ascofuranone
CHEBI:156148 EXACT SEEDED antiparasiticenzyme inhibitor
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.
Structure
| Standard InChIKey | VGYPZLGWVQQOST-JUERRSSISA-N |
|---|---|
| SMILES | CC1=C(C(=C(C(=C1Cl)O)C/C=C(\C)/CC/C=C(\C)/[C@@H]2CC(=O)C(O2)(C)C)O)C=O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:6434242 |
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, 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:BGC0001924 | DOI:10.1002/ijc.24259 |
Occurrences 7
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 |
|---|---|---|
| Acremonium NCBITaxon:159075 |
LOTUS | DOI:10.1021/NP8006793 |
| Ascochyta viciae NCBITaxon:1677696 |
LOTUS | DOI:10.1016/S1383-5769(97)82566-4 |
| Ascochyta viciae NCBITaxon:1677696 |
LOTUS | DOI:10.7164/ANTIBIOTICS.26.676 |
| Ascochyta viciae NCBITaxon:1677696 |
CHEBI | PMID:4792115 |
| Acremonium sp. NCBITaxon:2046025 |
CHEBI | 10.1021/np8006793 |
| Acremonium sclerotigenum NCBITaxon:261921 |
CHEBI | PMID:27804952 |
| Acremonium egyptiacum NCBITaxon:749675 |
LOTUS | DOI:10.1073/PNAS.1819254116 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001924 | Acremonium egyptiacum NCBITaxon:749675 |
CLUSTER_UNSTATED | genbank:LC406757.1 |
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 |
|---|---|---|
| Inhibitory Effects on Recombinant AOX Protein from US Patent US11565996: "Compounds for use as inhibitors of alternative oxidase or cytochrome bc1 complex" | IC50 0.187 uM | pubchem.aid:1919245 |
| Inhibitory Effects on Recombinant AOX Protein from US Patent US11565996: "Compounds for use as inhibitors of alternative oxidase or cytochrome bc1 complex" | IC50 0.5 uM | pubchem.aid:1919245 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:156148 (same structure, same inchikey)
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001924 | MIBIG | 3 |
| CHEBI:156148 | CHEBI | 3-star |
This page is generated from data/natural_products/unclassified/ascofuranone.yaml, which is generated from the committed inventories. Neither is edited by hand.