9186
Context
Vitamin A Deficiency
Vitamin A deficiency can be caused by many causes. A defect in the BCMO1 gene which codes for beta,beta-carotene 15,15’-monooxygenase is one of them. Beta,beta-carotene 15,15’-monooxygenase catalyzes the chemical reaction where the two substrates are beta-carotene and O2, whereas its product is retinal. A defect in this enzyme results in decrease of levels of retinal and vitamin A in serum; Signs and symptoms include night blindness, poor adaptation to darkness, dry skin and hair.
Disease
PW121979
Center
PathwayVisualizationContext122255
2380
4300
#000099
PathwayVisualization88128
88254
Retinol Metabolism
Retinol, the animal form of vitamin A, is a fat-soluble vitamin important in vision and bone growth. Retinol is among the most usable forms of vitamin A, which also include retinal (aldehyde form), retinoic acid (acid form) and retinyl ester (ester form). Retinol is normaly ingested in a precursor form. Typically animal sources (liver and eggs) contain retinyl esters, whereas plants (carrots, spinach) contain pro-vitamin A carotenoids. Hydrolysis of retinyl esters results in retinol, while pro-vitamin A carotenoids can be cleaved to produce retinal. Retinal (retinaldehyde) can be reversibly reduced to produce retinol or it can be irreversibly oxidized to produce retinoic acid. Retinoic acid is derived from retinol by oxidation through retinol and retinal dehydrogenases and several cytochrome p450s (CYPs). Many different geometric isomers of retinol, retinal and retinoic acid are possible as a result of either a trans or cis configuration of four of the five double bonds found in the polyene chain. The cis isomers are less stable and can readily convert to the all-trans configuration. Nevertheless, some cis isomers are found naturally and carry out essential functions. For example, the 11-cis-retinal isomer is the chromophore of rhodopsin, the vertebrate photoreceptor molecule. Retinoic acid plays an important role in regulating cell growth and differentiation. Retinoic acid can be oxidized to several metabolites by a panel of CYPs that differs for the different retinoic acid isomers. CYP26A1 is involved in the metabolic breakdown of retinoic acid by 4-hydroxylation. CYP26A1-mediated 4-hydroxylation is specific for all-trans-retinoic acid but not for the isomers 13-cis-retinoic acid and 9-cis-retinoic acid. CYP26C1 can also hydroxylate the trans form of retinoic acid it is unique in hydroxylating the 9-cis isomer of retinoic acid. CYP26B1 can also deactivate all-trans-retinoic acid by 4-hydroxylation. Another recently discovered cytochrome P450, called CYP2S1 is expressed in skin cells and is inducible by UV radiation, coal tar and all-trans retinoate. All trans retinoic acid also serves as a substrate for this enzyme. Phase II metabolism, mainly glucuronidation, is also observed for retinoic acid.
Metabolic
17
1
Cell
CL:0000000
5
Hepatocyte
CL:0000182
4
Cardiomyocyte
CL:0000746
3
Neuron
CL:0000540
7
Epithelial Cell
CL:0000066
2
Platelet
CL:0000233
6
Myocyte
CL:0000187
1
Homo sapiens
9606
Eukaryote
Human
12
Mus musculus
10090
Eukaryote
Mouse
5
Bos taurus
9913
Eukaryote
Cattle
17
Rattus norvegicus
10116
Eukaryote
Rat
10
Drosophila melanogaster
7227
Eukaryote
Fruit fly
6
Caenorhabditis elegans
6239
Eukaryote
Roundworm
2
Bacteria
2
Prokaryote
Bacteria
3
Escherichia coli
562
Prokaryote
19
Schizosaccharomyces pombe
4896
Eukaryote
24
Solanum lycopersicum
4081
Eukaryote
Tomato
4
Arabidopsis thaliana
3702
Eukaryote
Thale cress
18
Saccharomyces cerevisiae
4932
Eukaryote
Yeast
21
Xenopus laevis
8355
Eukaryote
African clawed frog
23
Pseudomonas aeruginosa
287
Prokaryote
60
Nitzschia sp.
0001
Eukaryote
Nitzschia4
25
Escherichia coli (strain K12)
83333
Prokaryote
49
Bathymodiolus platifrons
220390
Eukaryote
Deep sea mussel
1
Cytosol
GO:0005829
3
Mitochondrial Matrix
GO:0005759
2
Mitochondrion
GO:0005739
5
Cytoplasm
GO:0005737
7
Endoplasmic Reticulum Membrane
GO:0005789
25
Golgi apparatus
GO:0005794
4
Peroxisome
GO:0005777
12
Mitochondrial Inner Membrane
GO:0005743
6
Lysosome
GO:0005764
13
Endoplasmic Reticulum
GO:0005783
16
Lysosomal Lumen
GO:0043202
35
Chloroplast
GO:0009507
10
Cell Membrane
GO:0005886
31
Periplasmic Space
GO:0005620
19
sarcoplasmic reticulum
GO:0016529
36
Membrane
GO:0016020
39
Mitochondrial membrane
GO:0031966
8
Smooth Endoplasmic Reticulum
GO:0005790
14
Mitochondrial Outer Membrane
GO:0005741
27
Peroxisome Membrane
GO:0005778
11
Extracellular Space
GO:0005615
18
Melanosome Membrane
GO:0033162
20
Endoplasmic Reticulum Lumen
GO:0005788
21
Synapse
GO:0045202
15
Nucleus
GO:0005634
53
Endoplasmic Reticulum Body
GO:0010168
34
Plant-Type Vacuole
GO:0000325
40
Periplasm
GO:0042597
24
Mitochondrial Intermembrane Space
GO:0005758
37
Basolateral cell membrane
GO:0016323
1
Liver
BTO:0000759
72
9
11
Heart
BTO:0000562
73
10
5
cardiocyte
BTO:0001539
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
3
Sympathetic Nervous System
BTO:0001832
2
Endothelium
BTO:0000393
9
Muscle
BTO:0000887
141
18
2
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1
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PW_BS000159
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PW_BS000024
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PW_BS000024
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PW_BS000170
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10
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PW_BS000024
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PW_BS000164
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PW_BS000024
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PW_BS000115
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PW_BS000053
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PW_BS000011
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14
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PW_BS000112
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14
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PW_BS000113
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14
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1448
11-cis-Retinaldehyde
HMDB0002152
Vitamin A (all-trans retinol) is converted in the retina to the 11-cis-isomer of retinaldehyde or 11-cis-retinal. 11-cis-retinal functions in the retina in the transduction of light into the neural signals necessary for vision. 11-cis-retinal, while attached to opsin in rhodopsin is isomerized to all-trans-retinal by light. This is the event that triggers the nerve impulse to the brain which allows for the perception of light. All-trans-retinal is then released from opsin and reduced to all-trans-retinol. All-trans-retinol is isomerized to 11-cis-retinol in the dark, and then oxidized to 11-cis-retinal. 11-cis-retinal recombines with opsin to re-form rhodopsin. Night blindness or defective vision at low illumination results from a failure to resynthesize 11-cis retinal rapidly (http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/vit_0260.shtml).
564-87-4
C02110
5280490
16066
CPD-881
4444130
C/C(/C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=O
C20H28O
InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6-,12-11+,16-8+,17-13+
NCYCYZXNIZJOKI-IOUUIBBYSA-N
(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal
284.4357
284.214015518
-4.83
0
11-cis-retinal
0
0
FDB022871
11-cis-retinal;Cis-11-retinal;(2e,4z,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal;11-cis-retinene;11-cis-vitamin a aldehyde
PW_C001448
C-RetAl
3189
2
78782
132
122528
124
125089
118
126680
299
128260
388
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
1048
Retinal
HMDB0001358
Retinal is a carotenoid constituent of visual pigments. It is the oxidized form of retinol which functions as the active component of the visual cycle. It is bound to the protein opsin forming the complex rhodopsin. When stimulated by visible light, the retinal component of the rhodopsin complex undergoes isomerization at the 11-position of the double bond to the cis-form; this is reversed in "dark" reactions to return to the native trans-configuration.
116-31-4
C00376
638015
17898
CPD-881
553582
C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O
C20H28O
InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
NCYCYZXNIZJOKI-OVSJKPMPSA-N
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal
284.4357
284.214015518
-4.83
0
retinaldehyde
0
0
FDB022576
3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal;All-e-retinal;All-epsilon-retinal;All-trans-retinal;All-trans-retinaldehyde;All-trans-vitamin a aldehyde;All-trans-retinene;Axerophthal;E-retinal;Retinal;Retinaldehyde;Retinene;Retinene 1;Vitamin a aldehyde;Vitamin a1 aldehyde;Alpha-retinene;Epsilon-retinal;Trans-retinal;Trans-vitamin a aldehyde
PW_C001048
Retinal
3190
2
78783
132
122529
124
125090
118
126681
299
128261
388
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
9795
Zinc
HMDB0015532
Zinc is an essential element, necessary for sustaining all life. It is a trace element in the diet, forming an essential part of many enzymes, and playing an important role in protein synthesis and in cell division. Physiologically, it exists as an ion in the body. It is estimated that 3000 of the hundreds of thousands of proteins in the human body contain zinc prosthetic groups. In addition, there are over a dozen cell types in the human body that secrete zinc ions, and the roles of these secreted zinc signals in medicine and health are now being actively studied. Intriguingly, brain cells in the mammalian forebrain are one type of cell that secretes zinc, along with its other neuronal messenger substances. Cells in the salivary gland, prostate, immune system, and intestine are other types that secrete zinc. Obtaining a sufficient zinc intake during pregnancy and in young children is a problem, especially among those who cannot afford a good and varied diet. Zinc deficiency is associated with anemia, short stature, hypogonadism, impaired wound healing, and geophagia. Brain development is stunted by zinc deficiency in utero and in youth. Zinc is an activator of certain enzymes, such as carbonic anhydrase. Carbonic anhydrase is important in the transport of carbon dioxide in vertebrate blood. Even though zinc is an essential requirement for a healthy body, too much zinc can be harmful. Excessive absorption of zinc can also suppress copper and iron absorption. The free zinc ion in solution is highly toxic to plants, invertebrates, and even vertebrate fish. The Free Ion Activity Model (FIAM) is well-established in the literature and shows that just micromolar amounts of the free ion kill some organisms.
7440-66-6
23994
27363
22430
DB01593
[Zn]
Zn
InChI=1S/Zn
HCHKCACWOHOZIP-UHFFFAOYSA-N
zinc(2+) ion
65.409
63.929146578
0
zinc(2+) ion
2
2
30zn;Cinc;Zincum;Zink;Zn;Zn(ii);Zn2+
PW_C009795
Zinc
57
8
1711
2
1904
3
2137
17
2154
49
3610
29
4083
7
4469
18
4543
14
4999
31
6689
107
6690
101
6699
108
7020
160
11758
115
12229
151
12633
65
42397
315
42399
318
77030
253
78023
132
78328
112
78811
111
120119
124
120898
122
122308
407
122852
118
123469
135
124860
119
125486
299
126474
481
127023
388
127317
205
128043
206
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
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
2665
11-cis-Retinol
HMDB0006216
Cis-11-retinol is produce from vitamin A cycle driven by interphotoreceptor retinoid binding protein(IRBP). cis-11-retinol is released from retinal pigment epithelium(RPE) membranes. (PMID: 10655150). Retinoid metabolism of RPE cells freshly isolated by trypsinization showed no 11- cis -retinal and little 11- cis -retinol formation. Nondamaged cells cultured on thermally responsive surfaces detached in sheets upon temperature change. They showed metabolism similar to that of cells freshly isolated by nonenzymatic means. After trypsinization, confluent cultures dissociated into individual cells, but these cells showed poor retinoid metabolism, including no detectable retinyl esters or 11- cis -retinoid isomers. (PMID: 10375454).
22737-96-8
C00899
5280382
16302
CPD-882
4444073
[H]\C(CO)=C(\C)/C(/[H])=C(/[H])C([H])=C(C)C(\[H])=C(/[H])C1=C(C)CCCC1(C)C
C20H30O
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6-,12-11+,16-8+,17-13+
FPIPGXGPPPQFEQ-IOUUIBBYSA-N
(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
286.4516
286.229665582
-4.58
1
vitamin a
0
0
FDB023840
11-cis-vitamin a alcohol;Cis-11-retinol
PW_C002665
C-retol
3198
2
78784
132
122536
124
125097
118
126686
299
128265
388
4838
PC(24:1(15Z)/15:0)
HMDB0008790
PC(24:1(15Z)/15:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(24:1(15Z)/15:0), in particular, consists of one chain of nervonic acid at the C-1 position and one chain of pentadecanoic acid at the C-2 position. The nervonic acid moiety is derived from fish oils, while the pentadecanoic acid moiety is derived from dairy products and milk fat. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.
C00157
53479491
PHOSPHATIDYLCHOLINE
24767449
CCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCCCCCC\C=C/CCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
C47H92NO8P
InChI=1S/C47H92NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-28-30-31-33-35-37-39-46(49)53-43-45(44-55-57(51,52)54-42-41-48(3,4)5)56-47(50)40-38-36-34-32-29-19-17-15-13-11-9-7-2/h20-21,45H,6-19,22-44H2,1-5H3/b21-20-/t45-/m1/s1
SKYTWJRHKLHTDQ-ULOIKCHLSA-N
trimethyl(2-{[(2R)-2-(pentadecanoyloxy)-3-[(15Z)-tetracos-15-enoyloxy]propyl phosphonato]oxy}ethyl)azanium
830.209
829.656055437
-7.71
0
lecithin
0
0
C00157
1-nervonoyl-2-pentadecanoyl-sn-glycero-3-phosphocholine;Gpcho(24:1/15:0);Gpcho(24:1n9/15:0);Gpcho(24:1w9/15:0);Gpcho(39:1);Lecithin;Pc(24:1/15:0);Pc(24:1n9/15:0);Pc(24:1w9/15:0);Pc(39:1);Phosphatidylcholine(24:1/15:0);Phosphatidylcholine(24:1n9/15:0);Phosphatidylcholine(24:1w9/15:0);Phosphatidylcholine(39:1)
PW_C004838
PC241
3200
2
21892
49
21893
309
25365
18
78785
132
122537
124
125098
118
126687
299
128266
388
1948
Retinyl palmitate
HMDB0003648
Retinyl palmitate, or vitamin A palmitate, is a common vitamin supplement, with formula C36H60O2. It is available in both oral and injectable forms for treatment of vitamin A deficiency, under the brand names Aquasol and Palmitate. Retinyl palmitate is an alternate for retinyl acetate in vitamin A supplements, and is available in oily or dry forms. It is a pre-formed version of vitamin A, and can thus be realistically over-dosed, unlike beta-carotene.
79-81-2
C02588
5280531
17616
CPD-523
4444162
CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
C36H60O2
InChI=1S/C36H60O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-35(37)38-30-28-32(3)23-20-22-31(2)26-27-34-33(4)24-21-29-36(34,5)6/h20,22-23,26-28H,7-19,21,24-25,29-30H2,1-6H3/b23-20+,27-26+,31-22+,32-28+
VYGQUTWHTHXGQB-FFHKNEKCSA-N
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl hexadecanoate
524.8604
524.459331164
-6.81
0
vitamin a palmitate
0
0
FDB013831
All-trans-retinol palmitate;All-trans-retinyl palmitate;All-trans-vitamin a palmitate;Aquapalm;Aquasol a;Arovit;Axerophthol palmitate;Dispatabs tabs;Ester found in fish liver oils;Lutavit a 500 plus;Myvak;Myvax;Optovit a;Optovit-a;Retinol palmitate;Retinyl hexadecanoate;Retinyl hexadecanoic acid;Retinyl palmitate;Retinyl palmitic acid;Testavol s;Vitamin a palmitate;Vitazyme a;Trans-retinol palmitate;Trans-retinyl palmitate;All-trans-retinyl hexadecanoate;All-trans-retinyl hexadecanoic acid;All-trans-retinyl palmitic acid;Retinol palmitic acid;Vitamin a palmitic acid
PW_C001948
Retylpm
3201
2
78786
132
122538
124
125099
118
126688
299
128267
388
59
Glycerophosphocholine
HMDB0000086
Glycerophosphorylcholine (GPC) is a choline derivative and one of the two major forms of choline storage (along with phosphocholine) in the cytosol. Glycerophosphorylcholine is also one of the four major organic osmolytes in renal medullary cells, changing their intracellular osmolyte concentration in parallel with extracellular tonicity during cellular osmoadaptation. As an osmolyte, Glycerophosphorylcholine counteracts the effects of urea on enzymes and other macromolecules. Kidneys (especially medullar cells), which are exposed under normal physiological conditions to widely fluctuating extracellular solute concentrations, respond to hypertonic stress by accumulating the organic osmolytes glycerophosphorylcholine (GPC), betaine, myo-inositol, sorbitol and free amino acids. Increased intracellular contents of these osmolytes are achieved by a combination of increased uptake (myo-inositol and betaine) and synthesis (sorbitol, GPC), decreased degradation (GPC) and reduced osmolyte release. GPC is formed in the breakdown of phosphatidylcholine (PtC). This pathway is active in many body tissues, including mammary tissue.
28319-77-9
C00670
71920
16870
GLYCERYLPHOSPHORYLCHOLINE
64931
C[N+](C)(C)CCOP([O-])(=O)OC[C@@H](O)CO
C8H20NO6P
InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/t8-/m0/s1
SUHOQUVVVLNYQR-QMMMGPOBSA-N
(2-{[(2R)-2,3-dihydroxypropyl phosphono]oxy}ethyl)trimethylazanium
257.2213
257.102823889
-1.54
2
(2-{[(2R)-2,3-dihydroxypropyl phosphono]oxy}ethyl)trimethylazanium
0
0
FDB021802
2-[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]-n,n,n-trimethyl-ethanaminium inner salt;Choline alfoscerate;Choline glycerophosphate;Gpc;Gpcho;Glycerol 3-phosphocholine;Glycerol phosphorylcholine;Glycerol-3-phosphatidylcholine;Glycerophosphatidylcholine;Glycerophosphocholine;Glycerophosphorylcholine;Hydrogen glycerophosphate choline;L-choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner salt;L-alpha-glycerophosphocholine;L-alpha-glycerophosphorylcholine;L-alpha-glycerylphosphorylcholine;Sn-glycero-3-phosphocholine;A-glycerophosphorylcholine;A-glycerylphosphorylcholine;Alpha-glycerophosphorylcholine;Alpha-glycerylphosphorylcholine
PW_C000059
GPC
3202
2
68683
225
78787
132
122539
124
125100
118
126689
299
128268
388
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
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
1935
Retinyl ester
HMDB0003598
Retinyl ester, also known as all-E-retinoate, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Retinyl ester is considered to be a practically insoluble (in water) and relatively neutral molecule. Retinyl ester has been found throughout most human tissues, and has also been primarily detected in blood. Within the cell, retinyl ester is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, retinyl ester is involved in the retinol metabolism pathway. Retinyl ester is also involved in the metabolic disorder called vitamin a deficiency. Retinyl ester is a substrate for Lecithin retinol acyltransferase and Retinal pigment epithelium-specific 65 kDa protein.
C02075
5460164
545914
CPD-437
10607936
CC1CCCC(C)(C)C1\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O
C20H30O2
InChI=1S/C20H30O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14,17-18H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
WWDMJSSVVPXVSV-YCNIQYBTSA-N
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,2,6-trimethylcyclohexyl)nona-2,4,6,8-tetraenoic acid
302.451
302.224580204
-5.54
1
retinyl ester
0
-1
FDB023204
All-trans-retinyl ester;56-dihydroretinoic acid;All-e-retinoic acid;56-dihydroretinoate;All-e-retinoate
PW_C001935
RetEst
3210
2
78788
132
122543
124
125104
118
126692
299
128272
388
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
544
Fe2+
HMDB0000692
Iron is a chemical element with the symbol Fe and atomic number 26. Iron makes up 5% of the Earth's crust and is second in abundance to aluminium among the metals and fourth in abundance among the elements. Physiologically, it. exists as an ion in the body. Iron (as Fe2+, ferrous ion) is a necessary trace element used by all known living organisms. Iron-containing enzymes, usually containing heme prosthetic groups, participate in catalysis of oxidation reactions in biology, and in transport of a number of soluble gases. Iron is an essential constituent of hemoglobin, cytochrome, and other components of respiratory enzyme systems. Its chief functions are in the transport of oxygen to tissue (hemoglobin) and in cellular oxidation mechanisms. Inorganic iron involved in redox reactions is also found in the iron-sulfur clusters of many enzymes, such as nitrogenase (involved in the synthesis of ammonia from nitrogen and hydrogen) and hydrogenase. A class of non-heme iron proteins is responsible for a wide range of functions such as ribonucleotide reductase (reduces ribose to deoxyribose; DNA biosynthesis) and purple acid phosphatase (hydrolysis of phosphate esters). When the body is fighting a bacterial infection, the body sequesters iron inside of cells (mostly stored in the storage molecule ferritin) so that it cannot be used by bacteria. Depletion of iron stores may result in iron-deficiency anemia. Iron is used to build up the blood in anemia. Humans experience iron toxicity above 20 milligrams of iron for every kilogram of weight, and 60 milligrams per kilogram is a lethal dose. Over-consumption of iron, often the result of children eating large quantities of ferrous sulfate tablets intended for adult consumption, is the most common toxicological cause of death in children under six. The DRI lists the Tolerable Upper Intake Level (UL) for adults as 45 mg/day. For children under fourteen years old the UL is 40 mg/day. Iron is a metal extracted from iron ore, and is almost never found in the free elemental state.
15438-31-0
C14818
27284
29033
Ferric-Hydroxamate-Complexes
25394
DB01592
[Fe++]
Fe
InChI=1S/Fe/q+2
CWYNVVGOOAEACU-UHFFFAOYSA-N
lambda2-iron(2+) ion
55.845
55.934942133
0
lambda2-iron(2+) ion
2
2
FDB016251
Armco iron;Carbonyl iron;Fe;Ferrovac e;Hematite;Infed;Loha;Limonite;Magnetite;Malleable iron;Metopirone;Metyrapone;Pzho;Pzh2m;Remko;Suy-b 2;Taconite;Venofer;Wrought iron;Fe (ii) ion;Fe(ii);Fe2+;Fe(2+);Ferrous ion;Iron ion(2+)
PW_C000544
Fe2+
398
19
641
3
678
31
692
20
709
8
1777
2
7041
163
7052
160
12060
225
12143
151
77179
132
77740
112
77751
129
77760
341
77782
111
120544
407
120557
414
120570
122
121765
124
123178
119
123191
450
123204
135
124316
118
126143
299
126185
481
127650
388
209
Vitamin A
HMDB0000305
Vitamin A (retinol) is a yellow fat-soluble, antioxidant vitamin important in vision and bone growth. It belongs to the family of chemical compounds known as retinoids. Retinol is ingested in a precursor form; animal sources (milk and eggs) contain retinyl esters, whereas plants (carrots, spinach) contain pro-vitamin A carotenoids. Hydrolysis of retinyl esters results in retinol while pro-vitamin A carotenoids can be cleaved to produce retinal. Retinal, also known as retinaldehyde, can be reversibly reduced to produce retinol or it can be irreversibly oxidized to produce retinoic acid. Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of carotenoids found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.
68-26-8
C00473
445354
17336
RETINOL
393012
DB00162
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
C20H30O
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
FPIPGXGPPPQFEQ-OVSJKPMPSA-N
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
286.4516
286.229665582
-4.58
1
α-sol
0
0
FDB013828
(all-e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol;All-trans-retinol;Retinol;Vitamin a1;B-retinol;Beta-retinol;Trans-retinol;(2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol;All-trans-retinyl alcohol;All-trans-vitamin a alcohol;Alphalin;Chocola a
PW_C000209
Retinol
3220
2
78789
132
122545
124
125106
118
126694
299
128274
388
3195
DG(16:1(9Z)/22:0/0:0)
HMDB0007144
DG(16:1(9Z)/22:0/0:0) belongs to the family of Diacylglycerols. These are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. DG(16:1(9Z)/22:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.
C00165
9543771
DIACYLGLYCEROL
7822721
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
C41H78O5
InChI=1S/C41H78O5/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h14,16,39,42H,3-13,15,17-38H2,1-2H3/b16-14-/t39-/m0/s1
BZRVDTDUKMXTCU-QZEPCWIRSA-N
(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl docosanoate
651.055
650.584925606
-7.62
1
diacylglycerol
0
0
FDB024338
1-palmitoleoyl-2-behenoyl-sn-glycerol;Dag(16:1/22:0);Dag(16:1n7/22:0);Dag(16:1w7/22:0);Dag(38:1);Dg(16:1/22:0);Dg(16:1n7/22:0);Dg(16:1w7/22:0);Dg(38:1);Diacylglycerol;Diacylglycerol(16:1/22:0);Diacylglycerol(16:1n7/22:0);Diacylglycerol(16:1w7/22:0);Diacylglycerol(38:1);Diglyceride
PW_C003195
DG38:1
3228
2
16473
49
78790
132
84038
331
97837
383
117182
398
122546
124
125107
118
126695
299
128275
388
29134
TG(16:1(9Z)/22:0/16:1(9Z))
HMDB0048523
TG(16:1(9Z)/22:0/16:1(9Z)) is a dipalmitoleic acid triglyceride. Triglycerides (TGs or TAGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid trimesters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(16:1(9Z)/22:0/16:1(9Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position, one chain of behenic acid at the C-2 position and one chain of palmitoleic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)<br />TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols.
30777879
[H]C(COC(=O)CCCCCCC\C=C/CCCCCC)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
C57H106O6
InChI=1S/C57H106O6/c1-4-7-10-13-16-19-22-25-26-27-28-29-30-33-36-39-42-45-48-51-57(60)63-54(52-61-55(58)49-46-43-40-37-34-31-23-20-17-14-11-8-5-2)53-62-56(59)50-47-44-41-38-35-32-24-21-18-15-12-9-6-3/h20-21,23-24,54H,4-19,22,25-53H2,1-3H3/b23-20-,24-21-
SCKPWGYVJPFAGF-XFUYORNGSA-N
1,3-bis[(9Z)-hexadec-9-enoyloxy]propan-2-yl docosanoate
887.4479
886.798941124
-8.06
0
1,3-bis[(9Z)-hexadec-9-enoyloxy]propan-2-yl docosanoate
0
0
1-(9z-hexadecenoyl)-2-docosanoyl-3-(9z-hexadecenoyl)-glycerol;1-palmitoleoyl-2-behenoyl-3-palmitoleoyl-glycerol;Tag(16:1/22:0/16:1);Tag(54:2);Tg(16:1/22:0/16:1);Tg(54:2);Tracylglycerol(16:1/22:0/16:1);Tracylglycerol(54:2);Triacylglycerol;Triglyceride
PW_C029134
TG54:2
3229
2
31230
49
78791
132
122547
124
125108
118
126696
299
128276
388
2666
9-cis-Retinol
HMDB0006217
9-cis-retinol is a retinoid. Retinoids (vitamin A and its analogs) are essential dietary substances that are needed by mammals for reproduction, normal embryogenesis, growth, vision, and maintaining normal cellular differentiation and the integrity of the immune system. Within cells, retinoids regulate gene transcription acting through ligand-dependent transcription factors, the retinoic acid receptors (RARs), and the retinoid X receptors (RXRs). All-trans-retinoic acid binds only to RARs with high affinity, whereas its 9-cis isomer binds with high affinity to both RARs and RXRs. The actions of all-trans- and 9-cis-retinoic acid in regulating cellular responses are distinct and not interchangeable. (PMID: 9115228).
22737-97-9
C16682
9947823
78272
8123435
C\C(=C\CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
C20H30O
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13-
FPIPGXGPPPQFEQ-HWCYFHEPSA-N
(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
286.4516
286.229665582
-4.58
1
9-cis-retinol
0
0
FDB010848
9-cis retinol;9-cis-retinol;(2e,4e,6z,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol;(9cis)-retinol
PW_C002666
9-c-Rol
3231
2
78792
132
122549
124
125110
118
126698
299
128278
388
437
B-Carotene
HMDB0000561
B-Carotene is a carotenoid that is a precursor of vitamin A. It is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (porphyria, erythropoietic). (From Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Engewood, CO, 1995.) -- Pubchem; Carotene is an orange photosynthetic pigment important for photosynthesis. It is responsible for the orange colour of the carrot and many other fruits and vegetables. It contributes to photosynthesis by transmitting the light energy it absorbs to chlorophyll. Chemically, carotene is a terpene. It is the dimer of retinol (vitamin A) and comes in two primary forms: alpha- and beta-carotene. gamma-, delta- and epsilon-carotene also exist. Carotene can be stored in the liver and converted to vitamin A as needed. Beta-carotene is an anti-oxidant and such can be useful for curbing the excess of damaging free radicals in the body. However, the usefulness of beta-carotene as a dietary supplement (i.e. taken as a pill) is still subject to debate. Beta-carotene is fat-soluble, so a small amount of fat is needed to absorb it into the body. -- Wikipedia.
7235-40-7
C02094
5280489
17579
CPD1F-129
4444129
C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C
C40H56
InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+
OENHQHLEOONYIE-JLTXGRSLSA-N
1,3,3-trimethyl-2-[(1E,3E,5E,7E,9Z,11Z,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene
536.888
536.438201803
-6.14
0
1,3,3-trimethyl-2-[(1E,3E,5E,7E,9Z,11Z,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene
0
0
FDB014613
(all-e)-1,1'-(3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis;(all-e)-1,1'-(3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis[2,6,6-trimethyl-cyclohexene;All-e-b-carotene;All-epsilon-beta-carotene;All-trans-b-carotene;All-trans-beta-carotene;Betavit;Betacarotene;Carotaben;Carotene base 80s;Food orange 5;Kpmk;Lucaratin;Lucarotin;Lurotin;Provatene;Provatenol;Rovimix b-carotene;Serlabo;Solatene;B-carotene;Beta-carotene;1,1'-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(2,6,6-trimethylcyclohexene);Beta-karotin
PW_C000437
b-carot
3233
2
12054
225
73014
27
78793
132
122550
124
125111
118
126699
299
128279
388
1065
Oxygen
HMDB0001377
Oxygen is the third most abundant element in the universe after hydrogen and helium and the most abundant element by mass in the Earth's crust. Diatomic oxygen gas constitutes 20.9% of the volume of air. All major classes of structural molecules in living organisms, such as proteins, carbohydrates, and fats, contain oxygen, as do the major inorganic compounds that comprise animal shells, teeth, and bone. Oxygen in the form of O2 is produced from water by cyanobacteria, algae and plants during photosynthesis and is used in cellular respiration for all living organisms. Green algae and cyanobacteria in marine environments provide about 70% of the free oxygen produced on earth and the rest is produced by terrestrial plants. Oxygen is used in mitochondria to help generate adenosine triphosphate (ATP) during oxidative phosphorylation. For animals, a constant supply of oxygen is indispensable for cardiac viability and function. To meet this demand, an adult human, at rest, inhales 1.8 to 2.4 grams of oxygen per minute. This amounts to more than 6 billion tonnes of oxygen inhaled by humanity per year. At a resting pulse rate, the heart consumes approximately 8-15 ml O2/min/100 g tissue. This is significantly more than that consumed by the brain (approximately 3 ml O2/min/100 g tissue) and can increase to more than 70 ml O2/min/100 g myocardial tissue during vigorous exercise. As a general rule, mammalian heart muscle cannot produce enough energy under anaerobic conditions to maintain essential cellular processes; thus, a constant supply of oxygen is indispensable to sustain cardiac function and viability. However, the role of oxygen and oxygen-associated processes in living systems is complex, and they and can be either beneficial or contribute to cardiac dysfunction and death (through reactive oxygen species). Reactive oxygen species (ROS) are a family of oxygen-derived free radicals that are produced in mammalian cells under normal and pathologic conditions. Many ROS, such as the superoxide anion (O2-)and hydrogen peroxide (H2O2), act within blood vessels, altering mechanisms mediating mechanical signal transduction and autoregulation of cerebral blood flow. Reactive oxygen species are believed to be involved in cellular signaling in blood vessels in both normal and pathologic states. The major pathway for the production of ROS is by way of the one-electron reduction of molecular oxygen to form an oxygen radical, the superoxide anion (O2-). Within the vasculature there are several enzymatic sources of O2-, including xanthine oxidase, the mitochondrial electron transport chain, and nitric oxide (NO) synthases. Studies in recent years, however, suggest that the major contributor to O2- levels in vascular cells is the membrane-bound enzyme NADPH-oxidase. Produced O2- can react with other radicals, such as NO, or spontaneously dismutate to produce hydrogen peroxide (H2O2). In cells, the latter reaction is an important pathway for normal O2- breakdown and is usually catalyzed by the enzyme superoxide dismutase (SOD). Once formed, H2O2 can undergo various reactions, both enzymatic and nonenzymatic. The antioxidant enzymes catalase and glutathione peroxidase act to limit ROS accumulation within cells by breaking down H2O2 to H2O. Metabolism of H2O2 can also produce other, more damaging ROS. For example, the endogenous enzyme myeloperoxidase uses H2O2 as a substrate to form the highly reactive compound hypochlorous acid. Alternatively, H2O2 can undergo Fenton or Haber-Weiss chemistry, reacting with Fe2+/Fe3+ ions to form toxic hydroxyl radicals (-.OH). (PMID: 17027622, 15765131).
7782-44-7
C00007
977
15379
CPD-6641
952
O=O
O2
InChI=1S/O2/c1-2
MYMOFIZGZYHOMD-UHFFFAOYSA-N
oxidanone
31.9988
31.989829244
0
singlet oxygen
0
0
FDB022589
Dioxygen;Molecular oxygen;O2;Oxygen;Oxygen molecule;[oo];Dioxygene;Disauerstoff;E 948;E-948;E948
PW_C001065
O2
95
9
110
5
245
16
500
18
505
8
549
14
625
28
638
3
649
10
674
31
688
20
754
15
763
4
769
33
836
2
1375
49
2016
24
2531
22
2803
29
4260
42
4747
13
5467
123
5480
125
5493
126
5508
127
5809
108
5973
147
6129
159
7006
188
7032
163
7050
160
7319
213
7533
210
7560
212
8395
151
11816
216
11864
198
11883
215
11894
211
12057
225
12063
164
12247
286
12279
226
12325
249
12706
291
12716
292
13004
298
13016
300
13026
301
13038
302
13260
223
42276
17
42657
315
76910
293
77044
294
77214
134
77350
111
77363
130
77377
331
77395
332
77497
113
77512
115
77537
334
77626
336
77723
337
77736
112
77747
129
77756
341
77805
114
77812
133
78070
329
78151
132
78381
345
78805
343
79111
360
120047
408
120383
122
120426
405
120542
407
120553
414
120594
409
120601
406
120883
415
121045
124
121104
383
121605
434
121656
429
122117
382
122573
418
122689
384
122798
374
122822
443
123027
135
123060
376
123128
447
123139
136
123163
448
123176
119
123187
450
123219
137
123226
120
123459
451
123609
118
123669
398
124163
469
124214
464
124669
399
125145
454
125275
121
125425
482
125706
478
125731
483
125737
297
125740
479
125884
481
126100
299
126272
484
126522
495
126721
489
126825
480
126964
502
126986
207
127198
209
127214
208
127219
205
127222
501
127305
504
127345
206
127557
388
127574
515
127835
389
128081
395
128095
390
128312
506
128432
391
2667
9-cis-Retinal
HMDB0006218
In vivo, 9-cis-retinal is formed through oxidation of 9-cis-retinol by cis-retinol dehydrogenase (cRDH). (PMID: 15572038). The generation of retinoic acid from retinol is a two-step reaction, with the rate-limiting step being the oxidation of retinol into the intermediate retinaldehyde. Two classes of. unrelated enzymes have been implicated in the oxidation of retinol, the classical cytosolic medium chain alcohol dehydrogenases and recently identified microsomal members of the short chain alcohol dehydrogenase reductase (SDR) superfamily. Further oxidation of the retinaldehyde to the retinoic acid is believed to be catalyzed by several cytosolic aldehyde dehydrogenases. Retinoids are micronutrients required to maintain and promote health of vertebrates. They act physiologically by participating in the visual cycle, in regulating cell differentiation, in embryonic development (PMID: 10893430), in maintaining normal reproduction, and in the immune response (PMID: 8882153). In non-ocular tissues, the effects of retinoids within the body are mediated through retinoic acid receptors (RARs) and retinoid X receptors (RXRs), which act to regulate gene expression as ligand-dependent transcription factors. The naturally occurring ligands for these nuclear receptors are thought to be all-trans-retinoic acid for RARs and 9-cis-retinoic acid for RXRs (PMID: 10322133). While many details of the molecular actions of the RARs and RXRs in regulating gene transcription are understood (PMID: 10418975), tissue-specific synthetic pathway(s) of their ligands has not been adequately defined. Nevertheless, the therapeutic efficacy of retinoids, including 9-cis-retinoic acid, is well established in both tissue culture and animal models of breast cancer (PMID: 8825126, PMID: 12743994).
514-85-2
C16681
6436082
78273
4940758
C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=O
C20H28O
InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13-
NCYCYZXNIZJOKI-HWCYFHEPSA-N
(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal
284.4357
284.214015518
-4.83
0
9-cis-retinal
0
0
FDB023842
9-cis-retinal;9-cis-retinaldehyde;9-cis-vitamin a aldehyde;Isoretinene a;Cis-9-retinal;(2e,4e,6z,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal;(9cis)-retinal;9-c-retinal;9-cis-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal;9-cis-7,11,13-trans-retinal
PW_C002667
9-c-Ral
3235
2
78794
132
122551
124
125113
118
126700
299
128280
388
1600
9-cis-Retinoic acid
HMDB0002369
9-cis-Retinoic acid is an active retinoid that regulates expression of retinoid responsive genes, serving as a ligand for two classes of ligand-dependent transcription factors: the retinoic acid receptors and retinoid X receptors. Retinoids (vitamin A and its analogs) are essential dietary substances that are needed by mammals for reproduction, normal embryogenesis, growth, vision, and maintaining normal cellular differentiation and the integrity of the immune system. Within cells, retinoids regulate gene transcription acting through ligand-dependent transcription factors, the retinoic acid receptors (RARs), and the retinoid X receptors (RXRs). all-trans-Retinoic acid binds only to RARs with high affinity, whereas its 9-cis isomer binds with high affinity to both RARs and RXRs. The actions of all-trans- and 9-cis-retinoic acid in regulating cellular responses are distinct and not interchangeable (PMID: 9115228).
5300-03-8
C15493
449171
50648
395778
DB00523
C\C(\C=C\C1=C(C)CCCC1(C)C)=C\C=C\C(\C)=C\C(O)=O
C20H28O2
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+
SHGAZHPCJJPHSC-ZVCIMWCZSA-N
(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
300.4351
300.20893014
-4.80
1
alitretinoin
0
-1
FDB022982
15-apo-beta-caroten-15-oate;15-apo-beta-caroten-15-oic acid;9-retinoate;9-retinoic acid;9-cis-retinoate;9-cis-retinoic acid;9-cis-tretinoin;A-acido (argentina);Aberel;Aberela [norway];Acide retinoique (french) (dsl);Airol;Aknoten;Alitretinoin;Alitretinoin (usan);Alitretinoin [usan];All-trans- vitamin a1 acid;All-trans-b-retinoate;All-trans-b-retinoic acid;All-trans-beta-retinoate;All-trans-beta-retinoic acid;All-trans-vitamin a acid;Atragen;Avita;Avitoin [norway];B-retinoate;B-retinoic acid;Dermairol;Effederm;Effederm [france];Epi-aberel;Eudyna;Isotretinoin retinoate;Isotretinoin retinoic acid;Panretin;Panretin (tn);Panretin gel;Panretyn;Panrexin;Renova;Retacnyl;Retin a;Retin a (tn);Retin-a;Retin-a micro;Retinoate;Retinoic acid;Retinova;Trans-retinoate;Trans-retinoic acid;Tretinoin;Tretinoin (tn);Tretinoin (jan/usp);Tretinoin [usan:ban:inn];Tretinoin/all-trans retinoate;Tretinoin/all-trans retinoic acid;Tretinoina [inn-spanish];Tretinoine (french) (einecs);Tretinoine [inn-french];Tretinoino [inn-spanish];Tretinoinum [inn-latin];Tretinon;Vesanoid;Vesnaroid;Alpha-acido (argentina);Alpha-vitaminsyre [denmark];Beta-retinoate;Beta-retinoic acid;Trans-vitamin a acid;(2e,4e,6z,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid;(7e,9z,11e,13e)-retinoic acid;9(z)-retinoic acid;Alitretinoina;Alitretinoine;Alitretinoinum;(2e,4e,6z,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate;(7e,9z,11e,13e)-retinoate;9(z)-retinoate;Aberela;Alpha-vitaminsyre;Avitoin
PW_C001600
Airol
3243
2
78795
132
122552
124
125114
118
126701
299
128281
388
1227
all-trans-Retinoic acid
HMDB0001852
all-trans-Retinoic acid (ATRA) is an isomer of retinoic acid, the oxidized form of vitamin A. Retinoic acid functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID: 17495912). It is an important regulator of gene expression during growth and development, and in neoplasms. As a drug, all-trans-retinoic acid is known as tretinoin. Tretinoin is derived from maternal vitamin A and is essential for normal growth and embryonic development. An excess of tretinoin can be teratogenic. Tretinoin is used in the treatment of psoriasis, acne vulgaris, and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute).
302-79-4
C00777
444795
15367
392618
DB00755
C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
C20H28O2
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
SHGAZHPCJJPHSC-YCNIQYBTSA-N
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
300.442
300.208930142
-4.80
1
tretinoin
0
-1
FDB022710
(all-e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate;(all-e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid;3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate;3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid;Acide retinoique (french);All-(e)-retinoate;All-(e)-retinoic acid;All-trans-retinoate;All-trans-retinoic acid;All-trans-tretinoin;All-trans-vitamin a acid;All-trans-vitamin a1 acid;Retinoate;Retinoic acid;Tretin m;Tretinoine (french);Vitamin a acid;Beta-retinoate;Beta-retinoic acid;Trans-retinoate;Trans-retinoic acid
PW_C001227
T-RetcA
3246
2
78796
132
122554
124
125117
118
126703
299
128282
388
7859
4-Oxoretinol
HMDB0012329
4-oxo-retinol, a metabolite of retinol synthesized in mouse embryonal carcinoma F9 cells,is active in inducing differentiation of these cells. It also functions as a ligand of retinoic acid receptors and a transcriptional activator of reporter. genes.[PMID: 9110564]. 4-Oxoretinol is a metabolite of retinol in the human promyelocytic leukemia cell line NB4 which induces cell growth arrest and granulocytic differentiation.[PMID: 9581846].
62702-55-0
C16683
5289090
4451124
DB02699
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C
C20H28O2
InChI=1S/C20H28O2/c1-15(7-6-8-16(2)12-14-21)9-10-18-17(3)19(22)11-13-20(18,4)5/h6-10,12,21H,11,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-12+
PLIUCYCUYQIBDZ-RMWYGNQTSA-N
3-[(1E,3E,5E,7E)-9-hydroxy-3,7-dimethylnona-1,3,5,7-tetraen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one
300.4351
300.20893014
-4.39
1
4-oxoretinol
0
0
C16683
3,7-dimethyl-9-(3-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraen-1-ol;4-ketoretinol;4-ketovitamin a(1);4-ketovitamin-a-alcohol;4-ketovitamin-alpha-alcohol;4-oxo-retinol;4-oxorol;4-oxovitamin a1;4-oxovitamin-a-alcohol;4-oxovitamin-alpha-alcohol;4ova1;All-trans-4-oxoretinol;Oxr
PW_C007859
4ORetol
3247
2
78797
132
122555
124
125118
118
126704
299
128284
388
1799
Heme
HMDB0003178
Heme is the color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins. A heme or haem is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. Not all porphyrins contain iron, but a substantial fraction of porphyrin-containing metalloproteins have heme as their prosthetic subunit; these are known as hemoproteins.
14875-96-8
C00032
17627
HEME_A
24604415
DB02577
CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C=C)C8=[N+]7[Fe--]4(N2C1=C8)N56)C(C)=C3CCC(O)=O
C34H32FeN4O4
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);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;
KABFMIBPWCXCRK-RGGAHWMASA-L
4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide
616.487
616.177297665
-5.48
2
4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide
0
-2
FDB016272
(protoporphyrinato)iron;Ferroheme;Ferroheme b;Ferroprotoheme;Ferroprotoporphyrin;Ferroprotoporphyrin ix;Ferrous protoheme;Ferrous protoheme ix;Haem;Hem;Heme;Iron protoporphyrin;Iron protoporphyrin ix;Iron(ii) protoporphyrin ix;Protoferroheme;Protohaem;Protoheme;Protoheme ix;Reduced hematin
PW_C001799
Heme
247
16
308
10
324
8
608
2
766
5
1244
3
1354
49
1413
36
1963
18
2806
29
2938
9
3238
11
3367
26
3421
14
3734
4
4043
31
4823
28
5170
95
5472
123
5485
125
5517
129
5830
141
6246
78
6283
1
6597
151
7044
160
7060
161
7326
213
11835
198
11898
211
12065
164
13009
298
13021
300
42278
17
76915
293
76931
249
77351
111
77364
130
77367
331
77398
332
77517
115
77629
336
77813
334
78380
133
78602
132
78963
112
79932
134
120431
405
120603
408
120955
407
121085
383
121658
429
121746
124
121910
122
122570
406
122691
384
123065
376
123133
447
123144
136
123228
374
123521
119
123650
398
124216
464
124297
118
124463
135
125142
120
125277
121
125742
482
125896
481
126196
299
126499
297
126512
495
126718
479
126827
480
127224
502
127357
206
127632
388
128070
205
128083
395
128086
390
128309
501
128434
391
7207
All-trans-13,14-dihydroretinol
HMDB0011618
All-trans-13,14-dihydroretinol is involved in the retinol metabolism pathway. In this pathway, all-trans-13,14-dihydroretinol and an acceptor molecule is reversibly converted to retinol (vitamin A) plus reduced acceptor via the enzyme all-trans-retinol 13,14-reductase (EC 1.3.99.23). (KEGG).
115797-14-3
C15492
446798
52075
CPD-7247
394057
CC(CCO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
C20H32O
InChI=1S/C20H32O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-12,17,21H,7,10,13-15H2,1-5H3/b9-6+,12-11+,16-8+
OVBOQVAIYMSUDT-HRYGCDPOSA-N
(4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-4,6,8-trien-1-ol
288.4675
288.245315646
-4.66
1
13,14-dihydroretinol
0
0
C15492
13,14-dihydro-retinol;13,14-dihydro-all-trans-retinol;13,14-dihydroretinol;All-trans-13,14-dihydroretinol
PW_C007207
ATdhret
3249
2
78798
132
122557
124
125120
118
126706
299
128286
388
1786
Retinoyl b-glucuronide
HMDB0003141
Retinoyl beta-glucuronide is a naturally occurring, biologically active metabolite of vitamin A. Although retinoyl beta-glucuronide is regarded as a detoxification product of retinoic acid, it plays several roles in the functions of vitamin A. It can serve as a source of retinoic acid, and it may be a vehicle for transport of retinoic acid to target tissues. Topically applied retinoyl beta-glucuronide is comparable in efficacy to retinoic acid in the treatment of acne in humans, without the same side effects. Retinoyl beta-glucuronide may or may not be teratogenic, depending on the mode of administration and the species in which it is used. It may be a valuable therapeutic compound for the treatment of skin disorders and certain types of cancers.
401-10-5
C11061
5281877
28870
Beta-D-Glucuronides
4445170
O[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
C26H36O8
InChI=1S/C26H36O8/c1-15(11-12-18-17(3)10-7-13-26(18,4)5)8-6-9-16(2)14-19(27)33-25-22(30)20(28)21(29)23(34-25)24(31)32/h6,8-9,11-12,14,20-23,25,28-30H,7,10,13H2,1-5H3,(H,31,32)/b9-6+,12-11+,15-8+,16-14+/t20-,21-,22+,23-,25+/m0/s1
MTGFYEHKPMOVNE-NEFMKCFNSA-N
(2S,3S,4S,5R,6S)-6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
476.5592
476.241018128
-4.01
4
glucuronide
0
-1
DBMET00561
FDB023112
13-cis-retinoate;13-cis-retinoic acid;13-cis-retinoic acid acyl beta-d-glucuronide;13-cis-retinoic acid acyl beta-delta-glucuronide;13-cis-retinoyl glucuronide;13-cis-retinoyl-beta-d-glucuronide;13-cis-retinoyl-beta-delta-glucuronide;13-cis-retinoyl-beta-glucuronide;9-cis-retinoyl-beta-d-glucuronide;9-cis-retinoyl-beta-delta-glucuronide;All-trans-retinoyl-beta-d-glucuronide;All-trans-retinoyl-beta-delta-glucuronide;All-trans-retinoyl-beta-glucuronide;Glucuronide;Retinoate;Retinoic acid;Retinoic acid beta-d-glucuronide;Retinoic acid beta-delta-glucuronide;Retinoyl beta-glucuronide;Retinoyl glucuronide;Retinoyl-beta-glucuronide;All-trans-retinoyl-b-glucuronide;All-trans-retinoyl-β-glucuronide;1-o-all-trans-retinoyl-b-glucuronate;1-o-all-trans-retinoyl-b-glucuronic acid;1-o-all-trans-retinoyl-beta-glucuronate;1-o-all-trans-retinoyl-β-glucuronate;1-o-all-trans-retinoyl-β-glucuronic acid
PW_C001786
RetybGu
3251
2
78799
132
125122
118
128288
388
2690
4-Hydroxyretinoic acid
HMDB0006254
4-Hydroxyretinoic acid is an NADPH-dependent hydroxylation metabolite of retinoic acid in the microsomes, via the cytochrome P-450 system. Retinoic acid is an activated metabolite of retinol that supports the systemic functions of vitamin A in vivo. (PMID: 1538719, 1932598, 2851384).
66592-72-1
C16677
6438629
63795
4943093
C\C(\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
C20H28O3
InChI=1S/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+
KGUMXGDKXYTTEY-FRCNGJHJSA-N
(2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
316.4345
316.203844762
-4.55
2
4-hydroxyretinoic acid
0
-1
DBMET00298
FDB023862
4-hydroxy-13-cis-retinoate;4-hydroxy-13-cis-retinoic acid;4-hydroxy-retinoate;4-hydroxy-retinoic acid;4-hydroxy-all-trans-retinoate;4-hydroxy-all-trans-retinoic acid;4-oh-retinoate;4-oh-retinoic acid;All-trans-4-hydroxyretinoate;All-trans-4-hydroxyretinoic acid;Rac-4-hydroxy-all-trans-retinoate;Rac-4-hydroxy-all-trans-retinoic acid;(2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid;(2e,4e,6e,8e)-9-(3-hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid;(7e,9e,11e,13e)-4-hydroxyretinoic acid;4-hydroxy-(7e,9e,11e,13e)-retinoic acid;(2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate;(2e,4e,6e,8e)-9-(3-hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoate;(7e,9e,11e,13e)-4-hydroxyretinoate;4-hydroxy-(7e,9e,11e,13e)-retinoate
PW_C002690
4HRetA
3263
2
78800
132
122559
124
125132
118
126707
299
128297
388
2706
4-oxo-Retinoic acid
HMDB0006285
4-oxo-Retinoic acid is a biologically active geometric isomer of retinoic acid (RA). 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in cells. Metabolic transformation of all-trans RA to 4-hydroxylated RA appears to be primarily catalyzed by the cytochrome P 450 (CYP) 26AI in human skin cells. Cellular levels of all-trans RA are meticulously regulated utilizing an array of systems to balance uptake, biosynthesis, catabolism, and efflux transport. RA is a critical regulator of gene expression during embryonic development and in the maintenance of adult epithelial tissues. (PMID: 8794203, 7893159, 17330217, 16778795, 17460545).
38030-57-8
C16678
6437063
269971
4941652
C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
C20H26O3
InChI=1S/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+
GGCUJPCCTQNTJF-FRCNGJHJSA-N
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
314.4186
314.188194698
-4.71
1
4-oxo-retinoic acid
0
-1
DBMET00455
FDB023877
4-keto-retinoate;4-keto-retinoic acid;4-ketoretinoate;4-ketoretinoic acid;4-oxo-all-trans-retinoate;4-oxo-all-trans-retinoic acid;4-oxoretinoate;4-oxoretinoic acid;4-oxotretinoin;All-trans-4-oxoretinoate;All-trans-4-oxoretinoic acid;Ro 11-4824;Ro 12-4824
PW_C002706
4ORetA
3264
2
78801
132
122560
124
125133
118
126708
299
128298
388
7979
all-trans-18-Hydroxyretinoic acid
HMDB0012452
all-trans-18-Hydroxyretinoic acid, also known as 18-hydroxy-all-trans-retinoic acid or 18-hydroxyretinoate, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. all-trans-18-Hydroxyretinoic acid is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, all-trans-18-hydroxyretinoic acid is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, all-trans-18-hydroxyretinoic acid is involved in the retinol metabolism pathway. all-trans-18-Hydroxyretinoic acid is also involved in the metabolic disorder called vitamin a deficiency.
C16679
6506224
5005673
C\C(\C=C\C1=C(CO)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
C20H28O3
InChI=1S/C20H28O3/c1-15(7-5-8-16(2)13-19(22)23)10-11-18-17(14-21)9-6-12-20(18,3)4/h5,7-8,10-11,13,21H,6,9,12,14H2,1-4H3,(H,22,23)/b8-5+,11-10+,15-7+,16-13+
XSJOIRFEYHJNAW-FCKHSPHMSA-N
(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid
316.4345
316.203844762
-4.57
2
(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid
0
-1
C16679
18-hydroxy-all-trans-retinoate;18-hydroxy-all-trans-retinoic acid;Rac-18-hydroxy-all-trans-retinoate;Rac-18-hydroxy-all-trans-retinoic acid
PW_C007979
AT18HA
3265
2
78802
132
122561
124
125134
118
126709
299
128299
388
7978
all-trans-5,6-Epoxyretinoic acid
HMDB0012451
all-trans-5,6-Epoxyretinoic acid, also known as 5,6-epoxyretinoic acid, sodium salt or 5,6-epoxy-5,6-dihydro-retinoate, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. all-trans-5,6-Epoxyretinoic acid is considered to be a practically insoluble (in water) and relatively neutral molecule. all-trans-5,6-Epoxyretinoic acid has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, all-trans-5,6-epoxyretinoic acid is primarily located in the cytoplasm and membrane (predicted from logP). In humans, all-trans-5,6-epoxyretinoic acid is involved in the retinol metabolism pathway. all-trans-5,6-Epoxyretinoic acid is also involved in the metabolic disorder called vitamin a deficiency.
C16680
5363137
545933
4515523
C\C(\C=C\C12OC1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(O)=O
C20H28O3
InChI=1S/C20H28O3/c1-15(8-6-9-16(2)14-17(21)22)10-13-20-18(3,4)11-7-12-19(20,5)23-20/h6,8-10,13-14H,7,11-12H2,1-5H3,(H,21,22)/b9-6+,13-10+,15-8+,16-14+
KEEHJLBAOLGBJZ-WEDZBJJJSA-N
(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid
316.4345
316.203844762
-4.91
1
(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid
0
-1
DBMET00454
C16680
5,6-epoxy-5,6-dihydro-retinoate;5,6-epoxy-5,6-dihydro-retinoic acid;All-trans-5,6-epoxy-5,6-dihydroretinoate;All-trans-5,6-epoxy-5,6-dihydroretinoic acid;All-trans-5,6-epoxyretinoate
PW_C007978
alt56eA
3266
2
78803
132
25
Fatty Acid
Compound
145
Compound
PW_EC000025
35366
ChEBI
FA
40
Reduced acceptor
Compound
PW_EC000040
15022
ChEBI
RA
41
Acceptor
Compound
PW_EC000041
15339
ChEBI
Accepto
59
Rhodopsin
Compound
PW_EC000059
P08100
UniProt
Rhodops
60
Bathorodopsin
Compound
PW_EC000060
2998
ChEBI
Bathoro
61
iodopsin
Compound
PW_EC000061
5949
ChEBI
Iodopsi
62
Lumirodopsin
Compound
PW_EC000062
6562
ChEBI
Lumirod
63
Metarodopsin
Compound
PW_EC000063
6796
ChEBI
Metarod
15525
Alcohol dehydrogenase 1
P06757
Adh1
17
1.1.1.1
123237
135
124194
118
132606
464
17416
Retinol dehydrogenase 2
P50170
Acts on retinol bound on cellular retinol-binding protein (CRBP). Has higher activity with NADP rather than NAD.
Rdh2
17
1.1.1.105
125091
118
17420
Dehydrogenase/reductase SDR family member 4
Q6IRD4
Reduces all-trans-retinal and 9-cis retinal. Can also catalyze the oxidation of all-trans-retinol with NADP as co-factor, but with much lower efficiency. Reduces alkyl phenyl ketones and alpha-dicarbonyl compounds with aromatic rings, such as pyrimidine-4-aldehyde, 3-benzoylpyridine, 4-benzoylpyridine, menadione and 4-hexanoylpyridine. Has no activity towards aliphatic aldehydes and ketones (By similarity).
Dhrs4
17
1.1.1.184
125092
118
17422
Retinol dehydrogenase 7
Q4KMB6
Acts on retinol bound on cellular retinol-binding protein (CRBP).
Rdh7
17
1.1.1.105
125093
118
17262
Estradiol 17-beta-dehydrogenase 1
P51657
Favors the reduction of estrogens and androgens. Uses preferentially NADH.
Hsd17b1
17
1.1.1.62
124885
135
125094
118
17427
Retinol dehydrogenase 10
Q80ZF7
Retinol dehydrogenase with a clear preference for NADP. Converts all-trans-retinol to all-trans-retinal.
Rdh10
17
1.1.1.300
125095
118
17431
Dehydrogenase/reductase SDR family member 9
Q8VD48
3-alpha-hydroxysteroid dehydrogenase that converts 3-alpha-tetrahydroprogesterone (allopregnanolone) to dihydroxyprogesterone and 3-alpha-androstanediol to dihydroxyprogesterone. May play a role in the biosynthesis of retinoic acid from retinaldehyde, but seems to have low activity with retinoids. Can utilize both NADH and NADPH (By similarity).
Dhrs9
17
1.1.-.-
125096
118
17012
Dehydrogenase/reductase SDR family member 7B
A4GWE3
Putative oxidoreductase.
Dhrs7b
17
1.1.-.-
124612
118
17434
Lecithin retinol acyltransferase
Q9JI61
Transfers the acyl group from the sn-1 position of phosphatidylcholine to all-trans retinol, producing all-trans retinyl esters. Retinyl esters are storage forms of vitamin A. LRAT plays a critical role in vision (By similarity). It provides the all-trans retinyl ester substrates for the isomerohydrolase which processes the esters into 11-cis-retinol in the retinal pigment epithelium; due to a membrane-associated alcohol dehydrogenase, 11 cis-retinol is oxidized and converted into 11-cis-retinaldehyde which is the chromophore for rhodopsin and the cone photopigments.
Lrat
17
2.3.1.135
125101
118
17437
Diacylglycerol O-acyltransferase 2
Q8K4Y4
Essential acyltransferase that catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. Required for synthesis and storage of intracellular triglycerides. Probably plays a central role in cytosolic lipid accumulation. In liver, is primarily responsible for incorporating endogenously synthesized fatty acids into triglycerides. Functions also as an acyl-CoA retinol acyltransferase (ARAT) (By similarity).
Dgat2
17
2.3.1.20; 2.3.1.76
125102
118
17704
O-acyltransferase
Q8K1M9
17
115848
398
125103
118
17445
Retinoid isomerohydrolase
F1M8Q2
Critical isomerohydrolase in the retinoid cycle involved in regeneration of 11-cis-retinal, the chromophore of rod and cone opsins. Catalyzes the cleavage and isomerization of all-trans-retinyl fatty acid esters to 11-cis-retinol which is further oxidized by 11-cis retinol dehydrogenase to 11-cis-retinal for use as visual chromophore. Essential for the production of 11-cis retinal for both rod and cone photoreceptors. Also capable of catalyzing the isomerization of lutein to meso-zeaxanthin an eye-specific carotenoid. The soluble form binds vitamin A (all-trans-retinol), making it available for LRAT processing to all-trans-retinyl ester. The membrane form, palmitoylated by LRAT, binds all-trans-retinyl esters, making them available for IMH (isomerohydrolase) processing to all-cis-retinol. The soluble form is regenerated by transferring its palmitoyl groups onto 11-cis-retinol, a reaction catalyzed by LRAT.
Rpe65
17
3.1.1.64; 5.3.3.-
125105
118
17451
Patatin-like phospholipase domain-containing protein 2
P0C548
Catalyzes the initial step in triglyceride hydrolysis in adipocyte and non-adipocyte lipid droplets. Also has acylglycerol transacylase activity. May act coordinately with LIPE/HLS within the lipolytic cascade. Regulates adiposome size and may be involved in the degradation of adiposomes. May play an important role in energy homeostasis. May play a role in the response of the organism to starvation, enhancing hydrolysis of triglycerides and providing free fatty acids to other tissues to be oxidized in situations of energy depletion.
Pnpla2
17
3.1.1.3
125109
118
17455
Beta,beta-carotene 15,15'-dioxygenase
Q91XT5
Symmetrically cleaves beta-carotene into two molecules of retinal using a dioxygenase mechanism.
Bco1
17
1.13.11.63
125112
118
17457
Retinal dehydrogenase 1
O09184
Can convert/oxidize retinaldehyde to retinoic acid. Binds free retinal and cellular retinol-binding protein-bound retinal (PubMed:7832787). May have a broader specificity and oxidize other aldehydes in vivo (By similarity).
Aldh1a1
17
1.2.1.-; 1.2.1.36
125115
118
17458
Retinal dehydrogenase 2
Q4FZY8
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Does metabolize octanal and decanal but does not metabolize citral, benzaldehyde, acetaldehyde and propanal efficiently.
Aldh1a2
17
1.2.1.36
125116
118
17461
Cytochrome P450 26B1
Q80YE5
Involved in the metabolism of retinoic acid (RA), rendering this classical morphogen inactive through oxidation. Involved in the specific inactivation of all-trans-retinoic acid (all-trans-RA), with a preference for the following substrates: all-trans-RA > 9-cis-RA > 13-cis-RA. Generates several hydroxylated forms of RA, including 4-OH-RA, 4-oxo-RA, and 18-OH-RA. Essential for postnatal survival. Plays a central role in germ cell development: acts by degrading RA in the developing testis, preventing STRA8 expression, thereby leading to delay of meiosis. Required for the maintenance of the undifferentiated state of male germ cells during embryonic development in Sertoli cells, inducing arrest in G0 phase of the cell cycle and preventing meiotic entry. Plays a role in skeletal development, both at the level of patterning and in the ossification of bone and the establishment of some synovial joints (By similarity).
Cyp26b1
17
1.14.13.-
125119
118
17465
All-trans-retinol 13,14-reductase
Q8VHE9
Catalyzes the saturation of all-trans-retinol to all-trans-13,14-dihydroretinol. Does not exhibit any activity toward all-trans-retinoic acid, nor 9-cis, 11-cis or 13-cis-retinol isomers. May play a role in the metabolism of vitamin A. Independently of retinol conversion, may regulate liver metabolism upstream of MLXIPL/ChREBP. May play a role in adipocyte differentiation.
Retsat
17
1.3.99.23
125121
118
17468
DnaJ homolog subfamily B member 11
Q6TUG0
Serves as a co-chaperone for HSPA5. Binds directly to both unfolded proteins that are substrates for ERAD and nascent unfolded peptide chains, but dissociates from the HSPA5-unfolded protein complex before folding is completed. May help recruiting HSPA5 and other chaperones to the substrate. Stimulates HSPA5 ATPase activity (By similarity).
Dnajb11
17
125123
118
125259
398
7758
Unknown
Unknown
17
3.1.1.1, 3.1.1.56
5435
118
5460
120
80644
375
80655
135
80666
376
123808
443
123811
464
124957
473
124970
121
125260
398
131937
444
131983
470
132254
119
132257
529
132260
457
132605
137
132607
447
132609
138
132610
136
132612
452
132616
549
132621
552
132622
462
132623
553
132624
555
133143
400
135385
465
17474
Endoplasmic reticulum chaperone BiP
P06761
Endoplasmic reticulum chaperone that plays a key role in protein folding and quality control in the endoplasmic reticulum lumen (By similarity). Involved in the correct folding of proteins and degradation of misfolded proteins via its interaction with DNAJC10/ERdj5, probably to facilitate the release of DNAJC10/ERdj5 from its substrate (By similarity). Acts as a key repressor of the ERN1/IRE1-mediated unfolded protein response (UPR). In the unstressed endoplasmic reticulum, recruited by DNAJB9/ERdj4 to the luminal region of ERN1/IRE1, leading to disrupt the dimerization of ERN1/IRE1, thereby inactivating ERN1/IRE1. Accumulation of misfolded protein in the endoplasmic reticulum causes release of HSPA5/BiP from ERN1/IRE1, allowing homodimerization and subsequent activation of ERN1/IRE1 (By similarity).
Hspa5
17
3.6.4.10
125124
118
125261
398
17480
Protein disulfide-isomerase
P13700
This multifunctional protein catalyzes the formation, breakage and rearrangement of disulfide bonds. At the cell surface, seems to act as a reductase that cleaves disulfide bonds of proteins attached to the cell. May therefore cause structural modifications of exofacial proteins. Inside the cell, seems to form/rearrange disulfide bonds of nascent proteins. At high concentrations, functions as a chaperone that inhibits aggregation of misfolded proteins. At low concentrations, facilitates aggregation (anti-chaperone activity). May be involved with other chaperones in the structural modification of the TG precursor in hormone biogenesis. Also acts a structural subunit of various enzymes such as prolyl 4-hydroxylase and microsomal triacylglycerol transfer protein MTTP. Receptor for LGALS9; the interaction retains P4HB at the cell surface of Th2 T helper cells, increasing disulfide reductase activity at the plasma membrane, altering the plasma membrane redox state and enhancing cell migration.
P4hb
17
5.3.4.1
125125
118
125262
398
17484
Protein disulfide-isomerase A4
Q6P7S5
Pdia4
17
5.3.4.1
125126
118
125263
398
17488
Protein disulfide-isomerase A6
Q641Y3
May function as a chaperone that inhibits aggregation of misfolded proteins. Negatively regulates the unfolded protein response (UPR) through binding to UPR sensors such as ERN1, which in turn inactivates ERN1 signaling. May also regulate the UPR via the EIF2AK3 UPR sensor. Plays a role in platelet aggregation and activation by agonists such as convulxin, collagen and thrombin.
Pdia6
17
5.3.4.1
125127
118
125264
398
17492
Peptidyl-prolyl cis-trans isomerase B
O88541
PPIase that catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptides and may therefore assist protein folding.
Ppib
17
5.2.1.8
125128
118
125265
398
17498
RCG36668
D4A9Y0
Sdf2l1
17
125129
118
125266
398
17501
UDP-glucuronosyltransferase 1-1
Q64635
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Glucuronates opioids and bilirubin.
Ugt1a1
17
2.4.1.17
125130
118
125267
398
17503
Endoplasmic reticulum resident protein 29
Q5BKC2
Does not seem to be a disulfide isomerase. Plays an important role in the processing of secretory proteins within the endoplasmic reticulum (ER), possibly by participating in the folding of proteins in the ER.
Erp29
17
125131
118
125268
398
15447
Cytochrome P450 2A3
P20812
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Cyp2a3
17
1.14.14.1
123161
447
133599
118
16068
Cytochrome P450 2B12
P33272
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. This isozyme seems responsible for metabolism of 2,2',4,4',5,5'-hexachlorobiphenyl.
Cyp2b12
17
1.14.14.1
123677
398
132613
464
132615
447
133600
118
15432
Cytochrome P450 3A9
Q64631
This isozyme seems to be implicated in olfaction. Active in the demethylation of erythromycin as well as benzphetamine.
Cyp3a9
17
1.14.14.1
123146
136
123158
447
124268
464
125297
398
133601
118
9189
Alcohol dehydrogenase 1A
17
PW_P009189
17445
15525
2
9409
Retinol dehydrogenase 12
17
PW_P009409
17690
17416
1
9410
Dehydrogenase/reductase SDR family member 4
17
PW_P009410
17691
17420
1
9411
Retinol dehydrogenase 16
17
PW_P009411
17692
17422
1
9412
Retinol dehydrogenase 8
17
PW_P009412
17693
17262
1
9413
Short-chain dehydrogenase/reductase 3
17
PW_P009413
17694
17427
1
9414
Dehydrogenase/reductase SDR family member 9
17
PW_P009414
17695
17431
1
9415
Retinol dehydrogenase 11
17
PW_P009415
17696
17012
1
9416
Lecithin retinol acyltransferase
17
PW_P009416
17697
17434
1
9417
Acyl-CoA wax alcohol acyltransferase 1
17
PW_P009417
17698
17437
1
9418
Diacylglycerol O-acyltransferase 1
17
PW_P009418
17699
17704
1
9419
Retinoid isomerohydrolase
17
PW_P009419
17700
17445
1
9420
Patatin-like phospholipase domain-containing protein 4
17
PW_P009420
17701
17451
1
9421
Beta,beta-carotene 15,15'-monooxygenase
17
PW_P009421
17702
17455
1
9422
Retinal dehydrogenase 1
17
PW_P009422
17703
17457
4
9423
Retinal dehydrogenase 2
17
PW_P009423
17704
17458
1
9424
Cytochrome P450 26A1
17
PW_P009424
17705
17461
1
9425
All-trans-retinol 13,14-reductase
17
PW_P009425
17706
17465
1
9426
UDP-glucuronosyltransferase 1-1
17
PW_P009426
17707
17468
1
17708
7758
1
17709
17474
1
17710
7758
1
17711
17480
1
17712
17484
1
17713
17488
1
17714
17492
1
17715
17498
1
17716
17501
1
17717
17503
1
11467
Cytochrome P450
17
PW_P011467
20438
15447
1
20439
16068
1
20440
15432
1
967
1799
1
148057
false
PW_R148057
Right
552182
1448
1
Compound
false
552183
721
1
Compound
true
552184
1048
1
Compound
false
552185
1144
1
Compound
true
138323
9189
1.1.1.1
148058
false
PW_R148058
Right
552186
1448
1
Compound
false
552187
1048
1
Compound
false
138324
9409
1.1.1.-
148059
false
PW_R148059
Right
552188
1448
1
Compound
false
552189
143
1
Compound
true
552190
1048
1
Compound
false
552191
146
1
Compound
true
138325
9410
1.1.1.184
148060
false
PW_R148060
Right
552192
1448
1
Compound
false
552193
1048
1
Compound
false
138326
9411
1.1.-.-
148061
false
PW_R148061
Right
552194
1448
1
Compound
false
552195
143
1
Compound
true
552196
1048
1
Compound
false
552197
146
1
Compound
true
138327
9412
1.1.1.300
148062
false
PW_R148062
Right
552198
1448
1
Compound
false
552199
143
1
Compound
true
552200
1048
1
Compound
false
552201
146
1
Compound
true
138328
9413
1.1.1.300
148063
false
PW_R148063
Right
552202
1448
1
Compound
false
552203
1048
1
Compound
false
138329
9414
1.1.-.-
148064
false
PW_R148064
Right
552204
1448
1
Compound
false
552205
143
1
Compound
true
552206
2665
1
Compound
false
552207
146
1
Compound
true
138330
9415
1.1.1.300
148065
false
PW_R148065
Right
552208
2665
1
Compound
false
552209
4838
1
Compound
false
552210
1948
1
Compound
false
552211
59
1
Compound
true
138331
9416
2.3.1.135
148066
false
PW_R148066
Right
552212
2665
1
Compound
false
552213
940
1
Compound
true
552214
1948
1
Compound
false
552215
1099
1
Compound
true
138332
9417
2.3.1.75
148067
false
PW_R148067
Right
552216
2665
1
Compound
false
552217
940
1
Compound
true
552218
1948
1
Compound
false
552219
1099
1
Compound
true
138333
9418
148068
false
PW_R148068
Right
552220
1935
1
Compound
false
552221
1420
1
Compound
true
552222
2665
1
Compound
false
552223
25
1
ElementCollection
true
138334
9419
3.1.1.64
148069
false
PW_R148069
Right
552224
209
1
Compound
false
552225
940
1
Compound
true
552226
1935
1
Compound
false
552227
1099
1
Compound
true
138335
9418
148070
false
PW_R148070
Right
552228
209
1
Compound
false
552229
940
1
Compound
true
552230
1935
1
Compound
false
552231
1099
1
Compound
true
138336
9417
2.3.1.75
148071
false
PW_R148071
Right
552232
209
1
Compound
false
552233
4838
1
Compound
false
552234
1935
1
Compound
false
552235
59
1
Compound
true
138337
9416
2.3.1.135
148072
false
PW_R148072
Right
552236
209
1
Compound
false
552237
143
1
Compound
true
552238
1048
1
Compound
false
552239
146
1
Compound
true
138338
9415
1.1.1.300
148073
false
PW_R148073
Right
552240
1935
1
Compound
false
552241
3195
1
Compound
false
552242
209
1
Compound
false
552243
29134
1
Compound
false
138339
9420
3.1.1.3
1693
PW_R001693
Right
6435
209
1
Compound
false
6436
2666
1
Compound
false
148074
false
PW_R148074
Right
552244
437
1
Compound
false
552245
1065
1
Compound
true
552246
1048
1
Compound
false
138340
9421
1.14.99.36
148075
false
PW_R148075
Right
552247
2666
1
Compound
false
552248
143
1
Compound
true
552249
2667
1
Compound
false
552250
146
1
Compound
true
138341
9415
1.1.1.300
148076
false
PW_R148076
Both
552251
2666
1
Compound
false
552252
143
1
Compound
true
552253
2667
1
Compound
false
552254
146
1
Compound
true
138342
9415
1.1.1.300
148077
false
PW_R148077
Both
552255
2666
1
Compound
false
552256
143
1
Compound
true
552257
2667
1
Compound
false
552258
146
1
Compound
true
138343
9410
1.1.1.184
148078
false
PW_R148078
Right
552259
2667
1
Compound
false
552260
721
1
Compound
true
552261
1420
1
Compound
true
552262
1600
1
Compound
false
552263
1144
1
Compound
true
138344
9422
1.2.1.36
148079
false
PW_R148079
Right
552264
2667
1
Compound
false
552265
721
1
Compound
true
552266
1420
1
Compound
true
552267
1600
1
Compound
false
552268
1144
1
Compound
true
138345
9423
1.2.1.36
148080
false
PW_R148080
Right
552269
209
1
Compound
false
552270
721
1
Compound
true
552271
1420
1
Compound
true
552272
1227
1
Compound
false
552273
1144
1
Compound
true
138346
9422
1.2.1.36
148081
false
PW_R148081
Right
552274
209
1
Compound
false
552275
721
1
Compound
true
552276
1420
1
Compound
true
552277
1227
1
Compound
false
552278
1144
1
Compound
true
138347
9423
1.2.1.36
1703
PW_R001703
Right
6474
1227
1
Compound
false
6475
1600
1
Compound
false
148082
false
PW_R148082
Right
552279
209
1
Compound
false
552280
7859
1
Compound
false
138348
9424
1.14.-.-
148083
false
PW_R148083
Right
552281
209
1
Compound
false
552282
40
1
ElementCollection
true
552283
7207
1
Compound
false
552284
41
1
ElementCollection
true
138349
9425
1.3.99.23
148084
false
PW_R148084
Right
552285
1227
1
Compound
false
552286
40
1
ElementCollection
true
552287
1786
1
Compound
false
552288
41
1
ElementCollection
true
138350
9426
5.3.4.1
148085
false
PW_R148085
Right
552289
1227
1
Compound
false
552290
2690
1
Compound
false
138351
9424
1.14.-.-
148086
false
PW_R148086
Right
552291
2690
1
Compound
false
552292
2706
1
Compound
false
138352
9424
1.14.-.-
148087
false
PW_R148087
Right
552293
1227
1
Compound
false
552294
7979
1
Compound
false
138353
9424
1.14.-.-
178657
false
PW_R178657
Right
674255
1227
1
Compound
false
674256
7978
1
Compound
false
168773
11467
1.14.13.-
1711
PW_R001711
Right
6494
1448
1
Compound
false
6495
59
1
ElementCollection
false
1712
PW_R001712
Right
6496
59
1
ElementCollection
false
6497
60
1
ElementCollection
false
1713
PW_R001713
Right
6498
59
1
ElementCollection
false
6499
61
1
ElementCollection
false
1714
PW_R001714
Right
6500
61
1
ElementCollection
false
6501
1448
1
Compound
false
1715
PW_R001715
Right
6502
60
1
ElementCollection
false
6503
62
1
ElementCollection
false
1716
PW_R001716
Right
6504
62
1
ElementCollection
false
6505
63
1
ElementCollection
false
1717
PW_R001717
Right
6506
63
1
ElementCollection
false
6507
1048
1
Compound
false
2663366
1448
118
81
false
480
640
10
regular
200
190
2663367
721
118
59
false
670
350
10
regular
50
30
2663368
1048
118
81
false
1025
640
10
regular
200
190
2663369
1144
118
60
false
955
340
10
regular
50
30
2663370
9795
118
9
false
790
365
10
regular
100
25
2663371
143
118
9
false
812
485
10
regular
100
25
2663372
143
118
61
false
715
630
10
regular
50
30
2663373
146
118
62
false
945
635
10
regular
50
30
2663374
721
118
9
false
805
825
10
regular
100
25
2663375
143
118
61
false
685
950
10
regular
50
30
2663376
146
118
62
false
990
950
10
regular
50
30
2663377
143
118
61
false
685
1050
10
regular
50
30
2663378
146
118
62
false
990
1050
10
regular
50
30
2663379
143
118
9
false
800
1210
10
regular
100
25
2663380
721
118
9
false
795
1135
10
regular
100
25
2663381
143
118
61
false
460
910
10
regular
50
30
2663382
2665
118
81
false
460
1185
10
regular
200
190
2663383
146
118
62
false
460
1110
10
regular
50
30
2663384
143
118
61
false
275
895
10
regular
50
30
2663385
146
118
62
false
275
1075
10
regular
50
30
2663386
4838
118
81
false
880
1310
10
regular
200
190
2663387
1948
118
82
false
465
1860
10
regular
300
280
2663388
59
118
81
false
880
1625
10
regular
200
190
2663389
940
118
81
false
120
1365
10
regular
200
190
2663390
1099
118
85
false
225
1660
10
regular
50
30
2663391
940
118
81
false
430
1390
10
regular
200
190
2663392
1099
118
85
false
525
1755
10
regular
50
30
2663393
1935
118
81
false
1365
1185
10
regular
200
190
2663394
1420
118
49
false
1255
1155
10
regular
78
78
2663395
544
118
9
false
1105
1235
10
regular
100
25
2663396
209
118
81
false
2180
1185
10
regular
200
190
2663397
940
118
81
false
1955
890
10
regular
200
190
2663398
1099
118
85
false
1750
1040
10
regular
50
30
2663399
940
118
3
false
2030
1145
10
regular
100
100
2663400
1099
118
85
false
1750
1205
10
regular
50
30
2663401
4838
118
81
false
1960
1460
10
regular
200
190
2663402
59
118
81
false
1690
1465
10
regular
200
190
2663403
143
118
61
false
2000
675
10
regular
50
30
2663404
146
118
62
false
1685
670
10
regular
50
30
2663405
3195
118
81
false
1435
1680
10
regular
200
190
2663406
29134
118
81
false
2155
1685
10
regular
200
190
2663407
2666
118
81
false
2310
655
10
regular
200
190
2663408
437
118
81
false
1118
165
10
regular
200
190
2663409
1065
118
65
false
1274
361
10
regular
78
78
2663410
544
118
9
false
1243
460
10
regular
100
25
2663411
143
118
61
false
2685
570
10
regular
50
30
2663412
2667
118
81
false
2310
195
10
regular
200
190
2663413
146
118
62
false
2675
430
10
regular
50
30
2663414
143
118
61
false
2305
595
10
regular
50
30
2663415
146
118
62
false
2305
415
10
regular
50
30
2663416
143
118
61
false
2060
585
10
regular
50
30
2663417
146
118
62
false
2055
440
10
regular
50
30
2663418
721
118
59
false
2595
365
10
regular
50
30
2663419
1420
118
49
false
2515
215
10
regular
78
78
2663420
1600
118
81
false
2945
185
10
regular
200
190
2663421
1144
118
60
false
2845
365
10
regular
50
30
2663422
721
118
59
false
2615
225
10
regular
50
30
2663423
1420
118
49
false
2580
100
10
regular
78
78
2663424
1144
118
60
false
2850
235
10
regular
50
30
2663425
721
118
59
false
2450
1190
10
regular
50
30
2663426
1420
118
49
false
2425
1320
10
regular
78
78
2663427
1227
118
81
false
2880
1185
10
regular
200
190
2663428
1144
118
60
false
2745
1190
10
regular
50
30
2663429
721
118
59
false
2410
1440
10
regular
50
30
2663430
1420
118
49
false
2450
1495
10
regular
78
78
2663431
1144
118
60
false
2815
1440
10
regular
50
30
2663432
7859
118
81
false
2375
1995
10
regular
200
190
2663433
1799
118
9
false
2500
1775
10
regular
100
25
2663434
7207
118
81
false
2605
1995
10
regular
200
190
2663435
721
118
9
false
2730
1787
10
regular
100
25
2663436
1786
118
81
false
2885
1765
10
regular
200
190
2663437
2690
118
81
false
3490
975
10
regular
200
190
2663438
1799
118
9
false
3290
1020
10
regular
100
25
2663439
2706
118
81
false
3990
975
10
regular
200
190
2663440
1799
118
9
false
3780
1025
10
regular
100
25
2663441
7979
118
81
false
3505
1175
10
regular
200
200
2663442
1799
118
9
false
3300
1230
10
regular
100
25
2663443
7978
118
81
false
3730
1305
10
regular
200
200
2663444
1799
118
9
false
3255
1360
10
regular
100
25
13728
25
37
118
false
1000
1145
12
regular
100
90
13729
40
37
118
false
2750
1655
12
regular
100
90
13730
41
37
118
false
2775
1885
12
regular
100
90
13731
40
37
118
false
3070
1395
12
regular
100
90
13732
41
37
118
false
3075
1565
12
regular
100
90
13733
59
37
false
205
685
12
regular
100
90
13734
60
37
false
205
200
12
regular
100
90
13735
61
37
false
335
460
12
regular
100
90
13736
62
37
false
555
195
12
regular
100
90
13737
63
37
false
810
195
12
regular
100
90
930487
15525
118
6
false
765
370
8
subunit
regular
160
80
930488
17416
118
2
false
782
500
8
subunit
regular
150
70
930489
17420
118
8
false
782
695
8
subunit
regular
140
85
930490
17422
118
2
false
785
840
8
subunit
regular
150
70
930491
17262
118
2
false
785
930
8
subunit
regular
150
70
930492
17427
118
2
false
780
1030
8
subunit
regular
150
70
930493
17431
118
2
false
775
1150
8
subunit
regular
150
70
930494
17012
118
2
false
485
995
8
subunit
regular
150
70
930495
17012
118
2
false
295
972
8
subunit
regular
150
70
930496
17434
118
2
false
735
1532
8
subunit
regular
150
70
930497
17437
118
2
false
265
1577
8
subunit
regular
150
70
930498
17704
118
2
false
565
1642
8
subunit
regular
150
70
930499
17445
118
2
false
1085
1245
8
subunit
regular
150
70
930500
17704
118
2
false
1840
1080
8
subunit
regular
150
70
930501
17437
118
2
false
1840
1245
8
subunit
regular
150
70
930502
17434
118
2
false
1840
1380
8
subunit
regular
150
70
930503
17012
118
2
false
1785
700
8
subunit
regular
150
70
930504
17451
118
2
false
1820
1745
8
subunit
regular
150
70
930505
17455
118
2
false
1143
465
8
subunit
regular
150
70
930506
17012
118
2
false
2560
490
8
subunit
regular
150
70
930507
17012
118
2
false
2335
495
8
subunit
regular
150
70
930508
17420
118
8
false
2075
485
8
subunit
regular
140
85
930509
17457
118
8
false
2675
290
8
subunit
regular
140
85
930510
17458
118
2
false
2677
165
8
subunit
regular
150
70
930511
17457
118
2
false
2575
1245
8
subunit
regular
150
70
930512
17458
118
2
false
2575
1425
8
subunit
regular
150
70
930513
17461
118
2
false
2405
1780
8
subunit
regular
150
70
930514
17465
118
2
false
2630
1797
8
subunit
regular
150
70
930515
17468
118
116
false
2910
1522
8
none
regular
160
80
930516
7758
118
124
false
2870
1502
8
none
regular
170
90
930517
17474
118
2
false
2880
1472
8
none
regular
150
70
930518
7758
118
119
false
2880
1517
8
none
regular
160
80
930519
17480
118
116
false
2880
1497
8
none
regular
160
80
930520
17484
118
124
false
2885
1472
8
none
regular
170
90
930521
17488
118
2
false
2920
1462
8
none
regular
150
70
930522
17492
118
119
false
2910
1442
8
none
regular
160
80
930523
17498
118
98
false
2900
1477
8
none
regular
150
70
930524
17501
118
97
false
2890
1482
8
none
regular
150
70
930525
17503
118
2
false
2905
1492
8
protein
regular
150
70
930526
17461
118
2
false
3260
1035
8
subunit
regular
150
70
930527
17461
118
2
false
3760
1035
8
subunit
regular
150
70
930528
17461
118
2
false
3280
1240
8
subunit
regular
150
70
930529
15447
118
119
false
3275
1365
8
none
regular
160
80
930530
15447
118
116
false
3270
1340
8
none
regular
160
80
930531
15447
118
113
false
3255
1370
8
none
regular
160
80
930532
16068
118
2
false
3245
1355
8
none
regular
150
70
930533
15432
118
119
false
3275
1365
8
none
regular
160
80
930534
15432
118
116
false
3255
1370
8
none
regular
160
80
930535
15432
118
124
false
3240
1350
8
none
regular
170
90
930536
15432
118
2
false
3240
1375
8
protein
regular
150
70
794807
9189
88128
118
926947
930487
33182
2663370
3627779
Cofactor
794808
9409
88128
118
926948
930488
33183
2663371
3627782
Cofactor
794809
9410
88128
118
926949
930489
794810
9411
88128
118
926950
930490
33184
2663374
3627789
Cofactor
794811
9412
88128
118
926951
930491
794812
9413
88128
118
926952
930492
794813
9414
88128
118
926953
930493
33185
2663379
3627800
Cofactor
33186
2663380
3627801
Cofactor
794814
9415
88128
118
926954
930494
794815
9415
88128
118
926955
930495
794816
9416
88128
118
926956
930496
794817
9417
88128
118
926957
930497
794818
9418
88128
118
926958
930498
794819
9419
88128
118
926959
930499
33187
2663395
3627826
Cofactor
794820
9418
88128
118
926960
930500
794821
9417
88128
118
926961
930501
794822
9416
88128
118
926962
930502
794823
9415
88128
118
926963
930503
794824
9420
88128
118
926964
930504
794825
9421
88128
118
926965
930505
33188
2663410
3627852
Cofactor
794826
9415
88128
118
926966
930506
794827
9415
88128
118
926967
930507
794828
9410
88128
118
926968
930508
794829
9422
88128
118
926969
930509
794830
9423
88128
118
926970
930510
794831
9422
88128
118
926971
930511
794832
9423
88128
118
926972
930512
794833
9424
88128
118
926973
930513
33189
2663433
3627889
Cofactor
794834
9425
88128
118
926974
930514
33190
2663435
3627894
Cofactor
794835
9426
88128
118
926975
930515
926976
930516
926977
930517
926978
930518
926979
930519
926980
930520
926981
930521
926982
930522
926983
930523
926984
930524
926985
930525
794836
9424
88128
118
926986
930526
33191
2663438
3627901
Cofactor
794837
9424
88128
118
926987
930527
33192
2663440
3627904
Cofactor
794838
9424
88128
118
926988
930528
33193
2663442
3627907
Cofactor
794839
11467
88128
118
926989
930529
926990
930530
926991
930531
926992
930532
926993
930533
926994
930534
926995
930535
926996
930536
33194
2663444
3627910
Cofactor
2880010
M3080 1331 C3134 1388 3210 1410 3240 1410
5
false
18
2880011
M3730 1405 C3700 1405 3420 1410 3390 1410
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
2880012
M3205 1390 L3205 1440 L3255 1390 z
10
true
18
3627775
M580 640 C588 543 640 410 765 410
5
false
18
true
M 573.593124483032 631.4371114392959 L 580 645 L 588.5423682837832 632.6700387630692
false
3627776
M695 380 C701 406 735 410 765 410
5
false
18
3627777
M1125 640 C1123 555 1041 405 925 410
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627778
M980 370 C967 400 955 410 925 410
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627779
M325 210 L325 260 L375 210 z
10
true
18
3627780
M633 645 C625 552 752 535 782 535
5
false
18
3627781
M1074 637 C1074 567 962 535 932 535
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627782
M150 150 L150 200 L200 150 z
10
true
18
3627783
M680 735 C710 735 752 735 782 735
5
false
18
3627784
M740 660 C736 691 752 735 782 735
5
false
18
3627785
M1025 735 C995 735 952 735 922 735
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627786
M970 665 C973 707 952 735 922 735
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627787
M681 801 C712 833 755 875 785 875
5
false
18
3627788
M1032 799 C1006 840 965 875 935 875
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627789
M150 150 L150 200 L200 150 z
10
true
18
3627790
M674 831 C684 867 755 965 785 965
5
false
18
3627791
M735 965 C765 965 755 965 785 965
5
false
18
3627792
M1037 825 C1043 882 965 965 935 965
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627793
M990 965 C960 965 965 965 935 965
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627794
M622 831 C649 973 724 1061 780 1065
5
false
18
3627795
M735 1065 C765 1065 750 1065 780 1065
5
false
18
3627796
M1093 831 C1081 1025 960 1065 930 1065
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627797
M990 1065 C960 1065 960 1065 930 1065
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627798
M580 830 C616 1020 714 1185 775 1185
5
false
18
3627799
M1125 830 C1140 1018 984 1188 925 1185
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627800
M150 150 L150 200 L200 150 z
10
true
18
3627801
M150 150 L150 200 L200 150 z
10
true
18
3627802
M556 830 C556 860 560 965 560 995
5
false
18
3627803
M510 925 C558 925 560 965 560 995
5
false
18
3627804
M560 1185 C560 1155 560 1095 560 1065
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627805
M510 1125 C536 1127 560 1095 560 1065
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627806
M480 735 C364 747 370 942 370 972
5
false
18
3627807
M325 910 C354 907 370 942 370 972
5
false
18
3627808
M460 1280 C355 1219 370 1072 370 1042
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627809
M325 1090 C358 1096 370 1072 370 1042
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627810
M660 1280 C731 1278 810 1502 810 1532
5
false
18
3627811
M810 1532 C809 1499 796 1411 880 1405
5
false
18
3627812
M703 1861 C821 1820 810 1632 810 1602
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627813
M880 1720 C818 1721 810 1632 810 1602
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627814
M459 1301 C411 1302 340 1547 340 1577
5
false
18
3627815
M320 1460 C357 1449 340 1547 340 1577
5
false
18
3627816
M465 1955 C371 1897 340 1677 340 1647
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627817
M275 1675 C315 1673 340 1677 340 1647
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627818
M639 1372 C639 1402 640 1612 640 1642
5
false
18
3627819
M530 1580 C530 1610 640 1612 640 1642
5
false
18
3627820
M642 1858 C642 1828 640 1742 640 1712
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627821
M575 1770 C591 1768 640 1742 640 1712
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627822
M1365 1280 C1335 1280 1265 1280 1235 1280
5
false
18
3627823
M1294 1233 C1294 1271 1265 1280 1235 1280
5
false
18
3627824
M660 1280 C690 1280 1055 1280 1085 1280
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627825
M1050 1245 C1056 1265 1055 1280 1085 1280
5
false
18
true
M 1060.9164556685216 1255.2874192894624 L 1050 1245 L 1046.5490613902043 1259.5976375729576
false
3627826
M150 150 L150 200 L200 150 z
10
true
18
3627827
M2280 1185 C2274 1120 2020 1115 1990 1115
5
false
18
3627828
M2055 1080 C2056 1117 2020 1115 1990 1115
5
false
18
3627829
M1562 1191 C1568 1135 1810 1115 1840 1115
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627830
M1775 1070 C1776 1091 1810 1115 1840 1115
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627831
M2180 1280 C2150 1280 2020 1280 1990 1280
5
false
18
3627832
M2080 1245 C2081 1273 2020 1280 1990 1280
5
false
18
3627833
M1565 1280 C1595 1280 1810 1280 1840 1280
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627834
M1775 1235 C1776 1267 1810 1280 1840 1280
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627835
M2179 1362 C2155 1407 2020 1415 1990 1415
5
false
18
3627836
M2060 1460 C2058 1416 2020 1415 1990 1415
5
false
18
3627837
M1561 1354 C1617 1418 1810 1415 1840 1415
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627838
M1790 1465 C1790 1433 1810 1415 1840 1415
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627839
M2301 1188 C2280 813 2033 735 1935 735
5
false
18
3627840
M2025 705 C2027 731 1965 735 1935 735
5
false
18
3627841
M1225 735 C1255 735 1755 735 1785 735
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627842
M1710 700 C1716 735 1755 735 1785 735
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627843
M1465 1375 C1527 1619 1751 1780 1820 1780
5
false
18
3627844
M1635 1775 C1665 1775 1790 1780 1820 1780
5
false
18
3627845
M2280 1375 C2295 1637 2044 1781 1970 1780
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627846
M2155 1780 C2125 1780 2000 1780 1970 1780
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627847
M2280 1185 C2280 1155 2206 1093 2230 1110
5
true
18
3627848
M2410 845 C2410 875 2343 1152 2330 1184
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627849
M1218 355 C1218 385 1218 435 1218 465
5
false
18
3627850
M1274 400 C1233 404 1218 435 1218 465
5
false
18
3627851
M1218 639 C1218 609 1218 565 1218 535
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627852
M1293 615 L1293 665 L1343 615 z
10
true
18
3627853
M2511 700 C2595 669 2635 590 2635 560
5
false
18
true
M 2520.590284247219 688.466290793611 L 2511 700 L 2525.783627296205 702.538575184411
false
3627854
M2685 585 C2661 587 2635 590 2635 560
5
false
18
true
M 2661.3278098408605 601.1701876999267 L 2675 595 L 2662.8203656261753 586.2446298467769
false
3627855
M2510 358 C2579 382 2635 460 2635 490
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627856
M2675 445 C2651 449 2635 460 2635 490
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627857
M2410 655 C2410 625 2410 595 2410 565
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627858
M2355 610 C2386 608 2410 595 2410 565
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627859
M2410 385 C2410 415 2410 465 2410 495
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627860
M2355 430 C2401 428 2407 465 2410 495
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627861
M2310 750 C2213 735 2145 600 2145 570
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627862
M2110 600 C2134 600 2145 600 2145 570
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627863
M2310 290 C2232 295 2145 455 2145 485
5
false
18
true
M 2297.5160111000605 248.31564917166372 L 2310 240 L 2296.5564421184104 233.34637305792145
false
3627864
M2105 455 C2137 450 2145 455 2145 485
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627865
M2508 327 C2538 327 2645 330 2675 330
5
false
18
3627866
M2620 365 C2619 339 2645 330 2675 330
5
false
18
3627867
M2554 293 C2552 325 2623 328 2675 330
5
false
18
3627868
M2949 333 C2919 333 2845 330 2815 330
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627869
M2870 365 C2873 330 2845 330 2815 330
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627870
M2504 200 C2562 199 2647 200 2677 200
5
false
18
3627871
M2640 225 C2632 204 2647 200 2677 200
5
false
18
3627872
M2619 178 C2633 192 2647 200 2677 200
5
false
18
3627873
M2946 200 C2907 201 2857 200 2827 200
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627874
M2875 235 C2879 203 2857 200 2827 200
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627875
M2380 1280 C2410 1280 2545 1280 2575 1280
5
false
18
3627876
M2475 1220 C2473 1263 2545 1280 2575 1280
5
false
18
3627877
M2464 1320 C2456 1294 2545 1280 2575 1280
5
false
18
3627878
M2880 1280 C2850 1280 2755 1280 2725 1280
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627879
M2770 1220 C2772 1266 2755 1280 2725 1280
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627880
M2371 1374 C2424 1419 2545 1460 2575 1460
5
false
18
3627881
M2460 1455 C2490 1455 2545 1460 2575 1460
5
false
18
3627882
M2489 1495 C2489 1479 2545 1460 2575 1460
5
false
18
3627883
M2885 1371 C2837 1421 2755 1460 2725 1460
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627884
M2815 1455 C2785 1455 2755 1460 2725 1460
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627885
M2980 1185 C2980 1155 2906 718 2930 735
5
true
18
3627886
M3045 375 C3045 405 3050 1131 3049 1187
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627887
M2305 1368 C2296 1489 2472 1661 2480 1780
5
false
18
3627888
M2475 1995 C2475 1965 2480 1880 2480 1850
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627889
M150 150 L150 200 L200 150 z
10
true
18
3627890
M2332 1374 C2406 1722 2702 1646 2705 1797
5
false
18
3627891
M2705 1995 C2705 1965 2705 1897 2705 1867
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627892
M2750 1710 C2691 1713 2705 1767 2705 1797
5
false
18
3627893
M2775 1935 C2727 1931 2705 1897 2705 1867
5
false
18
true
M 2761.4316497609916 1941.3953007584944 L 2775 1935 L 2762.677331958798 1926.4471143848214
false
3627894
M150 150 L150 200 L200 150 z
10
true
18
3627895
M2980 1375 C2980 1405 2980 1462 2980 1492
5
false
18
3627896
M2985 1765 C2985 1735 2980 1592 2980 1562
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627897
M3070 1450 C3034 1455 2980 1462 2980 1492
5
false
18
3627898
M3075 1615 C3025 1608 2980 1592 2980 1562
5
false
18
true
M 3061.0952245002686 1620.6264747668563 L 3075 1615 L 3063.174942168285 1605.7713485667412
false
3627899
M3072 1187 C3100 1094 3230 1070 3260 1070
5
false
18
3627900
M3490 1070 C3460 1070 3440 1070 3410 1070
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627901
M150 150 L150 200 L200 150 z
10
true
18
3627902
M3690 1070 C3720 1070 3730 1070 3760 1070
5
false
18
3627903
M3990 1070 C3960 1070 3940 1070 3910 1070
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627904
M150 150 L150 200 L200 150 z
10
true
18
3627905
M3080 1280 C3110 1280 3250 1275 3280 1275
5
false
18
3627906
M3505 1275 C3475 1275 3460 1275 3430 1275
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627907
M150 150 L150 200 L200 150 z
10
true
18
3627908
M3080 1331 C3134 1388 3210 1410 3240 1410
5
false
18
3627909
M3730 1405 C3700 1405 3420 1410 3390 1410
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627910
M3205 1390 L3205 1440 L3255 1390 z
10
true
18
3627911
M480 735 C450 735 345 733 305 735
5
false
18
true
M 317.3417711296125 726.4747032084352 L 305 735 L 318.5540091611033 741.4256389301554
false
3627912
M305 735 C335 735 381 673 405 690
5
true
18
3627913
M255 685 C255 655 254 352 255 300
5
false
18
true
M 261.4815918950292 488.5273414426594 L 255 475 L 246.52577461250553 487.3768939593884
false
3627914
M255 300 C255 330 231 593 255 610
5
true
18
3627915
M11 12 C34 28 74 55 98 72
5
true
18
3627916
M335 510 C281 510 288 650 286 685
5
false
18
true
M 392.5 572.9903810567666 L 385 560 L 377.5 572.9903810567666
false
3627917
M11 12 C34 28 74 55 98 72
5
true
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627918
M435 510 C463 518 490.5 581 489.5 641
5
false
18
true
M 482.2175177365858 627.8864401445276 L 489.5 641 L 497.21543483717977 628.1364054295375
false
3627919
M305 250 C335 250 356 318 380 335
5
true
18
3627920
M555 245 C525 245 362 251 305 250
5
false
18
true
M 537.0096189432334 251.5 L 550 244 L 537.0096189432334 236.5
false
3627921
M655 245 C685 245 706 228 730 245
5
true
18
3627922
M810 245 C780 245 703 243 655 245
5
false
18
true
M 792.0096189432334 252.5 L 805 245 L 792.0096189432334 237.5
false
3627923
M1148 638 C1149 602 1074 252 910 245
5
false
18
true
M 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345
false
3627924
M910 245 C940 245 943.5 223 967.5 240
5
true
18
792719
88128
148057
118
3208412
2663366
3627775
Left
3208413
2663367
3627776
Left
3208414
2663368
3627777
Right
3208415
2663369
3627778
Right
749179
138323
794807
792720
88128
148058
118
3208416
2663366
3627780
Left
3208417
2663368
3627781
Right
749180
138324
794808
792721
88128
148059
118
3208418
2663366
3627783
Left
3208419
2663372
3627784
Left
3208420
2663368
3627785
Right
3208421
2663373
3627786
Right
749181
138325
794809
792722
88128
148060
118
3208422
2663366
3627787
Left
3208423
2663368
3627788
Right
749182
138326
794810
792723
88128
148061
118
3208424
2663366
3627790
Left
3208425
2663375
3627791
Left
3208426
2663368
3627792
Right
3208427
2663376
3627793
Right
749183
138327
794811
792724
88128
148062
118
3208428
2663366
3627794
Left
3208429
2663377
3627795
Left
3208430
2663368
3627796
Right
3208431
2663378
3627797
Right
749184
138328
794812
792725
88128
148063
118
3208432
2663366
3627798
Left
3208433
2663368
3627799
Right
749185
138329
794813
792726
88128
148064
118
3208434
2663366
3627802
Left
3208435
2663381
3627803
Left
3208436
2663382
3627804
Right
3208437
2663383
3627805
Right
749186
138330
794814
792727
88128
148064
118
3208438
2663366
3627806
Left
3208439
2663384
3627807
Left
3208440
2663382
3627808
Right
3208441
2663385
3627809
Right
749187
138330
794815
792728
88128
148065
118
3208442
2663382
3627810
Left
3208443
2663386
3627811
Left
3208444
2663387
3627812
Right
3208445
2663388
3627813
Right
749188
138331
794816
792729
88128
148066
118
3208446
2663382
3627814
Left
3208447
2663389
3627815
Left
3208448
2663387
3627816
Right
3208449
2663390
3627817
Right
749189
138332
794817
792730
88128
148067
118
3208450
2663382
3627818
Left
3208451
2663391
3627819
Left
3208452
2663387
3627820
Right
3208453
2663392
3627821
Right
749190
138333
794818
792731
88128
148068
118
3208454
2663393
3627822
Left
3208455
2663394
3627823
Left
3208456
2663382
3627824
Right
13177
13728
3627825
Right
749191
138334
794819
792732
88128
148069
118
3208457
2663396
3627827
Left
3208458
2663397
3627828
Left
3208459
2663393
3627829
Right
3208460
2663398
3627830
Right
749192
138335
794820
792733
88128
148070
118
3208461
2663396
3627831
Left
3208462
2663399
3627832
Left
3208463
2663393
3627833
Right
3208464
2663400
3627834
Right
749193
138336
794821
792734
88128
148071
118
3208465
2663396
3627835
Left
3208466
2663401
3627836
Left
3208467
2663393
3627837
Right
3208468
2663402
3627838
Right
749194
138337
794822
792735
88128
148072
118
3208469
2663396
3627839
Left
3208470
2663403
3627840
Left
3208471
2663368
3627841
Right
3208472
2663404
3627842
Right
749195
138338
794823
792736
88128
148073
118
3208473
2663393
3627843
Left
3208474
2663405
3627844
Left
3208475
2663396
3627845
Right
3208476
2663406
3627846
Right
749196
138339
794824
792737
88128
1693
118
3208477
2663396
3627847
Left
3208478
2663407
3627848
Right
792738
88128
148074
118
3208479
2663408
3627849
Left
3208480
2663409
3627850
Left
3208481
2663368
3627851
Right
749197
138340
794825
792739
88128
148075
118
3208482
2663407
3627853
Left
3208483
2663411
3627854
Left
3208484
2663412
3627855
Right
3208485
2663413
3627856
Right
749198
138341
794826
792740
88128
148076
118
3208486
2663407
3627857
Left
3208487
2663414
3627858
Left
3208488
2663412
3627859
Right
3208489
2663415
3627860
Right
749199
138342
794827
792741
88128
148077
118
3208490
2663407
3627861
Left
3208491
2663416
3627862
Left
3208492
2663412
3627863
Right
3208493
2663417
3627864
Right
749200
138343
794828
792742
88128
148078
118
3208494
2663412
3627865
Left
3208495
2663418
3627866
Left
3208496
2663419
3627867
Left
3208497
2663420
3627868
Right
3208498
2663421
3627869
Right
749201
138344
794829
792743
88128
148079
118
3208499
2663412
3627870
Left
3208500
2663422
3627871
Left
3208501
2663423
3627872
Left
3208502
2663420
3627873
Right
3208503
2663424
3627874
Right
749202
138345
794830
792744
88128
148080
118
3208504
2663396
3627875
Left
3208505
2663425
3627876
Left
3208506
2663426
3627877
Left
3208507
2663427
3627878
Right
3208508
2663428
3627879
Right
749203
138346
794831
792745
88128
148081
118
3208509
2663396
3627880
Left
3208510
2663429
3627881
Left
3208511
2663430
3627882
Left
3208512
2663427
3627883
Right
3208513
2663431
3627884
Right
749204
138347
794832
792746
88128
1703
118
3208514
2663427
3627885
Left
3208515
2663420
3627886
Right
792747
88128
148082
118
3208516
2663396
3627887
Left
3208517
2663432
3627888
Right
749205
138348
794833
792748
88128
148083
118
3208518
2663396
3627890
Left
3208519
2663434
3627891
Right
13178
13729
3627892
Left
13179
13730
3627893
Right
749206
138349
794834
792749
88128
148084
118
3208520
2663427
3627895
Left
3208521
2663436
3627896
Right
13180
13731
3627897
Left
13181
13732
3627898
Right
749207
138350
794835
792750
88128
148085
118
3208522
2663427
3627899
Left
3208523
2663437
3627900
Right
749208
138351
794836
792751
88128
148086
118
3208524
2663437
3627902
Left
3208525
2663439
3627903
Right
749209
138352
794837
792752
88128
148087
118
3208526
2663427
3627905
Left
3208527
2663441
3627906
Right
749210
138353
794838
792753
88128
178657
118
3208528
2663427
3627908
Left
3208529
2663443
3627909
Right
749211
168773
794839
792754
88128
1711
3208530
2663366
3627911
Left
13182
13733
3627912
Right
792755
88128
1712
13183
13733
3627913
Left
13184
13734
3627914
Right
792756
88128
1713
13185
13733
3627915
Left
13186
13735
3627916
Right
792757
88128
1714
3208531
2663366
3627917
Right
13187
13735
3627918
Left
792758
88128
1715
13188
13734
3627919
Left
13189
13736
3627920
Right
792759
88128
1716
13190
13736
3627921
Left
13191
13737
3627922
Right
792760
88128
1717
3208532
2663368
3627923
Right
13192
13737
3627924
Left
185134
66
645
800
1.3
1.3
0
2
3
280
360
185135
66
435
875
0.8
0.8
0
2
3
280
360
185136
66
710
1165
1.9
1.9
60
2
3
280
360
185137
66
1705
1040
1.3
1.3
0
2
3
280
360
185138
66
1715
600
0.8
0.8
0
2
3
280
360
185139
66
2535
405
0.6
0.6
0
2
3
280
360
185140
66
2345
1675
0.8
0.8
0
2
3
280
360
185141
66
2815
1380
1.0
1.0
0
2
3
280
360
185142
66
3190
910
0.8
0.8
0
2
3
280
360
185143
66
3705
925
0.8
0.8
0
2
3
280
360
185144
66
3190
1190
1.0
1.0
0
2
3
280
360
368584
M78 156 C78 106 128 56 178 56 C1381 56 2945 56 4148 56 C4198 56 4248 106 4248 156 C4248 777 4248 1584 4248 2205 C4248 2255 4198 2305 4148 2305 C2945 2305 1381 2305 178 2305 C128 2305 78 2255 78 2205 C78 1584 78 777 78 156
1
true
6
4170.0
2249.0
447439
15
hv
385
555
20
1.0
1.0
160
15
447440
15
hv
170
370
20
1.0
1.0
160
15
447441
15
Intracellular Space
275
100
20
1.0
1.0
160
15
447442
15
Endoplasmic Reticulum
700
1080
20
1.0
1.0
160
15
447443
15
Endoplasmic Reticulum
350
1640
20
1.0
1.0
160
15
Vitamin A Deficiency
Vitamin A deficiency can be caused by many causes. A defect in the BCMO1 gene which codes for beta,beta-carotene 15,15’-monooxygenase is one of them. Beta,beta-carotene 15,15’-monooxygenase catalyzes the chemical reaction where the two substrates are beta-carotene and O2, whereas its product is retinal. A defect in this enzyme results in decrease of levels of retinal and vitamin A in serum; Signs and symptoms include night blindness, poor adaptation to darkness, dry skin and hair.
Disease
PW_X009186
Complete
Context9186
49773
209
Compound
Decreased
49774
1048
Compound
Decreased
49775
17455
Protein
Mutated
278251
18806089
Sommer A: Vitamin a deficiency and clinical disease: an historical overview. J Nutr. 2008 Oct;138(10):1835-9. doi: 10.1093/jn/138.10.1835.
9186
Context