ascochlorin
CHEBI:156219 EXACT SEEDED antifungalenzyme inhibitor
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.
Structure
| Standard InChIKey | SETVRSKZJJWOPA-FLDGXQSCSA-N |
|---|---|
| SMILES | C[C@@H]1CCC(=O)[C@@H]([C@@]1(C)/C=C/C(=C/CC2=C(C(=C(C(=C2O)Cl)C)C=O)O)/C)C |
| Stereochemistry | fully defined |
| Cross-references | pubchem:11258227 |
Filing pathway
Unclassified — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is terpene, pks, from MIBiG.
Producer organisms 1
A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| Acremonium egyptiacum NCBITaxon:749675 |
SOURCE_ASSERTION | mibig:BGC0001923 | DOI:10.1002/ijc.24259 |
Occurrences 11
Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.
| Taxon | Source | Reference |
|---|---|---|
| Verticillium NCBITaxon:1036719 |
LOTUS | DOI:10.1248/CPB.42.953 |
| Acremonium NCBITaxon:159075 |
LOTUS | DOI:10.1021/NP8006793 |
| Ascochyta viciae NCBITaxon:1677696 |
LOTUS | DOI:10.7164/ANTIBIOTICS.21.539 |
| Ascochyta viciae NCBITaxon:1677696 |
CHEBI | PMID:31028855 |
| Streptomyces NCBITaxon:1883 |
LOTUS | DOI:10.1080/14786419.2018.1556265 |
| Fusarium NCBITaxon:5506 |
LOTUS | DOI:10.1016/S0040-4020(01)82703-4 |
| Gliomastix luzulae NCBITaxon:61182 |
LOTUS | DOI:10.1039/P19770000351 |
| Nigrosabulum globosum NCBITaxon:95328 |
LOTUS | DOI:10.1021/NP000547R |
| Nigrosabulum globosum NCBITaxon:95328 |
CHEBI | PMID:11374942 |
| Acremonium egyptiacum NCBITaxon:749675 |
CHEBI | 10.1073/pnas.1819254116 |
| Acremonium egyptiacum NCBITaxon:749675 |
LOTUS | DOI:10.1073/PNAS.1819254116 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001923 | Acremonium egyptiacum NCBITaxon:749675 |
CLUSTER_UNSTATED | genbank:LC406756.1 |
A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.
Bioactivities 2
| Assay | Result | Reference |
|---|---|---|
| Luminescence Cell-Based Primary HTS to Identify Inhibitors of STK33 | ACTIVE | pubchem.aid:2330 |
| Luminescence Cell-Based Primary HTS to Identify Inhibitors of the Sonic Hedgehog Signaling Pathway | ACTIVE | pubchem.aid:2313 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:156219 (same structure, same inchikey)
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001923 | MIBIG | 3 |
| CHEBI:156219 | CHEBI | 3-star |
This page is generated from data/natural_products/unclassified/ascochlorin.yaml, which is generated from the committed inventories. Neither is edited by hand.