1.02011-09-21 00:29:27 UTC2015-07-21 06:57:41 UTCFDB023406Hepoxilin A3Hepoxilin A3 is an electrophilic eicosanoids synthesized during arachidonic acid oxidative metabolism, which can participate in the Michael addition reaction with glutathione (GSH, a major cellular antioxidant) catalyzed by the GSH-S-transferase (GST) family. GSH-adducts have been observed with molecules synthesized through the 12-lipoxygenase pathway. (PMID 12432937)
Hepoxilins have biological actions that appear to have, as their basis, changes in intracellular concentrations of ions including calcium and potassium ions as well as changes in second messenger systems. Recent evidence suggests that the biological actions of the hepoxilins may be receptor-mediated as indicated from data showing the existence of hepoxilin-specific binding proteins in the human neutrophils. Such evidence also implicates the association of G-proteins both in hepoxilin-binding as well as in hepoxilin action. (PMID 7947989) [HMDB](5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoate(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoic acid(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyicosa-5,9,14-trienoate(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyicosa-5,9,14-trienoic acid(5Z,9e,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyeicosa-5,9,14-trienoate(5Z,9e,14Z)-(8XI,11R,12S)-11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoic acid(5Z,9e,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoate(5Z,9e,14Z)-(8XI,11R,12S)-11,12-Epoxy-8-hydroxyicosa-5,9,14-trienoic acid(5Z,9E)-8-hydroxy-10-{(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,9-dienoate(5Z,9E)-8-hydroxy-10-{(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,9-dienoic acid8-hydroxy-11,12-epoxyeicosa-5,9,14-trienoate8-hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid8-hydroxy-11S,12S-epoxy-5Z,14Z,9E-eicosatrienoate8-hydroxy-11S,12S-epoxy-5Z,14Z,9E-eicosatrienoic acidC20H32O4336.4657336.2300595128-hydroxy-10-[(2R,3S)-3-(oct-2-en-1-yl)oxiran-2-yl]deca-5,9-dienoic acid8-hydroxy-10-[(2R,3S)-3-(oct-2-en-1-yl)oxiran-2-yl]deca-5,9-dienoic acid85589-24-8[H][C@@]1(CC=CCCCCC)O[C@]1([H])C=CC(O)CC=CCCCC(O)=OInChI=1S/C20H32O4/c1-2-3-4-5-6-10-13-18-19(24-18)16-15-17(21)12-9-7-8-11-14-20(22)23/h6-7,9-10,15-19,21H,2-5,8,11-14H2,1H3,(H,22,23)/t17?,18-,19+/m0/s1SGTUOBURCVMACZ-JLMCIHFGSA-N belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain.HepoxilinsOrganic compoundsLipids and lipid-like moleculesFatty AcylsEicosanoidsAliphatic heteromonocyclic compoundsCarbonyl compoundsCarboxylic acidsDialkyl ethersEpoxidesEpoxy fatty acidsHydrocarbon derivativesHydroxy fatty acidsMedium-chain fatty acidsMedium-chain hydroxy acids and derivativesMonocarboxylic acids and derivativesOrganic oxidesOxacyclic compoundsSecondary alcoholsUnsaturated fatty acidsAlcoholAliphatic heteromonocyclic compoundCarbonyl groupCarboxylic acidCarboxylic acid derivativeDialkyl etherEpoxy fatty acidEtherFatty acidHepoxilinHeterocyclic fatty acidHydrocarbon derivativeHydroxy fatty acidMedium-chain fatty acidMedium-chain hydroxy acidMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacycleOxiraneSecondary alcoholUnsaturated fatty acidSolidlogp5.57logs-4.56solubility9.36e-03 g/llogp4.57pka_strongest_acidic4.68pka_strongest_basic-2.9iupac8-hydroxy-10-[(2R,3S)-3-(oct-2-en-1-yl)oxiran-2-yl]deca-5,9-dienoic acidaverage_mass336.4657mono_mass336.230059512smiles[H][C@@]1(CC=CCCCCC)O[C@]1([H])C=CC(O)CC=CCCCC(O)=OformulaC20H32O4inchiInChI=1S/C20H32O4/c1-2-3-4-5-6-10-13-18-19(24-18)16-15-17(21)12-9-7-8-11-14-20(22)23/h6-7,9-10,15-19,21H,2-5,8,11-14H2,1H3,(H,22,23)/t17?,18-,19+/m0/s1inchikeySGTUOBURCVMACZ-JLMCIHFGSA-Npolar_surface_area70.06refractivity99.72polarizability40.18rotatable_bond_count14acceptor_count4donor_count2physiological_charge-1formal_charge0HMDB0468836190#<Reference:0x0000555675c44688>#<Reference:0x0000555675c444d0>#<Reference:0x0000555675c44318>#<Reference:0x0000555675c44160>#<Reference:0x0000555675c43f30>#<Reference:0x0000555675c43d50>#<Reference:0x0000555675c43b98>#<Reference:0x0000555675c439e0>#<Reference:0x0000555675c43828>#<Reference:0x0000555675c435d0>#<Reference:0x0000555675c433c8>#<Reference:0x0000555675c431e8>#<Reference:0x0000555675c43008>#<Reference:0x0000555675c42e28>#<Reference:0x0000555675c42c20>#<Reference:0x0000555675c429f0>#<Reference:0x0000555675c426f8>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