1.0 2011-09-21 00:29:27 UTC 2015-07-21 06:57:41 UTC FDB023406 Hepoxilin A3 Hepoxilin 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 acid 8-hydroxy-11,12-epoxyeicosa-5,9,14-trienoate 8-hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid 8-hydroxy-11S,12S-epoxy-5Z,14Z,9E-eicosatrienoate 8-hydroxy-11S,12S-epoxy-5Z,14Z,9E-eicosatrienoic acid C20H32O4 336.4657 336.230059512 8-hydroxy-10-[(2R,3S)-3-(oct-2-en-1-yl)oxiran-2-yl]deca-5,9-dienoic acid 8-hydroxy-10-[(2R,3S)-3-(oct-2-en-1-yl)oxiran-2-yl]deca-5,9-dienoic acid 85589-24-8 [H][C@@]1(CC=CCCCCC)O[C@]1([H])C=CC(O)CC=CCCCC(O)=O InChI=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/s1 SGTUOBURCVMACZ-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. Hepoxilins Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic heteromonocyclic compounds Carbonyl compounds Carboxylic acids Dialkyl ethers Epoxides Epoxy fatty acids Hydrocarbon derivatives Hydroxy fatty acids Medium-chain fatty acids Medium-chain hydroxy acids and derivatives Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Secondary alcohols Unsaturated fatty acids Alcohol Aliphatic heteromonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Dialkyl ether Epoxy fatty acid Ether Fatty acid Hepoxilin Heterocyclic fatty acid Hydrocarbon derivative Hydroxy fatty acid Medium-chain fatty acid Medium-chain hydroxy acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxirane Secondary alcohol Unsaturated fatty acid Solid logp 5.57 ALOGPS logs -4.56 ALOGPS solubility 9.36e-03 g/l ALOGPS logp 4.57 ChemAxon pka_strongest_acidic 4.68 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac 8-hydroxy-10-[(2R,3S)-3-(oct-2-en-1-yl)oxiran-2-yl]deca-5,9-dienoic acid ChemAxon average_mass 336.4657 ChemAxon mono_mass 336.230059512 ChemAxon smiles [H][C@@]1(CC=CCCCCC)O[C@]1([H])C=CC(O)CC=CCCCC(O)=O ChemAxon formula C20H32O4 ChemAxon inchi InChI=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/s1 ChemAxon inchikey SGTUOBURCVMACZ-JLMCIHFGSA-N ChemAxon polar_surface_area 70.06 ChemAxon refractivity 99.72 ChemAxon polarizability 40.18 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB04688 36190 #<Reference:0x000055ce31df0cc8> #<Reference:0x000055ce31df0b10> #<Reference:0x000055ce31df0958> #<Reference:0x000055ce31df07a0> #<Reference:0x000055ce31df0598> #<Reference:0x000055ce31df03e0> #<Reference:0x000055ce31df0200> #<Reference:0x000055ce31df0048> #<Reference:0x000055ce31defda0> #<Reference:0x000055ce31defbe8> #<Reference:0x000055ce31defa30> #<Reference:0x000055ce31def850> #<Reference:0x000055ce31def648> #<Reference:0x000055ce31def418> #<Reference:0x000055ce31def0a8> #<Reference:0x000055ce31deeea0> #<Reference:0x000055ce31deece8> 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