Showing metabocard for Anandamide (BMDB0004080)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:07:45 UTC
Update Date2020-04-22 15:13:16 UTC
BMDB IDBMDB0004080
Secondary Accession Numbers
  • BMDB04080
Metabolite Identification
Common NameAnandamide
DescriptionAnandamide, also known as AEA, 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. Thus, anandamide is considered to be a fatty amide lipid molecule. Anandamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5Z,8Z,11Z,14Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamideChEBI
(all-Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamideChEBI
AEAChEBI
Anandamide (20.4, N-6)ChEBI
Anandamide(20:4, N-6)ChEBI
Arachidonic acid N-(hydroxyethyl)amideChEBI
Arachidonoyl ethanolamideChEBI
ArachidonylethanolamideChEBI
N-(2-Hydroxyethyl)anachidonamideChEBI
N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-ethanolamineChEBI
N-(5Z,8Z,11Z,14Z-Icosatetraenoyl)-ethanolamideChEBI
N-Arachidonoyl ethanolamineChEBI
N-Arachidonoyl-2-hydroxyethylamideChEBI
N-ArachidonoylethanolamineChEBI
Arachidonate N-(hydroxyethyl)amideGenerator
N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl) ethanolamineHMDB
5,8,11,14-EicosatetraenoylethanolamideHMDB
N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide (all-Z)HMDB
N-(2-Hydroxyethyl)arachidonamideHMDB
Anandamide (20.4,N-6)HMDB
ArachidonoylethanolamideHMDB
N-ArachidonoylethanolamideHMDB
AnandamideMeSH
N-(2-Hydroxyethyl)arachidonylamideHMDB
N-ArachidonylethanolamideHMDB
N-ArachidonylethanolamineHMDB
AEA(22:6)HMDB
Acylethanolamine 22:6HMDB
Chemical FormulaC22H37NO2
Average Molecular Weight347.5347
Monoisotopic Molecular Weight347.282429433
IUPAC Name(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
Traditional Nameanandamide
CAS Registry Number94421-68-8
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO
InChI Identifier
InChI=1S/C22H37NO2/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/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-
InChI KeyLGEQQWMQCRIYKG-DOFZRALJSA-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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.98ALOGPS
logP5.31ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)15.44ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity112.97 m³·mol⁻¹ChemAxon
Polarizability43.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004080
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023303
KNApSAcK IDNot Available
Chemspider ID4445241
KEGG Compound IDC11695
BioCyc IDCPD-7598
BiGG IDNot Available
Wikipedia LinkAnandamide
METLIN IDNot Available
PubChem Compound5281969
PDB IDNot Available
ChEBI ID2700
References
Synthesis ReferenceQi, Longwu; Meijler, Michael M.; Lee, Sang-Hyeup; Sun, Chengzao; Janda, Kim D. Solid-Phase Synthesis of Anandamide Analogues. Organic Letters (2004), 6(10), 1673-1675.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available