1.0 2011-09-21 01:51:16 UTC 2015-07-21 06:59:39 UTC FDB029176 4-Oxoretinal 4-Oxoretinal is a predominant retinoids during morphogenesis in mouse skin in vivo. Topical 4-oxoretinal and 4-oxoretinol promoted significant epidermal hyperplasia and metaplasia in mouse tail. They induced a moderate response for epidermal inflammation, compared with retinal, whereas neither 4-oxoretinal nor 4-oxoretinol prevented menadione-induced epidermal lipid peroxidation, unlike retinal and retinol. As analyzed by quantitative PCR, 4-oxoretinal and 4-oxoretinol did not reproduce the significant increased expression of genes coding for keratin 4, amphiregulin, heparin-EGF and CYP26A1, that did induce retinal and retinol. However, both retinal and 4-oxoretinal significantly inhibited the lipopolysaccharide-induced maturation of human dendritic cells in vitro. As analyzed in vivo and in vitro, 4-oxoretinal and 4-oxoretinol were not converted into retinoic acid. We conclude that 4-oxoretinal and 4-oxoretinol exert a moderate direct retinoid-like activity in vivo, thus confirming previous in vitro studies in amphibians showing 4-oxometabolites of vitamin A as bioactive agents rather than inactive catabolites. [HMDB] 3,7-dimethyl-9-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-all-trans-2,4,6,8-nonatetraenal 4-ketoretinal 4-oxo-all-trans-retinal 4OVA C20H26O2 298.4192 298.193280076 (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal 33532-44-4 C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCC(=O)C1(C)C)=C/C=O InChI=1S/C20H26O2/c1-15(7-6-8-16(2)13-14-21)9-11-18-17(3)10-12-19(22)20(18,4)5/h6-9,11,13-14H,10,12H2,1-5H3/b8-6+,11-9+,15-7+,16-13+ ZORDCCAUKPDLPN-ZBSJWCJSSA-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 Cyclohexenones Diterpenoids Enals Hydrocarbon derivatives Organic oxides Aldehyde Aliphatic homomonocyclic compound Alpha,beta-unsaturated aldehyde Carbonyl group Cyclic ketone Cyclohexenone Diterpenoid Enal Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Retinoid skeleton Solid logp 5.47 ALOGPS logs -4.63 ALOGPS solubility 6.98e-03 g/l ALOGPS logp 4.19 ChemAxon pka_strongest_acidic 19.84 ChemAxon pka_strongest_basic -4.1 ChemAxon iupac (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal ChemAxon average_mass 298.4192 ChemAxon mono_mass 298.193280076 ChemAxon smiles C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCC(=O)C1(C)C)=C/C=O ChemAxon formula C20H26O2 ChemAxon inchi InChI=1S/C20H26O2/c1-15(7-6-8-16(2)13-14-21)9-11-18-17(3)10-12-19(22)20(18,4)5/h6-9,11,13-14H,10,12H2,1-5H3/b8-6+,11-9+,15-7+,16-13+ ChemAxon inchikey ZORDCCAUKPDLPN-ZBSJWCJSSA-N ChemAxon polar_surface_area 34.14 ChemAxon refractivity 97.56 ChemAxon polarizability 35.76 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 13740 Specdb::CMs 133432 Specdb::CMs 141166 Specdb::MsMs 296293 Specdb::MsMs 296294 Specdb::MsMs 296295 Specdb::MsMs 337558 Specdb::MsMs 337559 Specdb::MsMs 337560 Specdb::MsMs 2739937 Specdb::MsMs 2739938 Specdb::MsMs 2739939 Specdb::MsMs 2938770 Specdb::MsMs 2938771 Specdb::MsMs 2938772 HMDB12794