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Showing Compound 20-Hydroxy-leukotriene E4 (FDB029162)

Record Information
Version1.0
Creation date2011-09-21 01:51:03 UTC
Update date2015-07-21 06:59:38 UTC
Primary IDFDB029162
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name20-Hydroxy-leukotriene E4
Description20-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. [HMDB]
CAS Number111844-33-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.0063 g/LALOGPS
logP0.3ALOGPS
logP0.58ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)2.39ChemAxon
pKa (Strongest Basic)9.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area141.08 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity129.55 m³·mol⁻¹ChemAxon
Polarizability52.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC23H37NO6S
IUPAC name(5S,6R,7E,9E,11Z,14Z)-6-[(2-amino-2-carboxyethyl)sulfanyl]-5,20-dihydroxyicosa-7,9,11,14-tetraenoic acid
InChI IdentifierInChI=1S/C23H37NO6S/c24-19(23(29)30)18-31-21(20(26)14-13-16-22(27)28)15-11-9-7-5-3-1-2-4-6-8-10-12-17-25/h2-5,7,9,11,15,19-21,25-26H,1,6,8,10,12-14,16-18,24H2,(H,27,28)(H,29,30)/b4-2-,5-3-,9-7+,15-11+/t19?,20-,21+/m0/s1
InChI KeyBJRMBXPQAMDCMG-QHZDNRHLSA-N
Isomeric SMILESNC(CS[C@H](\C=C\C=C\C=C/C\C=C/CCCCCO)[C@@H](O)CCCC(O)=O)C(O)=O
Average Molecular Weight455.608
Monoisotopic Molecular Weight455.234158611
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
  • Primary aliphatic amine
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary alcohol
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS20-Hydroxy-leukotriene E4, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000l-4319600000-1113fab95154d836ba62Spectrum
Predicted GC-MS20-Hydroxy-leukotriene E4, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-5900456000-c0b8c056c41214647966Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-1003900000-493268a38f604066df7e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kgc-1349500000-521c5e33aa901138ca342017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-6029000000-ec8690fcfdb723a0324a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0v4r-0104900000-34ec95a0fc67699e84832017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00rb-1219100000-83e18e503081a44552572017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9301000000-a23fd3dec462fedf26702017-09-01View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC03577
Pubchem Compound ID53481511
Pubchem Substance IDNot Available
ChEBI ID28700
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12639
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference