1.0 2011-09-21 01:50:48 UTC 2015-07-21 06:59:38 UTC FDB029148 18E-20-Oxo-20-CoA-LTE4 18E-20-oxo-20-CoA-LTE4 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] CoA-20-COOH-19E-LTE(,4) Coenzyme A-20-COOH-19E-LTE(,4) C44H63N8O22P3S2 1213.063 1212.271116656 3-({2-[(2-{[(2E,6Z,9Z,11E,13E,15R,16S)-15-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-19-carboxy-16-hydroxynonadeca-2,6,9,11,13-pentaenoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropyl ({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate 3-({2-[(2-{[(2E,6Z,9Z,11E,13E,15R,16S)-15-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-19-carboxy-16-hydroxynonadeca-2,6,9,11,13-pentaenoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropyl {[(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxyphosphonate O[C@@H](CCCC(O)=O)[C@H](SC[C@@H](N)C(O)=O)\C=C\C=C\C=C/C\C=C/CC\C=C\C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@@H](O)[C@H]1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N InChI=1S/C44H67N8O22P3S2/c1-44(2,25-71-77(68,69)74-76(66,67)70-23-30-37(73-75(63,64)65)36(58)42(72-30)52-27-51-35-39(46)49-26-50-40(35)52)38(59)41(60)48-20-19-32(54)47-21-22-78-34(57)18-13-11-9-7-5-3-4-6-8-10-12-16-31(79-24-28(45)43(61)62)29(53)15-14-17-33(55)56/h4-8,10,12-13,16,18,26-31,36-38,42,53,58-59H,3,9,11,14-15,17,19-25,45H2,1-2H3,(H,47,54)(H,48,60)(H,55,56)(H,61,62)(H,66,67)(H,68,69)(H2,46,49,50)(H2,63,64,65)/p-4/b6-4-,7-5-,10-8+,16-12+,18-13+/t28-,29+,30-,31-,36+,37+,38?,42-/m1/s1 KBFUWUDFICVJDA-KIHQUBHDSA-J belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aromatic heteropolycyclic compounds 1-benzopyrans Alkyl aryl ethers Aromatic monoterpenoids Benzenoids Carbonyl compounds Carboxylic acids Heterocyclic fatty acids Hydrocarbon derivatives Hydroxy fatty acids Medium-chain fatty acids Methyl-branched fatty acids Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Unsaturated fatty acids 1-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Aromatic monoterpenoid Benzenoid Benzopyran Bicyclic monoterpenoid Branched fatty acid Carbonyl group Carboxylic acid Carboxylic acid derivative Chromane Ether Fatty acid Fatty acyl Heterocyclic fatty acid Hydrocarbon derivative Hydroxy fatty acid Medium-chain fatty acid Methyl-branched fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Unsaturated fatty acid Solid logp 0.68 ALOGPS logs -3.53 ALOGPS solubility 3.83e-01 g/l ALOGPS logp -4.6 ChemAxon pka_strongest_acidic 0.81 ChemAxon pka_strongest_basic 9.13 ChemAxon iupac 3-({2-[(2-{[(2E,6Z,9Z,11E,13E,15R,16S)-15-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-19-carboxy-16-hydroxynonadeca-2,6,9,11,13-pentaenoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropyl ({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate ChemAxon average_mass 1213.063 ChemAxon mono_mass 1212.271116656 ChemAxon smiles O[C@@H](CCCC(O)=O)[C@H](SC[C@@H](N)C(O)=O)\C=C\C=C\C=C/C\C=C/CC\C=C\C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@@H](O)[C@H]1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N ChemAxon formula C44H63N8O22P3S2 ChemAxon inchi InChI=1S/C44H67N8O22P3S2/c1-44(2,25-71-77(68,69)74-76(66,67)70-23-30-37(73-75(63,64)65)36(58)42(72-30)52-27-51-35-39(46)49-26-50-40(35)52)38(59)41(60)48-20-19-32(54)47-21-22-78-34(57)18-13-11-9-7-5-3-4-6-8-10-12-16-31(79-24-28(45)43(61)62)29(53)15-14-17-33(55)56/h4-8,10,12-13,16,18,26-31,36-38,42,53,58-59H,3,9,11,14-15,17,19-25,45H2,1-2H3,(H,47,54)(H,48,60)(H,55,56)(H,61,62)(H,66,67)(H,68,69)(H2,46,49,50)(H2,63,64,65)/p-4/b6-4-,7-5-,10-8+,16-12+,18-13+/t28-,29+,30-,31-,36+,37+,38?,42-/m1/s1 ChemAxon inchikey KBFUWUDFICVJDA-KIHQUBHDSA-J ChemAxon polar_surface_area 495.8 ChemAxon refractivity 285.46 ChemAxon polarizability 116.7 ChemAxon rotatable_bond_count 38 ChemAxon acceptor_count 23 ChemAxon donor_count 9 ChemAxon physiological_charge -5 ChemAxon formal_charge -4 ChemAxon HMDB12610 #<Reference:0x000055ce32f6d348> #<Reference:0x000055ce32f6d118> #<Reference:0x000055ce32f6cf38>