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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:03:50 UTC
Update Date2020-02-26 21:37:48 UTC
HMDB IDHMDB0012607
Secondary Accession Numbers
  • HMDB12607
Metabolite Identification
Common Name18-Carboxy-dinor-LTE4
Description18-carboxy-dinor-LTE4 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.
Structure
Data?1582753068
Synonyms
ValueSource
Omega-COOH-dinor-lte(,4)HMDB
Chemical FormulaC21H31NO7S
Average Molecular Weight441.538
Monoisotopic Molecular Weight441.182123041
IUPAC Name(4Z,7Z,9E,11E,13R,14S)-13-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-14-hydroxyoctadeca-4,7,9,11-tetraenedioic acid
Traditional Name(4Z,7Z,9E,11E,13R,14S)-13-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-14-hydroxyoctadeca-4,7,9,11-tetraenedioic acid
CAS Registry NumberNot Available
SMILES
N[C@H](CS[C@H](\C=C\C=C\C=C/C\C=C/CCC(O)=O)[C@@H](O)CCCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C21H31NO7S/c22-16(21(28)29)15-30-18(17(23)11-10-14-20(26)27)12-8-6-4-2-1-3-5-7-9-13-19(24)25/h1-2,4-8,12,16-18,23H,3,9-11,13-15,22H2,(H,24,25)(H,26,27)(H,28,29)/b2-1-,6-4+,7-5-,12-8+/t16-,17+,18-/m1/s1
InChI KeyOXCSBZDIZXLXRX-CBAWHTJISA-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
Ontology
Disposition

Source:

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 Solubility0.02 g/LALOGPS
logP-0.52ALOGPS
logP-0.19ChemAxon
logS-4.3ALOGPS
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 Count17ChemAxon
Refractivity120.08 m³·mol⁻¹ChemAxon
Polarizability47.55 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xv-1119100000-55262482c3c4667acd5fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-8500759000-31c773f8df2c7f8e0048Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-1005900000-b4b6be43b987cd87e393Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05bn-1419100000-023ed9a04e058585d82bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00g3-4029000000-1c9031b45e84c4c5e3adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-0207900000-cbad47933e9081d722a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-1219000000-4a15a90800247cb7bbd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9302000000-b0d0e357f038327d49e9Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029145
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481489
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH 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. [PubMed:12607939 ]
  2. Evans JF: Cysteinyl leukotriene receptors. Prostaglandins Other Lipid Mediat. 2002 Aug;68-69:587-97. [PubMed:12432945 ]
  3. Hammarstrom S: Leukotrienes. Annu Rev Biochem. 1983;52:355-77. [PubMed:6311078 ]