1.0 2011-09-21 00:29:37 UTC 2015-07-21 06:57:42 UTC FDB023415 9,10-DHOME 9,10-DHOME is a derivative of linoleic acid diol that have been reported to be toxic in human's tissue preparations. 9,10-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation. 9,10-DHOME is the epoxide hydrolase metabolite of the leukotoxin 9,10--EpOME. 9,10-EpOMEs act as a protoxin, with the corresponding epoxide hydrolase 9,10-DiHOME specifically exerting toxicity. Both the 9,10-EpOME and the 9,10-DiHOME are shown to have neutrophil chemotactic activity. 9,10-DiHOME suppress the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4,which inhibit multiple aspects of neutrophil activation. (PMID: 12021203, 12127265, 17435320) [HMDB] (12Z)-9,10-Dihydroxyoctadec-12-enoate (12Z)-9,10-Dihydroxyoctadec-12-enoic acid 9,10-DHOA 9,10-DiHOME 9,10-dihydroxy-12Z-octadecenoate 9,10-dihydroxy-12Z-octadecenoic acid 9,10-hydroxyoctadec-12(Z)-enoate 9,10-hydroxyoctadec-12(Z)-enoic acid leukotoxin Leukotoxin diol C18H34O4 314.4602 314.245709576 (12E)-9,10-dihydroxyoctadec-12-enoic acid (12E)-9,10-dihydroxyoctadec-12-enoic acid CCCCC\C=C\CC(O)C(O)CCCCCCCC(O)=O InChI=1S/C18H34O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h7,10,16-17,19-20H,2-6,8-9,11-15H2,1H3,(H,21,22)/b10-7+ XEBKSQSGNGRGDW-JXMROGBWSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds 1,2-diols Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy 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 Hydrocarbon derivative Hydroxy fatty acid Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Unsaturated fatty acid Other Octadecanoids Solid logp 5.18 ALOGPS logs -3.89 ALOGPS solubility 4.01e-02 g/l ALOGPS logp 4.32 ChemAxon pka_strongest_acidic 4.62 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac (12E)-9,10-dihydroxyoctadec-12-enoic acid ChemAxon average_mass 314.4602 ChemAxon mono_mass 314.245709576 ChemAxon smiles CCCCC\C=C\CC(O)C(O)CCCCCCCC(O)=O ChemAxon formula C18H34O4 ChemAxon inchi InChI=1S/C18H34O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h7,10,16-17,19-20H,2-6,8-9,11-15H2,1H3,(H,21,22)/b10-7+ ChemAxon inchikey XEBKSQSGNGRGDW-JXMROGBWSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 90.43 ChemAxon polarizability 39.26 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 10961 Specdb::CMs 42575 Specdb::MsMs 83580 Specdb::MsMs 83581 Specdb::MsMs 83582 Specdb::MsMs 145218 Specdb::MsMs 145219 Specdb::MsMs 145220 Specdb::MsMs 435485 Specdb::MsMs 435486 Specdb::MsMs 435487 Specdb::MsMs 435488 Specdb::MsMs 435489 Specdb::MsMs 435490 Specdb::MsMs 435491 Specdb::MsMs 435492 Specdb::MsMs 435493 HMDB04704 #<Reference:0x000055ce2d04e150> #<Reference:0x000055ce2d04df98> #<Reference:0x000055ce2d04dde0> 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