ascofuranone

CHEBI:156148 EXACT SEEDED antiparasiticenzyme inhibitor

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

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.

Biosynthesis curated

Written by a curator with claim-level evidence on each step; not derived from a source. This is what the rest of the record exists to support.

Step	Enzyme	Reaction	Substrate → product	Evidence
1	AscJ short-chain dehydrogenase/reductase UniProtKB:A0A455R5K2	RHEA:63112	CHEBI:146279 → CHEBI:156148	DOI:10.1073/pnas.1819254116

Step 1: AscJ oxidizes AscI-derived ascofuranol to ascofuranone in the terminal step of the Acremonium egyptiacum ascofuranone branch. This single-step partial pathway leaves the upstream AscA-AscI steps uncurated.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Late Acremonium egyptiacum ascofuranone biosynthesis graph for AscJ-catalyzed ascofuranol oxidation to ascofuranone.

Subject	Predicate	Object	Notes	Evidence
ascofuranol	is oxidized by	AscJ short-chain dehydrogenase/reductase	AscJ oxidizes the AscI cyclization product ascofuranol in the terminal ascofuranone branch.	DOI:10.1073/pnas.1819254116 https://mite.lisc.univie.ac.at/repository/MITE0000382 https://www.uniprot.org/uniprotkb/A0A455R5K2 https://www.ncbi.nlm.nih.gov/protein/BBF25320.1 https://www.rhea-db.org/rhea/63112 reference DOI:10.1073/pnas.1819254116 evidence type PRIMARY_EXPERIMENT snippet which is oxidized into 1 by AscJ notes Araki et al. number ascofuranone as compound 1 and ascofuranol as compound 10. Their in vitro assay showed that cell-free Aspergillus sojae homogenate expressing ascJ oxidized ascofuranol into ascofuranone. reference https://mite.lisc.univie.ac.at/repository/MITE0000382 evidence type DATABASE_ASSERTION snippet Converts Ascofuranol to Ascofuranone by oxidation. retrieved on 2026-10-01 notes MITE0000382 is an active, non-intermediate AscJ entry for the oxidative terminal ascofuranone step. It links UniProtKB:A0A455R5K2, GenPept BBF25320.1, MIBiG BGC0001924, RHEA:63112 and the Araki et al. DOI. reference https://www.uniprot.org/uniprotkb/A0A455R5K2 evidence type DATABASE_ASSERTION snippet Short-chain dehydrogenase/reductase ascJ retrieved on 2026-10-01 notes Current Swiss-Prot UniProtKB:A0A455R5K2 resolves as Acremonium egyptiacum AscJ, length 296 aa, gene ascJ, EC 1.1.99.-. It cross-references EMBL LC406757 protein BBF25320.1 and annotates RHEA:63112 for AscJ-catalyzed ascofuranol oxidation to ascofuranone. reference https://www.ncbi.nlm.nih.gov/protein/BBF25320.1 evidence type DATABASE_ASSERTION snippet dehydrogenase [Acremonium egyptiacum] retrieved on 2026-10-01 notes GenPept BBF25320.1 is the 296 aa Acremonium egyptiacum F-1392 ascJ product encoded by LC406757.1. reference https://www.rhea-db.org/rhea/63112 evidence type DATABASE_ASSERTION snippet ascofuranol + A = ascofuranone + AH2 retrieved on 2026-10-01 notes RHEA:63112 is the curated ascofuranol oxidation reaction linked to Araki et al.; RHEA:63113 is its left-to-right physiological reaction.
AscJ short-chain dehydrogenase/reductase	forms	ascofuranone	AscJ forms CHEBI:156148 ascofuranone from ascofuranol.	DOI:10.1073/pnas.1819254116 https://mite.lisc.univie.ac.at/repository/MITE0000382 https://www.uniprot.org/uniprotkb/A0A455R5K2 https://www.ncbi.nlm.nih.gov/protein/BBF25320.1 https://www.rhea-db.org/rhea/63112 reference DOI:10.1073/pnas.1819254116 evidence type PRIMARY_EXPERIMENT snippet which is oxidized into 1 by AscJ notes Araki et al. number ascofuranone as compound 1 and ascofuranol as compound 10. Their in vitro assay showed that cell-free Aspergillus sojae homogenate expressing ascJ oxidized ascofuranol into ascofuranone. reference https://mite.lisc.univie.ac.at/repository/MITE0000382 evidence type DATABASE_ASSERTION snippet Converts Ascofuranol to Ascofuranone by oxidation. retrieved on 2026-10-01 notes MITE0000382 is an active, non-intermediate AscJ entry for the oxidative terminal ascofuranone step. It links UniProtKB:A0A455R5K2, GenPept BBF25320.1, MIBiG BGC0001924, RHEA:63112 and the Araki et al. DOI. reference https://www.uniprot.org/uniprotkb/A0A455R5K2 evidence type DATABASE_ASSERTION snippet Short-chain dehydrogenase/reductase ascJ retrieved on 2026-10-01 notes Current Swiss-Prot UniProtKB:A0A455R5K2 resolves as Acremonium egyptiacum AscJ, length 296 aa, gene ascJ, EC 1.1.99.-. It cross-references EMBL LC406757 protein BBF25320.1 and annotates RHEA:63112 for AscJ-catalyzed ascofuranol oxidation to ascofuranone. reference https://www.ncbi.nlm.nih.gov/protein/BBF25320.1 evidence type DATABASE_ASSERTION snippet dehydrogenase [Acremonium egyptiacum] retrieved on 2026-10-01 notes GenPept BBF25320.1 is the 296 aa Acremonium egyptiacum F-1392 ascJ product encoded by LC406757.1. reference https://www.rhea-db.org/rhea/63112 evidence type DATABASE_ASSERTION snippet ascofuranol + A = ascofuranone + AH2 retrieved on 2026-10-01 notes RHEA:63112 is the curated ascofuranol oxidation reaction linked to Araki et al.; RHEA:63113 is its left-to-right physiological reaction.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Bioactivities 2

Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.

Assay	Result	Target enzyme	Source detail
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; ACTIVE	UniProtKB:P22185	pubchem.aid:1919245 assay Inhibitory Effects on Recombinant AOX Protein from US Patent US11565996: "Compounds for use as inhibitors of alternative oxidase or cytochrome bc1 complex" evidence reference pubchem.aid:1919245 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1919245, deposited by BindingDB; assay type Confirmatory. call ACTIVE measurement type IC50 value 0.187 units uM target enzyme UniProtKB:P22185 activity class ENZYME_INHIBITOR
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; ACTIVE	UniProtKB:P22185	pubchem.aid:1919245 assay Inhibitory Effects on Recombinant AOX Protein from US Patent US11565996: "Compounds for use as inhibitors of alternative oxidase or cytochrome bc1 complex" evidence reference pubchem.aid:1919245 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1919245, deposited by BindingDB; assay type Confirmatory. call ACTIVE measurement type IC50 value 0.5 units uM target enzyme UniProtKB:P22185 activity class ENZYME_INHIBITOR

Elsewhere in the fleet

AntibioticMech — CHEBI:156148 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (ascofuranone) ↗ MediaIngredientMech (CHEBI:156148) ↗ TaxonMech: Acremonium egyptiacum (NCBITaxon:749675) ↗ PathwayMech (mibig:BGC0001924) ↗

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.