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Record Information
Creation Date2006-05-22 14:17:41 UTC
Update Date2017-03-02 21:26:55 UTC
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.
20-Hydroxy-leukotriene e4HMDB
20-OH-Leukotriene e4HMDB
[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
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLeukotrienes
Alternative Parents
  • Leukotriene
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Cysteine or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Hydroxy fatty acid
  • Thia fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Unsaturated fatty acid
  • Amino acid or derivatives
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
StatusDetected and Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.0018 mg/mLALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Smooth Muscle
Fc Epsilon Receptor I Signaling in Mast CellsSMP00358Not Available
Normal Concentrations
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
BloodDetected and Quantified<0.0006 uMAdult (>18 years old)Both
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
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
  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. [PubMed: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. [PubMed: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
BiGG ID2705740
Wikipedia LinkLeukotriene E4
NuGOwiki LinkHMDB02200
Metagene LinkHMDB02200
PubChem Compound5280749
PDB IDNot Available
ChEBI ID15650
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:8033491 ]
  6. Samuelsson B: Arachidonic acid metabolism: role in inflammation. Z Rheumatol. 1991;50 Suppl 1:3-6. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:12607939 ]
  10. Evans JF: Cysteinyl leukotriene receptors. Prostaglandins Other Lipid Mediat. 2002 Aug;68-69:587-97. [PubMed:12432945 ]
  11. Hammarstrom S: Leukotrienes. Annu Rev Biochem. 1983;52:355-77. [PubMed:6311078 ]


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