(±)-11(12)-EET ethanolamide (CHEM041408)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:28:18 UTC
Update Date2016-11-09 01:22:28 UTC
Accession NumberCHEM041408
Identification
Common Name(±)-11(12)-EET ethanolamide
ClassSmall Molecule
DescriptionAn N-(polyunsaturated fatty acyl)ethanolamine obtained by formal epoxidation across the 11,12-double bond of anandamide.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11(12)-EET-eaChEBI
11(12)-EpETrE-eaChEBI
11,12-EET-eaChEBI
N-(11,12-Epoxy-5Z,8Z,14Z-eicosatrienoyl)-ethanolamineChEBI
N-(11,12-Epoxy-5Z,8Z,14Z-icosatrienoyl)ethanolamineChEBI
(+/-)11(12)-epetre ethanolamideHMDB
Chemical FormulaC22H37NO3
Average Molecular Mass363.534 g/mol
Monoisotopic Mass363.277 g/mol
CAS Registry NumberNot Available
IUPAC Name(5Z,8Z)-N-(2-hydroxyethyl)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienamide
Traditional Name(5Z,8Z)-N-(2-hydroxyethyl)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienamide
SMILESCCCCC\C=C/CC1OC1C\C=C/C\C=C/CCCC(=O)NCCO
InChI IdentifierInChI=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 KeyTYRRSRADDAROSO-KROJNAHFSA-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
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00088 g/LALOGPS
logP5.43ALOGPS
logP4.38ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)15.44ChemAxon
pKa (Strongest Basic)-0.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area61.86 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity111.37 m³·mol⁻¹ChemAxon
Polarizability44.05 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-8694000000-6d3847325b2b7040cee2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-8796300000-08d23c6d3b184e010daeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4129000000-910d6ee245580b6ad5ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9311000000-c066370e8bc76292f791Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03kc-9400000000-719f47ab5fde92ea853eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0119000000-aee82aac64e21c8ff5e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-5219000000-5757c2d1716a1ad61a24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9300000000-dac6a7b4529aa109cd72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-ea75254cd356aac3e606Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3129000000-a8f779297baa545ea5beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9133000000-18b69b4fe133f3d381a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9117000000-938cc0536a78351d1651Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9001000000-f9d2451870ca0ec8533fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-2f1ee6d42f6b011c032eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0013652
FooDB IDFDB029622
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17220862
ChEBI ID136990
PubChem Compound ID16061183
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20702771
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21689782
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=27000802
4. 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.
5. 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.
6. 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.
7. Kozak KR, Marnett LJ: Oxidative metabolism of endocannabinoids. Prostaglandins Leukot Essent Fatty Acids. 2002 Feb-Mar;66(2-3):211-20.