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Record Information
Version3.6
Creation Date2009-07-25 00:04:32 UTC
Update Date2013-05-29 19:48:32 UTC
HMDB IDHMDB12642
Secondary Accession NumbersNone
Metabolite Identification
Common Name20-Oxo-leukotriene E4
Description20-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.
Structure
Thumb
Synonyms
  1. 20-Oxo-LTE(,4)
  2. 6-(S-Cysteinyl)-20-oxo-(5S)-hydroxy-(7E,9E,11Z,14Z)-eicosatetraenoate
  3. 6-(S-Cysteinyl)-20-oxo-(5S)-hydroxy-(7E,9E,11Z,14Z)-eicosatetraenoic acid
Chemical FormulaC23H35NO6S
Average Molecular Weight453.592
Monoisotopic Molecular Weight453.218508547
IUPAC Name(5S,6R,7E,9E,11Z,14Z)-6-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-5-hydroxy-20-oxoicosa-7,9,11,14-tetraenoic acid
Traditional IUPAC Name(5S,6R,7E,9E,11Z,14Z)-6-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-5-hydroxy-20-oxoicosa-7,9,11,14-tetraenoic acid
CAS Registry NumberNot Available
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
InChI Identifier
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
InChI KeyDXFWBOQUFGDWDP-HEZGWBLQSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassEicosanoids
Sub ClassLeukotrienes
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Thia Fatty Acids
  • Unsaturated Fatty Acids
Substituents
  • Acyclic Alkene
  • Aldehyde
  • Alpha Amino Acid Or Derivative
  • Carboxylic Acid Salt
  • Dicarboxylic Acid Derivative
  • Hydroxyeicosapolyenoic Acid
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Alcohol
  • Thioether
Direct ParentLeukotrienes
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.0047 g/LALOGPS
logP0.66ALOGPS
logP0.54ChemAxon
logS-5ALOGPS
pKa (strongest acidic)2.39ChemAxon
pKa (strongest basic)9.13ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count7ChemAxon
hydrogen donor count4ChemAxon
polar surface area137.92ChemAxon
rotatable bond count19ChemAxon
refractivity128.36ChemAxon
polarizability50.8ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029164
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12642
Metagene LinkHMDB12642
METLIN IDNot Available
PubChem Compound53481512
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mizutani N: [Studies on the experimental allergic rhinitis induced by Japanese cedar pollen--role of cysteinyl leukotrienes in nasal allergic symptoms]. Yakugaku Zasshi. 2003 Jan;123(1):1-8. Pubmed: 12607939
  2. Evans JF: Cysteinyl leukotriene receptors. Prostaglandins Other Lipid Mediat. 2002 Aug;68-69:587-97. Pubmed: 12432945
  3. Hammarstrom S: Leukotrienes. Annu Rev Biochem. 1983;52:355-77. Pubmed: 6311078