1.0 2011-09-21 01:51:04 UTC 2015-07-21 06:59:38 UTC FDB029164 20-Oxo-leukotriene E4 20-oxo-leukotriene E4 is a metabolite through lipid oxidation of Leukotriene E4 (LTE4).Leukotriene E4 (LTE4) is a cysteinyl leukotriene. Cysteinyl leukotrienes (CysLTs) are a family of potent inflammatory mediators that appear to contribute to the pathophysiologic features of allergic rhinitis. Nasal blockage induced by CysLTs is mainly due to dilatation of nasal blood vessels, which can be induced by the nitric oxide produced through CysLT1 receptor activation. LTE4, activate contractile and inflammatory processes via specific interaction with putative seven transmembrane-spanning receptors that couple to G proteins and subsequent intracellular signaling pathways. LTE4 is metabolized from leukotriene C4 in a reaction catalyzed by gamma-glutamyl transpeptidase and a particulate dipeptidase from kidney. (PMID: 12607939, 12432945, 6311078) 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] 20-oxo-LTE(,4) 6-(S-cysteinyl)-20-oxo-(5S)-hydroxy-(7E,9E,11Z,14Z)-eicosatetraenoate 6-(S-cysteinyl)-20-oxo-(5S)-hydroxy-(7E,9E,11Z,14Z)-eicosatetraenoic acid C23H35NO6S 453.592 453.218508547 (5S,6R,7E,9E,11Z,14Z)-6-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-5-hydroxy-20-oxoicosa-7,9,11,14-tetraenoic acid (5S,6R,7E,9E,11Z,14Z)-6-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-5-hydroxy-20-oxoicosa-7,9,11,14-tetraenoic acid N[C@H](CS[C@H](\C=C\C=C\C=C/C\C=C/CCCCC=O)[C@@H](O)CCCC(O)=O)C(O)=O InChI=1S/C23H35NO6S/c24-19(23(29)30)18-31-21(20(26)14-13-16-22(27)28)15-11-9-7-5-3-1-2-4-6-8-10-12-17-25/h2-5,7,9,11,15,17,19-21,26H,1,6,8,10,12-14,16,18,24H2,(H,27,28)(H,29,30)/b4-2-,5-3-,9-7+,15-11+/t19-,20+,21-/m1/s1 DXFWBOQUFGDWDP-HEZGWBLQSA-N belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated. Leukotrienes Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic acyclic compounds Alpha-hydrogen aldehydes Amino acids Carboxylic acids Cysteine and derivatives D-alpha-amino acids Dialkylthioethers Dicarboxylic acids and derivatives Hydrocarbon derivatives Hydroxy fatty acids Hydroxyeicosatetraenoic acids Long-chain fatty acids Monoalkylamines Organic oxides Organopnictogen compounds S-alkyl-L-cysteines Secondary alcohols Sulfenyl compounds Thia fatty acids Unsaturated fatty acids Alcohol Aldehyde Aliphatic acyclic compound Alpha-amino acid Alpha-amino acid or derivatives Alpha-hydrogen aldehyde Amine Amino acid Amino acid or derivatives Carbonyl group Carboxylic acid Carboxylic acid derivative Cysteine or derivatives D-alpha-amino acid Dialkylthioether Dicarboxylic acid or derivatives Fatty acid Hydrocarbon derivative Hydroxy fatty acid Hydroxyeicosatetraenoic acid Leukotriene Long-chain fatty acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Primary aliphatic amine Primary amine S-alkyl-l-cysteine Secondary alcohol Sulfenyl compound Thia fatty acid Thioether Unsaturated fatty acid Solid logp 0.66 ALOGPS logs -4.98 ALOGPS solubility 4.75e-03 g/l ALOGPS logp 0.54 ChemAxon pka_strongest_acidic 2.39 ChemAxon pka_strongest_basic 9.13 ChemAxon iupac (5S,6R,7E,9E,11Z,14Z)-6-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-5-hydroxy-20-oxoicosa-7,9,11,14-tetraenoic acid ChemAxon average_mass 453.592 ChemAxon mono_mass 453.218508547 ChemAxon smiles N[C@H](CS[C@H](\C=C\C=C\C=C/C\C=C/CCCCC=O)[C@@H](O)CCCC(O)=O)C(O)=O ChemAxon formula C23H35NO6S ChemAxon inchi InChI=1S/C23H35NO6S/c24-19(23(29)30)18-31-21(20(26)14-13-16-22(27)28)15-11-9-7-5-3-1-2-4-6-8-10-12-17-25/h2-5,7,9,11,15,17,19-21,26H,1,6,8,10,12-14,16,18,24H2,(H,27,28)(H,29,30)/b4-2-,5-3-,9-7+,15-11+/t19-,20+,21-/m1/s1 ChemAxon inchikey DXFWBOQUFGDWDP-HEZGWBLQSA-N ChemAxon polar_surface_area 137.92 ChemAxon refractivity 128.36 ChemAxon polarizability 50.8 ChemAxon rotatable_bond_count 19 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 22452 Specdb::CMs 39985 Specdb::CMs 171703 Specdb::MsMs 315907 Specdb::MsMs 315908 Specdb::MsMs 315909 Specdb::MsMs 362014 Specdb::MsMs 362015 Specdb::MsMs 362016 Specdb::MsMs 2813654 Specdb::MsMs 2813655 Specdb::MsMs 2813656 Specdb::MsMs 2891787 Specdb::MsMs 2891788 Specdb::MsMs 2891789 HMDB12642 #<Reference:0x000055ce32131a90> #<Reference:0x000055ce32131888> #<Reference:0x000055ce32131630>