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CHEBI:2700 - anandamide

ChEBI IDCHEBI:2700
ChEBI Nameanandamide
Stars
DefinitionAn N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.
Secondary ChEBI IDCHEBI:88116
Last Modified24 March 2022
SubmitterBijay
DownloadsMolfile
FormulaC22H37NO2
Net Charge0
Average Mass347.543
Monoisotopic Mass347.28243
SMILESCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO
InChIInChI=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-
InChIKeyLGEQQWMQCRIYKG-DOFZRALJSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606)
- DOI (10.1038/nbt.2488)
cerebrospinal fluid (UBERON:0001359) PubMed (19817812)
blood (UBERON:0000178) PubMed (16118355)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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.
cannabinoid receptor agonist  An agonist that binds to and activates cannabinoid receptors.
cannabinoid receptor agonist  An agonist that binds to and activates cannabinoid receptors.
Application:
vasodilator agent  A drug used to cause dilation of the blood vessels.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
AnandamideKEGG COMPOUND
ArachidonylethanolamideKEGG COMPOUND
N-(5Z,8Z,11Z,14Z-icosatetraenoyl)-ethanolamideKEGG COMPOUND
(all-Z)-N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamideChemIDplus
(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)-5,8,11,14-eicosatetraenamideChemIDplus
arachidonoyl ethanolamideChemIDplus
UniProt Name  Source
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamineUniProt
Manual XrefsDatabases
C11695KEGG COMPOUND
LMFA08040001LIPID MAPS
AnandamideWikipedia
HMDB0004080HMDB
CPD-7598MetaCyc
E7YPDBeChem
4445241ChemSpider
FDB023303FooDB
Registry NumbersSources
Reaxys:7079463Reaxys
CAS:94421-68-8KEGG COMPOUND
CAS:94421-68-8ChemIDplus
Citations