CHEBI:2700 - anandamide

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name anandamide
Definition An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Bijay
Secondary ChEBI IDs CHEBI:88116
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C22H37NO2
Net Charge 0
Average Mass 347.543
Monoisotopic Mass 347.28243
InChI 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-
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) See: DOI
Homo sapiens (NCBI:txid9606) Found in blood (UBERON:0000178). See: PubMed
Homo sapiens (NCBI:txid9606) Found in cerebrospinal fluid (UBERON:0001359). See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via endocannabinoid )
cannabinoid receptor agonist
An agonist that binds to and activates cannabinoid receptors.
(via cannabinoid )
Application(s): vasodilator agent
A drug used to cause dilation of the blood vessels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing anandamide (CHEBI:2700) has functional parent arachidonic acid (CHEBI:15843)
anandamide (CHEBI:2700) has role human blood serum metabolite (CHEBI:85234)
anandamide (CHEBI:2700) has role neurotransmitter (CHEBI:25512)
anandamide (CHEBI:2700) has role vasodilator agent (CHEBI:35620)
anandamide (CHEBI:2700) is a N-acylethanolamine 20:4 (CHEBI:134161)
anandamide (CHEBI:2700) is a endocannabinoid (CHEBI:67197)
Incoming N-(20-hydroxyarachidonoyl)ethanolamine (CHEBI:136992) has functional parent anandamide (CHEBI:2700)
N-[(5Z,11Z,14Z)-8,9-epoxyicosatrienoyl]ethanolamine (CHEBI:136989) has functional parent anandamide (CHEBI:2700)
N-[(5Z,8Z,11Z)-14,15-epoxyicosatrienoyl]ethanolamine (CHEBI:136991) has functional parent anandamide (CHEBI:2700)
N-[(5Z,8Z,14Z)-11,12-epoxyicosatrienoyl]ethanolamine (CHEBI:136990) has functional parent anandamide (CHEBI:2700)
N-[(8Z,11Z,14Z)-5,6-epoxyicosatrienoyl]ethanolamine (CHEBI:136988) has functional parent anandamide (CHEBI:2700)
N-arachidonoylethanolamine phosphate(2−) (CHEBI:131894) has functional parent anandamide (CHEBI:2700)
O-oleoylanandamide (CHEBI:76070) has functional parent anandamide (CHEBI:2700)
Synonyms Sources
(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide ChemIDplus
(all-Z)-N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamide ChemIDplus
Anandamide (20.4, N-6) HMDB
Anandamide(20:4, N-6) HMDB
Arachidonic acid N-(hydroxyethyl)amide HMDB
arachidonoyl ethanolamide ChemIDplus
Arachidonylethanolamide KEGG COMPOUND
N-(2-Hydroxyethyl)anachidonamide HMDB
N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-ethanolamine HMDB
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine UniProt
N-(5Z,8Z,11Z,14Z-icosatetraenoyl)-ethanolamide KEGG COMPOUND
N-arachidonoyl ethanolamine HMDB
N-arachidonoyl-2-hydroxyethylamide ChemIDplus
N-arachidonoylethanolamine ChEBI
Manual Xrefs Databases
4445241 ChemSpider
Anandamide Wikipedia
CPD-7598 MetaCyc
E7Y PDBeChem
FDB023303 FooDB
HMDB0004080 HMDB
View more database links
Registry Numbers Types Sources
7079463 Beilstein Registry Number Beilstein
7079463 Reaxys Registry Number Reaxys
94421-68-8 CAS Registry Number KEGG COMPOUND
94421-68-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15047233 PubMed citation Europe PMC
15797258 PubMed citation Europe PMC
15944392 PubMed citation Europe PMC
15997233 PubMed citation Europe PMC
16118355 PubMed citation Europe PMC
16957004 PubMed citation Europe PMC
18227059 PubMed citation Europe PMC
18691603 PubMed citation Europe PMC
19330032 PubMed citation Europe PMC
29363071 PubMed citation Europe PMC
29546791 PubMed citation Europe PMC
31610409 PubMed citation Europe PMC
32195347 PubMed citation Europe PMC
33551019 PubMed citation Europe PMC
33713246 PubMed citation Europe PMC
33731590 PubMed citation Europe PMC
Last Modified
24 March 2022