1.0 2011-09-21 00:19:17 UTC 2015-07-21 06:57:21 UTC FDB022768 Troxilin B3 Troxilin B3 is the enzymatically formed derivative of Hepoxilin B3. Normal human epidermis incubated with exogenous AA produces 12-oxo-eicosatetraenoic acid (12-oxo-ETE), hepoxilin A3 (HxA3), and hepoxilin B3 (HxB3) through the 12- Lipoxygenase (LO) pathway. 12-LO is the major arachidonic acid (AA) oxygenation pathway in epidermal cells with total product formation generally exceeding cyclooxygenase activity. Platelet-type 12-LO has been found to be the predominant isoenzyme expressed in human and murine skin epidermis. Increased levels of nonesterified hepoxilins and trioxilins occur in the psoriatic scales. Normal human epidermis synthesized only one of the two possible 10-hydroxy epimers of HxB3 whose formation is probably catalyzed by 12-LO. Hepoxilins exert action on plasma permeability on skin, and induce a specific-receptor-dependent Ca2+ mobilization from endogenous sources and the release of AA and diacylglycerols. (PMID: 11851887) [HMDB] (5Z,8Z,11S,12R,14Z)-10,11,12-trihydroxyicosa-5,8,14-trienoate (5Z,8Z,11S,12R,14Z)-10,11,12-trihydroxyicosa-5,8,14-trienoic acid (5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoate (5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoic acid (5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoicacid (5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoate (5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoic acid 10,11S,12R-trihydroxy-5Z,8Z,14Z-eicosatrienoate 10,11S,12R-trihydroxy-5Z,8Z,14Z-eicosatrienoic acid 10,11S,12R-TriOH all-cis-5,8,14-20:3 10,11S,12R-TriOH all-cis-5,8,14-C20:3 Trioxilin b3 C20H34O5 354.481 354.240624198 (11S,12R)-10,11,12-trihydroxyicosa-5,8,14-trienoic acid (11S,12R)-10,11,12-trihydroxyicosa-5,8,14-trienoic acid [H][C@@](O)(CC=CCCCCC)[C@]([H])(O)C(O)C=CCC=CCCCC(O)=O InChI=1S/C20H34O5/c1-2-3-4-5-8-11-14-17(21)20(25)18(22)15-12-9-6-7-10-13-16-19(23)24/h6-8,11-12,15,17-18,20-22,25H,2-5,9-10,13-14,16H2,1H3,(H,23,24)/t17-,18?,20+/m1/s1 GOHNIXDAQODZKP-IKCNDWCXSA-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 acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Polyols Secondary alcohols Unsaturated fatty acids Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Hydroxy fatty acid Hydroxyeicosatrienoic acid Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Polyol Secondary alcohol Unsaturated fatty acid Solid logp 4.76 ALOGPS logs -3.83 ALOGPS solubility 5.21e-02 g/l ALOGPS logp 3.57 ChemAxon pka_strongest_acidic 4.82 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (11S,12R)-10,11,12-trihydroxyicosa-5,8,14-trienoic acid ChemAxon average_mass 354.481 ChemAxon mono_mass 354.240624198 ChemAxon smiles [H][C@@](O)(CC=CCCCCC)[C@]([H])(O)C(O)C=CCC=CCCCC(O)=O ChemAxon formula C20H34O5 ChemAxon inchi InChI=1S/C20H34O5/c1-2-3-4-5-8-11-14-17(21)20(25)18(22)15-12-9-6-7-10-13-16-19(23)24/h6-8,11-12,15,17-18,20-22,25H,2-5,9-10,13-14,16H2,1H3,(H,23,24)/t17-,18?,20+/m1/s1 ChemAxon inchikey GOHNIXDAQODZKP-IKCNDWCXSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 103.08 ChemAxon polarizability 41.28 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB01965 #<Reference:0x000055ce302a4438> 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