1.0 2011-09-21 00:22:48 UTC 2025-11-19 02:42:57 UTC FDB022982 9-cis-Retinoic acid 9-cis-retinoic acid is an active retinoid that regulates expression of retinoid responsive genes, serving as ligand for two classes of ligand-dependent transcription factors, the retinoic acid receptors and retinoid X receptors. Retinoids (vitamin A and its analogs) are essential dietary substances that are needed by mammals for reproduction, normal embryogenesis, growth, vision, and maintaining normal cellular differentiation and the integrity of the immune system. Within cells, retinoids regulate gene transcription acting through ligand-dependent transcription factors, the retinoic acid receptors (RARs), and the retinoid X receptors (RXRs). All-trans-retinoic acid binds only to RARs with high affinity, whereas its 9-cis isomer binds with high affinity to both RARs and RXRs. The actions of all-trans- and 9-cis-retinoic acid in regulating cellular responses are distinct and not interchangeable. (PMID: 9115228) [HMDB] (2e,4e,6Z,8e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate (2e,4e,6Z,8e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid (7e,9Z,11e,13e)-Retinoate (7e,9Z,11e,13e)-Retinoic acid 15-Apo-beta-caroten-15-oate 15-Apo-beta-caroten-15-oic acid 9-cis-Retinoate 9-cis-Retinoic acid 9-cis-Tretinoin 9-Retinoate 9-Retinoic acid 9(Z)-Retinoate 9(Z)-Retinoic acid A-acido (argentina) Aberel Aberela Aberela [norway] acide retinoique (french) (DSL) Airol Aknoten Alitretinoin Alitretinoin (usan) Alitretinoin [usan] Alitretinoina Alitretinoine Alitretinoinum all-trans- Vitamin A1 acid All-trans-b-retinoate All-trans-b-retinoic acid All-trans-beta-retinoate All-trans-beta-retinoic acid alpha-acido (argentina) alpha-Vitaminsyre alpha-vitaminsyre [denmark] Atragen Avita Avitoin Avitoin [norway] B-retinoate B-retinoic acid Dermairol Effederm Effederm [france] Epi-aberel Eudyna Isotretinoin retinoate Isotretinoin retinoic acid Panretin Panretin (TN) Panretin gel Panretyn Panrexin Renova Retacnyl Retin a Retin a (TN) Retin-a Retin-a micro Retinoic acid Retinova trans-Vitamin a acid Tretinoin Tretinoin (jan/usp) Tretinoin (TN) Tretinoin [usan:ban:inn] Tretinoin/all-trans retinoate Tretinoin/all-trans retinoic acid Tretinoina [inn-spanish] Tretinoine (french) (einecs) Tretinoine [inn-french] Tretinoino [inn-spanish] Tretinoinum [inn-latin] Tretinon Vesanoid Vesnaroid C20H28O2 300.4351 300.20893014 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid isotretinoin 5300-03-8 CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(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) 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. 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 alpha,beta-unsaturated monocarboxylic acid retinoid 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 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 CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(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) ChemAxon inchikey SHGAZHPCJJPHSC-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 97.79 ChemAxon polarizability 36.93 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Retinol Metabolism SMP00074 map00830 Specdb::CMs 7235 Specdb::CMs 38146 Specdb::CMs 117959 Specdb::CMs 809298 Specdb::MsMs 252453 Specdb::MsMs 252454 Specdb::MsMs 252455 Specdb::MsMs 272394 Specdb::MsMs 272395 Specdb::MsMs 272396 Specdb::MsMs 3395149 Specdb::MsMs 3395150 Specdb::MsMs 3395151 Specdb::MsMs 3395152 Specdb::MsMs 3395153 Specdb::MsMs 3395154 HMDB02369 #<Reference:0x000055ce333814e8> Retinoic acid receptor RXR-alpha P19793 RXRA Retinoic acid receptor RXR-beta P28702 RXRB Retinoic acid receptor RXR-gamma P48443 RXRG