1.0 2011-09-21 00:35:37 UTC 2025-11-19 02:45:06 UTC FDB023841 9-cis-Retinol 9-cis-retinol is a retinoid. 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-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol (9cis)-Retinol 9-cis retinol 9-cis-Retinol C20H30O 286.4516 286.229665582 (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol α-sol 22737-97-9 C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+ FPIPGXGPPPQFEQ-OVSJKPMPSA-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 Diterpenoids Fatty alcohols Hydrocarbon derivatives Primary alcohols Alcohol Aliphatic homomonocyclic compound Diterpenoid Fatty acyl Fatty alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Primary alcohol Retinoid skeleton Fat-soluble vitamins Retinoids Retinoids retinol Solid logp 6.38 ALOGPS logs -4.58 ALOGPS solubility 7.58e-03 g/l ALOGPS logp 4.69 ChemAxon pka_strongest_acidic 16.44 ChemAxon pka_strongest_basic -2.2 ChemAxon iupac (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol ChemAxon average_mass 286.4516 ChemAxon mono_mass 286.229665582 ChemAxon smiles C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C ChemAxon formula C20H30O ChemAxon inchi InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+ ChemAxon inchikey FPIPGXGPPPQFEQ-OVSJKPMPSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 97.92 ChemAxon polarizability 36.54 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Retinol Metabolism SMP00074 map00830 Specdb::EiMs 432 Specdb::NmrTwoD 1267 Specdb::CMs 8618 Specdb::CMs 37414 Specdb::CMs 136707 Specdb::CMs 144441 Specdb::CMs 1057500 Specdb::NmrOneD 268188 Specdb::NmrOneD 268189 Specdb::NmrOneD 268190 Specdb::NmrOneD 268191 Specdb::NmrOneD 268192 Specdb::NmrOneD 268193 Specdb::NmrOneD 268194 Specdb::NmrOneD 268195 Specdb::NmrOneD 268196 Specdb::NmrOneD 268197 Specdb::NmrOneD 268198 Specdb::NmrOneD 268199 Specdb::NmrOneD 268200 Specdb::NmrOneD 268201 Specdb::NmrOneD 268202 Specdb::NmrOneD 268203 Specdb::NmrOneD 268204 Specdb::NmrOneD 268205 Specdb::NmrOneD 268206 Specdb::NmrOneD 268207 Specdb::MsMs 519 Specdb::MsMs 520 Specdb::MsMs 521 Specdb::MsMs 260733 Specdb::MsMs 260734 Specdb::MsMs 260735 Specdb::MsMs 280668 Specdb::MsMs 280669 Specdb::MsMs 280670 Specdb::MsMs 2473550 Specdb::MsMs 2473551 Specdb::MsMs 2473552 Specdb::MsMs 2489277 Specdb::MsMs 2489278 Specdb::MsMs 2489279 HMDB06217 #<Reference:0x000055ce306c02d8>