1.0 2011-09-21 01:50:22 UTC 2015-07-21 06:59:38 UTC FDB029117 12-Oxo-20-carboxy-leukotriene B4 12-oxo-20-carboxy-leukotriene B4 is the metabolite of lipid omega-oxidation of leukotriene B4 (LTB4). LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human 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: 7649996, 17623009, 2853166, 6088485) 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] (6Z,8E,10E,14Z)-(5S,12R)-12-oxo-5-hydroxyeicosa-6,8,10,14-tetraen-1,20-dioate (6Z,8E,10E,14Z)-(5S,12R)-12-oxo-5-hydroxyeicosa-6,8,10,14-tetraen-1,20-dioic acid 12-oxo-20-carboxy-LTB(,4) 12-oxo-20-COOH-leukotriene B(,4) 12-oxo-20-COOH-LTB(,4) C20H28O6 364.4327 364.188588628 (5R,6Z,8E,10E,14Z)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenedioic acid (5R,6Z,8E,10E,14Z)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenedioic acid O[C@H](CCCC(O)=O)\C=C/C=C/C=C/C(=O)C\C=C/CCCCC(O)=O InChI=1S/C20H28O6/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/h2,4-8,12-13,18,22H,1,3,9-11,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,12-7+,13-8-/t18-/m0/s1 VLMCDTMNMDDMLC-NZXMSVEXSA-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 Acryloyl compounds Carboxylic acids Dicarboxylic acids and derivatives Enones Hydrocarbon derivatives Hydroxy fatty acids Keto fatty acids Ketones Organic oxides Secondary alcohols Unsaturated fatty acids Acryloyl-group Alcohol Aliphatic acyclic compound Alpha,beta-unsaturated ketone Carbonyl group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Enone Hydrocarbon derivative Hydroxy fatty acid Keto fatty acid Ketone Long-chain fatty acid Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Unsaturated fatty acid Solid logp 3.20 ALOGPS logs -4.18 ALOGPS solubility 2.42e-02 g/l ALOGPS logp 3.22 ChemAxon pka_strongest_acidic 4.29 ChemAxon pka_strongest_basic -1.5 ChemAxon iupac (5R,6Z,8E,10E,14Z)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenedioic acid ChemAxon average_mass 364.4327 ChemAxon mono_mass 364.188588628 ChemAxon smiles O[C@H](CCCC(O)=O)\C=C/C=C/C=C/C(=O)C\C=C/CCCCC(O)=O ChemAxon formula C20H28O6 ChemAxon inchi InChI=1S/C20H28O6/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/h2,4-8,12-13,18,22H,1,3,9-11,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,12-7+,13-8-/t18-/m0/s1 ChemAxon inchikey VLMCDTMNMDDMLC-NZXMSVEXSA-N ChemAxon polar_surface_area 111.9 ChemAxon refractivity 103.75 ChemAxon polarizability 39.68 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 20755 Specdb::CMs 39950 Specdb::CMs 173658 Specdb::MsMs 312247 Specdb::MsMs 312248 Specdb::MsMs 312249 Specdb::MsMs 357451 Specdb::MsMs 357452 Specdb::MsMs 357453 Specdb::MsMs 2663782 Specdb::MsMs 2663783 Specdb::MsMs 2663784 Specdb::MsMs 3015186 Specdb::MsMs 3015187 Specdb::MsMs 3015188 HMDB12550 #<Reference:0x000055ce31e0a790> #<Reference:0x000055ce31e0a5d8> #<Reference:0x000055ce31e0a420> #<Reference:0x000055ce31e0a218>