1.0 2011-09-21 01:50:57 UTC 2015-07-21 06:59:38 UTC FDB029158 20-COOH-10,11-dihydro-LTB4 20-COOH-10,11-dihydro-LTB4 is formed when leukotriene B4 (LTB4) is metabolized by beta-oxidation. LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. (PMID: 8632343, 9667737) 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,12R)-dihydroxy-(6Z,8E,14Z)-eicosatrien-1,20-dicarboxylic acid anion 10,11-dihydro-20-COOH-leukotriene B(,4) 20-carboxy-10,11-dihydro-LTB(,4) C20H32O6 368.4645 368.219888756 (5R,6Z,8E,12R,14Z)-5,12-dihydroxyicosa-6,8,14-trienedioic acid (5R,6Z,8E,12R,14Z)-5,12-dihydroxyicosa-6,8,14-trienedioic acid O[C@H](CC\C=C\C=C/[C@H](O)CCCC(O)=O)C\C=C/CCCCC(O)=O InChI=1S/C20H32O6/c21-17(11-6-2-1-3-9-15-19(23)24)12-7-4-5-8-13-18(22)14-10-16-20(25)26/h2,4-6,8,13,17-18,21-22H,1,3,7,9-12,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,13-8-/t17-,18-/m0/s1 BCZGHMCTSJAJRR-NSBXBVANSA-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 Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Hydroxy fatty acids Organic oxides Secondary alcohols Unsaturated fatty acids Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Hydrocarbon derivative Hydroxy fatty acid Long-chain fatty acid Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Unsaturated fatty acid Solid logp 3.17 ALOGPS logs -3.96 ALOGPS solubility 4.04e-02 g/l ALOGPS logp 3.01 ChemAxon pka_strongest_acidic 4.27 ChemAxon pka_strongest_basic -1.1 ChemAxon iupac (5R,6Z,8E,12R,14Z)-5,12-dihydroxyicosa-6,8,14-trienedioic acid ChemAxon average_mass 368.4645 ChemAxon mono_mass 368.219888756 ChemAxon smiles O[C@H](CC\C=C\C=C/[C@H](O)CCCC(O)=O)C\C=C/CCCCC(O)=O ChemAxon formula C20H32O6 ChemAxon inchi InChI=1S/C20H32O6/c21-17(11-6-2-1-3-9-15-19(23)24)12-7-4-5-8-13-18(22)14-10-16-20(25)26/h2,4-6,8,13,17-18,21-22H,1,3,7,9-12,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,13-8-/t17-,18-/m0/s1 ChemAxon inchikey BCZGHMCTSJAJRR-NSBXBVANSA-N ChemAxon polar_surface_area 115.06 ChemAxon refractivity 103.69 ChemAxon polarizability 41.85 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 13179 Specdb::CMs 39979 Specdb::CMs 149359 Specdb::MsMs 294961 Specdb::MsMs 294962 Specdb::MsMs 294963 Specdb::MsMs 335848 Specdb::MsMs 335849 Specdb::MsMs 335850 Specdb::MsMs 2714137 Specdb::MsMs 2714138 Specdb::MsMs 2714139 Specdb::MsMs 2965236 Specdb::MsMs 2965237 Specdb::MsMs 2965238 HMDB12633 #<Reference:0x000055ce32ce1570> #<Reference:0x000055ce32ce1368>