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Record Information
Version3.6
Creation Date2009-07-25 00:01:48 UTC
Update Date2013-05-29 19:48:02 UTC
HMDB IDHMDB12501
Secondary Accession NumbersNone
Metabolite Identification
Common Name10,11-Dihydro-12R-hydroxy-leukotriene E4
Description10,11-dihydro-12R-hydroxy-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. (5S,6R,12R)-dihydroxy-6-(S-cysteinyl)-(7E,9E,14Z)-eicosatrienoate
  2. (5S,6R,12R)-dihydroxy-6-(S-cysteinyl)-(7E,9E,14Z)-eicosatrienoic acid
  3. 5,12-Dihydroxy-6-cysteinyl-7,9,14-eicosatrienoate
  4. 5,12-Dihydroxy-6-cysteinyl-7,9,14-eicosatrienoic acid
  5. 5S,12R-Dihydroxy-6-S-cysteinyl-7E,9E,14Z-eicosatrienoate
  6. 5S,12R-Dihydroxy-6-S-cysteinyl-7E,9E,14Z-eicosatrienoic acid
  7. e-LTB(,3)
  8. ELTB3
  9. epsilon-LTB(,3)
Chemical FormulaC23H39NO6S
Average Molecular Weight457.624
Monoisotopic Molecular Weight457.249808675
IUPAC Name(5S,6R,7E,9E,12S,14Z)-6-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-5,12-dihydroxyicosa-7,9,14-trienoic acid
Traditional Name(5S,6R,7E,9E,12S,14Z)-6-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-5,12-dihydroxyicosa-7,9,14-trienoic acid
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C[C@H](O)C\C=C\C=C\[C@@H](SC[C@@H](N)C(O)=O)[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C23H39NO6S/c1-2-3-4-5-6-8-12-18(25)13-9-7-10-15-21(31-17-19(24)23(29)30)20(26)14-11-16-22(27)28/h6-10,15,18-21,25-26H,2-5,11-14,16-17,24H2,1H3,(H,27,28)(H,29,30)/b8-6-,9-7+,15-10+/t18-,19+,20-,21+/m0/s1
InChI KeyInChIKey=FZJOTYMARNGISF-YXSOTRFDSA-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
  • Hydroxyeicosatrienoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • D-alpha-amino 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
StatusExpected but 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 Solubility0.0073 mg/mLALOGPS
logP0.45ALOGPS
logP1ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)2.35ChemAxon
pKa (Strongest Basic)9.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area141.08 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity128.17 m3·mol-1ChemAxon
Polarizability53.02 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 IDFDB029103
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12501
Metagene LinkHMDB12501
METLIN IDNot Available
PubChem Compound53481446
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. [12607939 ]
  2. Evans JF: Cysteinyl leukotriene receptors. Prostaglandins Other Lipid Mediat. 2002 Aug;68-69:587-97. [12432945 ]
  3. Hammarstrom S: Leukotrienes. Annu Rev Biochem. 1983;52:355-77. [6311078 ]