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Record Information
Version4.0
Creation Date2009-07-25 00:01:48 UTC
Update Date2017-10-23 19:06:05 UTC
HMDB IDHMDB0012501
Secondary Accession Numbers
  • HMDB12501
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
ValueSource
(5S,6R,12R)-Dihydroxy-6-(S-cysteinyl)-(7E,9E,14Z)-eicosatrienoateHMDB
(5S,6R,12R)-Dihydroxy-6-(S-cysteinyl)-(7E,9E,14Z)-eicosatrienoic acidHMDB
5,12-Dihydroxy-6-cysteinyl-7,9,14-eicosatrienoateHMDB
5,12-Dihydroxy-6-cysteinyl-7,9,14-eicosatrienoic acidHMDB
5S,12R-Dihydroxy-6-S-cysteinyl-7E,9E,14Z-eicosatrienoateHMDB
5S,12R-Dihydroxy-6-S-cysteinyl-7E,9E,14Z-eicosatrienoic acidHMDB
e-LTB(,3)HMDB
ELTB3HMDB
epsilon-LTB(,3)HMDB
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 KeyFZJOTYMARNGISF-YXSOTRFDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentHydroxyeicosatrienoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatrienoic acid
  • Long-chain fatty acid
  • Cysteine or derivatives
  • S-alkyl-l-cysteine
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • D-alpha-amino acid
  • 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
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity128.17 m³·mol⁻¹ChemAxon
Polarizability53.02 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8609600000-829d3a3140784324f4e8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0bu3-9321628000-159928b6a9d6ef324490View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-1003900000-3662f1010244672e3b0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06xx-2449500000-9e3bab4974cbb68b1ef4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-7129000000-bb7a104823dfe693df55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0abi-0204900000-3873c5cb609a5c92b2caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-1219100000-f64640a3f32d659df5a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9301000000-1a8d02aa6c0936d575b1View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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
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. [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 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.