1.02011-09-21 00:35:39 UTC2015-10-09 22:33:12 UTCFDB02384313-cis-Retinoic acidA topical dermatologic agent that is used in the treatment of acne vulgaris and several other skin diseases. The drug has teratogenic and other adverse effects. (PubChem)
13-cis-retinoic acid is also a naturally occurring retinoid that is present in the circulation. Although 13-cis-retinoic acid (isotretinoin) does not have the potent gene regulatory activity of other isomers, it is an effective pharmacologic agent for treating a variety of dermatologic conditions. (PMID: 11606944)
The steric conversion of 13-cis-retinoic acid (13-cRA) to all-trans-retinoic acid (t-RA) has been proposed as an activation mechanism for the observed therapeutic and teratogenic activities of 13-cRA. (PMID: 9806904)
13-cis retinoic acid exerts its specific activity on human sebocytes through selective intracellular isomerization to all-trans retinoic acid and binding to retinoid acid receptors. (PMID: 10951254) [HMDB](13-cis)-Retinoate(13-cis)-Retinoic acid(13cis)-Retinoate(13cis)-Retinoic acid(7e,9e,11e,13Z)-Retinoate(7e,9e,11e,13Z)-Retinoic acid13-cis-Vitamin A acid13-RAAccutaneAccutane (TN)AmnesteemCIP-Isotretinoincis-RAcis-Retinoatecis-Retinoic acidClaravisIsotretinoinIsotretinoin (USP)Isotretinoin [USAN:BAN:INN]IsotretinoinaIsotretinoineIsotretinoine [INN-French]IsotretinoinoIsotretinoino [INN-Spanish]IsotretinoinumIsotretinoinum [INN-Latin]IsotrexNeovitamin A acidRoaccutanRoaccutaneRoacutanSotretTeriosalC20H28O2300.4351300.208930143,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acidisotretinoin4759-48-2CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(O)=OInChI=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)SHGAZHPCJJPHSC-UHFFFAOYSA-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 compoundsCarbonyl compoundsCarboxylic acidsDiterpenoidsHydrocarbon derivativesMedium-chain fatty acidsMethyl-branched fatty acidsMonocarboxylic acids and derivativesOrganic oxidesUnsaturated fatty acidsAliphatic homomonocyclic compoundBranched fatty acidCarbonyl groupCarboxylic acidCarboxylic acid derivativeDiterpenoidFatty acidFatty acylHydrocarbon derivativeMedium-chain fatty acidMethyl-branched fatty acidMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganooxygen compoundRetinoic acidRetinoid skeletonUnsaturated fatty acidalpha,beta-unsaturated monocarboxylic acidretinoidSolidlogp5.66logs-4.80solubility4.77e-03 g/llogp5.01pka_strongest_acidic5iupac3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acidaverage_mass300.4351mono_mass300.20893014smilesCC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(O)=OformulaC20H28O2inchiInChI=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)inchikeySHGAZHPCJJPHSC-UHFFFAOYSA-Npolar_surface_area37.3refractivity97.79polarizability36.93rotatable_bond_count5acceptor_count2donor_count1physiological_charge-1formal_charge0Specdb::MsMs252453Specdb::MsMs252454Specdb::MsMs252455Specdb::MsMs272394Specdb::MsMs272395Specdb::MsMs272396Specdb::MsMs3395149Specdb::MsMs3395150Specdb::MsMs3395151Specdb::MsMs3395152Specdb::MsMs3395153Specdb::MsMs3395154Specdb::CMs7235Specdb::CMs38146Specdb::CMs117959Specdb::CMs809298HMDB06219#<Reference:0x00005556761c0dc8>#<Reference:0x00005556761c0b70>#<Reference:0x00005556761c0940>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