1.0 2011-09-21 00:35:38 UTC 2015-07-21 06:57:54 UTC FDB023842 9-cis-Retinal In vivo, 9-cis-retinal is formed through oxidation of 9-cis-retinol by cis-retinol dehydrogenase (cRDH). (PMID: 15572038). The generation of retinoic acid from retinol is a two-step reaction, with the rate-limiting step being the oxidation of retinol into the intermediate retinaldehyde. Two classes of unrelated enzymes have been implicated in the oxidation of retinol, the classical cytosolic medium chain alcohol dehydrogenases and recently identified microsomal members of the short chain alcohol dehydrogenase reductase (SDR) superfamily. Further oxidation of the retinaldehyde to the retinoic acid is believed to be catalyzed by several cytosolic aldehyde dehydrogenases. Retinoids are micronutrients required to maintain and promote health of vertebrates. They act physiologically by participating in the visual cycle, in regulating cell differentiation, in embryonic development (PMID: 10893430), in maintaining normal reproduction, and in the immune response (PMID: 8882153). In non-ocular tissues, the effects of retinoids within the body are mediated through retinoic acid receptors (RARs) and retinoid X receptors (RXRs), which act to regulate gene expression as ligand-dependent transcription factors. The naturally occurring ligands for these nuclear receptors are thought to be all-trans-retinoic acid for RARs and 9-cis-retinoic acid for RXRs (PMID: 10322133). While many details of the molecular actions of the RARs and RXRs in regulating gene transcription are understood (PMID: 10418975), tissue-specific synthetic pathway(s) of their ligands has not been adequately defined. Nevertheless, the therapeutic efficacy of retinoids, including 9-cis-retinoic acid, is well established in both tissue culture and animal models of breast cancer (PMID: 8825126, PMID: 12743994) [HMDB] (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-Retinal 9-cis-Retinaldehyde 9-cis-Vitamin A aldehyde cis-9-Retinal Isoretinene A 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-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 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 Retinoids Retinoids retinal Solid logp 6.62 ALOGPS logs -4.83 ALOGPS solubility 4.20e-03 g/l 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-OVSJKPMPSA-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 Retinol Metabolism SMP00074 map00830 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 HMDB06218 #<Reference:0x000055ce32435a70> #<Reference:0x000055ce32435840> #<Reference:0x000055ce32435688> #<Reference:0x000055ce324354d0> #<Reference:0x000055ce324352f0> #<Reference:0x000055ce32435138> #<Reference:0x000055ce32434f80> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 A-kinase anchor protein 10, mitochondrial O43572 AKAP10