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Retinol Metabolism 1.0 Cytochrome P450 3A43 HMDB03648 HMDB Retinol dehydrogenase 8 C23H38N7O17P3S Acetyl-CoA 809.1258 4-Hydroxyretinoic acid Dehydrogenase/reductase SDR family member 4 4451124 ChemSpider 937 ChemSpider 1.0 C00670 KEGG Compound O95237 UniProt 439153 PubChem-compound 1.0 C57H106O6 TG(16:1(9Z)/22:0/16:1(9Z)) 886.79895 HMDB01358 HMDB 66592-72-1 CAS PC(24:1(15Z)/15:0) 1.0 38030-57-8 CAS PW000164 PathWhiz P07327 UniProt Acyl-CoA wax alcohol acyltransferase 1 Retinoyl b-glucuronide 1.0 CHEBI:545914 ChEBI HMDB01206 HMDB Retinal dehydrogenase 1 116-31-4 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 952 ChemSpider 11-cis-Retinaldehyde C20H32O All-trans-13,14-dihydroretinol 288.24533 1.0 CHEBI:17336 ChEBI CHEBI:17579 ChEBI HMDB12329 HMDB Q6IN67 UniProt 64931 ChemSpider 6436082 PubChem-compound HMDB12452 HMDB 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(O)C(=O)NCCC(=O)NCCS HMDB12451 HMDB TG(16:1(9Z)/22:0/16:1(9Z)) 22737-96-8 CAS Q9HCN8 UniProt 28319-77-9 CAS 1.0 1.0 HMDB01423 HMDB 1.0 1.0 HMDB00217 HMDB C00473 KEGG Compound Cytosol 1.0 PHOSPHATIDYLCHOLINE BioCyc 1.0 Alcohol dehydrogenase 1A SMILES CC(CCO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C UDP-glucuronosyltransferase 1-1 Lecithin retinol acyltransferase CHEBI:63795 ChEBI HMDB00221 HMDB C00007 KEGG Compound C00006 KEGG Compound Q9BPW9 UniProt 9-cis-Retinal Cytochrome P450 2B6 CHEBI:18009 ChEBI C00001 KEGG Compound Protein disulfide-isomerase A2 C20H28O2 9-cis-Retinoic acid 300.20892 Beta-D-Glucuronides BioCyc Acceptor CHEBI:16066 ChEBI C00005 KEGG Compound Diacylglycerol O-acyltransferase 1 C00004 KEGG Compound C00003 KEGG Compound NADPH 1.0 Cytochrome P450 2A6 62702-55-0 CAS 1.0 Retinol dehydrogenase 12 302-79-4 CAS 1.0 1.0 Coenzyme A C21H28N7O14P2 NAD 664.11694 C00010 KEGG Compound Q58HT5 UniProt C20H30O2 Retinyl ester 302.22458 C00376 KEGG Compound Patatin-like phospholipase domain-containing protein 4 NAD(P) BioCyc 1.0 7822721 ChemSpider C36H60O2 Retinyl palmitate 524.45935 Stromal cell-derived factor 2-like protein 1 53-84-9 CAS C00024 KEGG Compound HMDB00561 HMDB P20853 UniProt SMILES [H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC All-trans-retinol 13,14-reductase NADP 1.0 Q9BTZ2 UniProt CL:0000000 CELL TYPE ONTOLOGY 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 Retinal dehydrogenase 1 SMILES C[N+](C)(C)CCOP([O-])(=O)OC[C@@H](O)CO 1.0 1.0 C40H56 B-Carotene 536.4382 Retinal 1.0 C11061 KEGG Compound 1.0 HMDB00305 HMDB 1.0 1.0 C02588 KEGG Compound O75452 UniProt 11-cis-Retinol Diacylglycerol O-acyltransferase 1 Protein disulfide-isomerase A6 Glycerophosphocholine Retinoid isomerohydrolase Cytochrome P450 DnaJ homolog subfamily B member 11 514-85-2 CAS Q6NUM9 UniProt C02110 KEGG Compound 7732-18-5 CAS HMDB07144 HMDB C20H26O3 4-oxo-Retinoic acid 314.1882 Retinal dehydrogenase 2 1.0 Retinoid isomerohydrolase 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 HMDB01852 HMDB Q96NR8 UniProt Cytochrome P450 2A13 4445170 ChemSpider Fatty Acid all-trans-18-Hydroxyretinoic acid P20815 UniProt 1.0 Beta,beta-carotene 15,15'-monooxygenase P20813 UniProt 962 PubChem-compound 79-81-2 CAS SMILES O=O 1.0 1.0 BiologicalState2 HMDB11618 HMDB 1.0 C20H28O 11-cis-Retinaldehyde 284.21402 1.0 HMDB06285 HMDB C47H92NO8P PC(24:1(15Z)/15:0) 829.65607 Cytochrome P450 3A7 CHEBI:269971 ChEBI SMILES C\C(\C=C\C12OC1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(O)=O SMILES C\C(\C=C\C1=C(CO)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O 5289090 PubChem-compound C20H30O 11-cis-Retinol 286.22968 22737-97-9 CAS C20H30O Vitamin A 286.22968 C16681 KEGG Compound C16682 KEGG Compound C16683 KEGG Compound 444493 PubChem-compound C16680 KEGG Compound 11-cis-Retinaldehyde 446798 PubChem-compound HMDB06254 HMDB 1.0 5363137 PubChem-compound 22833512 PubChem-compound HMDB08790 HMDB 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 Alcohol dehydrogenase 1A 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 Q15084 UniProt P23284 UniProt CHEBI:6562 ChEBI 6506224 PubChem-compound RETINOL BioCyc 8123435 ChemSpider 9-cis-Retinol C15492 KEGG Compound 17215925 ChemSpider 24767449 ChemSpider Cytochrome P450 26A1 UDP-glucuronosyltransferase 1-1 Lecithin retinol acyltransferase Cytochrome P450 3A43 P00352 UniProt C15493 KEGG Compound Acyl-CoA wax alcohol acyltransferase 1 P13667 UniProt SMILES C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C 4.0 HSP90B1 protein ReactionCatalysis1445 ACTIVATION ReactionCatalysis1444 ACTIVATION 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 Retinol dehydrogenase 16 SMILES O Acetyl-CoA ReactionCatalysis1441 ACTIVATION ReactionCatalysis1440 ACTIVATION ReactionCatalysis1443 ACTIVATION ReactionCatalysis1442 ACTIVATION C20H28O3 4-Hydroxyretinoic acid 316.20386 115797-14-3 CAS Cytochrome P450 2A13 Cytochrome P450 3A7 1.0 Cytochrome P450 3A4 Cytochrome P450 2B6 Cytochrome P450 3A5 1.0 C02075 KEGG Compound 6816 PubChem-compound all-trans-5,6-Epoxyretinoic acid 1.0 CHEBI:15846 ChEBI DG(16:1(9Z)/22:0/0:0) HMDB06218 HMDB HMDB06217 HMDB HMDB06216 HMDB Alcohol dehydrogenase 1A 53-59-8 CAS Cytochrome P450 2A6 Reaction1716 false Lumirodopsin → Metarodopsin LEFT_TO_RIGHT Beta,beta-carotene 15,15'-monooxygenase 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 P24462 UniProt 5280382 PubChem-compound Q9HAY6 UniProt All-trans-retinol 13,14-reductase Cytochrome P450 2A7 Rhodopsin 4444130 ChemSpider GO:0005829 GENE ONTOLOGY 78 kDa glucose-regulated protein Vitamin A Cytochrome P450 26A1 Reaction1712 false Rhodopsin → Bathorodopsin LEFT_TO_RIGHT Reaction1713 false Rhodopsin → iodopsin LEFT_TO_RIGHT HMDB00902 HMDB P11021 UniProt 1.14.13.- false 1.14.13.- All-trans-retinoic acid → all-trans-5,6-Epoxyretinoic acid LEFT_TO_RIGHT Reaction1711 false 11-cis-Retinaldehyde → Rhodopsin LEFT_TO_RIGHT CHEBI:16908 ChEBI 4940758 ChemSpider 1.14.-.- false 1.14.-.- All-trans-retinoic acid → all-trans-18-Hydroxyretinoic acid LEFT_TO_RIGHT Metarodopsin CPD-523 BioCyc 1.14.-.- false 1.14.-.- All-trans-retinoic acid → 4-Hydroxyretinoic acid LEFT_TO_RIGHT iodopsin 1.14.-.- false 1.14.-.- 4-Hydroxyretinoic acid → 4-oxo-Retinoic acid LEFT_TO_RIGHT Lumirodopsin 1.3.99.23 false 1.3.99.23 Reduced acceptor + Vitamin A → Acceptor + All-trans-13,14-dihydroretinol LEFT_TO_RIGHT Protein disulfide-isomerase A4 5.3.4.1 false 5.3.4.1 All-trans-retinoic acid + Reduced acceptor → Acceptor + Retinoyl b-glucuronide LEFT_TO_RIGHT CPD-882 BioCyc Retinyl palmitate Reaction1703 false All-trans-retinoic acid → 9-cis-Retinoic acid LEFT_TO_RIGHT 1.14.-.- false 1.14.-.- Vitamin A → 4-Oxoretinol 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 1.0 C02094 KEGG Compound C21H30N7O17P3 NADPH 745.0911 1.2.1.36 false 1.2.1.36 NAD + Vitamin A + Water → All-trans-retinoic acid + NADH LEFT_TO_RIGHT 1.2.1.36 false 1.2.1.36 NAD + Vitamin A + Water → All-trans-retinoic acid + NADH LEFT_TO_RIGHT 4444129 ChemSpider C21H29N7O17P3 NADP 744.08325 1.2.1.36 false 1.2.1.36 9-cis-Retinal + NAD + Water → 9-cis-Retinoic acid + NADH LEFT_TO_RIGHT 393012 ChemSpider 4515523 ChemSpider Bathorodopsin NADPH BioCyc Retinol dehydrogenase 8 1.0 Retinol dehydrogenase 11 Retinol dehydrogenase 11 Retinol dehydrogenase 12 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 53479491 PubChem-compound C20H28O Retinal 284.21402 Q8TC12 UniProt Q96GW1 UniProt 5460164 PubChem-compound 1.0 395778 ChemSpider Q13087 UniProt Q9UBS4 UniProt 1.0 SMILES CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(O)=O CHEBI:35366 ChEBI 10607936 ChemSpider ReactionCatalysis1412 ACTIVATION 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 ReactionCatalysis1411 ACTIVATION ReactionCatalysis1414 ACTIVATION ReactionCatalysis1413 ACTIVATION ReactionCatalysis1416 ACTIVATION 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 ReactionCatalysis1415 ACTIVATION 401-10-5 CAS ReactionCatalysis1418 ACTIVATION CHEBI:26536 ChEBI ReactionCatalysis1417 ACTIVATION 53-57-6 CAS CPD-437 BioCyc 4-oxo-Retinoic acid DnaJ homolog subfamily B member 11 O43174 UniProt HSP90B1 protein HMDB03141 HMDB Retinal Q9NYR8 UniProt 5005673 ChemSpider ReactionCatalysis1422 ACTIVATION ReactionCatalysis1425 ACTIVATION ReactionCatalysis1424 ACTIVATION C21H29N7O14P2 NADH 665.12476 ReactionCatalysis1427 ACTIVATION ReactionCatalysis1426 ACTIVATION 9-cis-Retinoic acid ReactionCatalysis1429 ACTIVATION ReactionCatalysis1428 ACTIVATION ReactionCatalysis1421 ACTIVATION ReactionCatalysis1420 ACTIVATION 1.0 4-Oxoretinol GLYCERYLPHOSPHORYLCHOLINE BioCyc Q16696 UniProt Stromal cell-derived factor 2-like protein 1 C8H20NO6P Glycerophosphocholine 257.1028 Endoplasmic reticulum resident protein 29 Protein disulfide-isomerase A4 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 Protein disulfide-isomerase A6 Peptidyl-prolyl cis-trans isomerase B HYOU1 protein Protein disulfide-isomerase A2 9543771 PubChem-compound 4444162 ChemSpider 78 kDa glucose-regulated protein ReactionCatalysis1434 ACTIVATION ReactionCatalysis1433 ACTIVATION SMILES C\C(=C/CO)\C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C ReactionCatalysis1436 ACTIVATION SMILES C\C(=C/CO)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C ReactionCatalysis1435 ACTIVATION ReactionCatalysis1438 ACTIVATION ReactionCatalysis1437 ACTIVATION ReactionCatalysis1439 ACTIVATION CHEBI:78273 ChEBI CHEBI:78272 ChEBI Short-chain dehydrogenase/reductase 3 ReactionCatalysis1430 ACTIVATION ReactionCatalysis1431 ACTIVATION 1.0 HMDB02152 HMDB 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 O94788 UniProt CHEBI:1146900 ChEBI 1.0 9947823 PubChem-compound 2.0 1.0 B-Carotene P30040 UniProt P22309 UniProt CHEBI:16302 ChEBI Rhodopsin Dehydrogenase/reductase SDR family member 4 CO-A BioCyc CHEBI:15339 ChEBI 1.0 Dehydrogenase/reductase SDR family member 9 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 Q9HB55 UniProt CHEBI:28870 ChEBI Cell 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 Retinal dehydrogenase 2 O2 Oxygen 31.98983 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 638015 PubChem-compound 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 SMILES CCCCCCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)CCCCCCC\C=C/CCCCCC)COC(=O)CCCCCCC\C=C/CCCCCC CHEBI:5949 ChEBI 1.1.1.1 false 1.1.1.1 11-cis-Retinaldehyde + NAD → NADH + Retinal LEFT_TO_RIGHT Water HMDB03598 HMDB O75911 UniProt 5337 ChemSpider CHEBI:17616 ChEBI HMDB00086 HMDB 7782-44-7 CAS 1.0 Patatin-like phospholipase domain-containing protein 4 All-trans-13,14-dihydroretinol Peptidyl-prolyl cis-trans isomerase B C20H28O3 all-trans-5,6-Epoxyretinoic acid 316.20386 5280531 PubChem-compound O75907 UniProt 1.0 9606 TAXONOMY CHEBI:545933 ChEBI CPD1F-129 BioCyc CHEBI:50648 ChEBI Short-chain dehydrogenase/reductase 3 392413 ChemSpider 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 1.0 5893 PubChem-compound 1.0 HMDB02111 HMDB Reaction1693 false Vitamin A → 9-cis-Retinol LEFT_TO_RIGHT 1.14.99.36 false 1.14.99.36 B-Carotene + Oxygen → Retinal LEFT_TO_RIGHT 1.1.1.300 false 1.1.1.300 NADP + Vitamin A → NADPH + Retinal LEFT_TO_RIGHT 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 2.3.1.135 false 2.3.1.135 PC(24:1(15Z)/15:0) + Vitamin A → Glycerophosphocholine + Retinyl ester LEFT_TO_RIGHT 5538 PubChem-compound 1.0 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 1.1.1.184 false 1.1.1.184 9-cis-Retinol + NADP ↔ 9-cis-Retinal + NADPH REVERSIBLE 1.1.1.300 false 1.1.1.300 9-cis-Retinol + NADP → 9-cis-Retinal + NADPH LEFT_TO_RIGHT 449171 PubChem-compound Retinyl ester CHEBI:15377 ChEBI RETINOATE BioCyc CHEBI:15379 ChEBI HMDB02369 HMDB 30777879 ChemSpider P08684 UniProt UDP-glucuronosyltransferase 1-1 5886 PubChem-compound 1.0 Endoplasmic reticulum resident protein 29 1.0 HMDB48523 HMDB 1.0 2.3.1.135 false 2.3.1.135 11-cis-Retinol + PC(24:1(15Z)/15:0) → Glycerophosphocholine + Retinyl palmitate LEFT_TO_RIGHT Oxygen 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 → 11-cis-Retinol + NADPH LEFT_TO_RIGHT 6437063 PubChem-compound 1.0 Q16518 UniProt Reaction1688 false Acetyl-CoA + Vitamin A → Coenzyme A + Retinyl ester LEFT_TO_RIGHT Retinal dehydrogenase 1 5300-03-8 CAS 2.3.1.75 false 2.3.1.75 Acetyl-CoA + Vitamin A → Coenzyme A + Retinyl ester LEFT_TO_RIGHT SMP00074 SMPDB 1.0 3.1.1.64 false 3.1.1.64 Retinyl ester + Water → 11-cis-Retinol + Fatty Acid LEFT_TO_RIGHT 2.3.1.75 false 2.3.1.75 11-cis-Retinol + Acetyl-CoA → Coenzyme A + Retinyl palmitate LEFT_TO_RIGHT Reaction1685 false 11-cis-Retinol + Acetyl-CoA → Coenzyme A + Retinyl palmitate LEFT_TO_RIGHT C41H78O5 DG(16:1(9Z)/22:0/0:0) 650.5849 HMDB01487 HMDB C00899 KEGG Compound C00777 KEGG Compound Retinol dehydrogenase 16 P11509 UniProt Cytochrome P450 3A4 Dehydrogenase/reductase SDR family member 9 1.0 1.0 1.0 P41247 UniProt 7235-40-7 CAS CHEBI:2998 ChEBI HMDB01377 HMDB 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 HYOU1 protein Cytochrome P450 2A7 All-trans-retinoic acid 1.0 85-61-0 CAS 68-26-8 CAS Cytochrome P450 3A5