20-COOH-leukotriene E4 (CHEM040981)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:07:07 UTC
Update Date2016-11-09 01:22:22 UTC
Accession NumberCHEM040981
Identification
Common Name20-COOH-leukotriene E4
ClassSmall Molecule
Description20-COOH-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 signalling pathways.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
20-COOH-LTE4HMDB
6-(S-Cysteinyl)-(5S)-hydroxy-(7E,9E,11Z,14Z)-eicosatetraenedioateHMDB
6-(S-Cysteinyl)-(5S)-hydroxy-(7E,9E,11Z,14Z)-eicosatetraenedioic acidHMDB
Chemical FormulaC23H35NO7S
Average Molecular Mass469.592 g/mol
Monoisotopic Mass469.213 g/mol
CAS Registry NumberNot Available
IUPAC Name(6Z,9Z,11E,13E,15R,16S)-15-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-16-hydroxyicosa-6,9,11,13-tetraenedioic acid
Traditional Name(6Z,9Z,11E,13E,15R,16S)-15-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-16-hydroxyicosa-6,9,11,13-tetraenedioic acid
SMILESN[C@H](CS[C@H](\C=C\C=C\C=C/C\C=C/CCCCC(O)=O)[C@@H](O)CCCC(O)=O)C(O)=O
InChI IdentifierInChI=1S/C23H35NO7S/c24-18(23(30)31)17-32-20(19(25)13-12-16-22(28)29)14-10-8-6-4-2-1-3-5-7-9-11-15-21(26)27/h2-6,8,10,14,18-20,25H,1,7,9,11-13,15-17,24H2,(H,26,27)(H,28,29)(H,30,31)/b4-2-,5-3-,8-6+,14-10+/t18-,19+,20-/m1/s1
InChI KeyHVLRBLGTGJGVCX-RHSCJZQUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCysteine and derivatives
Alternative Parents
Substituents
  • Cysteine or derivatives
  • S-alkyl-l-cysteine
  • Alpha-amino acid
  • D-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Hydroxy fatty acid
  • Thia fatty acid
  • Fatty acyl
  • Secondary alcohol
  • Amino acid
  • Carboxylic acid
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0068 g/LALOGPS
logP0.18ALOGPS
logP0.7ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)2.38ChemAxon
pKa (Strongest Basic)9.13ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area158.15 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity129.29 m³·mol⁻¹ChemAxon
Polarizability51.75 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ukc-3219600000-afc81424c577c7c73830Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00dl-8400918000-987eca40d2a4c9ab31e8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0001900000-a9aa6251a352d0e8e2a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0lk9-1249700000-127f1da4ed2b24fdf00fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cmv-4019200000-c4f5f9fd8da1131bd7f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gir-0103900000-46c830f394a499c0440dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03l9-1219200000-0336064a6d9bcaf9f0c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9302000000-10f31ff39e1d782b7a27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ul0-0029500000-a97dae5c18a6435b7889Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kur-0039500000-4b7053be1be20c285946Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01e9-4910000000-2ad4c146132a94fd0587Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01x0-2309400000-bcb027d5a55752e9a430Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1219000000-43c90b9b27b55393b866Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xr-5559000000-5e7c46a6b1b8554d75a6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0012634
FooDB IDFDB029159
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776643
ChEBI IDNot Available
PubChem Compound ID53481508
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
2. Evans JF: Cysteinyl leukotriene receptors. Prostaglandins Other Lipid Mediat. 2002 Aug;68-69:587-97.
3. Hammarstrom S: Leukotrienes. Annu Rev Biochem. 1983;52:355-77.
4. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19.