1.0 2011-09-21 00:26:47 UTC 2015-07-21 06:57:36 UTC FDB023240 13-L-Hydroperoxylinoleic acid 13-L-Hydroperoxylinoleic acid (13(S)-HPODE) is one of the primary products of the major polyunsaturated fatty acids (linoleic acid and arachidonic acid) from the 15-1ipoxygenase pathway (EC: 1.13.11.31). 13(S)-HPODE is a rather unstable metabolite and is rapidly metabolized to more stable secondary products such as diverse forms of hydroxy fatty acids (via reduction of the hydroperoxy group), alkoxy radicals (via homolytic cleavage of the peroxy group), forms of dihydro(pero)xy fatty acids (via lipoxygenase-catalysed double and triple oxygenation), or epoxy leukotrienes (via a hydrogen abstraction from a doubly allylic methylene group and a homolytic cleavage of the hydroperoxy group). (PMID 9082450) [HMDB] (13S,9z,11e)-13-hydroperoxy-9,11-octadecadienoate (13S,9z,11e)-13-hydroperoxy-9,11-octadecadienoic acid (9Z,11e,13S)-13-Hydroperoxyoctadeca-9,11-dienoate (9Z,11e,13S)-13-Hydroperoxyoctadeca-9,11-dienoic acid (9Z,11e)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate (9Z,11e)-(13S)-13-hydroperoxyoctadeca-9,11-dienoic acid 13-hpod 13-hpode 13-l-hydroperoxy-9-cis,11-trans-octadecadienoate 13-l-hydroperoxy-9-cis,11-trans-octadecadienoic acid 13-l-hydroperoxy-cis-9,trans-11-octadecadienoate 13-l-hydroperoxy-cis-9,trans-11-octadecadienoic acid 13(s)-hpode 13(s)-hydroperoxy-9Z,11e-octadecadienoate 13(s)-hydroperoxy-9Z,11e-octadecadienoic acid 13(s)-hydroperoxylinoleic acid 13S-hydroperoxy-9Z,11e-octadecadienoate 13S-hydroperoxy-9Z,11e-octadecadienoic acid Hpode Linoleic acid 13(s)-hydroperoxide C18H32O4 312.4443 312.230059512 (13S)-13-hydroperoxyoctadeca-9,11-dienoic acid (13S)-13-hydroperoxyoctadeca-9,11-dienoic acid 33964-75-9 [H][C@@](CCCCC)(OO)C=CC=CCCCCCCCC(O)=O InChI=1S/C18H32O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)/t17-/m0/s1 JDSRHVWSAMTSSN-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 5.76 ALOGPS logs -4.98 ALOGPS solubility 3.28e-03 g/l ALOGPS logp 5.64 ChemAxon pka_strongest_acidic 4.99 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (13S)-13-hydroperoxyoctadeca-9,11-dienoic acid ChemAxon average_mass 312.4443 ChemAxon mono_mass 312.230059512 ChemAxon smiles [H][C@@](CCCCC)(OO)C=CC=CCCCCCCCC(O)=O ChemAxon formula C18H32O4 ChemAxon inchi InChI=1S/C18H32O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)/t17-/m0/s1 ChemAxon inchikey JDSRHVWSAMTSSN-KRWDZBQOSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 91.38 ChemAxon polarizability 39.18 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB03871 15655 13S #<Reference:0x000055ce31829b00>