1.0 2011-09-21 00:21:58 UTC 2015-07-21 06:57:25 UTC FDB022935 14,15-DiHETrE 14,15-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Eicosanoids generated from arachidonic acid metabolism by cytochrome P450 (P450) enzymes are important autocrine and paracrine factors that have diverse biological functions. P450 eicosanoids are involved in the regulation of vascular tone, renal tubular transport, cardiac contractility, cellular proliferation, and inflammation. Regulation of P450 eicosanoid levels is determined by many factors, including the induction or repression of the P450 enzymes responsible for their formation. Fibrate drugs are part of a diverse group of compounds known as peroxisome proliferators, which also include herbicides and phthalate ester plasticizers. Peroxisome proliferators act via peroxisome proliferator-activated receptor (PPAR ). This receptor is a member of the PPAR nuclear receptor family that also consists of the PPAR and PPAR isoforms. PPAR is mainly expressed in the heart, liver, and kidney, whereas the expression of PPAR is predominantly in the adipose tissue. The biological role of PPAR as a lipid sensor has been well established. 14,15-DiHETrE is a potent activators of PPAR and PPAR . shown to induce the binding of PPAR to a peroxisome proliferator response element (PPRE). Furthermore, 14,15-DiHETrE behaves like peroxisome proliferators in that is able to alter apoA-I and apoA-II mRNA expression. 14,15-DiHETrE is the most potent PPARalpha activator in a COS-7 cell expression system producing a 12-fold increase in PPARalpha-mediated luciferase activity. (PMID: 17431031, 16113065) [HMDB] (+/-)14,15-DiHETrE (5Z,8Z,11Z)-14,15-Dihydroxyeicosa-5,8,11-trienoate (5Z,8Z,11Z)-14,15-Dihydroxyeicosa-5,8,11-trienoic acid (5Z,8Z,11Z)-14,15-Dihydroxyicosa-5,8,11-trienoate (5Z,8Z,11Z)-14,15-Dihydroxyicosa-5,8,11-trienoic acid 14,15-DHET 14,15-dihydroxy-5Z,8Z,11Z-eicosatrienoate 14,15-dihydroxy-5Z,8Z,11Z-eicosatrienoic acid 14,15-dihydroxyeicosatrienoate 14,15-dihydroxyeicosatrienoic acid C20H34O4 338.4816 338.245709576 14,15-dihydroxyicosa-5,8,11-trienoic acid 14,15-dihydroxyicosa-5,8,11-trienoic acid 77667-09-5 CCCCCC(O)C(O)CC=CCC=CCC=CCCCC(O)=O InChI=1S/C20H34O4/c1-2-3-12-15-18(21)19(22)16-13-10-8-6-4-5-7-9-11-14-17-20(23)24/h4,6-7,9-10,13,18-19,21-22H,2-3,5,8,11-12,14-17H2,1H3,(H,23,24) SYAWGTIVOGUZMM-UHFFFAOYSA-N belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds. Hydroxyeicosatrienoic acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic acyclic compounds 1,2-diols Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Secondary alcohols Unsaturated fatty acids 1,2-diol Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Hydroxy fatty acid Hydroxyeicosatrienoic acid Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Unsaturated fatty acid Solid logp 5.28 ALOGPS logs -4.39 ALOGPS solubility 1.39e-02 g/l ALOGPS logp 4.49 ChemAxon pka_strongest_acidic 4.82 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac 14,15-dihydroxyicosa-5,8,11-trienoic acid ChemAxon average_mass 338.4816 ChemAxon mono_mass 338.245709576 ChemAxon smiles CCCCCC(O)C(O)CC=CCC=CCC=CCCCC(O)=O ChemAxon formula C20H34O4 ChemAxon inchi InChI=1S/C20H34O4/c1-2-3-12-15-18(21)19(22)16-13-10-8-6-4-5-7-9-11-14-17-20(23)24/h4,6-7,9-10,13,18-19,21-22H,2-3,5,8,11-12,14-17H2,1H3,(H,23,24) ChemAxon inchikey SYAWGTIVOGUZMM-UHFFFAOYSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 101.87 ChemAxon polarizability 39.78 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arachidonic Acid Metabolism SMP00075 map00590 Specdb::CMs 104908 Specdb::CMs 116935 Specdb::CMs 121293 Specdb::MsMs 3396406 Specdb::MsMs 3396407 Specdb::MsMs 3396408 Specdb::MsMs 3396409 Specdb::MsMs 3396410 Specdb::MsMs 3396411 HMDB02265 #<Reference:0x000055ce32b4d128> #<Reference:0x000055ce32b4cf20> 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