1.0
C23H38N7O17P3S
Acetyl-CoA
809.1258
4-Hydroxyretinoic acid
4451124
ChemSpider
937
ChemSpider
C00670
KEGG Compound
392618
ChemSpider
Unknown
Unknown
Unknown
439153
PubChem-compound
ReactionCatalysis100737
ACTIVATION
HMDB0002152
HMDB
C57H106O6
TG(16:1(9Z)/22:0/16:1(9Z))
886.79895
66592-72-1
CAS
PC(24:1(15Z)/15:0)
38030-57-8
CAS
5.3.4.1
false
5.3.4.1
Reduced acceptor + all-trans-Retinoic acid → Acceptor + Retinoyl b-glucuronide
LEFT_TO_RIGHT
Retinoyl b-glucuronide
CHEBI:545914
ChEBI
ReactionCatalysis100749
ACTIVATION
116-31-4
CAS
NADH
SMILES
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C
CHEBI:16474
ChEBI
CHEBI:15022
ChEBI
ReactionCatalysis100751
ACTIVATION
952
ChemSpider
ReactionCatalysis100750
ACTIVATION
11-cis-Retinaldehyde
1.1.1.300
false
1.1.1.300
9-cis-Retinol + NADP → 9-cis-Retinal + NADPH
LEFT_TO_RIGHT
C20H32O
All-trans-13,14-dihydroretinol
288.24533
1.2.1.36
false
1.2.1.36
9-cis-Retinal + NAD + Water → 9-cis-Retinoic acid + NADH
LEFT_TO_RIGHT
ReactionCatalysis100759
ACTIVATION
HMDB0003141
HMDB
ReactionCatalysis100758
ACTIVATION
1.2.1.36
false
1.2.1.36
9-cis-Retinal + NAD + Water → 9-cis-Retinoic acid + NADH
LEFT_TO_RIGHT
1.1.1.300
false
1.1.1.300
9-cis-Retinol + NADP ↔ 9-cis-Retinal + NADPH
REVERSIBLE
ReactionCatalysis100757
ACTIVATION
ReactionCatalysis100756
ACTIVATION
1.1.1.184
false
1.1.1.184
9-cis-Retinol + NADP ↔ 9-cis-Retinal + NADPH
REVERSIBLE
ReactionCatalysis100755
ACTIVATION
1.14.-.-
false
1.14.-.-
Vitamin A → 4-Oxoretinol
LEFT_TO_RIGHT
ReactionCatalysis100754
ACTIVATION
1.3.99.23
false
1.3.99.23
Reduced acceptor + Vitamin A → Acceptor + All-trans-13,14-dihydroretinol
LEFT_TO_RIGHT
ReactionCatalysis100753
ACTIVATION
1.2.1.36
false
1.2.1.36
NAD + Vitamin A + Water → NADH + all-trans-Retinoic acid
LEFT_TO_RIGHT
ReactionCatalysis100752
ACTIVATION
1.2.1.36
false
1.2.1.36
NAD + Vitamin A + Water → NADH + all-trans-Retinoic acid
LEFT_TO_RIGHT
1.0
CHEBI:17336
ChEBI
CHEBI:17579
ChEBI
1.0
ReactionCatalysis100739
ACTIVATION
ReactionCatalysis100738
ACTIVATION
64931
ChemSpider
6436082
PubChem-compound
ReactionCatalysis100740
ACTIVATION
SMILES
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
1.14.-.-
false
1.14.-.-
all-trans-Retinoic acid → 4-Hydroxyretinoic acid
LEFT_TO_RIGHT
1.14.-.-
false
1.14.-.-
4-Hydroxyretinoic acid → 4-oxo-Retinoic acid
LEFT_TO_RIGHT
ReactionCatalysis100748
ACTIVATION
ReactionCatalysis100747
ACTIVATION
TG(16:1(9Z)/22:0/16:1(9Z))
ReactionCatalysis100746
ACTIVATION
1.14.-.-
false
1.14.-.-
all-trans-Retinoic acid → all-trans-18-Hydroxyretinoic acid
LEFT_TO_RIGHT
Mus musculus
ReactionCatalysis100745
ACTIVATION
1.14.13.-
false
1.14.13.-
all-trans-Retinoic acid → all-trans-5,6-Epoxyretinoic acid
LEFT_TO_RIGHT
ReactionCatalysis100744
ACTIVATION
22737-96-8
CAS
ReactionCatalysis100743
ACTIVATION
28319-77-9
CAS
ReactionCatalysis100742
ACTIVATION
1.0
ReactionCatalysis100741
ACTIVATION
1.1.1.300
false
1.1.1.300
11-cis-Retinaldehyde + NADP → 11-cis-Retinol + NADPH
LEFT_TO_RIGHT
1.0
1.1.1.300
false
1.1.1.300
11-cis-Retinaldehyde + NADP → NADPH + Retinal
LEFT_TO_RIGHT
1.1.-.-
false
1.1.-.-
11-cis-Retinaldehyde → Retinal
LEFT_TO_RIGHT
1.0
C00473
KEGG Compound
Cytosol
444795
PubChem-compound
1.0
PHOSPHATIDYLCHOLINE
BioCyc
1.0
SMILES
CC(CCO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
1.1.1.1
false
1.1.1.1
11-cis-Retinaldehyde + NAD → NADH + Retinal
LEFT_TO_RIGHT
1.1.-.-
false
1.1.-.-
11-cis-Retinaldehyde → Retinal
LEFT_TO_RIGHT
1.1.1.300
false
1.1.1.300
11-cis-Retinaldehyde + NADP → NADPH + Retinal
LEFT_TO_RIGHT
1.1.1.-
false
1.1.1.-
11-cis-Retinaldehyde → Retinal
LEFT_TO_RIGHT
1.1.1.184
false
1.1.1.184
11-cis-Retinaldehyde + NADP → NADPH + Retinal
LEFT_TO_RIGHT
CHEBI:63795
ChEBI
3.1.1.3
false
3.1.1.3
DG(16:1(9Z)/22:0/0:0) + Retinyl ester → TG(16:1(9Z)/22:0/16:1(9Z)) + Vitamin A
LEFT_TO_RIGHT
C00007
KEGG Compound
C00006
KEGG Compound
1.14.99.36
false
1.14.99.36
B-Carotene + Oxygen → Retinal
LEFT_TO_RIGHT
9-cis-Retinal
CHEBI:18009
ChEBI
C00001
KEGG Compound
C20H28O2
9-cis-Retinoic acid
300.20892
Beta-D-Glucuronides
BioCyc
Acceptor
CHEBI:16066
ChEBI
C00005
KEGG Compound
C00004
KEGG Compound
C00003
KEGG Compound
NADPH
1.0
1.0
Reaction110432
false
11-cis-Retinol + Acetyl-CoA → Coenzyme A + Retinyl palmitate
LEFT_TO_RIGHT
3.1.1.64
false
3.1.1.64
Retinyl ester + Water → 11-cis-Retinol + Fatty Acid
LEFT_TO_RIGHT
2.3.1.135
false
2.3.1.135
11-cis-Retinol + PC(24:1(15Z)/15:0) → Glycerophosphocholine + Retinyl palmitate
LEFT_TO_RIGHT
2.3.1.75
false
2.3.1.75
11-cis-Retinol + Acetyl-CoA → Coenzyme A + Retinyl palmitate
LEFT_TO_RIGHT
2.3.1.135
false
2.3.1.135
PC(24:1(15Z)/15:0) + Vitamin A → Glycerophosphocholine + Retinyl ester
LEFT_TO_RIGHT
62702-55-0
CAS
1.1.1.300
false
1.1.1.300
NADP + Vitamin A → NADPH + Retinal
LEFT_TO_RIGHT
1.0
Reaction110434
false
Acetyl-CoA + Vitamin A → Coenzyme A + Retinyl ester
LEFT_TO_RIGHT
2.3.1.75
false
2.3.1.75
Acetyl-CoA + Vitamin A → Coenzyme A + Retinyl ester
LEFT_TO_RIGHT
302-79-4
CAS
1.0
1.0
Coenzyme A
C21H28N7O14P2
NAD
664.11694
C00010
KEGG Compound
HMDB0000902
HMDB
C20H30O2
Retinyl ester
302.22458
C00376
KEGG Compound
PW121754
PathWhiz
NAD(P)
BioCyc
HMDB0006216
HMDB
HMDB0006217
HMDB
HMDB0006218
HMDB
1.0
7822721
ChemSpider
C36H60O2
Retinyl palmitate
524.45935
53-84-9
CAS
C00024
KEGG Compound
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
NADP
1.0
DIACYLGLYCEROL
BioCyc
CHEBI:52075
ChEBI
C00157
KEGG Compound
SMILES
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
1.0
HMDB0003648
HMDB
SMILES
C[N+](C)(C)CCOP([O-])(=O)OC[C@@H](O)CO
1.0
C40H56
B-Carotene
536.4382
Retinal
1.0
4.0
C11061
KEGG Compound
1.0
C02588
KEGG Compound
C00165
KEGG Compound
HMDB0001358
HMDB
11-cis-Retinol
Glycerophosphocholine
514-85-2
CAS
C02110
KEGG Compound
7732-18-5
CAS
C20H26O3
4-oxo-Retinoic acid
314.1882
HMDB0001487
HMDB
SMILES
C\C(\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
394057
ChemSpider
NAD
4445170
ChemSpider
Fatty Acid
HMDB0001377
HMDB
all-trans-18-Hydroxyretinoic acid
1.0
962
PubChem-compound
79-81-2
CAS
SMILES
O=O
1.0
1.0
HMDB0002111
HMDB
2.0
C20H28O
11-cis-Retinaldehyde
284.21402
1.0
C47H92NO8P
PC(24:1(15Z)/15:0)
829.65607
CHEBI:269971
ChEBI
ReactionCatalysis100762
ACTIVATION
SMILES
C\C(\C=C\C12OC1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(O)=O
HMDB0002369
HMDB
ReactionCatalysis100761
ACTIVATION
SMILES
C\C(\C=C\C1=C(CO)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
ReactionCatalysis100760
ACTIVATION
5289090
PubChem-compound
C20H30O
11-cis-Retinol
286.22968
22737-97-9
CAS
ReactionCatalysis100768
ACTIVATION
ReactionCatalysis100767
ACTIVATION
ReactionCatalysis100766
ACTIVATION
ReactionCatalysis100765
ACTIVATION
ReactionCatalysis100764
ACTIVATION
ReactionCatalysis100763
ACTIVATION
C20H30O
Vitamin A
286.22968
C16681
KEGG Compound
C16682
KEGG Compound
Retinal dehydrogenase 1
C16683
KEGG Compound
444493
PubChem-compound
C16680
KEGG Compound
11-cis-Retinaldehyde
446798
PubChem-compound
1.0
5363137
PubChem-compound
22833512
PubChem-compound
ACETYL-COA
BioCyc
SMILES
C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O
H2O
Water
18.010565
CHEBI:6796
ChEBI
C16678
KEGG Compound
4941652
ChemSpider
C16679
KEGG Compound
NADH
BioCyc
6438629
PubChem-compound
NAD
BioCyc
C16677
KEGG Compound
977
PubChem-compound
1.0
C26H36O8
Retinoyl b-glucuronide
476.24103
445354
PubChem-compound
HMDB0003598
HMDB
CHEBI:6562
ChEBI
6506224
PubChem-compound
RETINOL
BioCyc
HMDB0000086
HMDB
8123435
ChemSpider
9-cis-Retinol
C15492
KEGG Compound
UDP-glucuronosyltransferase 1-1
17215925
ChemSpider
24767449
ChemSpider
C15493
KEGG Compound
SMILES
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
564-87-4
CAS
5280489
PubChem-compound
SMILES
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
SMILES
O
Acetyl-CoA
C20H28O3
4-Hydroxyretinoic acid
316.20386
115797-14-3
CAS
1.0
1.0
C02075
KEGG Compound
6816
PubChem-compound
all-trans-5,6-Epoxyretinoic acid
HMDB0000305
HMDB
CHEBI:15846
ChEBI
DG(16:1(9Z)/22:0/0:0)
10090
TAXONOMY
53-59-8
CAS
Reaction1716
false
Lumirodopsin → Metarodopsin
LEFT_TO_RIGHT
Reaction1717
false
Metarodopsin → Retinal
LEFT_TO_RIGHT
Reaction1714
false
iodopsin → 11-cis-Retinaldehyde
LEFT_TO_RIGHT
Reaction1715
false
Bathorodopsin → Lumirodopsin
LEFT_TO_RIGHT
C20H30O
9-cis-Retinol
286.22968
C20H28O
9-cis-Retinal
284.21402
5280382
PubChem-compound
Rhodopsin
4444130
ChemSpider
GO:0005829
GENE ONTOLOGY
Vitamin A
Reaction1712
false
Rhodopsin → Bathorodopsin
LEFT_TO_RIGHT
Reaction1713
false
Rhodopsin → iodopsin
LEFT_TO_RIGHT
Reaction1711
false
11-cis-Retinaldehyde → Rhodopsin
LEFT_TO_RIGHT
CHEBI:16908
ChEBI
4940758
ChemSpider
Metarodopsin
CPD-523
BioCyc
iodopsin
Lumirodopsin
CPD-882
BioCyc
Retinyl palmitate
Reaction1703
false
all-trans-Retinoic acid → 9-cis-Retinoic acid
LEFT_TO_RIGHT
SMILES
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
CPD-881
BioCyc
71920
PubChem-compound
C20H28O2
all-trans-Retinoic acid
300.20892
5280490
PubChem-compound
C02094
KEGG Compound
C21H30N7O17P3
NADPH
745.0911
4444129
ChemSpider
C21H29N7O17P3
NADP
744.08325
393012
ChemSpider
4515523
ChemSpider
Bathorodopsin
HMDB0000561
HMDB
NADPH
BioCyc
1.0
CPD-6641
BioCyc
SMILES
C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=O
4444073
ChemSpider
58-68-4
CAS
HMDB0001423
HMDB
53479491
PubChem-compound
HMDB0000217
HMDB
C20H28O
Retinal
284.21402
5460164
PubChem-compound
1.0
395778
ChemSpider
1.0
1.0
SMILES
C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
CHEBI:35366
ChEBI
10607936
ChemSpider
SMILES
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
HMDB0000221
HMDB
SMILES
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
401-10-5
CAS
HMDB0048523
HMDB
53-57-6
CAS
CPD-437
BioCyc
4-oxo-Retinoic acid
Vitamin A Deficiency
1.0
Cytochrome P450
Retinal
5005673
ChemSpider
HMDB0012451
HMDB
HMDB0012452
HMDB
C21H29N7O14P2
NADH
665.12476
9-cis-Retinoic acid
HMDB0001206
HMDB
HMDB0012329
HMDB
1.0
4-Oxoretinol
Unknown
GLYCERYLPHOSPHORYLCHOLINE
BioCyc
C8H20NO6P
Glycerophosphocholine
257.1028
Unknown
SMILES
C/C(/C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=O
SMILES
CCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCCCCCC\C=C/CCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
9543771
PubChem-compound
4444162
ChemSpider
SMILES
[H]\C(CO)=C(\C)/C(/[H])=C(/[H])C([H])=C(C)C(\[H])=C(/[H])C1=C(C)CCCC1(C)C
SMILES
C\C(=C\CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
CHEBI:78273
ChEBI
CHEBI:78272
ChEBI
SMILES
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
C20H28O2
4-Oxoretinol
300.20892
C20H28O3
all-trans-18-Hydroxyretinoic acid
316.20386
Metarodopsin
Lumirodopsin
SMILES
CC1CCCC(C)(C)C1\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O
5682
ChemSpider
CHEBI:1146900
ChEBI
1.0
9947823
PubChem-compound
1.0
B-Carotene
CHEBI:16302
ChEBI
Rhodopsin
CO-A
BioCyc
CHEBI:15339
ChEBI
1.0
5675
ChemSpider
SMILES
CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
72-89-9
CAS
4943093
ChemSpider
iodopsin
C21H36N7O16P3S
Coenzyme A
767.11523
Bathorodopsin
1.0
CHEBI:28870
ChEBI
HMDB0008790
HMDB
6557
ChemSpider
SMILES
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
388299
ChemSpider
Acceptor
Reduced acceptor
CHEBI:16870
ChEBI
5281877
PubChem-compound
O2
Oxygen
31.98983
638015
PubChem-compound
SMILES
[H]C(COC(=O)CCCCCCC\C=C/CCCCCC)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
CHEBI:5949
ChEBI
HMDB0006254
HMDB
Water
Unknown
CHEBI:17616
ChEBI
Unknown
7782-44-7
CAS
1.0
All-trans-13,14-dihydroretinol
C20H28O3
all-trans-5,6-Epoxyretinoic acid
316.20386
5280531
PubChem-compound
1.0
Alcohol dehydrogenase 1A
CHEBI:15367
ChEBI
CHEBI:545933
ChEBI
CPD1F-129
BioCyc
CHEBI:50648
ChEBI
392413
ChemSpider
Unknown
Fatty Acid
SMILES
C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
553582
ChemSpider
5893
PubChem-compound
1.0
Reaction1693
false
Vitamin A → 9-cis-Retinol
LEFT_TO_RIGHT
Unknown
HMDB0011618
HMDB
SMP0120500
SMPDB
449171
PubChem-compound
Retinyl ester
CHEBI:15377
ChEBI
CHEBI:15379
ChEBI
30777879
ChemSpider
5886
PubChem-compound
Unknown
1.0
Oxygen
6437063
PubChem-compound
5300-03-8
CAS
1.0
HMDB0006285
HMDB
C41H78O5
DG(16:1(9Z)/22:0/0:0)
650.5849
C00899
KEGG Compound
C00777
KEGG Compound
1.0
1.0
1.0
HMDB0007144
HMDB
7235-40-7
CAS
CHEBI:2998
ChEBI
CHEBI:17898
ChEBI
CPD-7247
BioCyc
Reduced acceptor
SMILES
C\C(\C=C\C1=C(C)CCCC1(C)C)=C\C=C\C(\C)=C\C(O)=O
P08100
UniProt
CHEBI:15351
ChEBI
HMDB0001852
HMDB
all-trans-Retinoic acid
85-61-0
CAS
68-26-8
CAS