1.0 2016-09-30 23:20:28 UTC 2020-05-21 16:29:06 UTC BMDB0006218 BMDB06218 9-cis-Retinal 13-cis-13-cis-13-cis-retinal, also known as 13Z-13-cis-retinal or 13-cis-retinal, 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. Thus, 13-cis-13-cis-retinal is considered to be an isoprenoid lipid molecule. 13-cis-13-cis-13-cis-retinal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 13-cis-13-cis-13-cis-retinal exists in all living organisms, ranging from bacteria to humans. In cattle, 13-cis-13-cis-retinal is involved in the metabolic pathway called the retinol metabolism pathway. (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal (9cis)-Retinal 9-C-Retinal 9-cis-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal 9-cis-7,11,13-trans-Retinal 9-cis-Retinaldehyde 9-cis-Vitamin a aldehyde Isoretinene a cis-9-Retinal C20H28O 284.4357 284.214015518 (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal 9-cis-retinal 514-85-2 C/C(/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=O InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8-,17-13+ NCYCYZXNIZJOKI-MKOSUFFBSA-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. Organic compounds Lipids and lipid-like molecules Prenol lipids Retinoids Retinoids Aldehydes Diterpenoids Enals Hydrocarbon derivatives Organic oxides Aldehyde Aliphatic homomonocyclic compound Alpha,beta-unsaturated aldehyde Carbonyl group Diterpenoid Enal Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Retinoid skeleton Aliphatic homomonocyclic compounds Retinoids Retinoids retinal Solid logp 6.62 ALOGPS logs -4.83 ALOGPS logp 4.86 ChemAxon pka_strongest_basic -4.1 ChemAxon iupac (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal ChemAxon average_mass 284.4357 ChemAxon mono_mass 284.214015518 ChemAxon smiles C/C(/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C\C=O ChemAxon formula C20H28O ChemAxon inchi InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8-,17-13+ ChemAxon inchikey NCYCYZXNIZJOKI-MKOSUFFBSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 96.87 ChemAxon polarizability 34.99 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::NmrTwoD 2025 Specdb::NmrOneD 5188 Specdb::CMs 15090 Specdb::CMs 160210 Specdb::MsMs 299464 Specdb::MsMs 299465 Specdb::MsMs 299466 Specdb::MsMs 341485 Specdb::MsMs 341486 Specdb::MsMs 341487 Specdb::MsMs 2328204 Specdb::MsMs 2328205 Specdb::MsMs 2328206 Specdb::MsMs 2634910 Specdb::MsMs 2634911 Specdb::MsMs 2634912 FDB023842 C16681 4940758 6436082 78273 CPD-13536 2265509 Ostapenko, I. A.; Furaev, V. V. The 9-cis isomerization of all-trans-retinal during in vitro regeneration of visual pigment. Nature (London), New Biology (1973), 243(127), 185-6. BMDBP00601 Retinal dehydrogenase 1 P48644 ALDH1A1 Enzyme BMDBP01288 Retinol dehydrogenase 12 P59837 RDH12 Enzyme