ascochlorin

CHEBI:156219 ·resolve ·ANTIFUNGAL ·EXACT REVIEWED

A dihydroxybenzaldehyde that is 2,4-dihydroxybenzaldehyde which is substituted by a (1E,3E)-3-methyl-1-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-1,3-dien-5-yl group at position 3, chlorine at position 5, and a methyl group at position 6. A meroterpenoid produced by several fungi including Ascochyta viciae . It exhibits anticancer, antifungal and antiprotozoal activities. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:23482
Label unavailable CHEBI:26658
Label unavailable CHEBI:33572
Label unavailable CHEBI:50196
Label unavailable CHEBI:64419
Label unavailable CHEBI:78840
Label unavailable CHEBI:83403

Chemical structure

Computed structure properties
Molecular formula	C23H29ClO4
Charge	0
Average mass	404.934 Da
Monoisotopic mass	404.17544 Da
Source	ChEBI
InChIKey	SETVRSKZJJWOPA-FLDGXQSCSA-N

SMILES

[H]C(=O)c1c(C)c(Cl)c(O)c(C/C=C(C)/C=C/[C@@]2(C)[C@H](C)CCC(=O)[C@@H]2C)c1O

InChI

InChI=1S/C23H29ClO4/c1-13(10-11-23(5)14(2)7-9-19(26)16(23)4)6-8-17-21(27)18(12-25)15(3)20(24)22(17)28/h6,10-12,14,16,27-28H,7-9H2,1-5H3/b11-10+,13-6+/t14-,16+,23+/m1/s1

Also called

3-chloro-4,6-dihydroxy-2-methyl-5-{(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl}benzaldehyde (EXACT_SYNONYM)— chebi
(−)-ascochlorin (EXACT_SYNONYM)— chebi
LL-Z 1272 gamma (EXACT_SYNONYM)— chebi
antibiotic LL-Z1272 gamma (EXACT_SYNONYM)— chebi
antibiotic LL-Z1272γ (EXACT_SYNONYM)— chebi
ilicicolin D (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.

Activity roles

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

antifungal agent CHEBI:35718
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:156219`	ascochlorin	`antibioticmech:chebi-31a6bebed5`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

cytochrome bc1 complex Qi and Qo ubiquinone sites PROTEIN_COMPLEX DIRECT_BINDING_TARGET

Electron-transport assays used Pichia anomala mitochondria and purified bacterial and bovine complexes; EPR/kinetic experiments and a chicken bc1 crystal structure established occupation of both Qi and Qo sites. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2009-12 (retrieved 2026-09-02).

PMID:20025846 (Primary multi-system cytochrome-bc1 inhibition and cocrystal study (DOI:10.1016/j.bbabio.2009.12.003).)

Mechanism summary

Mode of action: ENERGY_METABOLISM_INHIBITION host shared target — CURATOR: PMID:20025846 measured ascochlorin inhibition of fungal, bacterial, and mammalian cytochrome bc1 complexes and resolved ascochlorin at both the Qi and Qo sites of chicken mitochondrial bc1. The combined kinetic, spectroscopic, and crystallographic evidence supports dual-site respiratory-chain inhibition and also shows that the target is host-shared.

Record-level evidence

PMID:20025846 (Primary ascochlorin dual-site cytochrome-bc1 mechanism study.)

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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI identity, structure, antifungal/antiprotozoal roles, and antifungal filing class; added dual-site respiratory-chain inhibition and direct cytochrome-bc1 target evidence with host-shared scope.

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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