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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:47 UTC
Update Date2019-07-23 05:45:27 UTC
HMDB IDHMDB0002304
Secondary Accession Numbers
  • HMDB02304
Metabolite Identification
Common NameLeukotriene B4 ethanolamide
DescriptionLeukotriene B4 ethanolamide is a synthetic agonist of leukotriene B4 (LTB4), that interacts with both leukotriene B4 receptors and Vanilloid TRPV1 receptors. Leukotriene B4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. Other specific pathways of leukotriene metabolism include the 12-hydroxydehydrogenase/ 15-oxo-prostaglandin-13-reductase that form a series of conjugated diene metabolites that have been observed to be excreted into human urine. Metabolism of LTC4 occurs by sequential peptide cleavage reactions involving a gamma-glutamyl transpeptidase that forms LTD4 (leukotriene D4) and a membrane-bound dipeptidase that converts LTD4 into LTE4 (leukotriene E4) before w-oxidation. These metabolic transformations of the primary leukotrienes are critical for termination of their biological activity, and defects in expression of participating enzymes may be involved in specific genetic disease. (PMID 17623009 , 16207832 )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?1563860727
Synonyms
ValueSource
LTB4 Ethanol amideHMDB
N-(2-Hydroxyethyl)-5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraen-1-amideHMDB
Chemical FormulaC22H37NO4
Average Molecular Weight379.5335
Monoisotopic Molecular Weight379.272258677
IUPAC Name(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-N-(2-hydroxyethyl)icosa-6,8,10,14-tetraenamide
Traditional NameLTB4 ethanol amide
CAS Registry Number877459-63-7
SMILES
CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(=O)NCCO
InChI Identifier
InChI=1S/C22H37NO4/c1-2-3-4-5-6-9-13-20(25)14-10-7-8-11-15-21(26)16-12-17-22(27)23-18-19-24/h6-11,14-15,20-21,24-26H,2-5,12-13,16-19H2,1H3,(H,23,27)/b8-7+,9-6-,14-10+,15-11-/t20-,21-/m1/s1
InChI KeyDQLVVNIINUTUIU-XLFGVTECSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentN-acylethanolamines
Alternative Parents
Substituents
  • N-acylethanolamine
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP3.99ALOGPS
logP2.85ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)15.39ChemAxon
pKa (Strongest Basic)-0.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area89.79 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity116 m³·mol⁻¹ChemAxon
Polarizability45.09 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fr-4569000000-07bbcd45df0fab107131JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00al-9403580000-183af0e09936b9778485JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2019000000-4f352551829a8f9e3932JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9114000000-a9957a9113512b82fed1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9211000000-bf01e60a47f738449f5cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-103935c4a5640462193dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3119000000-77b68bbcfe920f285fb9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9010000000-8161d2163618ea5160ceJSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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
FoodDB IDFDB022956
KNApSAcK IDNot Available
Chemspider ID4446251
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283127
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Murphy RC, Gijon MA: Biosynthesis and metabolism of leukotrienes. Biochem J. 2007 Aug 1;405(3):379-95. [PubMed:17623009 ]
  2. McHugh D, McMaster RS, Pertwee RG, Roy S, Mahadevan A, Razdan RK, Ross RA: Novel compounds that interact with both leukotriene B4 receptors and vanilloid TRPV1 receptors. J Pharmacol Exp Ther. 2006 Feb;316(2):955-65. Epub 2005 Oct 5. [PubMed:16207832 ]
  3. Lipid Maps (LMFA03020012) [Link]