1.02011-09-21 00:36:12 UTC2015-07-21 06:57:55 UTCFDB0238774-Oxo-retinoic acid4-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-Retinoate4-keto-Retinoic acid4-Ketoretinoate4-Ketoretinoic acid4-Oxo-all-trans-retinoate4-Oxo-all-trans-retinoic acid4-Oxoretinoate4-Oxoretinoic acid4-Oxotretinoinall-trans-4-Oxoretinoateall-trans-4-Oxoretinoic acidRo 11-4824Ro 12-4824C20H26O3314.4186314.188194698(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid4-oxo-retinoic acid38030-57-8C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=OInChI=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.RetinoidsOrganic compoundsLipids and lipid-like moleculesPrenol lipidsRetinoidsAliphatic homomonocyclic compoundsCarboxylic acidsCyclohexenonesDiterpenoidsHydrocarbon derivativesMedium-chain fatty acidsMethyl-branched fatty acidsMonocarboxylic acids and derivativesOrganic oxidesUnsaturated fatty acidsAliphatic homomonocyclic compoundBranched fatty acidCarbonyl groupCarboxylic acidCarboxylic acid derivativeCyclic ketoneCyclohexenoneDiterpenoidFatty acidFatty acylHydrocarbon derivativeKetoneMedium-chain fatty acidMethyl-branched fatty acidMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganooxygen compoundRetinoic acidRetinoid skeletonUnsaturated fatty acidRetinoidsRetinoidsretinoidSolidlogp4.94logs-4.71solubility6.20e-03 g/llogp4.35pka_strongest_acidic5pka_strongest_basic-4.8iupac(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acidaverage_mass314.4186mono_mass314.188194698smilesC\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=OformulaC20H26O3inchiInChI=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+inchikeyGGCUJPCCTQNTJF-FRCNGJHJSA-Npolar_surface_area54.37refractivity98.48polarizability36.62rotatable_bond_count5acceptor_count3donor_count1physiological_charge-1formal_charge0Retinol MetabolismSMP00074map00830Specdb::CMs20441Specdb::CMs38994Specdb::CMs156600Specdb::MsMs46329Specdb::MsMs46330Specdb::MsMs46331Specdb::MsMs158880Specdb::MsMs158881Specdb::MsMs158882Specdb::MsMs2319884Specdb::MsMs2319885Specdb::MsMs2319886Specdb::MsMs2618339Specdb::MsMs2618340Specdb::MsMs2618341HMDB06285#<Reference:0x0000555674582c60>#<Reference:0x0000555674582a58>#<Reference:0x00005556745827d8>#<Reference:0x00005556745825f8>#<Reference:0x0000555674582418>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823