Eicosapentaenoyl ethanolamide (CHEM041405)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:28:10 UTC
Update Date2016-11-09 01:22:28 UTC
Accession NumberCHEM041405
Identification
Common NameEicosapentaenoyl ethanolamide
ClassSmall Molecule
DescriptionAn N-(long-chain-acyl)ethanolamine that is the ethanolamide of (5Z,8Z,11Z,14Z17Z)-eicosapentaenoic acid.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoyl ethanolamideChEBI
(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl) ethanolamineChEBI
all-cis-Eicosa-5,8,11,14,17-pentaenoyl ethanolamideChEBI
all-cis-Icosa-5,8,11,14,17-pentaenoyl ethanolamideChEBI
Anandamide (20:5, N-3)ChEBI
EPEAChEBI
Icosapentaenoyl ethanolamideChEBI
N-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)ethanolamineChEBI
N-cis-5,8, 11,14,17-EicosapentaenoylethanolamineChEBI
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl ethanolamideChEBI, HMDB
Eicosapentaenoyl ethanolamideChEBI
N-(2-Hydroxyethyl)-5Z,8Z,11Z,14Z,17Z-eicosapentaenamideHMDB
N-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-ethanolamineHMDB
Chemical FormulaC22H35NO2
Average Molecular Mass345.519 g/mol
Monoisotopic Mass345.267 g/mol
CAS Registry Number109001-03-8
IUPAC Name(5Z,8Z,11Z,14Z,17Z)-N-(2-hydroxyethyl)icosa-5,8,11,14,17-pentaenamide
Traditional Name(5Z,8Z,11Z,14Z,17Z)-N-(2-hydroxyethyl)icosa-5,8,11,14,17-pentaenamide
SMILESCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO
InChI IdentifierInChI=1S/C22H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h3-4,6-7,9-10,12-13,15-16,24H,2,5,8,11,14,17-21H2,1H3,(H,23,25)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChI KeyOVKKNJPJQKTXIT-JLNKQSITSA-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
  • Carboxylic acid derivative
  • Alcohol
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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 Solubility0.0011 g/LALOGPS
logP5.78ALOGPS
logP4.95ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)15.44ChemAxon
pKa (Strongest Basic)-0.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity114.08 m³·mol⁻¹ChemAxon
Polarizability41.74 ųChemAxon
Number of Rings0ChemAxon
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, Positivesplash10-01p2-6594000000-f16f4f504f500b82ebdfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-9362200000-1320e1056324d323f57dSpectrum
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, Positivesplash10-01ot-5149000000-eed2dcb29f49f2289844Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9120000000-9305609c724a4878191aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9230000000-b5cc9e1615f5477bbea7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-d4f7e87c45bcc63e17d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-6029000000-a540e5c0d137b5a0ac56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9010000000-d0d8fe150594c5c85530Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-9328000000-0506718ab0ac845ed26cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9100000000-91289ad1e6e9f4611068Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9200000000-c7fc186fa971397efe35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-d32eeee3dd6dfdbb595fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-5129000000-f853d05861110dbe6a72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9020000000-d61a052479cd2fd9d23eSpectrum
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 IDHMDB0013649
FooDB IDFDB029619
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4446570
ChEBI ID71467
PubChem Compound ID5283450
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=20601112
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20660502
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21562563
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23168911
5. Balvers MG, Verhoeckx KC, Plastina P, Wortelboer HM, Meijerink J, Witkamp RF: Docosahexaenoic acid and eicosapentaenoic acid are converted by 3T3-L1 adipocytes to N-acyl ethanolamines with anti-inflammatory properties. Biochim Biophys Acta. 2010 Oct;1801(10):1107-14. doi: 10.1016/j.bbalip.2010.06.006. Epub 2010 Jun 27.