CHEBI:67373 - (R)-N-trans-feruloyloctopamine

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ChEBI Name (R)-N-trans-feruloyloctopamine
ChEBI ID CHEBI:67373
ChEBI ASCII Name (R)-N-trans-feruloyloctopamine
Definition A member of the class of cinnamamides that is an enamide obtained by the formal condensation of the amino group of (R)-octopamine with the carboxy group of ferulic acid. Isolated from Pisonia aculeata, it exhibits antitubercular activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C18H19NO5
Net Charge 0
Average Mass 329.34720
Monoisotopic Mass 329.12632
InChI InChI=1S/C18H19NO5/c1-24-17-10-12(2-8-15(17)21)3-9-18(23)19-11-16(22)13-4-6-14(20)7-5-13/h2-10,16,20-22H,11H2,1H3,(H,19,23)/b9-3+/t16-/m0/s1
InChIKey VJSCHQMOTSXAKB-CFZDNBDDSA-N
SMILES COc1cc(\C=C\C(=O)NC[C@H](O)c2ccc(O)cc2)ccc1O
Metabolite of Species Details
Pisonia aculeata (NCBI:txid363212) Found in stem (BTO:0001300). Cold methanolic extract of dried stems and roots See: PubMed
Pisonia aculeata (NCBI:txid363212) Found in root (BTO:0001188). Cold methanolic extract of dried stems and roots See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antitubercular agent
A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
Application(s): antitubercular agent
A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (R)-N-trans-feruloyloctopamine (CHEBI:67373) has functional parent (R)-octopamine (CHEBI:44715)
(R)-N-trans-feruloyloctopamine (CHEBI:67373) has functional parent ferulic acid (CHEBI:17620)
(R)-N-trans-feruloyloctopamine (CHEBI:67373) has role antitubercular agent (CHEBI:33231)
(R)-N-trans-feruloyloctopamine (CHEBI:67373) has role metabolite (CHEBI:25212)
(R)-N-trans-feruloyloctopamine (CHEBI:67373) has role plant metabolite (CHEBI:76924)
(R)-N-trans-feruloyloctopamine (CHEBI:67373) is a cinnamamides (CHEBI:23247)
(R)-N-trans-feruloyloctopamine (CHEBI:67373) is a monomethoxybenzene (CHEBI:25235)
(R)-N-trans-feruloyloctopamine (CHEBI:67373) is a phenols (CHEBI:33853)
(R)-N-trans-feruloyloctopamine (CHEBI:67373) is a secondary carboxamide (CHEBI:140325)
IUPAC Name
(2E)-N-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
Synonyms Sources
(2S,E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]ferulamide ChEBI
N-[2-(R)-hydroxy-2-(4-hydroxy-phenyl)ethyl]-3-(4-hydroxy-3-methoxy-phenyl)acrylamide ChEBI
Registry Number Type Source
9579371 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21542597 PubMed citation Europe PMC
Last Modified
07 March 2018