(R)-N-trans-feruloyloctopamine

CHEBI:67373 ·resolve ·ANTIMYCOBACTERIAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:140325 CHEBI:140325
CHEBI:23247 CHEBI:23247
CHEBI:25235 CHEBI:25235
CHEBI:33853 CHEBI:33853

Chemical structure

Computed structure properties
Molecular formula	C18H19NO5
Charge	0
Average mass	329.352 Da
Monoisotopic mass	329.12632 Da
Source	ChEBI
InChIKey	VJSCHQMOTSXAKB-CFZDNBDDSA-N

SMILES

COc1cc(/C=C/C(=O)NC[C@H](O)c2ccc(O)cc2)ccc1O

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

Also called

(2E)-N-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide (EXACT_SYNONYM)— chebi
(2S,E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]ferulamide (EXACT_SYNONYM)— chebi
N-[2-(R)-hydroxy-2-(4-hydroxy-phenyl)ethyl]-3-(4-hydroxy-3-methoxy-phenyl)acrylamide (EXACT_SYNONYM)— chebi
(R)-N-[(E)-feruloyl]octopamine (RELATED_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:9579371

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33231 CHEBI:33231

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:67373`	(R)-N-trans-feruloyloctopamine	`antibioticmech:chebi-323b67c54c`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.