1.0 2011-09-21 00:32:39 UTC 2015-07-21 06:57:47 UTC FDB023630 Thromboxane B3 Thromboxane B3 (TXB3) is a prostanoid that is formed by the hydrolysis of TXA3, a product of dietary eicosapentaenoic acid transformed in humans. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207, 2996649) Thromboxanes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. [HMDB] (5Z,9a,13E,15S,17Z)-9,11,15-trihydroxy-Thromboxa-5,13,17-trien-1-oate (5Z,9a,13E,15S,17Z)-9,11,15-trihydroxy-Thromboxa-5,13,17-trien-1-oic acid [2R(1E,3S,5Z),3S(Z),4S]-[partial]-7-[tetrahydro-4,6-dihydroxy-2-(3-hydroxy-1,5-octadienyl)-2H-pyran-3-yl]-5-Heptenoate [2R(1E,3S,5Z),3S(Z),4S]-[partial]-7-[tetrahydro-4,6-dihydroxy-2-(3-hydroxy-1,5-octadienyl)-2H-pyran-3-yl]-5-Heptenoic acid 9S,11,15S-trihydroxy-thromboxa-5Z,13E,17Z-trien-1-oate 9S,11,15S-trihydroxy-thromboxa-5Z,13E,17Z-trien-1-oic acid TXB3 C20H32O6 368.4645 368.219888756 (5E)-7-{4,6-dihydroxy-2-[(1E,5E)-3-hydroxyocta-1,5-dien-1-yl]oxan-3-yl}hept-5-enoic acid thromboxane B3 71953-80-5 CC\C=C\CC(O)\C=C\C1OC(O)CC(O)C1C\C=C\CCCC(O)=O InChI=1S/C20H32O6/c1-2-3-6-9-15(21)12-13-18-16(17(22)14-20(25)26-18)10-7-4-5-8-11-19(23)24/h3-4,6-7,12-13,15-18,20-22,25H,2,5,8-11,14H2,1H3,(H,23,24)/b6-3+,7-4+,13-12+ OYPPJMLKAYYWHH-OHVJZDGFSA-N belongs to the class of organic compounds known as thromboxanes. These are eicosanoids structurally characterized by the presence of a 6-member ether containing ring. Thromboxanes Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic heteromonocyclic compounds Carbonyl compounds Carboxylic acids Hemiacetals Heterocyclic fatty acids Hydrocarbon derivatives Hydroxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Oxanes Secondary alcohols Unsaturated fatty acids Alcohol Aliphatic heteromonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hemiacetal Heterocyclic fatty acid Hydrocarbon derivative Hydroxy fatty acid Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Secondary alcohol Thromboxane Unsaturated fatty acid Solid logp 3.11 ALOGPS logs -3.13 ALOGPS solubility 2.72e-01 g/l ALOGPS logp 2.56 ChemAxon pka_strongest_acidic 4.27 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac (5E)-7-{4,6-dihydroxy-2-[(1E,5E)-3-hydroxyocta-1,5-dien-1-yl]oxan-3-yl}hept-5-enoic acid ChemAxon average_mass 368.4645 ChemAxon mono_mass 368.219888756 ChemAxon smiles CC\C=C\CC(O)\C=C\C1OC(O)CC(O)C1C\C=C\CCCC(O)=O ChemAxon formula C20H32O6 ChemAxon inchi InChI=1S/C20H32O6/c1-2-3-6-9-15(21)12-13-18-16(17(22)14-20(25)26-18)10-7-4-5-8-11-19(23)24/h3-4,6-7,12-13,15-18,20-22,25H,2,5,8-11,14H2,1H3,(H,23,24)/b6-3+,7-4+,13-12+ ChemAxon inchikey OYPPJMLKAYYWHH-OHVJZDGFSA-N ChemAxon polar_surface_area 107.22 ChemAxon refractivity 102.3 ChemAxon polarizability 41.94 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 20425 Specdb::CMs 38864 Specdb::CMs 133964 Specdb::CMs 141698 Specdb::MsMs 311476 Specdb::MsMs 311477 Specdb::MsMs 311478 Specdb::MsMs 356488 Specdb::MsMs 356489 Specdb::MsMs 356490 Specdb::MsMs 2818923 Specdb::MsMs 2818924 Specdb::MsMs 2818925 Specdb::MsMs 2890453 Specdb::MsMs 2890454 Specdb::MsMs 2890455 HMDB05099 #<Reference:0x000055ce323e1998> #<Reference:0x000055ce323e17e0> #<Reference:0x000055ce323e15d8> 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