epidechlorogriseofulvin

naturalproductmech:mibig-ea4dc2a26d 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	QPCYNIYZPDJCMB-UHFFFAOYSA-N
SMILES	COC1=CC(OC)=C2C(OC3(C(C)CC(=O)C=C3OC)C2=O)=C1
Stereochemistry	undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers
Cross-references	npatlas:NPA019749

Filing pathway

Polyketides — 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 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
Penicillium aethiopicum NCBITaxon:36650	BGC_CHARACTERIZED	mibig:BGC0000070	DOI:10.1021/cb400541z

Occurrences 1

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
Axinella verrucosa NCBITaxon:237119	LOTUS	DOI:10.1021/NP030271Y

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000070	Penicillium aethiopicum NCBITaxon:36650	CLUSTER_DEMONSTRATED	genbank:GU574478.1

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	GsfE short-chain dehydrogenase UniProtKB:D7PI19		ungrounded → naturalproductmech:mibig-ea4dc2a26d	DOI:10.1021/cb400541z

Step 1: GsfE stereospecifically reduces dechloro-dehydrogriseofulvin, Cacho et al. compound 19, to epidechlorogriseofulvin, compound 2, with NADPH. The dechlorinated substrate is ungrounded locally, so this step names the exact substrate in notes rather than assigning a placeholder identifier.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Partial P. aethiopicum epidechlorogriseofulvin biosynthesis graph for GsfE-catalyzed final reduction.

Subject	Predicate	Object	Notes	Evidence
dechloro-dehydrogriseofulvin	is reduced by	GsfE short-chain dehydrogenase	GsfE reduces dechloro-dehydrogriseofulvin with NADPH in the terminal dechlorinated branch of griseofulvin biosynthesis.	DOI:10.1021/cb400541z https://mibig.secondarymetabolites.org/repository/BGC0000070.5/BGC0000070.gbk https://www.uniprot.org/uniprotkb/D7PI19 reference DOI:10.1021/cb400541z evidence type PRIMARY_EXPERIMENT snippet GsfE fully converted 18 or 19 to 1 or 2 notes Cacho et al. deleted gsfE and observed dehydrogriseofulvin and dechloro-dehydrogriseofulvin accumulation, then purified His-tagged GsfE and showed NADPH-dependent in vitro conversion of dechloro-dehydrogriseofulvin, compound 19, to epidechlorogriseofulvin, compound 2. reference https://mibig.secondarymetabolites.org/repository/BGC0000070.5/BGC0000070.gbk evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG BGC0000070.5 maps the P. aethiopicum GU574478.1 griseofulvin biosynthetic gene cluster CDS ADI24957.1 to GsfE and lists epidechlorogriseofulvin as a product. reference https://www.uniprot.org/uniprotkb/D7PI19 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes Reviewed UniProtKB:D7PI19 is the 377 aa P. aethiopicum GsfE short-chain dehydrogenase and cross-references GU574478 protein ADI24957.1.
GsfE short-chain dehydrogenase	forms	epidechlorogriseofulvin	His-tagged GsfE converted dechloro-dehydrogriseofulvin, compound 19, to epidechlorogriseofulvin, compound 2, in vitro.	DOI:10.1021/cb400541z https://mibig.secondarymetabolites.org/repository/BGC0000070.5/BGC0000070.gbk https://www.uniprot.org/uniprotkb/D7PI19 reference DOI:10.1021/cb400541z evidence type PRIMARY_EXPERIMENT snippet GsfE fully converted 18 or 19 to 1 or 2 notes Cacho et al. deleted gsfE and observed dehydrogriseofulvin and dechloro-dehydrogriseofulvin accumulation, then purified His-tagged GsfE and showed NADPH-dependent in vitro conversion of dechloro-dehydrogriseofulvin, compound 19, to epidechlorogriseofulvin, compound 2. reference https://mibig.secondarymetabolites.org/repository/BGC0000070.5/BGC0000070.gbk evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG BGC0000070.5 maps the P. aethiopicum GU574478.1 griseofulvin biosynthetic gene cluster CDS ADI24957.1 to GsfE and lists epidechlorogriseofulvin as a product. reference https://www.uniprot.org/uniprotkb/D7PI19 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes Reviewed UniProtKB:D7PI19 is the 377 aa P. aethiopicum GsfE short-chain dehydrogenase and cross-references GU574478 protein ADI24957.1.

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

Explore across X-Mech

AntibioticMech (epidechlorogriseofulvin) ↗ MediaIngredientMech (naturalproductmech:mibig-ea4dc2a26d) ↗ TaxonMech: Penicillium aethiopicum (NCBITaxon:36650) ↗ PathwayMech (mibig:BGC0000070) ↗

Provenance

Source concept	Source	Version
BGC0000070	MIBIG	5

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