CHEBI:31883 - N-oleoyldopamine

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ChEBI Name N-oleoyldopamine
ChEBI ID CHEBI:31883
ChEBI ASCII Name N-oleoyldopamine
Definition A fatty amide resulting from the formal condensation of the carboxy group of oleic acid with the amino group of dopamine. Synthesised in catecholaminergic neurons, it crosses the blood-brain barrier and might be considered as a carrier of dopamine into the brain. It is a transient receptor potential vanilloid type 1 (TRPV1) receptor agonist.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C26H43NO3
Net Charge 0
Average Mass 417.626
Monoisotopic Mass 417.32429
InChI InChI=1S/C26H43NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-26(30)27-21-20-23-18-19-24(28)25(29)22-23/h9-10,18-19,22,28-29H,2-8,11-17,20-21H2,1H3,(H,27,30)/b10-9-
InChIKey QQBPLXNESPTPNU-KTKRTIGZSA-N
SMILES C=1(C=CC(=CC1O)CCNC(CCCCCCC/C=C\CCCCCCCC)=O)O
Roles Classification
Biological Role(s): TRPV1 agonist
An agonist at the transient receptor potential vanilloid 1 (TRPV1).
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ChEBI Ontology
Outgoing N-oleoyldopamine (CHEBI:31883) has functional parent dopamine (CHEBI:18243)
N-oleoyldopamine (CHEBI:31883) has functional parent oleic acid (CHEBI:16196)
N-oleoyldopamine (CHEBI:31883) has role TRPV1 agonist (CHEBI:140535)
N-oleoyldopamine (CHEBI:31883) is a N-(fatty acyl)-dopamine (CHEBI:157740)
N-oleoyldopamine (CHEBI:31883) is a catechols (CHEBI:33566)
N-oleoyldopamine (CHEBI:31883) is a fatty amide (CHEBI:29348)
N-oleoyldopamine (CHEBI:31883) is a secondary carboxamide (CHEBI:140325)
IUPAC Name
(9Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]octadec-9-enamide
Synonyms Sources
N-(9Z-octadecanoyl)-dopamine UniProt
N-[2-(3,4-dihydroxyphenyl)ethyl]-9Z-octadecenamide LIPID MAPS
N-oleoyl dopamine KEGG COMPOUND
OLDA LIPID MAPS
Manual Xrefs Databases
C12272 KEGG COMPOUND
LMFA08020140 LIPID MAPS
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Registry Number Type Source
105955-11-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
17166411 PubMed citation Europe PMC
19309549 PubMed citation Europe PMC
19901198 PubMed citation Europe PMC
24817351 PubMed citation Europe PMC
28400256 PubMed citation Europe PMC
Last Modified
10 April 2018