1.0 2011-09-21 00:36:12 UTC 2015-07-21 06:57:55 UTC FDB023877 4-Oxo-retinoic acid 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) [HMDB] 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 C20H26O3 314.4186 314.188194698 (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 4-oxo-retinoic acid 38030-57-8 C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O 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 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. Retinoids Organic compounds Lipids and lipid-like molecules Prenol lipids Retinoids Aliphatic homomonocyclic compounds Carboxylic acids Cyclohexenones 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 Cyclic ketone Cyclohexenone Diterpenoid Fatty acid Fatty acyl Hydrocarbon derivative Ketone 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 Retinoids Retinoids retinoid Solid logp 4.94 ALOGPS logs -4.71 ALOGPS solubility 6.20e-03 g/l ALOGPS logp 4.35 ChemAxon pka_strongest_acidic 5 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac (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 ChemAxon average_mass 314.4186 ChemAxon mono_mass 314.188194698 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 C20H26O3 ChemAxon inchi 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+ ChemAxon inchikey GGCUJPCCTQNTJF-FRCNGJHJSA-N ChemAxon polar_surface_area 54.37 ChemAxon refractivity 98.48 ChemAxon polarizability 36.62 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Retinol Metabolism SMP00074 map00830 Specdb::CMs 20441 Specdb::CMs 38994 Specdb::CMs 156600 Specdb::MsMs 46329 Specdb::MsMs 46330 Specdb::MsMs 46331 Specdb::MsMs 158880 Specdb::MsMs 158881 Specdb::MsMs 158882 Specdb::MsMs 2319884 Specdb::MsMs 2319885 Specdb::MsMs 2319886 Specdb::MsMs 2618339 Specdb::MsMs 2618340 Specdb::MsMs 2618341 HMDB06285 #<Reference:0x000055ce323e7f50> #<Reference:0x000055ce323e7d98> #<Reference:0x000055ce323e7be0> #<Reference:0x000055ce323e7a28> #<Reference:0x000055ce323e7870> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823