kavapyrone

CHEBI:6116 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

A pyranone that is 2H-pyran-2-one substituted by a methoxy group at position 4 and a 3-phenyloxiran-2-yl group at position 6 (the 2R,3S stereoisomer). Isolated from Didymocarpus aurantiacus and Piper rusbyi, it exhibits antileishmanial 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:25698 CHEBI:25698
CHEBI:32955 CHEBI:32955
CHEBI:75885 CHEBI:75885

Chemical structure

Computed structure properties
Molecular formula	C14H12O4
Charge	0
Average mass	244.246 Da
Monoisotopic mass	244.07356 Da
Source	ChEBI
InChIKey	MLGUXXSGWWCJQW-KBPBESRZSA-N

SMILES

COc1cc([C@@H]2O[C@H]2c2ccccc2)oc(=O)c1

InChI

InChI=1S/C14H12O4/c1-16-10-7-11(17-12(15)8-10)14-13(18-14)9-5-3-2-4-6-9/h2-8,13-14H,1H3/t13-,14-/m0/s1

Also called

4-methoxy-6-[(2R,3S)-3-phenyloxiran-2-yl]-2H-pyran-2-one (EXACT_SYNONYM)— chebi
(+)-(7R,8S)-epoxy-5,6-didehydrokavain (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:11152408

Activity roles

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

CHEBI:70868 CHEBI:70868

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:6116`	kavapyrone	`antibioticmech:chebi-b3e1fe9872`	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.