CHEBI:143514 - N-arachidonoyl-L-serine

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ChEBI Name N-arachidonoyl-L-serine
ChEBI ID CHEBI:143514
ChEBI ASCII Name N-arachidonoyl-L-serine
Definition An N-acyl-amino acid resulting from the formal condensation of the carboxy group of arachidonic acid with the amino group of L-serine. It is an endocannabinoid-like lipid isolated from bovine brains.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter TheOtherDave
Supplier Information
Download Molfile XML SDF
Formula C23H37NO4
Net Charge 0
Average Mass 391.552
Monoisotopic Mass 391.27226
InChI InChI=1S/C23H37NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(26)24-21(20-25)23(27)28/h6-7,9-10,12-13,15-16,21,25H,2-5,8,11,14,17-20H2,1H3,(H,24,26)(H,27,28)/b7-6-,10-9-,13-12-,16-15-/t21-/m0/s1
InChIKey FQUVPTVNRMUOPO-UPQKDGGNSA-N
SMILES C(CCC)C/C=C\C/C=C\C/C=C\C/C=C\CCCC(N[C@H](C(=O)O)CO)=O
Metabolite of Species Details
Bos taurus (NCBI:txid9913) Found in brain (BTO:0000142). See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): cannabinoid receptor agonist
An agonist that binds to and activates cannabinoid receptors.
mammalian metabolite
Any animal metabolite produced during a metabolic reaction in mammals.
Application(s): vasodilator agent
A drug used to cause dilation of the blood vessels.
pro-angiogenic agent
Any compound that promotes the growth of new blood vessels from pre-existing vessels.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing N-arachidonoyl-L-serine (CHEBI:143514) has functional parent L-serine (CHEBI:17115)
N-arachidonoyl-L-serine (CHEBI:143514) has functional parent arachidonic acid (CHEBI:15843)
N-arachidonoyl-L-serine (CHEBI:143514) has role cannabinoid receptor agonist (CHEBI:67072)
N-arachidonoyl-L-serine (CHEBI:143514) has role mammalian metabolite (CHEBI:75768)
N-arachidonoyl-L-serine (CHEBI:143514) has role neuroprotective agent (CHEBI:63726)
N-arachidonoyl-L-serine (CHEBI:143514) has role pro-angiogenic agent (CHEBI:72571)
N-arachidonoyl-L-serine (CHEBI:143514) has role vasodilator agent (CHEBI:35620)
N-arachidonoyl-L-serine (CHEBI:143514) is a N-(fatty acyl)-L-α-amino acid (CHEBI:137550)
N-arachidonoyl-L-serine (CHEBI:143514) is conjugate acid of N-arachidonoyl-L-serine(1−) (CHEBI:149697)
Incoming N-arachidonoyl-L-serine(1−) (CHEBI:149697) is conjugate base of N-arachidonoyl-L-serine (CHEBI:143514)
IUPAC Name
N-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]-L-serine
Synonyms Sources
(2S)-3-hydroxy-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenamido]propanoic acid ChEBI
(2S)-3-hydroxy-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propanoic acid ChEBI
ARA-S SUBMITTER
C20:4(5Z,8Z,11Z,14Z)-L-Ser ChEBI
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serine SUBMITTER
N-(5Z,8Z,11Z,14Z-icosatetraenoyl)-L-serine ChEBI
N-[(5Z,8Z,11Z,14Z)-1-Oxo-5,8,11,14-icosatetraenyl]-L-serine ChEBI
Manual Xref Database
LMFA08020073 LIPID MAPS
View more database links
Registry Number Type Source
187224-29-9 CAS Registry Number SUBMITTER
Citations Waiting for Citations Types Sources
16467152 PubMed citation SUBMITTER
18234973 PubMed citation Europe PMC
18923087 PubMed citation Europe PMC
20649562 PubMed citation Europe PMC
20649563 PubMed citation Europe PMC
21505478 PubMed citation Europe PMC
23695434 PubMed citation Europe PMC
28955964 PubMed citation Europe PMC
Last Modified
23 June 2020