1.0 2011-09-21 00:29:28 UTC 2015-07-21 06:57:41 UTC FDB023407 Hepoxilin B3 Hepoxilin B3 is a normal human epidermis eicosanoid. Hepoxilin B3 is dramatically elevated in psoriatic lesions. The primary biological action of the hepoxilins appears to relate to their ability to release calcium from intracellular stores through a receptor-mediated action. The receptor is intracellular, and appears to be G-protein coupled. The conversion of hepoxilin into its omega-hydroxy catabolite has recently been demonstrated through the action of an omega-hydroxylase. This enzyme is different from that which oxidizes leukotriene B4, as the former activity is lost when the cell is disrupted, while leukotriene B4-catabolic activity is recovered in both the intact and disrupted cell. Additionally, hepoxilin catabolism is inhibited by CCCP, a mitochondrial uncoupler, while leukotriene catabolism is unaffected. As hepoxilins cause the translocation of calcium from intracellular stores in the endoplasmic reticulum to the mitochondria, it is speculated that hepoxilin omega-oxidation takes place in the mitochondria, and the omega-oxidation product facilitates accumulation of the elevated cytosolic calcium by the mitochondria. (PMID 10692117, 11851887, 10086189) [HMDB] (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoate (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoic acid (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoicacid (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoate (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoic acid (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoicacid (5Z,8Z)-10-hydroxy-10-{(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoate (5Z,8Z)-10-hydroxy-10-{(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid 10-hydroxy-11R,12S-epoxy-5Z,8Z,14Z-eicosatrienoate 10-hydroxy-11R,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid HxB3 C20H32O4 336.4657 336.230059512 10-hydroxy-10-[(2R,3S)-3-(oct-2-en-1-yl)oxiran-2-yl]deca-5,8-dienoic acid 10-hydroxy-10-[(2R,3S)-3-(oct-2-en-1-yl)oxiran-2-yl]deca-5,8-dienoic acid 71799-95-6 [H][C@@]1(CC=CCCCCC)O[C@]1([H])C(O)C=CCC=CCCCC(O)=O InChI=1S/C20H32O4/c1-2-3-4-5-9-12-15-18-20(24-18)17(21)14-11-8-6-7-10-13-16-19(22)23/h6-7,9,11-12,14,17-18,20-21H,2-5,8,10,13,15-16H2,1H3,(H,22,23)/t17?,18-,20+/m0/s1 DWNBPRRXEVJMPO-AQCCAAQSSA-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 5.11 ALOGPS logs -4.56 ALOGPS solubility 9.24e-03 g/l ALOGPS logp 4.73 ChemAxon pka_strongest_acidic 4.82 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac 10-hydroxy-10-[(2R,3S)-3-(oct-2-en-1-yl)oxiran-2-yl]deca-5,8-dienoic acid ChemAxon average_mass 336.4657 ChemAxon mono_mass 336.230059512 ChemAxon smiles [H][C@@]1(CC=CCCCCC)O[C@]1([H])C(O)C=CCC=CCCCC(O)=O ChemAxon formula C20H32O4 ChemAxon inchi InChI=1S/C20H32O4/c1-2-3-4-5-9-12-15-18-20(24-18)17(21)14-11-8-6-7-10-13-16-19(22)23/h6-7,9,11-12,14,17-18,20-21H,2-5,8,10,13,15-16H2,1H3,(H,22,23)/t17?,18-,20+/m0/s1 ChemAxon inchikey DWNBPRRXEVJMPO-AQCCAAQSSA-N ChemAxon polar_surface_area 70.06 ChemAxon refractivity 99.57 ChemAxon polarizability 39.55 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB04690 34784 #<Reference:0x000055ce326bbb28> #<Reference:0x000055ce326bb970> #<Reference:0x000055ce326bb7b8> 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