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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gb9-1910000000-79c55260280d43c9a900View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fs7-5900000000-75831770c51e1d2f739dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gb9-1910000000-79c55260280d43c9a900View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fs7-5900000000-75831770c51e1d2f739dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02a5-7493000000-c585906fb5c6d8aa4ff3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fki-9353100000-6c635dea7003727f3b83View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-1029000000-acb4551dcc9e3f6e05ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03xr-9000000000-45148e922a9fd54fabf5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-9230000000-c1ae6b0473246ef09b54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03xr-9000000000-100fb9f29334308faa9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-5149000000-76b6af47eca436d3e5ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9131000000-069d65af4be10e925d42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9230000000-3590307e1cf3aab76689View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-004521084d25577be5feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r2-5019000000-1c63bb1751f58bf91f0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9010000000-161a34c3d66caea4a293View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-9328000000-b4562c25b6933ac7a7baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000000000-4d45bc23e3d763bd083bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9100000000-ed96624588d13e15a5bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-a3f88dce43caba26e0b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-5129000000-5f007c24785520e490c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9010000000-868cfda7283947a9fbc4View in MoNA
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