1.0 2011-09-21 00:29:40 UTC 2015-07-21 06:57:42 UTC FDB023417 8R-Hydroperoxylinoleic acid 8(R)-hydroperoxylinoleic acid (8(R)-EPODE) is an oxidized product of linoleic acid. Oxidized lipids such as 8(R)-HPODE can decrease cellular proteoglycan metabolism in endothelial monolayers and alter mRNA levels of major specific proteoglycans in a concentration-dependent manner. This may have implications in lipid-mediated disruption of endothelial barrier function and atherosclerosis. (PMID: 8645361, 9507987) [HMDB] (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoic acid (8R)-8-Hydroperoxylinoleate (8R)-8-Hydroperoxylinoleic acid (9Z,12Z)-(8R)-8-Hydroperoxyoctadeca-9,12-dienoate (9Z,12Z)-(8R)-8-Hydroperoxyoctadeca-9,12-dienoic acid (R-(Z,Z))-8-Hydroperoxy-9,12-octadecadienoate (R-(Z,Z))-8-Hydroperoxy-9,12-octadecadienoic acid 8-HPODE 8-Hydroperoxylinoleic acid 8(R)-HPODE 8R-HPODE 8R-Hydroperoxy-9Z,12Z-octadecadienoate 8R-Hydroperoxy-9Z,12Z-octadecadienoic acid C18H32O4 312.4443 312.230059512 (8R)-8-hydroperoxyoctadeca-9,12-dienoic acid (8R)-8-hydroperoxyoctadeca-9,12-dienoic acid 143343-95-7 [H][C@](CCCCCCC(O)=O)(OO)C=CCC=CCCCCC InChI=1S/C18H32O4/c1-2-3-4-5-6-7-8-11-14-17(22-21)15-12-9-10-13-16-18(19)20/h6-7,11,14,17,21H,2-5,8-10,12-13,15-16H2,1H3,(H,19,20)/t17-/m0/s1 RGJSGXNKRWWCOQ-KRWDZBQOSA-N belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Lineolic acids and derivatives Organic compounds Lipids and lipid-like molecules Fatty Acyls Lineolic acids and derivatives Aliphatic acyclic compounds Alkyl hydroperoxides Allylic hydroperoxides Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroperoxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Peroxols Unsaturated fatty acids Aliphatic acyclic compound Alkyl hydroperoxide Allylic hydroperoxide Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Hydroperoxide Hydroperoxy fatty acid Long-chain fatty acid Monocarboxylic acid or derivatives Octadecanoid Organic oxide Organic oxygen compound Organooxygen compound Peroxol Unsaturated fatty acid Solid logp 5.68 ALOGPS logs -4.88 ALOGPS solubility 4.10e-03 g/l ALOGPS logp 5.64 ChemAxon pka_strongest_acidic 4.45 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (8R)-8-hydroperoxyoctadeca-9,12-dienoic acid ChemAxon average_mass 312.4443 ChemAxon mono_mass 312.230059512 ChemAxon smiles [H][C@](CCCCCCC(O)=O)(OO)C=CCC=CCCCCC ChemAxon formula C18H32O4 ChemAxon inchi InChI=1S/C18H32O4/c1-2-3-4-5-6-7-8-11-14-17(22-21)15-12-9-10-13-16-18(19)20/h6-7,11,14,17,21H,2-5,8-10,12-13,15-16H2,1H3,(H,19,20)/t17-/m0/s1 ChemAxon inchikey RGJSGXNKRWWCOQ-KRWDZBQOSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 91.38 ChemAxon polarizability 37.42 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB04706 34485 #<Reference:0x000055ce31681078> #<Reference:0x000055ce31680e98>