aspyrone

CHEBI:156387 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A member of the class of 2-pyranones that is 5,6-dihydro-2H-pyran-2-one in which the hydrogens at positions 3, 5S and 6R are replaced by (2S,3S)-3-methyloxiran-2-yl, hydroxy and methyl groups, respectively. It is a fungal metabolite isolated from Aspergillus melleus and exhibits nematicidal, antibacterial and antifungal properties. — 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:26188 CHEBI:26188
CHEBI:32955 CHEBI:32955
CHEBI:35681 CHEBI:35681
CHEBI:75885 CHEBI:75885
CHEBI:86478 CHEBI:86478

Chemical structure

Computed structure properties
Molecular formula	C9H12O4
Charge	0
Average mass	184.191 Da
Monoisotopic mass	184.07356 Da
Source	ChEBI
InChIKey	RCAULRNMJFUWRP-HETMPLHPSA-N

SMILES

[H][C@@]1(C2=C[C@H](O)[C@@H](C)OC2=O)O[C@@]1([H])C

InChI

InChI=1S/C9H12O4/c1-4-7(10)3-6(9(11)13-4)8-5(2)12-8/h3-5,7-8,10H,1-2H3/t4-,5+,7+,8-/m1/s1

Also called

(5S,6R)-5-hydroxy-6-methyl-3-[(2S,3S)-3-methyloxiran-2-yl]-5,6-dihydro-2H-pyran-2-one (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:17398-00-4

Activity roles

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

CHEBI:33282 CHEBI:33282
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:156387`	aspyrone	`antibioticmech:chebi-ee352b983d`	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.