common bean, and citrus. This makes D-threo-isocitric acid a potential biomarker for the consumption of these food products. Threo-Isocitric acid is the substrate of isocitrate dehydrogenase (IDH), a NADP-dependent IDH that occurs in 2 structurally distinct forms: mitochondrial (OMIM 147650) and soluble (also called supernatant or cytoplasmic, OMIM 147700).
6061-97-8
C00451
5318532
151
CPD-1941
4477081
O[C@H]([C@H](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)/t2-,4+/m0/s1
ODBLHEXUDAPZAU-ZAFYKAAXSA-N
(1R,2S)-1-hydroxypropane-1,2,3-tricarboxylic acid
192.1235
192.02700261
-0.56
4
threo-DS(+)-isocitrate
0
-3
FDB012771
(+)-threo-isocitrate;(+)-threo-isocitric acid;(1r,2s)-1-hydroxypropane-1,2,3-tricarboxylate;(1r,2s)-1-hydroxypropane-1,2,3-tricarboxylic acid;(2r,3s)-isocitrate;3-carboxy-2,3-dideoxy-l-threo-pentaric acid;D-(+)-threo-isocitric acid(2r,3s)-isocitric acid;D-threo-isocitrate;Ds-threo-isocitrate;Ds-threo-isocitric acid;Ici;Ict;Isocitric acid;Threo-d-(+)-isocitrate;Threo-d-(+)-isocitric acid;Threo-ds(+)-isocitrate;Threo-ds(+)-isocitric acid;Threo-isocitrate
PW_C001246
D-TIsoA
143
NADP
HMDB0000217
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).
53-59-8
C00006
5886
18009
NAD(P)
5675
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](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-1lambda5-pyridin-1-ylium
744.4129
744.083277073
-2.27
9
1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
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;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acid
PW_C000143
NADP
183
8
191
3
768
5
780
10
824
18
839
2
1611
29
1617
49
4685
31
4796
14
4801
14
5308
111
5790
108
6017
147
6132
159
6273
35
6778
117
7069
188
7105
163
7152
205
7206
160
7317
213
7346
210
7562
212
7589
170
8197
225
8220
151
8419
224
11811
198
11897
211
12008
222
12152
164
12249
286
12597
226
12650
249
42344
315
43745
322
76913
293
77164
132
77384
331
77396
332
77461
130
77515
115
77624
336
77814
334
77870
112
80713
119
113165
94
120106
407
120429
405
120450
122
120604
408
120618
123
121142
125
121277
429
121401
124
121485
383
123063
376
123084
135
123229
374
123243
447
123713
136
123848
464
123960
118
124043
398
125473
481
125694
297
125743
482
126215
299
126528
495
127010
206
127225
502
127570
388
128100
390
1316
Carbon dioxide
HMDB0001967
Carbon dioxide is a colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbon dioxide is produced during respiration by all animals, fungi and microorganisms that depend on living and decaying plants for food, either directly or indirectly. It is, therefore, a major component of the carbon cycle. Additionally, carbon dioxide is used by plants during photosynthesis to make sugars which may either be consumed again in respiration or used as the raw material to produce polysaccharides such as starch and cellulose, proteins and the wide variety of other organic compounds required for plant growth and development. When inhaled at concentrations much higher than usual atmospheric levels, it can produce a sour taste in the mouth and a stinging sensation in the nose and throat. These effects result from the gas dissolving in the mucous membranes and saliva, forming a weak solution of carbonic acid. Carbon dioxide is used by the food industry, the oil industry, and the chemical industry. Carbon dioxide is used to produce carbonated soft drinks and soda water. Traditionally, the carbonation in beer and sparkling wine comes about through natural fermentation, but some manufacturers carbonate these drinks artificially.
124-38-9
C00011
280
16526
274
O=C=O
CO2
InChI=1S/CO2/c2-1-3
CURLTUGMZLYLDI-UHFFFAOYSA-N
methanedione
44.0095
43.989829244
0.63
0
carbon dioxide
0
0
DBMET00423
FDB014084
Carbon oxide;Carbon-12 dioxide;Carbonic acid anhydride;Carbonic acid gas;Carbonic anhydride;[co2];Co2;E 290;E-290;E290;R-744
PW_C001316
CO2
50
8
121
1
204
4
480
13
503
18
640
3
677
31
695
20
806
5
1133
43
1638
49
1745
2
2551
17
3144
70
5283
103
5320
111
5750
108
5771
101
5968
100
6026
155
6078
161
6471
178
6637
107
6922
190
7017
160
7035
163
7061
188
7163
205
7308
198
7333
213
7461
222
7530
210
8215
225
8223
151
9158
249
11849
277
11908
170
12464
226
12688
290
42626
315
43523
318
76994
293
77122
133
77170
132
77470
333
77739
112
77750
129
77763
341
78077
134
78405
356
78427
334
78941
331
79227
130
80008
368
80675
119
80717
135
94836
384
113291
391
115549
121
119954
406
120089
122
120155
407
120364
412
120556
414
120833
419
120922
124
120991
408
121284
125
121505
383
122744
120
123011
446
123190
450
123418
455
123489
118
123556
374
123855
136
124063
398
125344
479
125460
297
125516
481
125824
490
125870
299
125931
482
126280
480
126887
501
127052
206
127277
507
127331
388
127390
502
146
NADPH
HMDB0000221
Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).
53-57-6
C00005
22833512
16474
NADPH
17215925
NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=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
NADPH
185
8
190
3
778
10
796
5
821
18
837
2
1609
29
1615
49
4687
31
4793
14
4797
14
5310
111
5789
108
5972
147
6128
159
6271
35
6779
117
7068
188
7103
163
7154
205
7205
160
7315
213
7345
210
7559
212
7591
170
8194
225
8219
151
8421
224
11812
198
11893
211
12006
222
12150
164
12245
286
12596
226
12648
249
42343
315
43746
322
76911
293
77166
132
77385
331
77394
332
77460
130
77504
112
77511
115
77623
336
80712
119
113164
94
120105
407
120425
405
120452
122
120616
123
121141
125
121275
429
121402
124
121483
383
123059
376
123086
135
123241
447
123712
136
123846
464
123961
118
124041
398
125472
481
125696
297
126214
299
126529
495
127009
206
127572
388
128101
390
134
Oxoglutaric acid
HMDB0000208
Oxoglutaric acid, also known as alpha-ketoglutarate, alpha-ketoglutaric acid, AKG, or 2-oxoglutaric acid, is classified as a gamma-keto acid or a gamma-keto acid derivative. gamma-Keto acids are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. alpha-Ketoglutarate is considered to be soluble (in water) and acidic. alpha-Ketoglutarate is a key molecule in the TCA cycle, playing a fundamental role in determining the overall rate of this important metabolic process (PMID: 26759695). In the TCA cycle, AKG is decarboxylated to succinyl-CoA and carbon dioxide by AKG dehydrogenase, which functions as a key control point of the TCA cycle. Additionally, AKG can be generated from isocitrate by oxidative decarboxylation catalyzed by the enzyme known as isocitrate dehydrogenase (IDH). In addition to these routes of production, AKG can be produced from glutamate by oxidative deamination via glutamate dehydrogenase, and as a product of pyridoxal phosphate-dependent transamination reactions (mediated by branched-chain amino acid transaminases) in which glutamate is a common amino donor. AKG is a nitrogen scavenger and a source of glutamate and glutamine that stimulates protein synthesis and inhibits protein degradation in muscles. In particular, AKG can decrease protein catabolism and increase protein synthesis to enhance bone tissue formation in skeletal muscles (PMID: 26759695). Interestingly, enteric feeding of AKG supplements can significantly increase circulating plasma levels of hormones such as insulin, growth hormone, and insulin-like growth factor-1 (PMID: 26759695). It has recently been shown that AKG can extend the lifespan of adult C. elegans by inhibiting ATP synthase and TOR (PMID: 24828042). In combination with molecular oxygen, alpha-ketoglutarate is required for the hydroxylation of proline to hydroxyproline in the production of type I collagen. A recent study has shown that alpha-ketoglutarate promotes TH1 differentiation along with the depletion of glutamine thereby favouring Treg (regulatory T-cell) differentiation (PMID: 26420908). alpha-Ketoglutarate has been found to be associated with fumarase deficiency, 2-ketoglutarate dehydrogenase complex deficiency, and D-2-hydroxyglutaric aciduria, which are all inborn errors of metabolism (PMID: 8338207).
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;Alpha-ketoglutaric acid;Oxoglutaric acid;A-ketoglutarate;A-ketoglutaric acid;Alpha-ketoglutarate;α-ketoglutarate;α-ketoglutaric acid
PW_C000134
AKG
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
7471
222
7515
224
7519
151
8209
225
8374
220
11863
198
12681
289
77054
253
77135
133
77481
111
77523
112
77746
129
77967
345
77970
346
77976
327
77984
347
78425
334
80018
368
80694
135
113162
94
119972
406
120022
124
120084
407
120174
122
120552
414
120814
418
120989
408
121146
423
121152
424
121160
425
122757
120
122831
119
123186
450
123399
454
123554
374
123718
458
123724
459
123732
460
125357
479
125400
299
125455
481
125533
297
125800
489
125929
482
126900
501
126940
388
126993
206
127066
205
127255
506
127388
502
721
NAD
HMDB0000902
NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).
53-84-9
C00003
5893
15846
NAD
5682
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
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-1lambda5-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-1lambda5-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;Dpn;Nad;Nad+;Nadide;B-nad;β-nad
PW_C000721
NAD
140
4
150
3
353
8
651
10
1114
2
1134
43
1273
5
1466
54
2229
49
2779
17
2835
29
3107
9
4807
18
4813
18
4819
28
4902
6
4960
31
5167
95
5238
103
5334
111
5360
112
5469
123
5482
125
5590
135
5610
118
5696
100
5738
108
5827
141
5912
147
5942
151
6024
155
6072
157
6076
161
6385
1
6469
178
6772
117
6890
160
7012
188
7097
163
7174
205
7197
206
7405
198
7459
222
8241
226
8359
225
9085
224
11819
216
12322
249
13006
298
13018
300
13256
223
42404
322
42619
315
77104
132
77120
133
77209
134
77370
331
77650
336
77667
334
77702
332
77709
130
77915
113
77983
347
78406
356
80006
368
80690
119
93825
124
110552
388
112750
166
112853
94
119929
122
119952
406
120171
407
120834
419
120984
408
121159
425
121242
126
121259
429
121817
383
122614
384
122742
120
123130
447
123141
136
123419
455
123549
374
123731
460
123812
443
123829
464
124370
398
125187
121
125319
297
125342
479
125530
481
125806
299
125825
490
125924
482
126515
495
126765
480
126885
501
127278
507
127383
502
128089
390
128360
391
128428
395
1099
Coenzyme A
HMDB0001423
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. It is also a parent compound for other transformation products, including but not limited to, phenylglyoxylyl-CoA, tetracosanoyl-CoA, and 6-hydroxyhex-3-enoyl-CoA. 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 the 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 proteins 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@@H](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-IBOSZNHHSA-N
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-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
CoA
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
7458
222
8229
151
9081
226
9090
224
9124
170
9215
195
13013
299
15318
249
25488
49
42616
315
76907
293
77119
133
77222
134
77230
329
77292
111
77550
132
77555
334
77563
112
77633
336
77672
129
77996
115
78047
332
78056
350
78413
335
78567
130
79259
333
79974
331
80005
368
80620
118
80627
374
80635
119
80665
376
93828
382
93834
383
98674
288
110555
389
110561
390
115842
399
115847
398
119951
406
120147
405
120231
384
120305
122
120634
407
120762
117
121406
123
121421
433
121521
125
121666
429
121682
408
121714
414
122404
422
122741
120
122904
121
122960
135
123965
447
123979
468
124079
136
124220
464
124265
450
124974
375
125341
479
125509
478
125579
480
125592
484
125634
297
126084
481
126549
491
126560
482
126746
300
126884
501
127046
209
127109
391
127301
205
127540
206
127667
388
128121
508
128133
502
128340
395
1144
NADH
HMDB0001487
NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).
58-68-4
C00004
439153
16908
NADH
388299
DB00157
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
C21H29N7O14P2
InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
BOPGDPNILDQYTO-NNYOXOHSSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid
665.441
665.124771695
-2.35
8
NADH
0
-2
FDB022649
1,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotide
PW_C001144
NADH
143
4
153
3
490
8
648
10
1115
2
1275
5
1469
54
2230
49
2781
17
2836
29
3109
9
4806
18
4812
18
4821
28
4904
6
4959
31
5169
95
5240
103
5332
111
5358
112
5466
123
5479
125
5593
135
5698
100
5737
108
5829
141
5915
147
5945
151
6027
155
6079
161
6387
1
6472
178
6771
117
6893
160
7011
188
7099
163
7172
205
7195
206
7462
222
8244
226
8360
225
9086
224
11809
198
11821
216
12320
249
13003
298
13015
300
13255
223
42403
322
42618
315
77107
132
77123
133
77208
134
77371
331
77651
336
77668
334
77700
332
77707
130
77917
113
77986
347
80009
368
80691
119
93822
124
110549
388
112854
94
115838
118
119955
406
120172
407
120378
122
120986
408
121162
425
121244
126
121693
429
121818
383
122616
384
122745
120
123127
447
123138
136
123551
374
123734
460
123814
443
124242
464
124371
398
125189
121
125345
479
125531
481
125762
297
125808
299
125926
482
126516
495
126767
480
126888
501
127385
502
128090
390
128362
391
128429
395
808
Succinyl-CoA
HMDB0001022
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;Succinylcoenzyme a
PW_C000808
Suc-CoA
233
4
1055
3
3669
2
5378
103
6039
155
6097
161
6485
178
7015
160
7361
163
7474
222
77140
133
78101
112
78576
132
80021
368
119978
406
120769
407
122014
124
122763
120
123365
119
124568
118
125358
479
126164
299
126306
481
126901
501
127868
206
1034
Adenosine diphosphate
HMDB0001341
Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.
58-64-0
C00008
6022
16761
ADP
5800
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H15N5O10P2
InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
XTWYTFMLZFPYCI-KQYNXXCUSA-N
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
427.2011
427.029414749
-2.12
6
adenosine-diphosphate
0
-2
FDB021817
Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acid
PW_C001034
ADP
23
4
134
8
415
22
482
13
801
5
963
15
978
3
1061
14
1518
2
1901
49
2104
18
2113
10
2161
58
2408
59
2435
27
2728
47
2736
46
2855
29
3165
72
3635
61
4400
23
4476
31
4770
91
5036
26
5157
7
5208
97
5217
100
5315
111
5349
112
5392
103
5446
120
5544
129
5572
133
5624
108
5741
117
5764
101
5849
143
5856
146
5878
107
5899
147
5926
151
6050
155
6111
161
6231
166
6495
178
6700
94
6841
188
6872
160
7159
205
7187
206
7208
210
7226
213
7231
211
7300
198
7303
216
7391
217
7410
218
7433
163
7483
222
8187
225
11851
277
11905
170
12013
281
12180
285
13262
223
15329
308
42328
315
42398
313
42622
322
42696
318
77029
253
77087
132
77216
134
77306
329
77472
333
77663
336
78039
332
78043
350
78170
128
78215
351
78244
353
78414
335
78495
115
78705
331
78849
130
78920
334
80030
368
80622
118
80651
135
80676
119
94827
124
113283
388
116204
109
119944
122
119994
406
120156
407
120318
382
120366
412
121248
429
121394
123
121399
433
121472
408
121899
383
121976
410
122064
125
122085
405
122405
422
122445
435
122973
399
123013
446
123818
464
123953
447
123958
468
124030
374
124452
398
124529
444
124615
136
124636
376
124947
472
124975
375
125012
470
125334
297
125373
479
125492
299
125517
481
125645
484
126125
485
126219
300
126235
495
126242
478
126550
491
126597
499
126915
501
127733
516
127780
395
127797
390
127803
209
128122
508
128168
517
128313
389
1104
Phosphate
HMDB0001429
Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.
14265-44-2
C00009
1061
18367
CPD-8587
1032
[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
phosphoric acid
94.9714
94.95342
3
phosphoric acid
0
-2
DBMET00532
FDB022617
Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ion
PW_C001104
Pi
24
4
84
8
814
5
818
18
831
2
980
3
1763
14
1767
49
2500
10
2729
47
2737
46
3129
29
3166
72
3636
61
3851
23
4249
22
4475
31
5031
27
5158
7
5207
97
5216
100
5317
111
5351
112
5381
103
5447
120
5543
129
5573
133
5605
135
5625
108
5693
6
5848
143
5855
146
5911
147
5941
151
6040
155
6100
161
6294
107
6487
178
6691
101
6714
117
6842
188
6889
160
7161
205
7189
206
7212
211
7306
198
7389
210
7402
212
7436
163
7475
222
8196
225
8258
227
10118
241
10134
257
11748
132
11761
115
11773
213
11904
170
11927
164
12014
281
12728
290
13263
223
34819
17
42255
304
42350
315
42435
318
43692
322
77018
253
77194
293
77217
134
77940
336
77966
130
78048
332
78057
329
78245
353
78669
331
80022
368
89279
308
93831
383
94796
384
110558
390
110640
391
113235
94
115845
398
116206
109
119982
406
120069
122
120699
407
121057
124
121216
125
121268
429
121352
121
121409
123
121423
382
121852
405
123304
119
123621
118
123786
136
123838
464
123968
447
123981
399
124405
376
124948
472
125362
479
125446
297
125774
481
125954
299
126221
478
126594
300
126604
298
126723
484
126904
501
127413
388
127783
209
128166
395
128177
513
128315
389
414
Adenosine triphosphate
HMDB0000538
Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).
56-65-5
C00002
5957
15422
ATP
5742
DB00171
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
C10H16N5O13P3
InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
ZKHQWZAMYRWXGA-KQYNXXCUSA-N
({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
507.181
506.995745159
-2.05
7
adenosine triphosphate
0
-3
FDB021813
5'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acid
PW_C000414
ATP
9
2
21
4
60
8
266
16
414
22
478
13
733
32
799
5
934
39
976
3
2105
18
2112
10
2146
49
2156
14
2160
58
2405
59
2434
27
2726
46
2812
29
3029
66
3163
72
3616
61
3617
51
4399
23
4474
31
4768
91
4864
54
5032
89
5035
26
5155
7
5205
97
5215
100
5250
104
5291
101
5313
111
5346
112
5390
103
5406
117
5430
118
5443
120
5542
129
5556
132
5569
133
5603
135
5621
108
5846
143
5854
146
5876
107
5897
147
5924
151
6048
155
6109
161
6230
166
6493
178
6839
188
6870
160
6976
199
7157
205
7184
206
7209
210
7225
213
7229
211
7298
198
7302
216
7390
217
7408
218
7432
163
7481
222
7499
190
8186
225
11847
277
11903
170
12010
281
12039
164
12178
285
12578
226
12691
290
13264
223
15327
308
42326
315
42621
322
42694
318
77028
253
77218
134
77233
329
77468
333
77632
336
78037
332
78041
350
78168
128
78214
351
78240
353
78411
335
78494
115
78850
130
78865
331
78919
334
80028
368
80046
184
80674
119
85629
1
94826
124
113234
94
113282
388
116280
109
119914
122
119992
406
120154
407
120245
382
120362
412
121246
429
121392
123
121397
433
121471
408
121974
410
122065
125
122079
383
122083
405
122402
422
122444
435
122919
399
123009
446
123816
464
123951
447
123956
468
124029
374
124527
444
124616
136
124630
398
124634
376
124943
472
124972
375
125011
470
125304
297
125371
479
125392
299
125515
481
125595
484
126123
485
126220
300
126234
495
126240
478
126547
491
126596
499
126913
501
127123
389
127731
516
127781
395
127796
390
127801
209
128119
508
128167
517
174
Succinic acid
HMDB0000254
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;Acide butanedioique;Acide succinique;Acidum succinicum;Bernsteinsaeure;Butandisaeure;Butanedionic acid;E363;Ethylenesuccinic acid;Hooc-ch2-ch2-cooh;Spirit of amber;Butanedionate;Ethylenesuccinate
PW_C000174
Succini
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
7455
219
7456
220
7477
222
11866
198
12142
151
13259
223
42368
318
42369
315
42402
322
77143
133
77213
134
77483
111
77738
112
77749
129
78426
334
80024
368
80721
119
112846
308
113428
1
119984
406
120192
407
120385
122
120555
414
120990
408
122565
384
122767
120
123029
135
123189
450
123555
374
125138
121
125364
479
125549
481
125930
482
126713
480
126906
501
127082
206
127389
502
128304
391
101
L-Malic acid
HMDB0000156
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;L-2-hydroxybutanedioic acid;L-malic acid;Malate;(-)-l-malate;(s)-malate;L-2-hydroxybutanedioate;L-malate
PW_C000101
Malate
262
4
1098
3
1721
8
2387
2
5387
103
5735
108
6046
155
6106
161
6453
107
6491
178
7451
219
7452
220
7479
222
42455
318
42456
315
77147
133
78766
111
79051
132
79057
112
80026
368
119988
406
121441
122
122394
124
122401
407
122771
120
123999
135
124964
118
124971
119
125368
479
126066
297
126535
299
126546
481
126910
501
127519
205
128108
388
128118
206
1860
Quinone
HMDB0003364
Quinone is also called 1,4-benzoquinone or cyclohexadienedione. Quinones are oxidized derivatives of aromatic compounds and are often readily made from reactive aromatic compounds with electron-donating substituents such as phenols and catechols, which increase the nucleophilicity of the ring and contributes to the large redox potential needed to break aromaticity. Derivatives of quinones are common constituents of biologically relevant molecules. Some serve as electron acceptors in electron transport chains such as those in photosynthesis (plastoquinone, phylloquinone), and aerobic respiration (ubiquinone). Quinone is a common constituent of biologically relevant molecules (e.g. Vitamin K1 is phylloquinone). A natural example of quinones as oxidizing agents is the spray of bombardier beetles. Hydroquinone is reacted with hydrogen peroxide to produce a fiery blast of steam, a strong deterent in the animal world.
106-51-4
C00472
4650
16509
CPD-8130
4489
O=C1C=CC(=O)C=C1
C6H4O2
InChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H
AZQWKYJCGOJGHM-UHFFFAOYSA-N
cyclohexa-2,5-diene-1,4-dione
108.0948
108.021129372
-0.38
0
quinone
0
0
FDB005755
1,4-benzoquine;1,4-benzoquinone;1,4-cyclohexadiene dioxide;1,4-cyclohexadienedione;1,4-diossibenzene;1,4-dioxy-benzol;1,4-dioxybenzene;2,5-cyclohexadiene-1,4-dione;2,5-cyclohexadiene-1-4-dione;Benzo-1,4-quinone;Benzo-chinon;Benzoquinone;Benzoquinone [un2587];Chinon;Chinone;Cyclohexadiene-1,4-dione;Cyclohexadienedione;Eldoquin;Para-benzoquinone;Para-quinone;Quinone1,4-benzoquinone;Semiquinone anion;Semiquinone radicals;P-benzoquinone;P-chinon;P-quinone;1,4-benzochinon;Quinone
PW_C001860
Quinone
1184
33
2707
2
3835
14
4622
22
4900
3
5891
95
78031
112
78051
329
78728
132
78806
343
120758
407
120884
415
121414
382
122203
124
123355
119
123460
451
123973
399
124755
118
125790
481
126365
299
127245
206
127306
504
127928
388
148
Oxalacetic acid
HMDB0000223
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;3-carboxy-3-oxopropanoic acid;Keto-succinic acid;Oxalacetic acid;Oxobutanedioic acid;3-carboxy-3-oxopropanoate;Keto-succinate;Oxobutanedioate
PW_C000148
Oaa
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
7468
222
7513
224
7517
151
8372
220
8378
225
11744
117
11891
160
12707
291
12717
292
43792
322
77508
132
77533
113
77538
334
77958
112
78009
111
78290
345
80015
368
80700
135
119964
406
120048
408
120062
126
120180
122
120419
124
120815
418
121207
407
122799
374
122813
443
123055
118
123400
454
123777
119
125354
479
125426
482
125439
301
125537
297
125801
489
125807
299
126897
501
126965
502
126977
207
127070
205
127256
506
127261
388
1632
Hydroquinone
HMDB0002434
Hydroquinone, also known as benzene-1,4-diol, is an aromatic organic compound which is a type of phenol, having the chemical formula C6H4(OH)2. Its chemical structure has two hydroxyl groups bonded to a benzene ring in a para position. Hydroquinone is commonly used as a biomarker for benzene exposure. The presence of hydroquinone in normal individuals stems mainly from direct dietary ingestion, catabolism of tyrosine and other substrates by gut bacteria, ingestion of arbutin-containing foods, cigarette smoking, and the use of some over-the-counter medicines. Hydroquinone is a white granular solid at room temperature and pressure. The hydroxyl groups of hydroquinone are quite weakly acidic. Hydroquinone can lose an H+ from one of the hydroxyls to form a monophenolate ion or lose an H+ from both to form a diphenolate ion. Hydroquinone has a variety of uses principally associated with its action as a reducing agent which is soluble in water. It is a major component of most photographic developers where, with the compound Metol, it reduces silver halides to elemental silver.
123-31-9
C00530
785
17594
236-TRICHLOROHYDROQUINONE
764
OC1=CC=C(O)C=C1
C6H6O2
InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H
QIGBRXMKCJKVMJ-UHFFFAOYSA-N
benzene-1,4-diol
110.1106
110.036779436
-0.06
2
α-hydroquinone
0
0
FDB000885
1,4-benzenediol;1,4-dihydroxy-benzeen;1,4-dihydroxy-benzol;1,4-dihydroxybenzen;1,4-diidrobenzene;4-hydroxyphenol;Benzene-1,4-diol;Benzohydroquinone;Benzoquinol;Dihydroquinone;Dihydroxybenzene;Hydrochinon;Hydrochinone;Hydroquinol;Hydroquinole;Hydroquinone;Hydroquinone for synthesis;Hydroquinone gr;Hydroquinoue;Idrochinone;Melanex;Phiaquin;Quinol;Solaquin forte;A-hydroquinone;Alpha-hydroquinone;B-quinol;Beta-quinol;P-benzenediol;P-dihydroxybenzene;P-dioxobenzene;P-dioxybenzene;P-hydroquinone;P-hydroxybenzene;P-hydroxyphenol;1,4-dihydroxybenzene;Eldoquin
PW_C001632
Quinol
1183
33
4623
22
4901
3
5894
95
78032
112
78053
329
78804
343
120759
407
120882
415
121416
382
123356
119
123458
451
123975
399
125791
481
127246
206
127304
504
40711
4Fe-4S
HMDB0061380
Tetrakis(λ¹-iron(1+) ion) tetrasulfane tetrasulfanide belongs to the class of inorganic compounds known as transition metal sulfides. These are inorganic compounds containing a sulfur atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen is a transition metal.
33723
S[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
tetrakis(lambda1-iron(1+) ion) tetrasulfane tetrasulfanide
483.932
483.54763418
0
tetrakis(lambda1-iron(1+) ion) tetrasulfane tetrasulfanide
0
1
PW_C040711
4Fe-4S
4738
3
4859
8
5051
4
5065
2
5403
110
6060
157
6124
163
6508
180
7493
224
12618
164
77160
112
78003
111
80040
370
80681
135
117797
133
117828
132
120009
407
120161
122
122658
406
122673
124
122784
119
125233
120
125248
118
125387
481
125522
297
126790
479
126806
299
126928
206
127057
205
128387
501
128404
388
964
FAD
HMDB0001248
FAD, also known as flavitan or adeflavin, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. FAD is a drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD is slightly soluble (in water) and a moderately acidic compound (based on its pKa). FAD has been found in human liver and muscle tissues, and has also been detected in multiple biofluids, such as feces and blood. Within the cell, FAD is primarily located in the cytoplasm, mitochondria, endoplasmic reticulum and peroxisome. FAD exists in all living organisms, ranging from bacteria to humans. In humans, FAD is involved in the risedronate action pathway, the ibandronate action pathway, the valine, leucine and isoleucine degradation pathway, and the pyrimidine metabolism pathway. FAD is also involved in several metabolic disorders, some of which include the oncogenic action OF L-2-hydroxyglutarate in hydroxygluaricaciduria pathway, gaba-transaminase deficiency, 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency, and the saccharopinuria/hyperlysinemia II pathway. FAD is a condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972).
146-14-5
C00016
643975
16238
FAD
559059
DB03147
CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)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}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
785.5497
785.157134455
-2.27
9
flavine-adenine dinucleotide
0
-3
FDB022511
1h-purin-6-amine flavin dinucleotide;1h-purin-6-amine flavine dinucleotide;Adenine-flavin dinucleotide;Adenine-flavine dinucleotide;Adenine-riboflavin dinuceotide;Adenine-riboflavin dinucleotide;Adenine-riboflavine dinucleotide;Fad;Flamitajin b;Flanin f;Flavin adenine dinucleotide;Flavin adenine dinucleotide oxidized;Flavin-adenine dinucleotide;Flavine adenosine diphosphate;Flavine-adenine dinucleotide;Flavitan;Flaziren;Isoalloxazine-adenine dinucleotide;Riboflavin 5'-adenosine diphosphate;Riboflavin-adenine dinucleotide;Riboflavine-adenine dinucleotide;Adeflavin
PW_C000964
FAD
99
9
114
5
186
8
192
3
216
4
253
17
628
28
825
18
840
2
1188
14
1489
42
1612
29
1622
49
2133
58
2536
22
3723
26
4602
36
4688
31
4741
13
4758
10
4881
6
5268
103
5285
102
5335
111
5496
126
5511
127
5613
118
6030
155
6054
156
6082
161
6116
162
6390
1
6475
178
6499
179
6666
107
7039
163
7175
205
7321
213
7465
222
7487
223
9076
224
11818
216
11887
215
11899
211
12296
225
12328
249
12443
151
12519
227
12595
226
12710
291
12720
292
13029
301
13041
302
43623
318
77080
293
77126
133
77152
134
77501
113
77507
112
77518
115
77541
334
77615
132
77726
337
78054
329
78375
345
78930
331
79222
336
79272
358
80012
368
80034
369
80714
119
119958
406
119999
384
120051
408
120107
407
120432
405
120453
122
120490
124
121278
429
121298
418
121417
382
121489
383
122748
120
122776
121
122802
374
122823
443
123066
376
123087
135
123166
448
123849
464
123868
454
123976
399
124047
398
125348
479
125378
480
125429
482
125474
481
125697
297
125979
489
126107
299
126277
484
126891
501
126920
391
126968
502
126987
207
127011
206
127310
209
127432
506
127602
388
127840
389
42924
ferroheme b
Ferroheme b belongs to the class of organic compounds known as metalloporphyrins. These are polycyclic compounds containing a porphyrin moiety and a metal atom. Ferroheme b is considered to be a practically insoluble (in water) and relatively neutral molecule. Ferroheme b may be a unique E.coli metabolite. Ferroheme b participates in a number of enzymatic reactions. In particular, Ferroheme b can be biosynthesized from protoporphyrin ix and fe2+; which is mediated by the enzyme ferrochelatase. In addition, Ferroheme b and farnesyl pyrophosphate can be converted into heme O; which is mediated by the enzyme heme O synthase.
53356674
[Fe].CC1=C(CCC([O-])=O)C2=N\C\1=C/C1=C(C=C)C(C)=C([N-]1)\C=C1/[N-]\C(=C/C3=N/C(=C\2)/C(CCC([O-])=O)=C3C)C(C)=C1C=C
C34H30FeN4O4
InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/p-4/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;
RNQMHXMGXVQRMV-RGGAHWMASA-J
5,9-bis(2-carboxylatoethyl)-14,19-diethenyl-4,10,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),4,6,8(23),9,11,13,15,17,19-undecaene-21,22-diide iron
614.485
614.163836
-4.07
0
5,9-bis(2-carboxylatoethyl)-14,19-diethenyl-4,10,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),4,6,8(23),9,11,13,15,17,19-undecaene-21,22-diide iron
-4
-2
Protoheme ix, ferroprotoporphyrin ix
PW_C042924
FB
6585
109
7007
189
42789
317
40558
2Fe-2S
HMDB0061344
Bis(λ²-iron(2+) ion) disulfane tetrasulfanide belongs to the class of inorganic compounds known as transition metal sulfides. These are inorganic compounds containing a sulfur atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen is a transition metal.
S[Fe]1(S)S[Fe](S)(S)S1
Fe2H4S6
InChI=1S/2Fe.4H2S.2S/h;;4*1H2;;/q2*+2;;;;;;/p-4
TUVRTRPESCSNGS-UHFFFAOYSA-J
bis(lambda2-iron(2+) ion) disulfane tetrasulfanide
308.112
307.733608534
0
bis(lambda2-iron(2+) ion) disulfane tetrasulfanide
0
2
PW_C040558
2Fe2S
3742
2
4012
8
4257
17
4389
3
4626
5
4754
31
4829
9
4837
28
5056
4
5497
126
5512
127
7046
160
13030
301
13042
302
77715
113
77727
337
78377
134
78386
132
79207
112
117811
133
121586
407
121795
124
122567
384
122664
406
123152
443
123167
448
124144
119
124346
118
125140
121
125239
120
126189
299
126715
480
126796
479
127680
388
128306
391
128394
501
42932
3Fe-4S iron-sulfur cluster
This compound belongs to the class of inorganic compounds known as transition metal hydrides. These are inorganic hydride compounds in which the heaviest metal atom is a transition metal. 3Fe-4S iron-sulfur cluster has the chemical formula Fe3H4S4, and an average molecular weight of 299.81. 3Fe-4S iron-sulfur cluster is involved in multiple pathways, some of which are TCA Cycle (Ubiquinol-8) Pathway, TCA Cycle (Ubiquinol-0) Pathway, TCA Cycle (Ubiquinol-2) Pathway, and TCA Cycle (Ubiquinol-4) Pathway.
6398952
[SH-].[SH-].[SH-].[SH-].[Fe].[Fe].[Fe++]
Fe3H4S4
InChI=1S/3Fe.4H2S/h;;;4*1H2/q;;+2;;;;/p-4
YXXKXRWWNBEVMU-UHFFFAOYSA-J
λ²-iron(2+) ion diiron tetrasulfanide
299.81
299.72549
0
λ²-iron(2+) ion diiron tetrasulfanide
-2
0
Fe3s4 cluster, fe3s4 center, fe3s4, fe3s4 iron-sulfur center, fe3s4 iron-sulfur cluster, [3fe-4s] iron-sulfur center, [3fe-4s]
PW_C042932
3F4Sisc
42958
Ubiquinone-9
Ubiquinone-9 is a member of the chemical class known as Polyprenylbenzoquinones. These are compounds containing a polyisoprene chain attached to a quinone at the second ring position. Ubiquione-9 has 9 isoprene units. Normally in E. coli the active form of Ubiquinone has 8 isoprene units (Ubiquinone-8) and in humans it normally has 10. Ubiquinone-9 is an extended version of Ubiquinone 8 that arises from conjugation by an extended prenyl tail via 4-hydroxybenzoate polyprenyltransferase. Ubiquionone is involved in cellular respiration. It is fat-soluble and is therefore mobile in cellular membranes; it plays a unique role in the electron transport chain (ETC). In the inner bacterial membrane, electrons from NADH and succinate pass through the ETC to the oxygen, which is then reduced to water. The transfer of electrons through ETC results in the pumping of H+ across the membrane creating a proton gradient across the membrane, which is used by ATP synthase (located on the membrane) to generate ATP.
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)CCC=C(C)C)=C(C)C1=O
C54H82O4
InChI=1S/C54H82O4/c1-40(2)22-14-23-41(3)24-15-25-42(4)26-16-27-43(5)28-17-29-44(6)30-18-31-45(7)32-19-33-46(8)34-20-35-47(9)36-21-37-48(10)38-39-50-49(11)51(55)53(57-12)54(58-13)52(50)56/h22,24,26,28,30,32,34,36,38H,14-21,23,25,27,29,31,33,35,37,39H2,1-13H3/b41-24+,42-26+,43-28+,44-30+,45-32+,46-34+,47-36+,48-38+
UUGXJSBPSRROMU-WJNLUYJISA-N
2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]cyclohexa-2,5-diene-1,4-dione
795.2265
794.621311112
-6.56
0
ubiquinone 9
0
0
PW_C042958
U9
42957
Ubiquinol-9
Ubiquinol-9 is a member of the chemical class known as Polyprenylbenzoquinols. They are reduced forms of polyprenylbenzoquinines (ubiquinones). These are compounds containing a polyisoprene chain attached to a quinol at the second ring position. Ubiquiol-9 has just 9 isoprene units. Normally in E. coli the active form of Ubiquinol has 8 isoprene units (Ubiquinol-8) and in humans it normally has 10. Ubiquinol-9 is an extended version of Ubiquinol 8 that arises from conjugation by an extended prenyl tail via 4-hydroxybenzoate polyprenyltransferase. Coenzyme Q(n) exists in three redox states, fully oxidized (ubiquinone), partially reduced (semiquinones or ubisemiquinones), and fully reduced (ubiquinols). The redox functions of ubiquinol in cellular energy production and antioxidant protection are based on the ability to exchange two electrons in a redox cycle between ubiquinol (reduced) and the ubiquinone (oxidized) form. Ubiquionols are important in cellular respiration. They are fat-soluble and therefore mobile in cellular membranes; they play a unique role in the electron transport chain (ETC). In the inner bacterial membrane, electrons from NADH and succinate pass through the ETC to the oxygen, which is then reduced to water. The transfer of electrons through ETC results in the pumping of H+ across the membrane creating a proton gradient across the membrane, which is used by ATP synthase (located on the membrane) to generate ATP.
[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=C(C)C(O)=C(OC)C(OC)=C1O)=C(\C)CCC=C(C)C
C54H84O4
InChI=1S/C54H84O4/c1-40(2)22-14-23-41(3)24-15-25-42(4)26-16-27-43(5)28-17-29-44(6)30-18-31-45(7)32-19-33-46(8)34-20-35-47(9)36-21-37-48(10)38-39-50-49(11)51(55)53(57-12)54(58-13)52(50)56/h22,24,26,28,30,32,34,36,38,55-56H,14-21,23,25,27,29,31,33,35,37,39H2,1-13H3/b41-24+,42-26+,43-28+,44-30+,45-32+,46-34+,47-36+,48-38+
NPCOQXAVBJJZBQ-WJNLUYJISA-N
2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]benzene-1,4-diol
797.2424
796.636961176
-6.51
2
2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]benzene-1,4-diol
0
0
PW_C042957
U9
88
Fumaric acid
HMDB0000134
Fumaric acid is a precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase. Fumarate is converted by fumarase to malate. A fumarate is a salt or ester of the organic compound fumaric acid, a dicarboxylic acid. (wikipedia).
110-17-8
C00122
21883788
18012
FUM
10197150
DB04299
OC(=O)\C=C\C(O)=O
C4H4O4
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
VZCYOOQTPOCHFL-OWOJBTEDSA-N
(2E)-but-2-enedioic acid
116.0722
116.010958616
2
fumaric acid
0
-2
FDB003291
(2e)-but-2-enedioate;(2e)-but-2-enedioic acid;(e)-2-butenedioate;(e)-2-butenedioic acid;2-(e)-butenedioate;2-(e)-butenedioic acid;Allomaleate;Allomaleic acid;Boletate;Boletic acid;Fc 33;Fumarate;Fumaric acid;Lichenate;Lichenic acid;Sodium fumarate;Trans-1,2-ethylenedicarboxylate;Trans-1,2-ethylenedicarboxylic acid;Trans-2-butenedioate;Trans-2-butenedioic acid;Trans-butenedioate;Trans-butenedioic acid;(2e)-2-butenedioic acid;E297;Fumarsaeure;Trans-but-2-enedioic acid;(2e)-2-butenedioate;Trans-but-2-enedioate
PW_C000088
Fumarat
102
8
254
17
2004
2
5053
4
5388
102
6047
156
6107
162
6458
107
6459
108
6492
179
6763
117
6837
166
7480
223
9065
151
11804
198
12713
290
42400
322
42496
318
42497
315
77148
134
77466
111
79107
132
80027
369
117808
133
119989
384
120043
122
121599
124
122661
406
122772
121
122794
135
124157
118
125236
120
125369
480
125421
297
126793
479
126911
391
126960
205
127565
388
128391
501
940
Acetyl-CoA
HMDB0001206
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;Accoa;Acetyl coenzyme a;S-acetyl-coa;S-acetyl-coenzyme a;Acetylcoenzyme a
PW_C000940
Ac-CoA
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
7460
222
8245
151
8277
210
12582
226
13012
299
42615
315
77121
133
77291
111
77562
112
77706
132
77994
115
78355
134
78433
334
80007
368
80634
119
80663
376
90124
170
119953
406
120145
405
120304
122
120632
407
122417
408
122626
384
122743
120
122959
135
123137
118
124986
374
125200
121
125343
479
125507
478
125633
297
126564
482
126572
481
126778
480
126886
501
127044
209
127394
205
127665
388
128137
502
128145
206
128374
391
63
Citric acid
HMDB0000094
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;2-hydroxytricarballylic acid;Citronensaeure;E330;H3cit;2-hydroxytricarballylate
PW_C000063
CA
219
4
2415
2
5372
103
6034
155
6089
161
6479
178
7469
222
77132
133
79053
132
80016
368
111712
8
119965
406
122397
124
122754
120
124967
118
125355
479
126538
299
126898
501
128111
388
40034
Hydrogen Ion
HMDB0059597
Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])
C00080
1038
15378
1010
[H+]
H
InChI=1S/p+1
GPRLSGONYQIRFK-UHFFFAOYSA-N
hydron
1.0079
1.007825032
0
hydron
1
0
H+;H(+);Hydrogen cation;Hydron;Proton
PW_C040034
H+
215
4
670
8
753
15
788
31
848
3
1116
2
1463
26
1464
54
2231
49
2780
17
4250
22
4254
42
4547
10
4576
18
4694
70
5241
103
5327
111
5353
112
5626
108
5639
107
5699
100
5720
105
5742
117
5963
147
6037
155
6070
157
6093
161
6130
159
6232
166
6483
178
6601
152
6692
101
6843
188
6910
187
7100
163
7168
205
7191
206
7453
219
7454
220
7472
222
7525
213
7532
210
7558
212
7572
160
7590
170
8195
225
8218
151
8243
226
8413
162
8420
224
9139
195
9155
249
11915
164
12015
281
12181
285
12246
286
12266
287
12521
227
13257
223
13325
294
15330
308
42329
315
42354
318
42401
322
42405
312
42454
320
76912
293
77136
133
77210
134
77372
331
77804
114
77955
132
77990
327
77991
347
78379
345
79929
130
80019
368
80387
310
80388
304
80722
119
93823
124
94823
383
110550
388
112855
94
113280
390
115537
398
115539
118
115856
336
116205
109
119973
406
120193
407
120549
122
120593
409
121170
424
121171
425
122569
418
122615
384
122687
125
122758
120
123183
135
123218
137
123742
459
123743
460
125141
454
125188
121
125273
136
125359
479
125550
481
125730
483
125736
297
125809
299
126517
495
126717
489
126766
480
126823
300
126902
501
127213
208
128308
506
128361
391
128430
395
6442
Aconitate hydratase 1
P25516
Involved in metabolic process. May have an iron-responsive regulatory function.
acnA
b1276
AP009048
3
4.2.1.3
6556
Aconitate hydratase 2
P36683
Involved in metabolic process. Citrate = isocitrate.
acnB
b0118
AP009048
3
4.2.1.3; 4.2.1.99
11746
117
5941
Isocitrate dehydrogenase [NADP]
P08200
Involved in magnesium ion binding. Isocitrate + NADP(+) = 2-oxoglutarate + CO(2) + NADPH.
icd
b1136
AF017587
3
1.1.1.42
6272
2-oxoglutarate dehydrogenase E1 component
P0AFG3
Involved in oxoglutarate dehydrogenase (succinyl-transferring) activity. 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).
sucA
b0726
AP009048
3
1.2.4.2
6273
Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex
P0AFG6
Involved in transferase activity, transferring acyl groups. 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).
sucB
b0727
AP009048
3
2.3.1.61
7773
lipoamide dehydrogenase
P0A9P0
lpd
3
11743
117
6289
Succinyl-CoA ligase [ADP-forming] subunit alpha
P0AGE9
Involved in catalytic activity. ATP + succinate + CoA = ADP + phosphate + succinyl-CoA.
sucD
b0729
AP009048
3
6.2.1.5
6067
Succinyl-CoA ligase [ADP-forming] subunit beta
P0A836
Involved in ATP binding. ATP + succinate + CoA = ADP + phosphate + succinyl-CoA.
sucC
b0728
AP009048
3
6.2.1.5
6548
Malate:quinone oxidoreductase
P33940
Involved in malate dehydrogenase (quinone) activity. (S)-malate + a quinone = oxaloacetate + reduced quinone.
mqo
b2210
AP009048
3
1.1.5.4
7788
succinate:quinone oxidoreductase, FAD binding protein
P0AC41
SdhA
3
8588
109
135552
285
135929
308
137247
101
138070
730
7789
succinate dehydrogenase, FeS subunit
P07014
3
8589
109
137248
101
138071
730
7790
succinate dehydrogenase
P69054
3
8590
109
137249
101
138072
730
7791
succinate dehydrogenase fumarate reductase, membrane anchor subunit
P0AC44
sdhD
3
8591
109
137250
101
138073
730
7757
Citrate synthase monomer
P0ABH7
gltA
3
138075
117
6671
Malate dehydrogenase
P61889
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor. Catalyzes the reversible oxidation of malate to oxaloacetate.
mdh
b3236
AP009048
3
1.1.1.37
6196
Fumarate hydratase class I, aerobic
P0AC33
Involved in lyase activity. It functions as an aerobic enzyme in the citric acid cycle. It accounts for about 80% of the fumarase activity when the bacteria grows aerobically.
fumA
b1612
AP009048
3
4.2.1.2; 5.3.2.2
6336
Fumarate hydratase class I, anaerobic
P14407
Involved in lyase activity. It functions in the generation of fumarate for use as an anaerobic electron acceptor.
fumB
b4122
AP009048
3
4.2.1.2; 4.2.1.81
5880
Fumarate hydratase class II
P05042
Involved in fumarate hydratase activity. (S)-malate = fumarate + H(2)O.
fumC
b1611
AP009048
3
4.2.1.2
8587
101
138074
731
1295
Citrate hydro-lyase (cis-aconitate-forming)
3
PW_P001295
1500
6442
2
1294
Citrate hydro-lyase
3
PW_P001294
1499
6556
2
1296
citrate dehydrogenase
3
PW_P001296
1501
5941
2
1312
2-oxoglutarate dehydrogenase
3
PW_P001312
1517
6272
12
1518
6273
24
1519
7773
2
1327
succinyl-CoA synthetase
3
PW_P001327
1544
6289
2
1545
6067
2
1334
malate:quinone oxidoreductase
3
PW_P001334
1557
6548
1328
succinate:quinone oxidoreductase
3
PW_P001328
1546
7788
1
1547
7789
1
1548
7790
1
1549
7791
1
527
40711
528
964
529
42924
530
40558
531
42932
1293
citrate synthase
3
PW_P001293
1498
7757
6
1333
malate dehydrogenase
3
PW_P001333
1556
6671
2
1332
fumarase hydratase
3
PW_P001332
1553
6196
2
1554
6336
2
1555
5880
4
183174
false
PW_R183174
Right
692524
51
1
Compound
false
692525
1420
1
Compound
false
692526
1246
1
Compound
false
172963
1295
183175
false
PW_R183175
Right
692527
51
1
Compound
false
692528
1420
1
Compound
false
692529
1246
1
Compound
false
172964
1294
2592
false
PW_R002592
Right
10102
1246
1
Compound
false
10103
143
1
Compound
false
10104
1316
1
Compound
false
10105
146
1
Compound
false
10106
134
1
Compound
false
2564
1296
1.1.1.42
2608
false
PW_R002608
Right
10191
134
1
Compound
false
10192
721
1
Compound
false
10193
1099
1
Compound
false
10194
1144
1
Compound
false
10195
1316
1
Compound
false
10196
808
1
Compound
false
2593
1312
1.2.4.2
2618
false
PW_R002618
Right
10233
808
1
Compound
false
10234
1034
1
Compound
false
10235
1104
1
Compound
false
10236
414
1
Compound
false
10237
1099
1
Compound
false
10238
174
1
Compound
false
2606
1327
6.2.1.5
2630
false
PW_R002630
Right
10283
101
1
Compound
false
10284
1860
1
Compound
false
10285
148
1
Compound
false
10286
1632
1
Compound
false
2620
1334
3752
false
PW_R003752
Right
15105
174
1
Compound
false
15106
42958
1
Compound
false
15107
88
1
Compound
false
15108
42957
1
Compound
false
3726
1328
2588
false
PW_R002588
Right
10085
148
1
Compound
false
10086
1420
1
Compound
false
10087
940
1
Compound
false
10088
63
1
Compound
false
10089
1099
1
Compound
false
10090
40034
1
Compound
false
2558
1293
2625
false
PW_R002625
Right
10258
101
1
Compound
false
10259
721
1
Compound
false
10260
148
1
Compound
false
10261
1144
1
Compound
false
10262
40034
1
Compound
false
2613
1333
1.1.1.37
2624
false
PW_R002624
Right
10255
88
1
Compound
false
10256
1420
1
Compound
false
10257
101
1
Compound
false
2612
1332
4.2.1.2
183176
false
PW_R183176
Right
692530
63
1
Compound
false
692531
1420
1
Compound
false
692532
51
1
Compound
false
172965
1295
4.2.1.3
183177
false
PW_R183177
Right
692533
63
1
Compound
false
692534
1420
1
Compound
false
692535
51
1
Compound
false
172966
1294
4.2.1.3
2718225
51
3
false
1802
928
10
regular
100
110
2718226
1420
49
false
1107
794
10
regular
78
78
2718227
1420
49
false
1674
790
10
regular
78
78
2718228
1420
49
false
1899
1094
10
regular
78
78
2718229
1420
49
false
324
1235
10
regular
78
78
2718230
1246
3
false
1799
1438
10
regular
100
110
2718231
143
61
false
1904
1593
10
regular
50
30
2718232
1316
52
false
1712
1789
10
regular
78
78
2718233
1316
52
false
1243
1888
10
regular
78
78
2718234
146
62
false
1912
1813
10
regular
50
30
2718235
134
3
false
1802
1983
10
regular
100
110
2718236
721
59
false
1632
2065
10
regular
50
30
2718237
721
59
false
507
659
10
regular
50
30
2718238
1099
85
false
1422
821
10
regular
50
30
2718239
1099
85
false
1667
1935
10
regular
50
30
2718240
1099
85
false
562
1924
10
regular
50
30
2718241
1144
60
false
1287
2083
10
regular
50
30
2718242
1144
60
false
852
809
10
regular
50
30
2718243
808
3
false
1102
1981
10
regular
100
100
2718244
1034
43
false
967
1943
10
regular
50
30
2718245
1104
46
false
965
2098
10
regular
44
43
2718246
414
42
false
572
2134
10
regular
50
30
2718247
174
3
false
402
1984
10
regular
100
100
2718248
101
3
false
402
879
10
regular
100
100
2718249
1860
3
false
342
319
10
regular
100
100
2718250
148
3
false
952
681
10
regular
100
110
2718251
1632
3
false
772
369
10
regular
100
100
2718252
40711
9
false
492
1719
10
regular
100
25
2718253
964
9
false
407
1674
20
regular
100
25
2718254
42924
9
false
397
1624
20
regular
100
25
2718255
40558
9
false
522
1609
10
regular
100
25
2718256
42932
9
false
587
1654
10
regular
100
45
2718257
42958
3
false
292
1839
10
regular
100
100
2718258
42957
3
false
292
1489
10
regular
100
100
2718259
88
3
false
397
1364
10
regular
100
100
2718260
940
3
false
1097
564
10
regular
100
100
2718261
63
3
false
1557
686
10
regular
100
100
2718262
40034
55
false
1457
596
10
regular
78
78
2718263
40034
55
false
853
604
10
regular
78
78
964244
6442
6
false
1717
1193
8
subunit
regular
160
80
964245
6556
6
false
1767
1248
19
subunit
regular
160
80
964246
5941
6
false
1767
1693
8
subunit
regular
160
80
964247
6272
136
false
1337
1890
8
subunit
regular
175
155
964248
6273
136
false
1467
1895
8
subunit
regular
175
155
964249
7773
6
false
1404
1995
8
subunit
regular
160
80
964250
6289
6
false
672
1952
8
subunit
regular
160
80
964251
6067
6
false
727
1992
8
subunit
regular
160
80
964252
6548
2
false
527
384
8
subunit
regular
150
70
964253
7788
109
2
false
492
1674
8
subunit
regular
150
70
964254
7789
109
2
false
492
1619
8
subunit
regular
150
70
964255
7790
109
2
false
377
1634
19
subunit
regular
150
70
964256
7791
109
2
false
377
1684
8
subunit
regular
150
70
964257
7757
17
false
1207
698
8
subunit
regular
180
85
964258
6671
6
false
592
696
8
subunit
regular
160
80
964259
6196
6
false
317
1031
8
subunit
regular
160
80
964260
6336
6
false
432
1036
8
subunit
regular
160
80
964261
5880
101
8
false
382
1083
8
subunit
regular
140
85
964262
6442
6
false
1772
636
12
subunit
regular
160
80
964263
6556
6
false
1772
696
19
subunit
regular
160
80
816457
1295
757
960009
964244
816458
1294
757
960010
964245
816459
1296
757
960011
964246
816460
1312
757
960012
964247
960013
964248
960014
964249
816461
1327
757
960015
964250
960016
964251
816462
1334
757
960017
964252
816463
1328
757
960018
964253
960019
964254
960020
964255
960021
964256
37014
2718252
3720506
Cofactor
37015
2718253
3720507
Cofactor
37016
2718254
3720508
Cofactor
37017
2718255
3720509
Cofactor
37018
2718256
3720510
Cofactor
816464
1293
757
960022
964257
816465
1333
757
960023
964258
816466
1332
757
960024
964259
960025
964260
960026
964261
816467
1295
757
960027
964262
816468
1294
757
960028
964263
3720476
M1002 791 C1001 878 1003 963 1002 995
5
false
18
true
M 995.3519105072328 981.5537028853234 L 1002 995 L 1010.3207901417596 982.5194370552929
false
3720477
M1147 564 C1147 519 1165 452 1272 449
5
false
18
true
M 986.1276983822503 690.1972439813574 L 992 704 L 1001.0173865455082 692.013059611023
false
3720478
M452 2084 C452 2114 452 2154 452 2184
5
false
18
true
M 554.5 1851.9903810567666 L 547 1839 L 539.5 1851.9903810567666
false
3720479
M1852 1038 C1852 1068 1847 1218 1847 1248
5
false
18
3720480
M1899 1133 C1841 1132 1847 1218 1847 1248
5
false
18
3720481
M1849 1438 C1849 1408 1847 1358 1847 1328
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720482
M1852 1038 C1852 1068 1847 1218 1847 1248
5
false
18
3720483
M1899 1133 C1841 1132 1847 1218 1847 1248
5
false
18
3720484
M1849 1438 C1849 1408 1847 1358 1847 1328
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720485
M1849 1548 C1849 1578 1847 1663 1847 1693
5
false
18
3720486
M1904 1608 C1838 1604 1847 1663 1847 1693
5
false
18
3720487
M1790 1828 C1846 1834 1847 1803 1847 1773
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720488
M1912 1828 C1874 1830 1847 1803 1847 1773
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720489
M1852 1983 C1852 1953 1847 1803 1847 1773
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720490
M1802 2038 C1772 2038 1594 2035 1564 2035
5
false
18
3720491
M1632 2080 C1622 2035 1627 2035 1564 2035
5
false
18
3720492
M1692 1965 C1694 2007 1594 2035 1564 2035
5
false
18
3720493
M1337 2098 C1337 2004 1374 2035 1404 2035
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720494
M1321 1927 C1327 2031 1374 2035 1404 2035
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720495
M1202 2031 C1232 2031 1374 2035 1404 2035
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720496
M1102 2031 C1072 2031 917 2032 887 2032
5
false
18
3720497
M992 1973 C1000 2033 914 2030 887 2032
5
false
18
3720498
M987 2098 C989 2035 910 2034 887 2032
5
false
18
3720499
M597 2134 C594 2071 697 2032 727 2032
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720500
M587 1954 C588 2029 697 2032 727 2032
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720501
M502 2034 C532 2034 697 2032 727 2032
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720502
M452 879 C450 749 449 451 449 419 C480 418 495 418 527 419
5
false
18
3720503
M442 369 C467 424 497 419 527 419
5
false
18
3720504
M1002 681 C1001 653 1003 480 1003 421 C970 421 930 418 872 419
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720505
M772 419 C730 419 707 419 677 419
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720506
M322 1809 L322 1859 L372 1809 z
10
true
18
3720507
M322 1789 L322 1839 L372 1789 z
10
true
18
3720508
M322 1769 L322 1819 L372 1769 z
10
true
18
3720509
M322 1749 L322 1799 L372 1749 z
10
true
18
3720510
M322 1709 L322 1759 L372 1709 z
10
true
18
3720511
M452 1984 C452 1954 452 1784 452 1754
5
false
18
3720512
M392 1889 C472 1887 452 1784 452 1754
5
false
18
3720513
M392 1539 C465 1539 451 1661 452 1684
5
false
18
true
M 25.946855044164835 1331.5948896296293 L 11 1330.3333333333333 L 17.380887721185843 1343.9084676564116
false
3720514
M447 1464 C447 1494 452 1654 452 1684
5
false
18
true
M 25.946855044164835 1331.5948896296293 L 11 1330.3333333333333 L 17.380887721185843 1343.9084676564116
false
3720515
M1052 736 C1082 736 1177 738 1207 738
5
false
18
3720516
M1146 794 C1144 732 1177 738 1207 738
5
false
18
3720517
M1147 664 C1137 749 1177 738 1207 738
5
false
18
3720518
M1557 736 C1527 736 1417 738 1387 738
5
false
18
true
M 248.94685504416483 496.261556296296 L 234 495 L 240.38088772118584 508.5751343230783
false
3720519
M1447 821 C1444 749 1417 738 1387 738
5
false
18
true
M 248.94685504416483 496.261556296296 L 234 495 L 240.38088772118584 508.5751343230783
false
3720520
M1496 674 C1486 738 1417 738 1387 738
5
false
18
true
M 248.94685504416483 496.261556296296 L 234 495 L 240.38088772118584 508.5751343230783
false
3720521
M452 879 C450 735 545 741 592 736
5
false
18
3720522
M532 689 C530 739 549 737 592 736
5
false
18
3720523
M952 736 C922 736 782 736 752 736
5
false
18
true
M 226.94685504416483 614.261556296296 L 212 613 L 218.38088772118584 626.5751343230784
false
3720524
M877 809 C870 778 799 735 752 736
5
false
18
true
M 226.94685504416483 614.261556296296 L 212 613 L 218.38088772118584 626.5751343230784
false
3720525
M892 682 C887 722 840 735 752 736
5
false
18
true
M 226.94685504416483 614.261556296296 L 212 613 L 218.38088772118584 626.5751343230784
false
3720526
M447 1364 C447 1334 452 1198 452 1168
5
false
18
3720527
M402 1274 C454 1272 452 1198 452 1168
5
false
18
3720528
M452 979 C452 1009 452 1053 452 1083
5
false
18
true
M 227.94685504416483 946.261556296296 L 213 945 L 219.38088772118584 958.5751343230784
false
3720529
M1657 736 C1687 736 1742 736 1772 736
5
false
18
3720530
M1713 790 C1713 758 1697 732 1657 736
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720531
M1852 928 C1854 838 1852 872 1852 776
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720532
M1657 736 C1687 736 1742 736 1772 736
5
false
18
3720533
M1713 790 C1713 758 1697 732 1657 736
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3720534
M1852 928 C1854 838 1852 872 1852 776
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
810550
757
183174
3274358
2718225
3720479
Left
3274359
2718228
3720480
Left
3274360
2718230
3720481
Right
765985
2561
816457
810551
757
183175
3274361
2718225
3720482
Left
3274362
2718228
3720483
Left
3274363
2718230
3720484
Right
765986
2562
816458
810552
757
2592
3274364
2718230
3720485
Left
3274365
2718231
3720486
Left
3274366
2718232
3720487
Right
3274367
2718234
3720488
Right
3274368
2718235
3720489
Right
765987
2564
816459
810553
757
2608
3274369
2718235
3720490
Left
3274370
2718236
3720491
Left
3274371
2718239
3720492
Left
3274372
2718241
3720493
Right
3274373
2718233
3720494
Right
3274374
2718243
3720495
Right
765988
2593
816460
810554
757
2618
3274375
2718243
3720496
Left
3274376
2718244
3720497
Left
3274377
2718245
3720498
Left
3274378
2718246
3720499
Right
3274379
2718240
3720500
Right
3274380
2718247
3720501
Right
765989
2606
816461
810555
757
2630
3274381
2718248
3720502
Left
3274382
2718249
3720503
Left
3274383
2718250
3720504
Right
3274384
2718251
3720505
Right
765990
2620
816462
810556
757
3752
3274385
2718247
3720511
Left
3274386
2718257
3720512
Left
3274387
2718258
3720513
Right
3274388
2718259
3720514
Right
765991
2607
816463
810557
757
2588
3274389
2718250
3720515
Left
3274390
2718226
3720516
Left
3274391
2718260
3720517
Left
3274392
2718261
3720518
Right
3274393
2718238
3720519
Right
3274394
2718262
3720520
Right
765992
2558
816464
810558
757
2625
3274395
2718248
3720521
Left
3274396
2718237
3720522
Left
3274397
2718250
3720523
Right
3274398
2718242
3720524
Right
3274399
2718263
3720525
Right
765993
2613
816465
810559
757
2624
3274400
2718259
3720526
Left
3274401
2718229
3720527
Left
3274402
2718248
3720528
Right
765994
2612
816466
810560
757
183176
3274403
2718261
3720529
Left
3274404
2718227
3720530
Right
3274405
2718225
3720531
Right
765995
2560
816467
810561
757
183177
3274406
2718261
3720532
Left
3274407
2718227
3720533
Right
3274408
2718225
3720534
Right
765996
2559
816468
110905
111203
757
14
false
927
995
16
regular
107583
2718250
3720476
Right
110906
111204
757
14
false
1272
414
16
regular
107584
2718260
3720477
Right
110907
111205
757
14
false
377
2184
16
regular
107585
2718247
3720478
Right
188174
760
1120
1.6
1.6
0
2
92
479
481
371786
M225 374 C225 324 275 274 325 274 C810 274 1440 274 1925 274 C1975 274 2025 324 2025 374 C2025 935 2025 1663 2025 2224 C2025 2274 1975 2324 1925 2324 C1440 2324 810 2324 325 2324 C275 2324 225 2274 225 2224 C225 1663 225 935 225 374
1
true
6
1800.0
2050.0
371787
M125 275 C125 225 175 175 225 175 C770 175 1480 175 2025 175 C2075 175 2125 225 2125 275 C2125 896 2125 1704 2125 2325 C2125 2375 2075 2425 2025 2425 C1480 2425 770 2425 225 2425 C175 2425 125 2375 125 2325 C125 1704 125 896 125 275
1
true
6
2000.0
2250.0