CHEBI:2700 - anandamide

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ChEBI Name anandamide
ChEBI ID CHEBI:2700
Definition An N-(polyunsaturated fatty acyl)ethanolamine resulting from the formal condensation of carboxy group of arachidonic acid with amino group of ethanolamine.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Bijay
Secondary ChEBI IDs CHEBI:88116
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Formula C22H37NO2
Net Charge 0
Average Mass 347.536
Monoisotopic Mass 347.282
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-
InChIKey LGEQQWMQCRIYKG-DOFZRALJSA-N
SMILES C(CCC)C/C=C\C/C=C\C/C=C\C/C=C\CCCC(NCCO)=O
Metabolite of Species Details
Homo sapiens (NCBI:9606) See: DOI
Homo sapiens (NCBI:9606) Found in blood (UBERON:0000178). See: PubMed
Homo sapiens (NCBI:9606) Found in cerebrospinal fluid (UBERON:0001359). See: PubMed
Roles Classification
Biological Role(s): human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
neurotransmitter
An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.
metabolite
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.
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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-(long-chain-acyl)ethanolamine (CHEBI:15897)
anandamide (CHEBI:2700) is a N-(polyunsaturated fatty acyl)ethanolamine (CHEBI:85281)
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)
IUPAC Name
(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
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
AEA KEGG COMPOUND
Anandamide KEGG COMPOUND
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
Database Links Databases
Anandamide Wikipedia
C11695 KEGG COMPOUND
CPD-7598 MetaCyc
HMDB0004080 HMDB
LMFA08040001 LIPID MAPS
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
15997233 PubMed citation Europe PMC
16118355 PubMed citation Europe PMC
16957004 PubMed citation Europe PMC
18691603 PubMed citation Europe PMC
19330032 PubMed citation Europe PMC
Last Modified
18 May 2017