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.

Label unavailable CHEBI:26658
Label unavailable CHEBI:33572
Label unavailable CHEBI:47016
Label unavailable CHEBI:50196
Label unavailable CHEBI:64419
Label unavailable CHEBI:78840
Label unavailable 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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

wikipedia.en:Ascofuranone

Activity roles

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

antiprotozoal drug 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
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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