conidiogenone

CHEBI:189095 EXACT SEEDED

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 diterpenoid with formula C20H32O2. It is isolated from Penicillium cyclopium and exhibits potent conidiation inducing activity.

Structure

Standard InChIKey	VXPSMCORCRBNAO-TYVLEIALSA-N
SMILES	C[C@H]1[C@@H](CC(=O)[C@]2([C@@]13C[C@]4(CCC([C@H]4[C@@H]3CC2)(C)C)C)C)O
Stereochemistry	fully defined
Cross-references	npatlas:NPA017609

Filing pathway

Terpenoids — 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
Penicillium rubens Wisconsin 54-1255 NCBITaxon:500485	SOURCE_ASSERTION	mibig:BGC0002320	PMID:30343633

Occurrences 5

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
Penicillium aurantiogriseum NCBITaxon:36655	LOTUS	DOI:10.1016/S0040-4039(02)01493-4
Penicillium aurantiogriseum NCBITaxon:36655	LOTUS	DOI:10.1128/EC.1.5.823-829.2002
Penicillium cyclopium NCBITaxon:60167	CHEBI	10.1016/S0040-4039(02)01493-4
Penicillium cyclopium NCBITaxon:60167	LOTUS	DOI:10.1016/S0040-4039(02)01493-4
Penicillium cyclopium NCBITaxon:60167	LOTUS	DOI:10.1128/EC.1.5.823-829.2002

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0002320	Penicillium rubens Wisconsin 54-1255 NCBITaxon:500485	CLUSTER_DEMONSTRATED	genbank:AM920435.1

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	PchDS UniProtKB:B6HFX8	RHEA:17653	CHEBI:175763 → CHEBI:58756	DOI:10.1080/09168451.2018.1536518
2	PchDS UniProtKB:B6HFX8		CHEBI:58756 → CHEBI:177897	DOI:10.1080/09168451.2018.1536518
3	PchP450 UniProtKB:B6HFX9		CHEBI:177897 → CHEBI:189095	DOI:10.1080/09168451.2018.1536518

Step 1: The C-terminal prenyltransferase domain of PchDS condenses isopentenyl diphosphate with (2E,6E)-farnesyl diphosphate to form (2E,6E,10E)-geranylgeranyl diphosphate in the conidiogenone pathway.

Step 2: The N-terminal terpene cyclase domain of PchDS cyclizes (2E,6E,10E)-geranylgeranyl diphosphate to deoxyconidiogenol.

Step 3: PchP450 is the Pc20g10870 P450 homolog proposed to catalyze the deoxyconidiogenol-to-conidiogenone oxidation in the Penicillium rubens AM920435.1 locus; the exact two-round oxidation was assayed with the Penicillium roqueforti PrP450 homolog, not directly with PchP450.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 6 nodes, 6 edges

Penicillium rubens conidiogenone biosynthesis graph for PchDS formation and cyclization of GGPP, followed by the inferred PchP450 oxidation of deoxyconidiogenol to conidiogenone.

Subject	Predicate	Object	Notes	Evidence
(2E,6E)-farnesyl diphosphate	is prenylated by	PchDS		DOI:10.1080/09168451.2018.1536518 https://www.uniprot.org/uniprotkb/B6HFX8 https://www.ncbi.nlm.nih.gov/protein/CAP86415.1 reference DOI:10.1080/09168451.2018.1536518 evidence type PRIMARY_EXPERIMENT notes Shiina et al. experimentally characterized the Penicillium rubens Wisconsin 54-1255 bifunctional diterpene synthase PchDS/Pc20g10860 that produces the conidiogenone precursor deoxyconidiogenol. reference https://www.uniprot.org/uniprotkb/B6HFX8 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes UniProtKB:B6HFX8 resolves PchDS to the reviewed Penicillium rubens Pc20g10860 protein and maps it to EMBL AM920435 protein CAP86415.1. reference https://www.ncbi.nlm.nih.gov/protein/CAP86415.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept CAP86415.1 is the AM920435.1 Pc20g10860 coding sequence cross-referenced from UniProtKB:B6HFX8.
PchDS	forms	(2E,6E,10E)-geranylgeranyl diphosphate		DOI:10.1080/09168451.2018.1536518 https://www.uniprot.org/uniprotkb/B6HFX8 https://www.ncbi.nlm.nih.gov/protein/CAP86415.1 reference DOI:10.1080/09168451.2018.1536518 evidence type PRIMARY_EXPERIMENT notes Shiina et al. experimentally characterized the Penicillium rubens Wisconsin 54-1255 bifunctional diterpene synthase PchDS/Pc20g10860 that produces the conidiogenone precursor deoxyconidiogenol. reference https://www.uniprot.org/uniprotkb/B6HFX8 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes UniProtKB:B6HFX8 resolves PchDS to the reviewed Penicillium rubens Pc20g10860 protein and maps it to EMBL AM920435 protein CAP86415.1. reference https://www.ncbi.nlm.nih.gov/protein/CAP86415.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept CAP86415.1 is the AM920435.1 Pc20g10860 coding sequence cross-referenced from UniProtKB:B6HFX8.
(2E,6E,10E)-geranylgeranyl diphosphate	is cyclized by	PchDS		DOI:10.1080/09168451.2018.1536518 https://www.uniprot.org/uniprotkb/B6HFX8 https://www.ncbi.nlm.nih.gov/protein/CAP86415.1 reference DOI:10.1080/09168451.2018.1536518 evidence type PRIMARY_EXPERIMENT notes Shiina et al. experimentally characterized the Penicillium rubens Wisconsin 54-1255 bifunctional diterpene synthase PchDS/Pc20g10860 that produces the conidiogenone precursor deoxyconidiogenol. reference https://www.uniprot.org/uniprotkb/B6HFX8 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes UniProtKB:B6HFX8 resolves PchDS to the reviewed Penicillium rubens Pc20g10860 protein and maps it to EMBL AM920435 protein CAP86415.1. reference https://www.ncbi.nlm.nih.gov/protein/CAP86415.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept CAP86415.1 is the AM920435.1 Pc20g10860 coding sequence cross-referenced from UniProtKB:B6HFX8.
PchDS	forms	deoxyconidiogenol		DOI:10.1080/09168451.2018.1536518 https://www.uniprot.org/uniprotkb/B6HFX8 https://www.ncbi.nlm.nih.gov/protein/CAP86415.1 reference DOI:10.1080/09168451.2018.1536518 evidence type PRIMARY_EXPERIMENT notes Shiina et al. experimentally characterized the Penicillium rubens Wisconsin 54-1255 bifunctional diterpene synthase PchDS/Pc20g10860 that produces the conidiogenone precursor deoxyconidiogenol. reference https://www.uniprot.org/uniprotkb/B6HFX8 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes UniProtKB:B6HFX8 resolves PchDS to the reviewed Penicillium rubens Pc20g10860 protein and maps it to EMBL AM920435 protein CAP86415.1. reference https://www.ncbi.nlm.nih.gov/protein/CAP86415.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept CAP86415.1 is the AM920435.1 Pc20g10860 coding sequence cross-referenced from UniProtKB:B6HFX8.
deoxyconidiogenol	is putatively oxidized by	PchP450	The P. rubens PchP450 function is inferred from the assayed P. roqueforti PrP450 homolog.	DOI:10.1080/09168451.2018.1536518 https://www.uniprot.org/uniprotkb/B6HFX9 https://www.ncbi.nlm.nih.gov/protein/CAP86416.1 reference DOI:10.1080/09168451.2018.1536518 evidence type PRIMARY_EXPERIMENT notes Shiina et al. identified PchP450/Pc20g10870 in the Penicillium rubens Wisconsin 54-1255 locus as the P450 homolog corresponding to the experimentally assayed PrP450 conidiogenone synthase. reference https://www.uniprot.org/uniprotkb/B6HFX9 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes UniProtKB:B6HFX9 resolves PchP450 to the reviewed Penicillium rubens Pc20g10870 protein, maps it to EMBL AM920435 protein CAP86416.1, and infers the conidiogenone oxidation function from the assayed Penicillium roqueforti PrP450 homolog. reference https://www.ncbi.nlm.nih.gov/protein/CAP86416.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept CAP86416.1 is the AM920435.1 Pc20g10870 coding sequence cross-referenced from UniProtKB:B6HFX9.
PchP450	putatively forms	conidiogenone	The P. rubens PchP450 function is inferred from the assayed P. roqueforti PrP450 homolog.	DOI:10.1080/09168451.2018.1536518 https://www.uniprot.org/uniprotkb/B6HFX9 https://www.ncbi.nlm.nih.gov/protein/CAP86416.1 reference DOI:10.1080/09168451.2018.1536518 evidence type PRIMARY_EXPERIMENT notes Shiina et al. identified PchP450/Pc20g10870 in the Penicillium rubens Wisconsin 54-1255 locus as the P450 homolog corresponding to the experimentally assayed PrP450 conidiogenone synthase. reference https://www.uniprot.org/uniprotkb/B6HFX9 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes UniProtKB:B6HFX9 resolves PchP450 to the reviewed Penicillium rubens Pc20g10870 protein, maps it to EMBL AM920435 protein CAP86416.1, and infers the conidiogenone oxidation function from the assayed Penicillium roqueforti PrP450 homolog. reference https://www.ncbi.nlm.nih.gov/protein/CAP86416.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept CAP86416.1 is the AM920435.1 Pc20g10870 coding sequence cross-referenced from UniProtKB:B6HFX9.

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

Explore across X-Mech

AntibioticMech (conidiogenone) ↗ MediaIngredientMech (CHEBI:189095) ↗ TaxonMech: Penicillium rubens Wisconsin 54-1255 (NCBITaxon:500485) ↗ PathwayMech (mibig:BGC0002320) ↗

Provenance

Source concept	Source	Version
BGC0002320	MIBIG	3
CHEBI:189095	CHEBI	3-star

This page is generated from data/natural_products/terpenoids/conidiogenone.yaml, which is generated from the committed inventories. Neither is edited by hand.