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Record Information
Version3.6
Creation Date2006-08-13 10:27:48 UTC
Update Date2013-05-29 19:39:34 UTC
HMDB IDHMDB04080
Secondary Accession NumbersNone
Metabolite Identification
Common NameAnandamide
DescriptionAnandamide is a highly potent endogenous agonist of the cannabinoid CB1 and CB2 receptors. CB1 receptors are predominantly found in the central nervous system (CNS) where they mainly mediate the psychotropic effects of Tetrahydrocannabinol (THC) and endocannabinoids, whereas the expression of the CB2 receptor is thought to be restricted to cells of the immune system. It was suggested that AEA might inhibit tumor cell proliferation or induce apoptosis independently of CB1 and CB2 receptors, via interaction with the type 1 vanilloid receptor (VR1). VR1 is an ion channel expressed almost exclusively by sensory neurons, activated by pH, noxious heat (>48 degree centigrade) and plant toxins and is thought to play an important role in nociception. Cervical cancer cells are sensitive to AEA-induced apoptosis via VR1 that is aberrantly expressed in vitro and in vivo while CB1 and CB2 receptors play a protective role. (PMID 15047233 ). Novel prostaglandins (prostaglandin glycerol esters and prostaglandin ethanolamides) are COX-2 oxidative metabolites of endogenous cannabinoids (such as Anandamide). Recent evidence suggests that these new types of prostaglandins are likely novel signaling mediators involved in synaptic transmission and plasticity. (PMID 16957004 ).
Structure
Thumb
Synonyms
  1. 5,8,11,14-Eicosatetraenoylethanolamide
  2. AEA
  3. Anandamide
  4. Anandamide (20.4, N-6)
  5. Anandamide(20:4, N-6)
  6. Arachidonic acid N-(hydroxyethyl)amide
  7. Arachidonylethanolamide
  8. N-(2-Hydroxyethyl)-5,8,11,14-Eicosatetraenamide (all-Z)
  9. N-(2-Hydroxyethyl)anachidonamide
  10. N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-ethanolamine
  11. N-(5Z,8Z,11Z,14Z-Icosatetraenoyl)-ethanolamide
  12. N-Arachidonoyl ethanolamine
  13. N-Arachidonoyl-2-hydroxyethylamide
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
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Amides
Sub ClassN-acyl Amines
Other Descriptors
  • Aliphatic Acyclic Compounds
  • a monocarboxylic-acid-amide(Cyc)
  • an N-acylethanolamine(Cyc)
Substituents
  • Acyclic Alkene
  • Carboxamide Group
  • N Acylethanolamine
  • Primary Alcohol
  • Secondary Carboxylic Acid Amide
Direct ParentN-acyl Amines
Ontology
StatusDetected and 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.700E-04 g/LALOGPS
logP5.98ALOGPS
logP5.31ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)15.44ChemAxon
pKa (Strongest Basic)-0.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity112.97ChemAxon
Polarizability43.93ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.008 +/- 0.016 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.99 +/- 5.39 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.12 +/- 1.2 uMAdult (>18 years old)Not Specified
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.01165 +/- 0.00753 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.00255 +/- 0.00178 uMAdult (>18 years old)BothEpilepsy details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023303
KNApSAcK IDNot Available
Chemspider ID4445241
KEGG Compound IDC11695
BioCyc IDCPD-7598
BiGG IDNot Available
Wikipedia LinkAnandamide
NuGOwiki LinkHMDB04080
Metagene LinkHMDB04080
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)Download (PDF)
General References
  1. Felder CC, Nielsen A, Briley EM, Palkovits M, Priller J, Axelrod J, Nguyen DN, Richardson JM, Riggin RM, Koppel GA, Paul SM, Becker GW: Isolation and measurement of the endogenous cannabinoid receptor agonist, anandamide, in brain and peripheral tissues of human and rat. FEBS Lett. 1996 Sep 16;393(2-3):231-5. Pubmed: 8814296
  2. Contassot E, Tenan M, Schnuriger V, Pelte MF, Dietrich PY: Arachidonyl ethanolamide induces apoptosis of uterine cervix cancer cells via aberrantly expressed vanilloid receptor-1. Gynecol Oncol. 2004 Apr;93(1):182-8. Pubmed: 15047233
  3. Sang N, Chen C: Lipid signaling and synaptic plasticity. Neuroscientist. 2006 Oct;12(5):425-34. Pubmed: 16957004

Enzymes

General function:
Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:
Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes polyunsaturated substrate anandamide preferentially as compared to monounsaturated substrates.
Gene Name:
FAAH
Uniprot ID:
O00519
Molecular weight:
63065.28
Reactions
Anandamide + Water → Arachidonic acid + Ethanolaminedetails
General function:
Involved in hydrolase activity
Specific function:
Lysophospholipase selective for N-acyl phosphatidylethanolamine (NAPE). Contributes to the biosynthesis of N-acyl ethanolamines, including the endocannabinoid anandamide by hydrolyzing the sn-1 and sn-2 acyl chains from N-acyl phosphatidylethanolamine (NAPE) generating glycerophospho-N-acyl ethanolamine (GP-NAE), an intermediate for N-acyl ethanolamine biosynthesis. Hydrolyzes substrates bearing saturated, monounsaturated, polyunsaturated N-acyl chains. Shows no significant activity towards other lysophospholipids, including lysophosphatidylcholine, lysophosphatidylethanolamine and lysophosphatidylserine
Gene Name:
ABHD4
Uniprot ID:
Q8TB40
Molecular weight:
38794.1
General function:
Involved in metal ion binding
Specific function:
Hydrolyzes N-acyl-phosphatidylethanolamines (NAPEs) to produce N-acylethanolamines (NAEs) and phosphatidic acid. Responsible for the generation of anandamide (N-arachidonoylethanolamine), the ligand of cannabinoid and vanilloid receptors (By similarity).
Gene Name:
NAPEPLD
Uniprot ID:
Q6IQ20
Molecular weight:
45595.15
General function:
Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:
Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes monounsaturated substrate anandamide preferentially as compared to polyunsaturated substrates.
Gene Name:
FAAH2
Uniprot ID:
Q6GMR7
Molecular weight:
58303.115
Reactions
Anandamide + Water → Arachidonic acid + Ethanolaminedetails
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered ligand binding
Gene Name:
CNR1
Uniprot ID:
P21554
Molecular weight:
52857.4