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Record Information
StatusDetected and Quantified
Creation Date2006-05-22 14:17:41 UTC
Update Date2018-03-12 21:33:49 UTC
Secondary Accession Numbers
  • HMDB0062487
  • HMDB02200
  • HMDB62487
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 activates 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 and are 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.
(5S-(5R*,6S*(s*),7E,9E,11Z,14Z))-6-((2-amino-2-carboxyethyl)thio)-5-hydroxy-7,9,11,14-eicosatetraenoic acidChEBI
5S-Hydroxy,6R-(S-cysteinyl),7E,9E,11Z,14Z-eicosatetraenoic acidChEBI
(7E,9E,11Z,14Z)-(5S,6R)-6-(Cystein-S-yl)-5-hydroxyeicosa-7,9,11,14-tetraenoic acidGenerator
(7E,9E,11Z,14Z)-(5S,6R)-6-(Cystein-S-yl)-5-hydroxyicosa-7,9,11,14-tetraenoic acidGenerator
Leukotriene eMeSH
Leukotriene e-4MeSH
Leukotrienes eMeSH
Leukotriene e 4MeSH
Chemical FormulaC23H37NO5S
Average Molecular Weight439.61
Monoisotopic Molecular Weight439.239244469
IUPAC Name(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-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 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentLeukotrienes
Alternative Parents
  • Leukotriene
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • L-cysteine-s-conjugate
  • Cysteine or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • 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 Descriptors
Physiological effect

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Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.0018 g/LALOGPS
pKa (Strongest Acidic)2.39ChemAxon
pKa (Strongest Basic)9.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120.85 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity127.62 m³·mol⁻¹ChemAxon
Polarizability50.83 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Smooth Muscle
Fc Epsilon Receptor I Signaling in Mast CellsThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
BloodDetected and Quantified0.00002 +/- 0.00001 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0300 +/- 0.00182 uMInfant (0-1 year old)Not SpecifiedNormal details
BloodDetected and Quantified0.000072 +/- 0.000082 uMAdult (>18 years old)Both
BloodDetected and Quantified<0.0006 uMAdult (>18 years old)Both
BloodDetected and Quantified0.000031 +/- 0.000015 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00008 +/- 0.0000323 uMInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified0.00003 +/- 0.000008 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.0000322 +/- 0.0000086 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
Abnormal Concentrations
BloodDetected and Quantified<0.00001137 uMInfant (0-1 year old)FemaleLeukotriene C4-Synthesis Deficiency details
BloodDetected and Quantified0.00013 +/- 0.00005 uMAdult (>18 years old)BothEczema details
Cerebrospinal Fluid (CSF)Detected and Quantified<0.00001137 uMInfant (0-1 year old)FemaleLeukotriene C4-Synthesis Deficiency details
UrineDetected and Quantified0.00003 +/- 0.000009 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedSjögren-Larsson syndrome details
UrineDetected and Quantified<0.000000005 umol/mmol creatinineInfant (0-1 year old)FemaleLeukotriene C4-Synthesis Deficiency 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 ]
Leukotriene C4-Synthesis Deficiency
  1. Mayatepek E, Flock B: Leukotriene C4-synthesis deficiency: a new inborn error of metabolism linked to a fatal developmental syndrome. Lancet. 1998 Nov 7;352(9139):1514-7. [PubMed:9820300 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4444402
KEGG Compound IDC05952
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280879
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 ]
  12. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  13. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  14. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  15. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  16. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.


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: