1.0 2011-09-21 00:29:18 UTC 2018-05-28 18:36:41 UTC FDB023395 13S-Hydroxyoctadecadienoic acid 13-hydroxyoctadecadienoic acid (13-HODE) is synthesized in the body from linoleic acid. 13-HODE prevents cell adhesion to endothelial cells and can inhibit cancer metastasis. 13-HODE synthesis is enhanced by cyclic AMP. Gamma-linolenic acid, a desaturated metabolite of linoleic acid, causes substantial stimulation of 13-HODE synthesis. A fall in gamma-linolenic acid synthesis with age may be related to the age-related fall in 13-HODE formation. (PMID 9561154) 13-HODE is considered an intermediate in Linoleic acid metabolism(KEGG ID C14762). It is generated from 13(S)-HPODE via the enzyme lipoxygenase [EC:1.13.11.12]. [HMDB] (13S)-Hydroxyoctadecadienoate (13S)-Hydroxyoctadecadienoic acid (9Z, 11e)-(13S)-13-Hydroxyoctadeca-9,11-dienoate (9Z, 11e)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acid (9Z,11e)-(13S)-13-Hydroxyoctadeca-9,11-dienoate (9Z,11e)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acid 13-HODE 13-Hydroxyoctadecadienoate 13-Hydroxyoctadecadienoic acid 13(S)-HODE C18H32O3 296.4449 296.23514489 (13S)-13-hydroxyoctadeca-9,11-dienoic acid (13S)-13-hydroxyoctadeca-9,11-dienoic acid 5204-88-6 [H][C@](O)(CCCCC)C=CC=CCCCCCCCC(O)=O InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/t17-/m0/s1 HNICUWMFWZBIFP-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 Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Secondary alcohols Unsaturated fatty acids Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Hydroxy fatty acid Long-chain fatty acid Monocarboxylic acid or derivatives Octadecanoid Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Unsaturated fatty acid logp 5.88 ALOGPS logs -5.00 ALOGPS solubility 2.98e-03 g/l ALOGPS logp 5.19 ChemAxon pka_strongest_acidic 4.99 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac (13S)-13-hydroxyoctadeca-9,11-dienoic acid ChemAxon average_mass 296.4449 ChemAxon mono_mass 296.23514489 ChemAxon smiles [H][C@](O)(CCCCC)C=CC=CCCCCCCCC(O)=O ChemAxon formula C18H32O3 ChemAxon inchi InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/t17-/m0/s1 ChemAxon inchikey HNICUWMFWZBIFP-KRWDZBQOSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 90.03 ChemAxon polarizability 38.26 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB61708 #<Reference:0x000055ce32210510>