1.0 2011-09-21 01:51:32 UTC 2017-03-11 23:00:53 UTC FDB029194 9,13-cis-Retinoate Tretinoin, also known as all-<i>trans</i>-retinoic acid (ATRA), is a naturally occurring derivative of vitamin A (retinol). Retinoids such as tretinoin are important regulators of cell reproduction, proliferation, and differentiation and are used to treat acne and photodamaged skin and to manage keratinization disorders such as ichthyosis and keratosis follicularis. Tretinoin also represents the class of anticancer drugs called differentiating agents and is used in the treatment of acute promyelocytic leukemia (APL). [HMDB] 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-(2E,4Z,6E,8Z)-nonatetraen-1-oate 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-(2E,4Z,6E,8Z)-nonatetraen-1-oic acid 9-cis,13-cis-retinoate 9-cis,13-cis-retinoic acid 9,13-cis-retinoate 9,13-cis-retinoic acid 9,13-cis-retinoic acid anion 9,13-cis-vitamin-A-acid 9,13-cis-vitamin-alpha-acid 9,13-di-cis-RA dcVA C20H28O2 300.4351 300.20893014 (2Z,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid 9,13-di-cis-retinoic acid 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-CDMOMSTLSA-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 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 Retinoids Solid logp 5.66 ALOGPS logs -4.80 ALOGPS solubility 4.77e-03 g/l ALOGPS logp 5.01 ChemAxon pka_strongest_acidic 5 ChemAxon iupac (2Z,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid ChemAxon average_mass 300.4351 ChemAxon mono_mass 300.20893014 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-CDMOMSTLSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 97.79 ChemAxon polarizability 35.87 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 23375 Specdb::CMs 40011 Specdb::CMs 165654 Specdb::MsMs 317833 Specdb::MsMs 317834 Specdb::MsMs 317835 Specdb::MsMs 364429 Specdb::MsMs 364430 Specdb::MsMs 364431 Specdb::MsMs 2763073 Specdb::MsMs 2763074 Specdb::MsMs 2763075 Specdb::MsMs 2941966 Specdb::MsMs 2941967 Specdb::MsMs 2941968 HMDB12874