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Record Information
Version3.6
Creation Date2006-05-22 14:17:41 UTC
Update Date2016-05-13 21:38:57 UTC
HMDB IDHMDB02200
Secondary Accession NumbersNone
Metabolite Identification
Common NameLeukotriene E4
DescriptionLeukotriene 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
ValueSource
20-Hydroxy-leukotriene e4HMDB
20-OH-Leukotriene e4HMDB
LTE4HMDB
[5S-[5R*,6S*(s*),7E,9E,11Z,14Z]]- 6-[(2-amino-2-carboxyethyl)thio]-5-hydroxy-7,9,11,14-eicosatetraenoateHMDB
[5S-[5R*,6S*(s*),7E,9E,11Z,14Z]]- 6-[(2-amino-2-carboxyethyl)thio]-5-hydroxy-7,9,11,14-eicosatetraenoic acidHMDB
Chemical FormulaC23H37NO5S
Average Molecular Weight439.609
Monoisotopic Molecular Weight439.239243989
IUPAC Name(5S,6R,7E,9E,11Z,14Z)-6-[(2-amino-2-carboxyethyl)sulfanyl]-5-hydroxyicosa-7,9,11,14-tetraenoic acid
Traditional Nameleukotriene E4
CAS Registry Number75715-89-8
SMILES
CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SCC(N)C(O)=O)[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C23H37NO5S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-21(30-18-19(24)23(28)29)20(25)15-14-17-22(26)27/h6-7,9-13,16,19-21,25H,2-5,8,14-15,17-18,24H2,1H3,(H,26,27)(H,28,29)/b7-6-,10-9-,12-11+,16-13+/t19?,20-,21+/m0/s1
InChI KeyInChIKey=OTZRAYGBFWZKMX-MPWKMEBCSA-N
Chemical Taxonomy
DescriptionThis compound 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. 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentLeukotrienes
Alternative Parents
Substituents
  • Leukotriene
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Thia fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and 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
  • Cytoplasm
  • 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 Solubility0.0018 mg/mLALOGPS
logP1.57ALOGPS
logP2.02ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)2.39ChemAxon
pKa (Strongest Basic)9.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120.85 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity127.62 m3·mol-1ChemAxon
Polarizability50.58 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Smooth Muscle
Pathways
NameSMPDB LinkKEGG Link
Fc Epsilon Receptor I Signaling in Mast CellsSMP00358Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2E-5 +/- 1E-5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified7.2-e5 +/- 8.2-e5 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified<0.0006 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified3.1-e5 +/- 1.5-e5 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified3-e5 +/- 8-e6 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00013 +/- 0.00005 uMAdult (>18 years old)BothEczema details
UrineDetected and Quantified0.00003 +/- 0.000009 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedSjögren-Larsson syndrome details
Associated Disorders and Diseases
Disease References
Eczema
  1. Hua Z, Fei H, Mingming X: Evaluation and interference of serum and skin lesion levels of leukotrienes in patients with eczema. Prostaglandins Leukot Essent Fatty Acids. 2006 Jul;75(1):51-5. Epub 2006 Jun 6. [16757158 ]
Sjögren-Larsson syndrome
  1. Willemsen MA, Rotteveel JJ, de Jong JG, Wanders RJ, IJlst L, Hoffmann GF, Mayatepek E: Defective metabolism of leukotriene B4 in the Sjogren-Larsson syndrome. J Neurol Sci. 2001 Jan 15;183(1):61-7. [11166796 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022901
KNApSAcK IDNot Available
Chemspider ID4444323
KEGG Compound IDC05952
BioCyc ID7E9E11Z14Z-5S6R-6-CYSTEIN-S-YL
BiGG ID2705740
Wikipedia LinkLeukotriene E4
NuGOwiki LinkHMDB02200
Metagene LinkHMDB02200
METLIN ID3536
PubChem Compound5280749
PDB IDNot Available
ChEBI ID15650
References
Synthesis ReferenceRosenberger, Michael; Newkom, Christian; Aig, Edward R. Total synthesis of leukotriene E4, a member of the SRS-A family. Journal of the American Chemical Society (1983), 105(11), 3656-61.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lambiase A, Bonini S, Rasi G, Coassin M, Bruscolini A, Bonini S: Montelukast, a leukotriene receptor antagonist, in vernal keratoconjunctivitis associated with asthma. Arch Ophthalmol. 2003 May;121(5):615-20. [12742837 ]
  2. Denzlinger C, Tetzloff W, Gerhartz HH, Pokorny R, Sagebiel S, Haberl C, Wilmanns W: Differential activation of the endogenous leukotriene biosynthesis by two different preparations of granulocyte-macrophage colony-stimulating factor in healthy volunteers. Blood. 1993 Apr 15;81(8):2007-13. [8386025 ]
  3. Uemura M, Buchholz U, Kojima H, Keppler A, Hafkemeyer P, Fukui H, Tsujii T, Keppler D: Cysteinyl leukotrienes in the urine of patients with liver diseases. Hepatology. 1994 Oct;20(4 Pt 1):804-12. [7927219 ]
  4. Keppler D: [The Heinrich-Wieland Prize presentation. Metabolism and analysis of leukotrienes in vivo] Klin Wochenschr. 1988 Oct 17;66(20):997-1005. [3070147 ]
  5. Depre M, Friedman B, Van Hecken A, de Lepeleire I, Tanaka W, Dallob A, Shingo S, Porras A, Lin C, de Schepper PJ: Pharmacokinetics and pharmacodynamics of multiple oral doses of MK-0591, a 5-lipoxygenase-activating protein inhibitor. Clin Pharmacol Ther. 1994 Jul;56(1):22-30. [8033491 ]
  6. Samuelsson B: Arachidonic acid metabolism: role in inflammation. Z Rheumatol. 1991;50 Suppl 1:3-6. [1907059 ]
  7. Mayatepek E, Badiou S, Bellet H, Lehmann WD: A patient with neurological symptoms and abnormal leukotriene metabolism: a new defect in leukotriene biosynthesis. Ann Neurol. 2005 Dec;58(6):968-70. [16315285 ]
  8. Jacques CA, Spur BW, Johnson M, Lee TH: The mechanism of LTE4-induced histamine hyperresponsiveness in guinea-pig tracheal and human bronchial smooth muscle, in vitro. Br J Pharmacol. 1991 Dec;104(4):859-66. [1667288 ]
  9. 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. [12607939 ]
  10. Evans JF: Cysteinyl leukotriene receptors. Prostaglandins Other Lipid Mediat. 2002 Aug;68-69:587-97. [12432945 ]
  11. Hammarstrom S: Leukotrienes. Annu Rev Biochem. 1983;52:355-77. [6311078 ]

Enzymes

General function:
Involved in metalloexopeptidase activity
Specific function:
Probable metalloprotease which hydrolyzes leukotriene D4 (LTD4) into leukotriene E4 (LTE4)
Gene Name:
DPEP2
Uniprot ID:
Q9H4A9
Molecular weight:
53305.5