2-oxocyclopiazonic acid

naturalproductmech:mibig-5209b855e4 MINTED SEEDED

Grounding review: No 3-star ChEBI entry shares this structure, so the record keeps a content-hashed identifier.

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

Structure

Standard InChIKey	MHEUVENJAVJAKO-FCONBKKXSA-N
SMILES	CC(C1=C(O)[C@@H]2C3[C@H](C(C)(C)N2C1=O)CC4=C5[C@@]3([H])C(NC5=CC=C4)=O)=O
Stereochemistry	undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers

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 nrps, 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
Aspergillus oryzae NCBITaxon:5062	BGC_CHARACTERIZED	mibig:BGC0000977	DOI:10.1002/cbic.201000672

Occurrences 0

None cited.

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000977	Aspergillus oryzae NCBITaxon:5062	CLUSTER_DEMONSTRATED	genbank:AB506492.1

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	CpaH cytochrome P450 monooxygenase UniProtKB:C9K202		CHEBI:22450 → naturalproductmech:mibig-5209b855e4	DOI:10.1002/cbic.201000672

Step 1: CpaH mediates the terminal conversion of Aspergillus oryzae cyclopiazonic acid into 2-oxocyclopiazonic acid. CHEBI:22450 is the exact local grounding for the BGC0000977 cyclopiazonic acid substrate structure; its ChEBI preferred label differs from MIBiG's cyclopiazonic acid label.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Aspergillus oryzae CpaH terminal oxidation of cyclopiazonic acid to 2-oxocyclopiazonic acid.

Subject	Predicate	Object	Notes	Evidence
cyclopiazonic acid	is oxidized by	CpaH cytochrome P450 monooxygenase		DOI:10.1002/cbic.201000672 https://mibig.secondarymetabolites.org/repository/BGC0000977.4/ https://www.uniprot.org/uniprotkb/C9K202 reference DOI:10.1002/cbic.201000672 evidence type PRIMARY_EXPERIMENT snippet cpaH-mediates the conversion of CPA into the less toxic 2-oxocyclopiazonic acid notes Kato et al. used targeted gene inactivation in Aspergillus oryzae, isolated the corresponding metabolite, and assigned CpaH to the terminal conversion of cyclopiazonic acid into 2-oxocyclopiazonic acid. reference https://mibig.secondarymetabolites.org/repository/BGC0000977.4/ evidence type DATABASE_ASSERTION retrieved on 2026-09-29 notes MIBiG BGC0000977.4 records Aspergillus oryzae AB506492.1 as the cyclopiazonic acid / 2-oxocyclopiazonic acid BGC and cites DOI:10.1002/cbic.201000672 as compound evidence. reference https://www.uniprot.org/uniprotkb/C9K202 evidence type DATABASE_ASSERTION retrieved on 2026-09-29 notes UniProtKB reviewed entry C9K202 resolves to the 509 aa Aspergillus oryzae CpaH cytochrome P450 monooxygenase, maps AB506492 to protein BAK26559.1, and annotates the CpaH function and disruption phenotype from PMID:21608094.
CpaH cytochrome P450 monooxygenase	produces	2-oxocyclopiazonic acid		DOI:10.1002/cbic.201000672 https://mibig.secondarymetabolites.org/repository/BGC0000977.4/ https://www.uniprot.org/uniprotkb/C9K202 reference DOI:10.1002/cbic.201000672 evidence type PRIMARY_EXPERIMENT snippet cpaH-mediates the conversion of CPA into the less toxic 2-oxocyclopiazonic acid notes Kato et al. used targeted gene inactivation in Aspergillus oryzae, isolated the corresponding metabolite, and assigned CpaH to the terminal conversion of cyclopiazonic acid into 2-oxocyclopiazonic acid. reference https://mibig.secondarymetabolites.org/repository/BGC0000977.4/ evidence type DATABASE_ASSERTION retrieved on 2026-09-29 notes MIBiG BGC0000977.4 records Aspergillus oryzae AB506492.1 as the cyclopiazonic acid / 2-oxocyclopiazonic acid BGC and cites DOI:10.1002/cbic.201000672 as compound evidence. reference https://www.uniprot.org/uniprotkb/C9K202 evidence type DATABASE_ASSERTION retrieved on 2026-09-29 notes UniProtKB reviewed entry C9K202 resolves to the 509 aa Aspergillus oryzae CpaH cytochrome P450 monooxygenase, maps AB506492 to protein BAK26559.1, and annotates the CpaH function and disruption phenotype from PMID:21608094.

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

Explore across X-Mech

AntibioticMech (2-oxocyclopiazonic acid) ↗ MediaIngredientMech (naturalproductmech:mibig-5209b855e4) ↗ TaxonMech: Aspergillus oryzae (NCBITaxon:5062) ↗ PathwayMech (mibig:BGC0000977) ↗

Provenance

Source concept	Source	Version
BGC0000977	MIBIG	4

This page is generated from data/natural_products/unclassified/2-oxocyclopiazonic-acid.yaml, which is generated from the committed inventories. Neither is edited by hand.