ascochlorin

CHEBI:156219 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

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

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

Equivalent identifiers for this same structure in other resources.

cas:26166-39-2
knapsack:C00018754
pdb-ccd:3H1

Activity roles

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

CHEBI:35718 CHEBI:35718
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:156219`	ascochlorin	`antibioticmech:chebi-31a6bebed5`	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.