1.0 2016-09-30 23:20:55 UTC 2020-05-21 16:29:07 UTC BMDB0006254 BMDB06254 4-Hydroxyretinoic acid 4-Hydroxyretinoic acid 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. 4-Hydroxyretinoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Hydroxyretinoic acid participates in a number of enzymatic reactions, within cattle. In particular, 4-Hydroxyretinoic acid can be biosynthesized from all-trans-retinoic acid; which is catalyzed by the enzyme cytochrome P450 26A1. In addition, 4-Hydroxyretinoic acid can be converted into 4-oxo-retinoic acid; which is mediated by the enzyme cytochrome P450 26A1. In cattle, 4-hydroxyretinoic acid is involved in the metabolic pathway called the retinol metabolism pathway. (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 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-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 4-Hydroxy-all-trans-retinoate 4-Hydroxyretinoate 4-Hydroxy-13-cis-retinoate 4-Hydroxy-13-cis-retinoic acid 4-Hydroxy-retinoate 4-Hydroxy-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 4-Hydroxy-13-retinoic acid 4-Hydroxyretinoic acid, (13-cis)-isomer C20H28O3 316.4345 316.203844762 (2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid 4-hydroxyretinoic acid 66592-72-1 C\C(\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O 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 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. Organic compounds Lipids and lipid-like molecules Prenol lipids Retinoids Retinoids Carbonyl compounds Carboxylic acids Diterpenoids Hydrocarbon derivatives Hydroxy fatty acids Medium-chain fatty acids Methyl-branched fatty acids Monocarboxylic acids and derivatives Organic oxides Secondary alcohols Unsaturated fatty acids Alcohol Aliphatic homomonocyclic compound Branched fatty acid Carbonyl group Carboxylic acid Carboxylic acid derivative Diterpenoid Fatty acid Fatty acyl Hydrocarbon derivative Hydroxy fatty acid Medium-chain fatty acid Methyl-branched fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Retinoic acid Retinoid skeleton Secondary alcohol Unsaturated fatty acid Aliphatic homomonocyclic compounds Retinoids Retinoids retinoid Solid logp 5.04 ALOGPS logs -4.55 ALOGPS logp 3.78 ChemAxon pka_strongest_acidic 5 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid ChemAxon average_mass 316.4345 ChemAxon mono_mass 316.203844762 ChemAxon smiles C\C(\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O ChemAxon formula C20H28O3 ChemAxon inchi 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+ ChemAxon inchikey KGUMXGDKXYTTEY-FRCNGJHJSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 99.31 ChemAxon polarizability 37.33 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Retinol Metabolism SMP0087260 Specdb::MsMs 106254 Specdb::MsMs 106255 Specdb::MsMs 106256 Specdb::MsMs 172938 Specdb::MsMs 172939 Specdb::MsMs 172940 Specdb::MsMs 2403623 Specdb::MsMs 2403624 Specdb::MsMs 2403625 Specdb::MsMs 2535887 Specdb::MsMs 2535888 Specdb::MsMs 2535889 Specdb::CMs 14985 Specdb::CMs 38982 Specdb::CMs 131006 Specdb::CMs 138740 Kidney Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 FDB023862 4943093 6438629 C16677 63795 2299866 Rosenberger, Michael. Retinoic acid metabolites. 1. Total synthesis of 4-hydroxy- and 4-oxoretinoic acid. Journal of Organic Chemistry (1982), 47(9), 1698-701. BMDBP02993 Cytochrome P450 26B1 E1BHJ4 CYP26B1 Enzyme