Record Information
Version1.0
Creation date2011-09-21 00:21:25 UTC
Update date2015-07-21 06:57:25 UTC
Primary IDFDB022901
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number75715-89-8
Structure
Thumb
Synonyms
SynonymSource
[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
20-Hydroxy-leukotriene e4HMDB
20-OH-Leukotriene e4HMDB
LTE4hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0018 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity127.62 m³·mol⁻¹ChemAxon
Polarizability51.15 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC23H37NO5S
IUPAC name(5S,6R,7E,9E)-6-[(2-amino-2-carboxyethyl)sulfanyl]-5-hydroxyicosa-7,9,11,14-tetraenoic acid
InChI IdentifierInChI=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-BGCYIFDCSA-N
Isomeric SMILES[H][C@](O)(CCCC(O)=O)[C@]([H])(SCC(N)C(O)=O)\C=C\C=C\C=CCC=CCCCCC
Average Molecular Weight439.609
Monoisotopic Molecular Weight439.239243989
Classification
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
  • 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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID4444323
ChEMBL IDNot Available
KEGG Compound IDC05952
Pubchem Compound ID5280749
Pubchem Substance IDNot Available
ChEBI ID15650
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02200
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2705740
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLeukotriene E4
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Dipeptidase 2DPEP2Q9H4A9
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference