ascochlorin

CHEBI:156219 EXACT SEEDED antifungalenzyme 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 (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.

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	AscG cytochrome P450 monooxygenase UniProtKB:A0A455R4X0	RHEA:63100	ungrounded → CHEBI:156219	DOI:10.1073/pnas.1819254116

Step 1: AscG oxidizes AscF-derived ilicicolin C to ascochlorin in the terminal step of the Acremonium egyptiacum ascochlorin branch. This single-step partial pathway leaves the upstream AscA-AscF steps uncurated.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Late Acremonium egyptiacum ascochlorin biosynthesis graph for AscG-catalyzed ilicicolin C oxidation to ascochlorin.

Subject	Predicate	Object	Notes	Evidence
ilicicolin C	is oxidized by	AscG cytochrome P450 monooxygenase	AscG oxidizes the AscF cyclization product ilicicolin C in the terminal ascochlorin branch.	DOI:10.1073/pnas.1819254116 https://mite.lisc.univie.ac.at/repository/MITE0000379 https://www.uniprot.org/uniprotkb/A0A455R4X0 https://www.ncbi.nlm.nih.gov/protein/BBF25319.1 https://mibig.secondarymetabolites.org/repository/BGC0001923.3/BGC0001923.gbk reference DOI:10.1073/pnas.1819254116 evidence type PRIMARY_EXPERIMENT snippet was oxidized into 2 by the P450 monooxygenase AscG notes Araki et al. reconstituted the Acremonium egyptiacum AscE, AscF and AscG reactions in vitro from ilicicolin A and identified the three-enzyme product as ascochlorin by MS/MS comparison and authentic-standard coinjection. reference https://mite.lisc.univie.ac.at/repository/MITE0000379 evidence type DATABASE_ASSERTION snippet Conversion of alicicolin C to ascochlorin. retrieved on 2026-10-01 notes MITE0000379 is an active, non-intermediate AscG entry for the oxidative terminal ascochlorin step. It links UniProtKB:A0A455R4X0, GenPept BBF25319.1, MIBiG BGC0001923, RHEA:63100 and the Araki et al. DOI. reference https://www.uniprot.org/uniprotkb/A0A455R4X0 evidence type DATABASE_ASSERTION snippet Cytochrome P450 monooxygenase ascG retrieved on 2026-10-01 notes Current Swiss-Prot UniProtKB:A0A455R4X0 resolves as Acremonium egyptiacum AscG, length 534 aa, gene ascG, EC 1.14.14.-. It cross-references EMBL LC406756 protein BBF25319.1 and annotates RHEA:63100 for AscG-catalyzed ilicicolin C oxidation to ascochlorin. reference https://www.ncbi.nlm.nih.gov/protein/BBF25319.1 evidence type DATABASE_ASSERTION snippet cytochrome P450 [Acremonium egyptiacum] retrieved on 2026-10-01 notes GenPept BBF25319.1 is the 534 aa Acremonium egyptiacum F-1392 ascG product encoded by LC406756.1. reference https://mibig.secondarymetabolites.org/repository/BGC0001923.3/BGC0001923.gbk evidence type DATABASE_ASSERTION snippet protein_id="BBF25319.1" retrieved on 2026-10-01 notes MIBiG BGC0001923.3 is the Acremonium egyptiacum F-1392 ascochlorin cluster record and places ascG/BBF25319.1 in the cluster.
AscG cytochrome P450 monooxygenase	forms	ascochlorin	AscG forms CHEBI:156219 ascochlorin from ilicicolin C.	DOI:10.1073/pnas.1819254116 https://mite.lisc.univie.ac.at/repository/MITE0000379 https://www.uniprot.org/uniprotkb/A0A455R4X0 https://www.ncbi.nlm.nih.gov/protein/BBF25319.1 https://mibig.secondarymetabolites.org/repository/BGC0001923.3/BGC0001923.gbk reference DOI:10.1073/pnas.1819254116 evidence type PRIMARY_EXPERIMENT snippet was oxidized into 2 by the P450 monooxygenase AscG notes Araki et al. reconstituted the Acremonium egyptiacum AscE, AscF and AscG reactions in vitro from ilicicolin A and identified the three-enzyme product as ascochlorin by MS/MS comparison and authentic-standard coinjection. reference https://mite.lisc.univie.ac.at/repository/MITE0000379 evidence type DATABASE_ASSERTION snippet Conversion of alicicolin C to ascochlorin. retrieved on 2026-10-01 notes MITE0000379 is an active, non-intermediate AscG entry for the oxidative terminal ascochlorin step. It links UniProtKB:A0A455R4X0, GenPept BBF25319.1, MIBiG BGC0001923, RHEA:63100 and the Araki et al. DOI. reference https://www.uniprot.org/uniprotkb/A0A455R4X0 evidence type DATABASE_ASSERTION snippet Cytochrome P450 monooxygenase ascG retrieved on 2026-10-01 notes Current Swiss-Prot UniProtKB:A0A455R4X0 resolves as Acremonium egyptiacum AscG, length 534 aa, gene ascG, EC 1.14.14.-. It cross-references EMBL LC406756 protein BBF25319.1 and annotates RHEA:63100 for AscG-catalyzed ilicicolin C oxidation to ascochlorin. reference https://www.ncbi.nlm.nih.gov/protein/BBF25319.1 evidence type DATABASE_ASSERTION snippet cytochrome P450 [Acremonium egyptiacum] retrieved on 2026-10-01 notes GenPept BBF25319.1 is the 534 aa Acremonium egyptiacum F-1392 ascG product encoded by LC406756.1. reference https://mibig.secondarymetabolites.org/repository/BGC0001923.3/BGC0001923.gbk evidence type DATABASE_ASSERTION snippet protein_id="BBF25319.1" retrieved on 2026-10-01 notes MIBiG BGC0001923.3 is the Acremonium egyptiacum F-1392 ascochlorin cluster record and places ascG/BBF25319.1 in the cluster.

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
Luminescence Cell-Based Primary HTS to Identify Inhibitors of STK33	ACTIVE	Not recorded	pubchem.aid:2330 assay Luminescence Cell-Based Primary HTS to Identify Inhibitors of STK33 evidence reference pubchem.aid:2330 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 2330, deposited by Broad Institute; assay type Screening. Target accession CAC29064 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE activity class ENZYME_INHIBITOR
Luminescence Cell-Based Primary HTS to Identify Inhibitors of the Sonic Hedgehog Signaling Pathway	ACTIVE	Not recorded	pubchem.aid:2313 assay Luminescence Cell-Based Primary HTS to Identify Inhibitors of the Sonic Hedgehog Signaling Pathway evidence reference pubchem.aid:2313 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 2313, deposited by Broad Institute; assay type Screening. call ACTIVE activity class ENZYME_INHIBITOR

Elsewhere in the fleet

AntibioticMech — CHEBI:156219 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (ascochlorin) ↗ MediaIngredientMech (CHEBI:156219) ↗ TaxonMech: Acremonium egyptiacum (NCBITaxon:749675) ↗ PathwayMech (mibig:BGC0001923) ↗

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.