5α-epoxyalantolactone

CHEBI:65856 ·resolve ·ANTIMYCOBACTERIAL ·EXACT SEEDED

A sesquiterpene lactone that is the 5α-epoxy derivative of alantolactone. Isolated from the root extracts of Inula helenium, it exhibits antimycobacterial 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:32955 CHEBI:32955
CHEBI:37667 CHEBI:37667
CHEBI:39270 CHEBI:39270

Chemical structure

Computed structure properties
Molecular formula	C15H20O3
Charge	0
Average mass	248.322 Da
Monoisotopic mass	248.14124 Da
Source	ChEBI
InChIKey	YIQKVCDNUFDAHB-HKKVUVRFSA-N

SMILES

[H][C@@]12C[C@@]3(C)CCC[C@H](C)[C@@]34O[C@H]4[C@]1([H])C(=C)C(=O)O2

InChI

InChI=1S/C15H20O3/c1-8-5-4-6-14(3)7-10-11(9(2)13(16)17-10)12-15(8,14)18-12/h8,10-12H,2,4-7H2,1,3H3/t8-,10+,11+,12-,14+,15-/m0/s1

Also called

(1aR,2S,5aR,6aR,9aR,9bS)-2,5a-dimethyl-9-methylideneoctahydro-2H-oxireno[4,4a]naphtho[2,3-b]furan-8(9H)-one (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:5031399

Activity roles

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

CHEBI:64912 CHEBI:64912

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:65856`	5α-epoxyalantolactone	`antibioticmech:chebi-332800b909`	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.