ascofuranone

CHEBI:156148 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

A dihydroxybenzaldehyde that is 2,4-dihydroxybenzaldehyde which is substituted by a (2E,6E)-7-[(2S)-5,5-dimethyl-4-oxotetrahydrofuran-2-yl]-3-methylocta-2,6-dien-1-yl group at position 3, chlorine at position 5, and a methyl group at position 6. A meroterpenoid produced by the soil fungus, Acremonium sclerotigenum. It is a promising drug candidate against the tropical disease, African trypanosomiasis. — 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:26658 CHEBI:26658
CHEBI:33572 CHEBI:33572
CHEBI:47016 CHEBI:47016
CHEBI:50196 CHEBI:50196
CHEBI:64419 CHEBI:64419
CHEBI:78840 CHEBI:78840
CHEBI:83403 CHEBI:83403

Chemical structure

Computed structure properties
Molecular formula	C23H29ClO5
Charge	0
Average mass	420.933 Da
Monoisotopic mass	420.17035 Da
Source	ChEBI
InChIKey	VGYPZLGWVQQOST-JUERRSSISA-N

SMILES

[H]C(=O)c1c(C)c(Cl)c(O)c(C/C=C(\C)CC/C=C(\C)[C@]2([H])CC(=O)C(C)(C)O2)c1O

InChI

InChI=1S/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1

Also called

3-chloro-5-{(2E,6E)-7-[(2S)-5,5-dimethyl-4-oxotetrahydrofuran-2-yl]-3-methylocta-2,6-dien-1-yl}-4,6-dihydroxy-2-methylbenzaldehyde (EXACT_SYNONYM)— chebi
(S)-ascofuranone (EXACT_SYNONYM)— chebi
(S-(E,E))-3-chloro-4,6-dihydroxy-2-methyl-5-(3-methyl-7-(tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)-2,6-octadienyl)-benzaldehyde (EXACT_SYNONYM)— chebi
(−)-ascofuranone (EXACT_SYNONYM)— chebi
ascofuranon (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:38462-04-3
knapsack:C00017973
wikipedia.en:Ascofuranone

Activity roles

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

CHEBI:35820 CHEBI:35820

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:156148`	ascofuranone	`antibioticmech:chebi-1fd877718e`	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.