1.0 2016-09-30 22:48:09 UTC 2020-05-21 16:29:27 UTC BMDB0001852 BMDB01852 Retinoic acid all-trans-All-trans-all-all-trans-retinoic acid, also known as all-all-trans-retinoic acid or all-trans-retinoic 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. all-trans-All-trans-all-all-trans-retinoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. all-trans-All-trans-all-all-trans-retinoic acid participates in a number of enzymatic reactions, within cattle. In particular, all-trans-All-trans-all-all-trans-retinoic acid can be biosynthesized from vitamin a through the action of the enzyme retinal dehydrogenase 1. In addition, all-trans-All-trans-all-all-trans-retinoic acid can be biosynthesized from vitamin a; which is mediated by the enzyme retinal dehydrogenase 2. In cattle, all-trans-all-all-trans-retinoic acid is involved in the metabolic pathway called the retinol metabolism pathway. all-trans-All-trans-all-all-trans-retinoic acid is a potentially toxic compound. (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-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ecl) AGN 100335 all-(e)-Retinoic acid all-trans-beta-Retinoic acid all-trans-Tretinoin all-trans-Vitamin a acid all-trans-Vitamin a1 acid beta-Retinoic acid Eudyna Renova Retin-a Retinoic acid Retisol-a Ro 1-5488 Solage Stieva-a trans-Retinoic acid Tretin m Tretinoin Vesanoid Vitamin a acid Vitinoin all-trans-Retinoate Avita Retin a (all-e)-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-cyclohexene-1-yl)-2,4,6,8-nonatetraenoate (ecl) all-(e)-Retinoate all-trans-b-Retinoate all-trans-b-Retinoic acid all-trans-beta-Retinoate all-trans-Β-retinoate all-trans-Β-retinoic acid b-Retinoate b-Retinoic acid beta-Retinoate Β-retinoate Β-retinoic acid Retinoate trans-Retinoate (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate Tretinoin zinc salt trans Retinoic acid Acid, all-trans-retinoic Salt, tretinoin sodium beta all trans Retinoic acid beta-all-trans-Retinoic acid Acid, vitamin a Potassium salt, tretinoin Sodium salt, tretinoin Acid, beta-all-trans-retinoic Tretinoin potassium salt Zinc salt, tretinoin Acid, retinoic Acid, trans-retinoic Salt, tretinoin potassium Salt, tretinoin zinc Tretinoin sodium salt all trans Retinoic acid Retin-a micro Atralin Tretin-X all-trans-Retinoic acid C20H28O2 300.442 300.208930142 (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid tretinoin 302-79-4 C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O 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 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 Medium-chain fatty acids Methyl-branched fatty acids Monocarboxylic acids and derivatives Organic oxides Unsaturated fatty acids Aliphatic homomonocyclic compound Branched fatty acid Carbonyl group Carboxylic acid Carboxylic acid derivative Diterpenoid Fatty acid Fatty acyl Hydrocarbon derivative Medium-chain fatty acid Methyl-branched fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Retinoic acid Retinoid skeleton Unsaturated fatty acid Aliphatic homomonocyclic compounds Retinoids Retinoids retinoic acid Solid logp 5.66 ALOGPS logs -4.80 ALOGPS logp 5.01 ChemAxon pka_strongest_acidic 5 ChemAxon iupac (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid ChemAxon average_mass 300.442 ChemAxon mono_mass 300.208930142 ChemAxon smiles C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O ChemAxon formula C20H28O2 ChemAxon inchi 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+ ChemAxon inchikey SHGAZHPCJJPHSC-YCNIQYBTSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 97.79 ChemAxon polarizability 36.85 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 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::CMs 91895 Specdb::CMs 151121 Specdb::NmrOneD 5195 Specdb::NmrTwoD 2031 Specdb::MsMs 95706 Specdb::MsMs 95707 Specdb::MsMs 95708 Specdb::MsMs 160026 Specdb::MsMs 160027 Specdb::MsMs 160028 Specdb::MsMs 1218340 Specdb::MsMs 1218341 Specdb::MsMs 1218342 Specdb::MsMs 2233615 Specdb::MsMs 2252520 Specdb::MsMs 2253293 Specdb::MsMs 2253949 Specdb::MsMs 2254559 Specdb::MsMs 2256027 Specdb::MsMs 2256601 Specdb::MsMs 2257973 Specdb::MsMs 2258638 Specdb::MsMs 2259946 Specdb::MsMs 2794304 Specdb::MsMs 2794305 Specdb::MsMs 2794306 Specdb::MsMs 2884046 Specdb::MsMs 2884047 Specdb::MsMs 2884048 Adipose Tissue 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 Adrenal Cortex 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 Adrenal Gland 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 Bladder 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 Brain 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 Epidermis 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 Fibroblasts 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 Intestine 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 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 Lung 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 Neuron 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 Pancreas 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 Placenta 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 Platelet 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 Prostate Tissue 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 Spleen 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 Testis 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 392618 FDB022710 C00777 15367 444795 Tretinoin Solladie, Guy; Girardin, Andre. Highly stereoselective synthesis of vitamin A and all-trans retinoic acid by low-valent titanium induced reductive elimination. Tetrahedron Letters (1988), 29(2), 213-16. BMDBP00016 Cytochrome P450 3A28 P79102 CYP3A28 Enzyme BMDBP00062 Cytochrome P450 2E1 O18963 CYP2E1 Enzyme BMDBP00102 Prostaglandin-H2 D-isomerase O02853 PTGDS Enzyme BMDBP00601 Retinal dehydrogenase 1 P48644 ALDH1A1 Enzyme BMDBP01877 Polycomb group RING finger protein 1 Q2YDF9 PCGF1 Enzyme BMDBP01878 Retinoic acid receptor responder (Tazarotene induced) 1 Q0P5D6 RARRES1 Enzyme BMDBP01879 Retinoic acid receptor beta Q45UD6 Enzyme BMDBP01880 Retinoic acid receptor responder protein 2 Q29RS5 RARRES2 Enzyme BMDBP01881 Retinoic acid receptor, alpha Q58DG3 RARA Enzyme BMDBP01882 RARG protein Q08DD4 RARG Enzyme BMDBP01883 Peroxisome proliferator-activated receptor gamma O18971 PPARG Enzyme BMDBP01884 Fatty acid-binding protein, adipocyte P48035 FABP4 Enzyme BMDBP01885 Cellular retinoic acid-binding protein 1 P62964 CRABP1 Enzyme BMDBP01886 LOC100138545 protein A6QQE3 LOC100138545 Enzyme BMDBP01887 Retinoic acid receptor RXR-gamma Q0VC20 RXRG Enzyme BMDBP01888 Cellular retinoic acid-binding protein 2 Q5PXY7 CRABP2 Enzyme BMDBP02993 Cytochrome P450 26B1 E1BHJ4 CYP26B1 Enzyme