Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:41 UTC
Update Date2021-09-14 14:59:13 UTC
HMDB IDHMDB0002200
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.
Structure
Data?1582752235
Synonyms
ValueSource
(5S-(5R*,6S*(s*),7E,9E,11Z,14Z))-6-((2-amino-2-carboxyethyl)thio)-5-hydroxy-7,9,11,14-eicosatetraenoic acidChEBI
(7E,9E,11Z,14Z)-(5S,6R)-6-(Cystein-S-yl)-5-hydroxyeicosa-7,9,11,14-tetraenoateChEBI
(7E,9E,11Z,14Z)-(5S,6R)-6-(Cystein-S-yl)-5-hydroxyicosa-7,9,11,14-tetraenoateChEBI
5S-Hydroxy,6R-(S-cysteinyl),7E,9E,11Z,14Z-eicosatetraenoic acidChEBI
LTE4ChEBI
(5S-(5R*,6S*(s*),7E,9E,11Z,14Z))-6-((2-amino-2-carboxyethyl)thio)-5-hydroxy-7,9,11,14-eicosatetraenoateGenerator
(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
5S-Hydroxy,6R-(S-cysteinyl),7E,9E,11Z,14Z-eicosatetraenoateGenerator
Leukotriene eHMDB
Leukotriene e-4HMDB
Leukotrienes eHMDB
Leukotriene e 4HMDB
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
SMILES
CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H](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 KeyOTZRAYGBFWZKMX-FRFVZSDQSA-N
Chemical Taxonomy
Description 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
Substituents
  • 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
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available213.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00001905
[M+H]+Not Available213.2http://allccs.zhulab.cn/database/detail?ID=AllCCS00001905
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0018 g/LALOGPS
logP10(1.57) g/LALOGPS
logP10(2.02) g/LChemAxon
logS10(-5.4) 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+215.8731661259
DarkChem[M-H]-211.6831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Leukotriene E4CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H](N)C(O)=O)[C@@H](O)CCCC(O)=O5882.9Standard polar33892256
Leukotriene E4CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H](N)C(O)=O)[C@@H](O)CCCC(O)=O3261.8Standard non polar33892256
Leukotriene E4CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H](N)C(O)=O)[C@@H](O)CCCC(O)=O3694.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Leukotriene E4,1TMS,isomer #1CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(=O)O[Si](C)(C)C)[C@@H](O)CCCC(=O)O3681.3Semi standard non polar33892256
Leukotriene E4,1TMS,isomer #2CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(=O)O)[C@H](CCCC(=O)O)O[Si](C)(C)C3756.7Semi standard non polar33892256
Leukotriene E4,1TMS,isomer #3CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(=O)O)[C@@H](O)CCCC(=O)O[Si](C)(C)C3723.7Semi standard non polar33892256
Leukotriene E4,1TMS,isomer #4CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C)C(=O)O)[C@@H](O)CCCC(=O)O3814.1Semi standard non polar33892256
Leukotriene E4,2TMS,isomer #1CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(=O)O[Si](C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C3696.6Semi standard non polar33892256
Leukotriene E4,2TMS,isomer #2CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(=O)O[Si](C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C3666.8Semi standard non polar33892256
Leukotriene E4,2TMS,isomer #3CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[C@@H](O)CCCC(=O)O3755.4Semi standard non polar33892256
Leukotriene E4,2TMS,isomer #4CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(=O)O)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3741.7Semi standard non polar33892256
Leukotriene E4,2TMS,isomer #5CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C)C(=O)O)[C@H](CCCC(=O)O)O[Si](C)(C)C3838.6Semi standard non polar33892256
Leukotriene E4,2TMS,isomer #6CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C)C(=O)O)[C@@H](O)CCCC(=O)O[Si](C)(C)C3794.7Semi standard non polar33892256
Leukotriene E4,2TMS,isomer #7CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)CCCC(=O)O3941.7Semi standard non polar33892256
Leukotriene E4,3TMS,isomer #1CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(=O)O[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3686.5Semi standard non polar33892256
Leukotriene E4,3TMS,isomer #2CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C3760.5Semi standard non polar33892256
Leukotriene E4,3TMS,isomer #3CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C3716.1Semi standard non polar33892256
Leukotriene E4,3TMS,isomer #4CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)CCCC(=O)O3879.9Semi standard non polar33892256
Leukotriene E4,3TMS,isomer #5CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C)C(=O)O)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3795.9Semi standard non polar33892256
Leukotriene E4,3TMS,isomer #6CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C3945.4Semi standard non polar33892256
Leukotriene E4,3TMS,isomer #7CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C3880.5Semi standard non polar33892256
Leukotriene E4,4TMS,isomer #1CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3712.6Semi standard non polar33892256
Leukotriene E4,4TMS,isomer #1CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3469.8Standard non polar33892256
Leukotriene E4,4TMS,isomer #1CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C4036.4Standard polar33892256
Leukotriene E4,4TMS,isomer #2CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C3876.7Semi standard non polar33892256
Leukotriene E4,4TMS,isomer #2CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C3560.7Standard non polar33892256
Leukotriene E4,4TMS,isomer #2CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C4182.3Standard polar33892256
Leukotriene E4,4TMS,isomer #3CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C3804.3Semi standard non polar33892256
Leukotriene E4,4TMS,isomer #3CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C3585.6Standard non polar33892256
Leukotriene E4,4TMS,isomer #3CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C4232.9Standard polar33892256
Leukotriene E4,4TMS,isomer #4CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3868.1Semi standard non polar33892256
Leukotriene E4,4TMS,isomer #4CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3571.2Standard non polar33892256
Leukotriene E4,4TMS,isomer #4CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C4197.3Standard polar33892256
Leukotriene E4,5TMS,isomer #1CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3781.6Semi standard non polar33892256
Leukotriene E4,5TMS,isomer #1CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3567.2Standard non polar33892256
Leukotriene E4,5TMS,isomer #1CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3870.2Standard polar33892256
Leukotriene E4,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O3919.6Semi standard non polar33892256
Leukotriene E4,1TBDMS,isomer #2CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(=O)O)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C4005.8Semi standard non polar33892256
Leukotriene E4,1TBDMS,isomer #3CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(=O)O)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C3981.6Semi standard non polar33892256
Leukotriene E4,1TBDMS,isomer #4CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[C@@H](O)CCCC(=O)O4032.6Semi standard non polar33892256
Leukotriene E4,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C4206.1Semi standard non polar33892256
Leukotriene E4,2TBDMS,isomer #2CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C4172.7Semi standard non polar33892256
Leukotriene E4,2TBDMS,isomer #3CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O4212.5Semi standard non polar33892256
Leukotriene E4,2TBDMS,isomer #4CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(=O)O)[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4261.0Semi standard non polar33892256
Leukotriene E4,2TBDMS,isomer #5CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C4288.7Semi standard non polar33892256
Leukotriene E4,2TBDMS,isomer #6CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C4248.6Semi standard non polar33892256
Leukotriene E4,2TBDMS,isomer #7CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O4366.5Semi standard non polar33892256
Leukotriene E4,3TBDMS,isomer #1CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4458.4Semi standard non polar33892256
Leukotriene E4,3TBDMS,isomer #2CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C4458.4Semi standard non polar33892256
Leukotriene E4,3TBDMS,isomer #3CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C4402.5Semi standard non polar33892256
Leukotriene E4,3TBDMS,isomer #4CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O4562.3Semi standard non polar33892256
Leukotriene E4,3TBDMS,isomer #5CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4494.4Semi standard non polar33892256
Leukotriene E4,3TBDMS,isomer #6CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C4615.7Semi standard non polar33892256
Leukotriene E4,3TBDMS,isomer #7CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C4572.2Semi standard non polar33892256
Leukotriene E4,4TBDMS,isomer #1CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4593.0Semi standard non polar33892256
Leukotriene E4,4TBDMS,isomer #1CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4146.5Standard non polar33892256
Leukotriene E4,4TBDMS,isomer #1CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4156.2Standard polar33892256
Leukotriene E4,4TBDMS,isomer #2CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C4787.7Semi standard non polar33892256
Leukotriene E4,4TBDMS,isomer #2CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C4229.1Standard non polar33892256
Leukotriene E4,4TBDMS,isomer #2CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C4263.0Standard polar33892256
Leukotriene E4,4TBDMS,isomer #3CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C4723.3Semi standard non polar33892256
Leukotriene E4,4TBDMS,isomer #3CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C4275.3Standard non polar33892256
Leukotriene E4,4TBDMS,isomer #3CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C4308.9Standard polar33892256
Leukotriene E4,4TBDMS,isomer #4CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4797.0Semi standard non polar33892256
Leukotriene E4,4TBDMS,isomer #4CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4227.0Standard non polar33892256
Leukotriene E4,4TBDMS,isomer #4CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4267.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Leukotriene E4 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leukotriene E4 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene E4 10V, Positive-QTOFsplash10-00dl-1006900000-d68d18c7b1314c206f8a2018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene E4 20V, Positive-QTOFsplash10-000i-2729200000-8a82a9c9671eeade77f62018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene E4 40V, Positive-QTOFsplash10-00bc-8139000000-7d6806220d99255232f02018-11-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene E4 10V, Negative-QTOFsplash10-000i-0003900000-b47de87fd8f2e68c72bc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene E4 20V, Negative-QTOFsplash10-0f89-0019000000-1a1077cfaeb6986463cf2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene E4 40V, Negative-QTOFsplash10-001r-7394000000-62b6156e2c3999245d3c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene E4 10V, Positive-QTOFsplash10-0uy3-1419200000-b5cfed69cbf94d9bec662021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene E4 20V, Positive-QTOFsplash10-00ku-3902000000-73d24883cf695b0534062021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene E4 40V, Positive-QTOFsplash10-05nf-3900000000-962d440d8077c0a892e22021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Smooth Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Normal
details
BloodDetected and Quantified<0.0006 uMAdult (>18 years old)Both
Normal
details
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
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. [PubMed:16757158 ]
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 ]
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
Phenol Explorer Compound IDNot Available
FooDB IDFDB022901
KNApSAcK IDNot Available
Chemspider ID4444402
KEGG Compound IDC05952
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLeukotriene E4
METLIN IDNot Available
PubChem Compound5280879
PDB IDNot Available
ChEBI ID15650
Food Biomarker OntologyNot Available
VMH IDLEUKTRE4
MarkerDB IDMDB00000384
Good Scents IDNot Available
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. [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.

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