Record Information
Version1.0
Creation date2011-09-21 00:27:47 UTC
Update date2015-07-21 06:57:38 UTC
Primary IDFDB023303
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number94421-68-8
Structure
Thumb
Synonyms
SynonymSource
(5Z,8Z,11Z,14Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamideChEBI
(all-Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamideChEBI
5,8,11,14-Eicosatetraenoylethanolamidehmdb
AEAhmdb
Anandamidehmdb
Anandamide (20.4, n-6)hmdb
Anandamide(20:4, n-6)hmdb
Arachidonic acid n-(hydroxyethyl)amidehmdb
Arachidonoyl ethanolamideChEBI
Arachidonylethanolamidehmdb
N-(2-hydroxyethyl)-5,8,11,14-Eicosatetraenamide (all-Z)hmdb
N-(2-Hydroxyethyl)anachidonamidehmdb
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolaminehmdb
N-(5Z,8Z,11Z,14Z-icosatetraenoyl)-ethanolamidehmdb
N-arachidonoyl ethanolaminehmdb
N-Arachidonoyl-2-hydroxyethylamidehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.00025 g/LALOGPS
logP6.22ALOGPS
logP6.13ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)4.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.82 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity113.49 m³·mol⁻¹ChemAxon
Polarizability42.69 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC22H37NO2
IUPAC nameN-(2-hydroxyethyl)icosa-5,8,11,14-tetraenimidic acid
InChI IdentifierInChI=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)
InChI KeyLGEQQWMQCRIYKG-UHFFFAOYSA-N
Isomeric SMILESCCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCO
Average Molecular Weight347.5347
Monoisotopic Molecular Weight347.282429433
Classification
DescriptionThis compound belongs to the class of chemical entities known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboximidic acids and derivatives
Direct ParentCarboximidic acids
Alternative Parents
Substituents
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid
  • Alkanolamine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID4445241
ChEMBL IDCHEMBL15848
KEGG Compound IDC11695
Pubchem Compound ID5281969
Pubchem Substance IDNot Available
ChEBI ID2700
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04080
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAnandamide
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Fatty-acid amide hydrolase 1FAAHO00519
Fatty-acid amide hydrolase 2FAAH2Q6GMR7
Abhydrolase domain-containing protein 4ABHD4Q8TB40
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference