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Human Metabolome Database Version 3.5

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Showing metabocard for Anandamide (HMDB04080)

Record Information
Version 3.5
Creation Date 2006-08-13 04:27:48 -0600
Update Date 2013-05-29 13:39:34 -0600
HMDB ID HMDB04080
Secondary Accession Numbers None
Metabolite Identification
Common Name Anandamide
Description Anandamide 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 Link_out). 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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C22H37NO2
Average Molecular Weight 347.5347
Monoisotopic Molecular Weight 347.282429433
IUPAC Name (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
Traditional IUPAC Name anandamide
CAS Registry Number 94421-68-8
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 Key LGEQQWMQCRIYKG-DOFZRALJSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Amides
Sub Class N-acyl Amines
Other Descriptors
  • Aliphatic Acyclic Compounds
  • a monocarboxylic-acid-amide(Cyc)
  • an <i>N</i>-acylethanolamine(Cyc)
Substituents
  • Acyclic Alkene
  • Carboxamide Group
  • N Acylethanolamine
  • Primary Alcohol
  • Secondary Carboxylic Acid Amide
Direct Parent N-acyl Amines
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 4.700E-04 g/L ALOGPS
LogP 5.98 ALOGPS
LogP 5.31 ChemAxon
LogS -5.87 ALOGPS
pKa (strongest acidic) 15.44 ChemAxon
pKa (strongest basic) -0.34 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 49.33 A2 ChemAxon
Rotatable Bond Count 16 ChemAxon
Refractivity 112.97 ChemAxon
Polarizability 43.93 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.008 +/- 0.016 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
2.99 +/- 5.39 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
3.12 +/- 1.2 uM Adult (>18 years old) Not Specified Comment Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.01165 +/- 0.00753 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00255 +/- 0.00178 uM Adult (>18 years old) Both epileptic patients
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023303
KNApSAcK ID Not Available
Chemspider ID 4445241 Link_out
KEGG Compound ID C11695 Link_out
BioCyc ID CPD-7598 Link_out
BiGG ID Not Available
Wikipedia Link Anandamide Link_out
NuGOwiki Link HMDB04080 Link_out
Metagene Link HMDB04080 Link_out
METLIN ID Not Available
PubChem Compound 5281969 Link_out
PDB ID Not Available
ChEBI ID 2700 Link_out
References
Synthesis Reference Qi, 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 Link_out
  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 Link_out
  3. Sang N, Chen C: Lipid signaling and synaptic plasticity. Neuroscientist. 2006 Oct;12(5):425-34. Pubmed: 16957004 Link_out
Enzymes
Name: Fatty-acid amide hydrolase 1
Reactions:
Anandamide + Water unknown Arachidonic acid + Ethanolamine details
Gene Name: FAAH
Uniprot ID: O00519 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Abhydrolase domain-containing protein 4
Reactions: Not Available
Gene Name: ABHD4
Uniprot ID: Q8TB40 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: N-acyl-phosphatidylethanolamine-hydrolyzing phospholipase D
Reactions: Not Available
Gene Name: NAPEPLD
Uniprot ID: Q6IQ20 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fatty-acid amide hydrolase 2
Reactions:
Anandamide + Water unknown Arachidonic acid + Ethanolamine details
Gene Name: FAAH2
Uniprot ID: Q6GMR7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cannabinoid receptor 1
Reactions: Not Available
Gene Name: CNR1
Uniprot ID: P21554 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA