Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for (±)11(12)-EET Ethanolamide (HMDB13652)

Record Information
Version 3.5
Creation Date 2011-07-07 04:24:13 -0600
Update Date 2013-02-08 17:30:44 -0700
HMDB ID HMDB13652
Secondary Accession Numbers None
Metabolite Identification
Common Name (±)11(12)-EET Ethanolamide
Description Arachidonoyl ethanolamide (AEA; anandamide) is an endogenous lipid neurotransmitter with cannibingeric activity, binding to both the central cannabinoid (CB1) and peripheral cannabinoid CB2 receptors.1,2 Fatty acid amide hydrolase (FAAH) is the enzyme responsible for the hydrolysis and inactivation of AEA.3 Metabolism of AEA by cyclooxygenase-2, leading to formation of prostaglandin ethanolamides, and by lipoxygenases has also been documented.4 (±)11(12)-EET ethanolamide is a potential cytochrome P450 (CYP450) metabolite of AEA, although specific stereochemistry rather than a racemic mixture would likely ensue from enzymatic metabolism. CYP450 metabolism of AEA may be particularly relevant under conditions of FAAH inhibition. Evidence for the formation of 11(12)-EET ethanolamide in vivo has not been documented.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (+/-)11(12)-EpETrE Ethanolamide
Chemical Formula C22H37NO3
Average Molecular Weight 363.5341
Monoisotopic Molecular Weight 363.277344055
IUPAC Name (5Z,8Z)-N-(2-hydroxyethyl)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienamide
Traditional IUPAC Name (5Z,8Z)-N-(2-hydroxyethyl)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienamide
CAS Registry Number Not Available
SMILES CCCCC\C=C/CC1OC1C\C=C/C\C=C/CCCC(=O)NCCO
InChI Identifier InChI=1S/C22H37NO3/c1-2-3-4-5-9-12-15-20-21(26-20)16-13-10-7-6-8-11-14-17-22(25)23-18-19-24/h6,8-10,12-13,20-21,24H,2-5,7,11,14-19H2,1H3,(H,23,25)/b8-6-,12-9-,13-10-
InChI Key TYRRSRADDAROSO-KROJNAHFSA-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 8.840E-04 g/L ALOGPS
LogP 5.43 ALOGPS
LogP 4.38 ChemAxon
LogS -5.61 ALOGPS
pKa (strongest acidic) 15.44 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 44.05 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
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029622
KNApSAcK ID Not Available
Chemspider ID 17220862 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB13652 Link_out
Metagene Link HMDB13652 Link_out
METLIN ID Not Available
PubChem Compound 16061183 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available