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CHEBI:143514 - N-arachidonoyl-L-serine

ChEBI IDCHEBI:143514
ChEBI NameN-arachidonoyl-L-serine
Stars
ASCII NameN-arachidonoyl-L-serine
DefinitionAn 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.
Last Modified23 June 2020
SubmitterTheOtherDave
DownloadsMolfile
FormulaC23H37NO4
Net Charge0
Average Mass391.552
Monoisotopic Mass391.27226
SMILESCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N[C@@H](CO)C(=O)O
InChIInChI=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
InChIKeyFQUVPTVNRMUOPO-UPQKDGGNSA-N
Species of MetaboliteComponentSourceComments
Bos taurus (ncbitaxon:9913) brain (BTO:0000142) PubMed (16467152)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
cannabinoid receptor agonist  An agonist that binds to and activates cannabinoid receptors.
mammalian metabolite  Any animal metabolite produced during a metabolic reaction in mammals.
Applications:
vasodilator agent  A drug used to cause dilation of the blood vessels.
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
pro-angiogenic agent  Any compound that promotes the growth of new blood vessels from pre-existing vessels.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
ARA-SSUBMITTER
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serineSUBMITTER
N-[(5Z,8Z,11Z,14Z)-1-Oxo-5,8,11,14-icosatetraenyl]-L-serineChEBI
(2S)-3-hydroxy-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenamido]propanoic acidChEBI
(2S)-3-hydroxy-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propanoic acidChEBI
N-(5Z,8Z,11Z,14Z-icosatetraenoyl)-L-serineChEBI
Manual XrefsDatabases
LMFA08020073LIPID MAPS
Registry NumbersSources
CAS:187224-29-9SUBMITTER
Citations