piperyline

CHEBI:9691 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A N-acylpyrrolidine that is pyrollidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum. — 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:140326 CHEBI:140326
CHEBI:26456 CHEBI:26456
CHEBI:38298 CHEBI:38298
CHEBI:46766 CHEBI:46766

Chemical structure

Computed structure properties
Molecular formula	C16H17NO3
Charge	0
Average mass	271.316 Da
Monoisotopic mass	271.12084 Da
Source	ChEBI
InChIKey	GQIJYUMTOUBHSH-IJIVKGSJSA-N

SMILES

O=C(/C=C/C=C/c1ccc2c(c1)OCO2)N1CCCC1

InChI

InChI=1S/C16H17NO3/c18-16(17-9-3-4-10-17)6-2-1-5-13-7-8-14-15(11-13)20-12-19-14/h1-2,5-8,11H,3-4,9-10,12H2/b5-1+,6-2+

Also called

(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one (EXACT_SYNONYM)— chebi
(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(1-pyrrolidinyl)-2,4-pentadien-1-one (EXACT_SYNONYM)— chebi
(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one (EXACT_SYNONYM)— chebi
1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]pyrrolidine (EXACT_SYNONYM)— chebi
piperiline (EXACT_SYNONYM)— chebi
piperylin (EXACT_SYNONYM)— chebi
pyrroperine (EXACT_SYNONYM)— chebi
trichostachin (EXACT_SYNONYM)— chebi
trichostachine (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:25924-78-1
chemspider:552302
foodb.food:FDB000444
hmdb:HMDB0029374
kegg.compound:C10174
knapsack:C00002076
reaxys:29164

Activity roles

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

CHEBI:35718 CHEBI:35718

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:9691`	piperyline	`antibioticmech:chebi-4c179b90c8`	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.