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Human Metabolome Database Version 3.5

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Showing metabocard for (±)8(9)-EET Ethanolamide (HMDB13659)

Record Information
Version 3.5
Creation Date 2011-07-12 04:28:56 -0600
Update Date 2013-06-04 14:53:59 -0600
HMDB ID HMDB13659
Secondary Accession Numbers None
Metabolite Identification
Common Name (±)8(9)-EET Ethanolamide
Description (±)8(9)-EET ethanolamide is a cytochrome P450 (CYP450) metabolite of arachidonoyl ethanolamide (AEA), although specific stereochemistry rather than a racemic mixture would likely ensue from enzymatic metabolism (PMID: 17272674 Link_out). AEA is an endogenous lipid neurotransmitter with cannabingeric activity, binding to both the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors (PMID: 8395053 Link_out, 16078824 Link_out). Fatty acid amide hydrolase (FAAH) is the enzyme responsible for the hydrolysis and inactivation of AEA (PMID: 12052036 Link_out). Metabolism of AEA by COX-2, lipoxygenases, and CYP450 enzymes has also been documented (PMID: 12052037 Link_out, 17272674 Link_out). Human liver microsomes metabolize AEA to 5,6-, 8,9-, 11,12-, and 14,15-EET ethanolamides in a time and protein concentration dependent manner (PMID: 17272674 Link_out). (±)8(9)-EET reduces glomerular filtration rate through cyclooxygenase dependent preglomerular vasoconstriction (PMID: 1928373 Link_out). The physiological actions of (±)8(9)-EET ethanolamide have not been examined.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (+/-)8(9)-EpETrE Ethanolamide
Chemical Formula C22H37NO3
Average Molecular Weight 363.5341
Monoisotopic Molecular Weight 363.277344055
IUPAC Name (5Z)-N-(2-hydroxyethyl)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enamide
Traditional IUPAC Name 8(9)-EpETrE-EA
CAS Registry Number Not Available
SMILES CCCCC\C=C/C\C=C/CC1OC1C\C=C/CCCC(=O)NCCO
InChI Identifier InChI=1S/C22H37NO3/c1-2-3-4-5-6-7-8-9-12-15-20-21(26-20)16-13-10-11-14-17-22(25)23-18-19-24/h6-7,9-10,12-13,20-21,24H,2-5,8,11,14-19H2,1H3,(H,23,25)/b7-6-,12-9-,13-10-
InChI Key BXHPMUQFGGSDAK-TYAUOURKSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Amides
Sub Class N-acyl Amines
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • N-acyl ethanolamines (endocannabinoids)(Lipidmaps)
Substituents
  • Carboxamide Group
  • Dialkyl Ether
  • N Acylethanolamine
  • Oxirane
  • Primary Alcohol
  • Secondary Carboxylic Acid Amide
Direct Parent N-acyl Amines
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 8.510E-04 g/L ALOGPS
LogP 5.42 ALOGPS
LogP 4.38 ChemAxon
LogS -5.63 ALOGPS
pKa (strongest acidic) 15.33 ChemAxon
pKa (strongest basic) -0.34 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 61.86 A2 ChemAxon
Rotatable Bond Count 16 ChemAxon
Refractivity 111.37 ChemAxon
Polarizability 44.21 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029629
KNApSAcK ID Not Available
Chemspider ID 17220861 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB13659 Link_out
Metagene Link HMDB13659 Link_out
METLIN ID Not Available
PubChem Compound 16061182 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Snider NT, Kornilov AM, Kent UM, Hollenberg PF: Anandamide metabolism by human liver and kidney microsomal cytochrome p450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. J Pharmacol Exp Ther. 2007 May;321(2):590-7. Epub 2007 Feb 1. Pubmed: 17272674 Link_out
  2. Felder CC, Briley EM, Axelrod J, Simpson JT, Mackie K, Devane WA: Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci U S A. 1993 Aug 15;90(16):7656-60. Pubmed: 8395053 Link_out
  3. Lambert DM, Fowler CJ: The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications. J Med Chem. 2005 Aug 11;48(16):5059-87. Pubmed: 16078824 Link_out
  4. Deutsch DG, Ueda N, Yamamoto S: The fatty acid amide hydrolase (FAAH). Prostaglandins Leukot Essent Fatty Acids. 2002 Feb-Mar;66(2-3):201-10. Pubmed: 12052036 Link_out
  5. Kozak KR, Marnett LJ: Oxidative metabolism of endocannabinoids. Prostaglandins Leukot Essent Fatty Acids. 2002 Feb-Mar;66(2-3):211-20. Pubmed: 12052037 Link_out
  6. Katoh T, Takahashi K, Capdevila J, Karara A, Falck JR, Jacobson HR, Badr KF: Glomerular stereospecific synthesis and hemodynamic actions of 8,9-epoxyeicosatrienoic acid in rat kidney. Am J Physiol. 1991 Oct;261(4 Pt 2):F578-86. Pubmed: 1928373 Link_out