aurafuron A

CHEBI:156298 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A polyketide that is 2,3-dihydrofuran substituted by hydroxy, methyl, oxo, methyl and (2S,3Z,5E,7R,8R,9E)-2,8-dihydroxy-7,9,12-trimethyltrideca-3,5,9-trien-1-yl groups at positions 2, 2, 3, 4, and 5, respectively. It is a cytotoxic natural product found in several myxobacteria species and inhibits the growth of some filamentous fungi. — 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:134396 CHEBI:134396
CHEBI:139592 CHEBI:139592
CHEBI:26188 CHEBI:26188
CHEBI:26912 CHEBI:26912
CHEBI:27136 CHEBI:27136
CHEBI:35681 CHEBI:35681
CHEBI:38131 CHEBI:38131

Chemical structure

Computed structure properties
Molecular formula	C22H34O5
Charge	0
Average mass	378.509 Da
Monoisotopic mass	378.24062 Da
Source	ChEBI
InChIKey	AQQYZHDRTDSOER-LYKBUVKOSA-N

SMILES

CC1=C(C[C@H](O)/C=C\C=C\[C@@H](C)[C@@H](O)/C(C)=C/CC(C)C)OC(C)(O)C1=O

InChI

InChI=1S/C22H34O5/c1-14(2)11-12-16(4)20(24)15(3)9-7-8-10-18(23)13-19-17(5)21(25)22(6,26)27-19/h7-10,12,14-15,18,20,23-24,26H,11,13H2,1-6H3/b9-7+,10-8-,16-12+/t15-,18-,20-,22?/m1/s1

Also called

5-[(2S,3Z,5E,7R,8R,9E)-2,8-dihydroxy-7,9,12-trimethyltrideca-3,5,9-trien-1-yl]-2-hydroxy-2,4-dimethylfuran-3(2H)-one (EXACT_SYNONYM)— chebi
(−)-aurafuron A (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

chemspider:9948038

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:156298`	aurafuron A	`antibioticmech:chebi-d81058d91e`	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.