1.02011-09-21 00:21:58 UTC2015-07-21 06:57:25 UTCFDB02293514,15-DiHETrE14,15-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 acid14,15-DHET14,15-dihydroxy-5Z,8Z,11Z-eicosatrienoate14,15-dihydroxy-5Z,8Z,11Z-eicosatrienoic acid14,15-dihydroxyeicosatrienoate14,15-dihydroxyeicosatrienoic acidC20H34O4338.4816338.24570957614,15-dihydroxyicosa-5,8,11-trienoic acid14,15-dihydroxyicosa-5,8,11-trienoic acid77667-09-5CCCCCC(O)C(O)CC=CCC=CCC=CCCCC(O)=OInChI=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 acidsOrganic compoundsLipids and lipid-like moleculesFatty AcylsEicosanoidsAliphatic acyclic compounds1,2-diolsCarbonyl compoundsCarboxylic acidsHydrocarbon derivativesHydroxy fatty acidsLong-chain fatty acidsMonocarboxylic acids and derivativesOrganic oxidesSecondary alcoholsUnsaturated fatty acids1,2-diolAlcoholAliphatic acyclic compoundCarbonyl groupCarboxylic acidCarboxylic acid derivativeFatty acidHydrocarbon derivativeHydroxy fatty acidHydroxyeicosatrienoic acidLong-chain fatty acidMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganooxygen compoundSecondary alcoholUnsaturated fatty acidSolidlogp5.28logs-4.39solubility1.39e-02 g/llogp4.49pka_strongest_acidic4.82pka_strongest_basic-3.1iupac14,15-dihydroxyicosa-5,8,11-trienoic acidaverage_mass338.4816mono_mass338.245709576smilesCCCCCC(O)C(O)CC=CCC=CCC=CCCCC(O)=OformulaC20H34O4inchiInChI=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)inchikeySYAWGTIVOGUZMM-UHFFFAOYSA-Npolar_surface_area77.76refractivity101.87polarizability39.78rotatable_bond_count15acceptor_count4donor_count3physiological_charge-1formal_charge0Arachidonic Acid MetabolismSMP00075map00590Specdb::MsMs3396406Specdb::MsMs3396407Specdb::MsMs3396408Specdb::MsMs3396409Specdb::MsMs3396410Specdb::MsMs3396411Specdb::CMs104908Specdb::CMs116935Specdb::CMs121293HMDB02265#<Reference:0x00007f3db99732b0>#<Reference:0x00007f3db9972e00>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823