1.0 2011-09-21 00:32:27 UTC 2015-07-21 06:57:47 UTC FDB023616 Leukotriene B5 Leukotriene B5 (LTB5) is a 5-lipoxygenase metabolite of arachidonic (AA) and eicosapentaenoic acid (EPA), involved in numerous inflammatory diseases and possesses a substantially less potent inflammatory effect than LTB4. Binding of LTB5 to human neutrophil LTB4 high affinity binding sites is lower than that of LTB4. Polymorphonuclear leukocytes isolated from volunteers who ingested eicosapentaenoic acid (EPA) form LTB5. Enrichment of human neutrophils with EPA, by dietary supplementation for at least 3 weeks, reduces their formation of LTB4 ex vivo. LTB5 is catabolized to 20-OH-LTB5, which in turn is metabolized to 20-COOH-LTB5. Presumably the same enzyme systems are involved in the catabolism of LTB5 that are responsible for catabolism of LTB4. Fish oil supplementation has a protective effect on exercise-induced bronchoconstriction (EIB) in elite athletes, which may be attributed to its antiinflammatory properties due to a significant reduction in LTB4 and a significant increase in LTB5 generation from activated polymorphonuclear leukocytes (PMNLs). (PMID: 1964169, 15866528, 2538061, 16424411) Leukotrienes 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] (5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-6,8,10,14,17-Eicosapentaenoate (5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-6,8,10,14,17-Eicosapentaenoic acid 5,12-DiHEPE 5,12-Dihydroxy-6-trans-leukotriene b(5) 5,12-dihydroxy-6E-LTB5 5,12-dihydroxy-6trans-leukotriene B(5) LTB5 C20H30O4 334.4498 334.214409448 (5S,12R)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid (5S,12R)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid 80445-66-5 [H]C(C=CC=C[C@]([H])(O)CC=CCC=CCC)=C[C@@]([H])(O)CCCC(O)=O InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h3-4,6-11,14-15,18-19,21-22H,2,5,12-13,16-17H2,1H3,(H,23,24)/t18-,19-/m1/s1 BISQPGCQOHLHQK-RTBURBONSA-N belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds. Hydroxyeicosapentaenoic 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 Secondary alcohols Unsaturated fatty acids Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Hydroxy fatty acid Hydroxyeicosapentaenoic acid Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Unsaturated fatty acid Solid logp 4.68 ALOGPS logs -4.32 ALOGPS solubility 1.62e-02 g/l ALOGPS logp 3.76 ChemAxon pka_strongest_acidic 4.65 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (5S,12R)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid ChemAxon average_mass 334.4498 ChemAxon mono_mass 334.214409448 ChemAxon smiles [H]C(C=CC=C[C@]([H])(O)CC=CCC=CCC)=C[C@@]([H])(O)CCCC(O)=O ChemAxon formula C20H30O4 ChemAxon inchi InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h3-4,6-11,14-15,18-19,21-22H,2,5,12-13,16-17H2,1H3,(H,23,24)/t18-,19-/m1/s1 ChemAxon inchikey BISQPGCQOHLHQK-RTBURBONSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 104.1 ChemAxon polarizability 40.8 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB05073 #<Reference:0x000055ce31f83928> #<Reference:0x000055ce31f83748> #<Reference:0x000055ce31f83540> #<Reference:0x000055ce31f83388> #<Reference:0x000055ce31f831a8> 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