flavoglaucin

naturalproductmech:mibig-be4adf1947 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	RGRXZGKXEJHPQQ-UHFFFAOYSA-N
SMILES	CCCCCCCC1=C(O)C=C(CC=C(C)C)C(O)=C1C=O
Stereochemistry	fully defined
Cross-references	pubchem:119037, npatlas:NPA033320

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
Aspergillus ruber CBS 135680 NCBITaxon:1388766	SOURCE_ASSERTION	mibig:BGC0002234	PMID:32134669

Occurrences 17

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 dierckxii NCBITaxon:121611	LOTUS	DOI:10.1248/CPB.20.2727
Aspergillus repens NCBITaxon:1405805	LOTUS	DOI:10.1021/NP200147C
Aspergillus chevalieri NCBITaxon:182096	LOTUS	DOI:10.1007/BF02540819
Aspergillus chevalieri NCBITaxon:182096	LOTUS	DOI:10.1271/BBB1961.45.313
Talipariti tiliaceum NCBITaxon:183267	LOTUS	DOI:10.1248/CPB.56.1282
Microsporum NCBITaxon:34392	LOTUS	DOI:10.1248/CPB.54.882
Aspergillus ruber NCBITaxon:396024	LOTUS	DOI:10.1080/00021369.1980.10864196
Aspergillus ruber NCBITaxon:396024	LOTUS	DOI:10.1248/CPB.37.621
Aspergillus ruber NCBITaxon:396024	LOTUS	DOI:10.1248/CPB.56.1282
Aspergillus ruber NCBITaxon:396024	LOTUS	DOI:10.1271/BBB1961.44.1685
Aspergillus glaucus NCBITaxon:41413	LOTUS	DOI:10.1002/CBER.19430760408
Aspergillus glaucus NCBITaxon:41413	LOTUS	DOI:10.1038/164026A0
Aspergillus glaucus NCBITaxon:41413	LOTUS	DOI:10.1039/JR9370000080
Aspergillus glaucus NCBITaxon:41413	LOTUS	DOI:10.1271/BBB.67.1443
Aspergillus glaucus NCBITaxon:41413	LOTUS	DOI:10.1271/BBB.80887
Aspergillus amstelodami NCBITaxon:5054	LOTUS	DOI:10.1248/CPB1953.1.160
Penicillium charlesii NCBITaxon:69767	LOTUS	DOI:10.1248/CPB.20.2727

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0002234	Aspergillus ruber CBS 135680 NCBITaxon:1388766	CLUSTER_DEMONSTRATED	genbank:KK088422.1

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	FogE cytochrome P450 monooxygenase UniProtKB:A0A017SFB8		ungrounded → ungrounded	DOI:10.1021/acs.orglett.0c00440

Step 1: FogE catalyzes aromatic C-3 hydroxylation of an alkylated salicyl alcohol intermediate in the flavoglaucin pathway. This single-step partial pathway leaves FogA-D formation of the salicyl alcohol substrate and the later FogH/FogF prenylation and reoxidation steps uncurated.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Partial Aspergillus ruber flavoglaucin biosynthesis graph for FogE-catalyzed C-3 hydroxylation upstream of FogH prenylation.

Subject	Predicate	Object	Notes	Evidence
alkylated salicyl alcohol flavoglaucin intermediate	is C-3-hydroxylated by	FogE cytochrome P450 monooxygenase	MITE records FogE as the cytochrome P450 for aromatic hydroxylation of a flavoglaucin biosynthetic intermediate.	DOI:10.1021/acs.orglett.0c00440 https://mite.lisc.univie.ac.at/repository/MITE0000457 https://mibig.secondarymetabolites.org/repository/BGC0002234.3/BGC0002234.gbk https://www.uniprot.org/uniprotkb/A0A017SFB8 https://www.ncbi.nlm.nih.gov/protein/EYE95339.1 reference DOI:10.1021/acs.orglett.0c00440 evidence type PRIMARY_EXPERIMENT snippet heterologous expression, precursor feeding, and biochemical characterization notes Nies et al. elucidated the Aspergillus ruber flavoglaucin and congener pathway; MITE and UniProtKB curate the FogE-specific C-3 aromatic hydroxylation from this same primary article. reference https://mite.lisc.univie.ac.at/repository/MITE0000457 evidence type DATABASE_ASSERTION snippet aromatic hydroxylation of flavoglaucin biosynthetic intermediate retrieved on 2026-10-01 notes MITE0000457 is an active FogE cytochrome P450 entry for hydroxylation of a flavoglaucin-pathway salicyl alcohol intermediate; it links UniProtKB:A0A017SFB8, GenPept EYE95339.1, MIBiG BGC0002234 and the Nies et al. DOI. reference https://mibig.secondarymetabolites.org/repository/BGC0002234.3/BGC0002234.gbk evidence type DATABASE_ASSERTION snippet locus_tag="EURHEDRAFT_455792" retrieved on 2026-10-01 notes MIBiG BGC0002234.3 places EYE95339.1 inside the active Aspergillus ruber CBS 135680 flavoglaucin cluster as the EURHEDRAFT_455792 cytochrome P450 CDS. reference https://www.uniprot.org/uniprotkb/A0A017SFB8 evidence type DATABASE_ASSERTION snippet Cytochrome P450 monooxygenase fogE retrieved on 2026-10-01 notes Reviewed UniProtKB:A0A017SFB8 resolves as Aspergillus ruber CBS 135680 FogE/FOGE_ASPRC, a 538 aa cytochrome P450 monooxygenase, and cross-references EMBL KK088422 protein EYE95339.1. reference https://www.ncbi.nlm.nih.gov/protein/EYE95339.1 evidence type DATABASE_ASSERTION snippet cytochrome P450 [Aspergillus ruber CBS 135680] retrieved on 2026-10-01 notes GenPept EYE95339.1 is the 538 aa Aspergillus ruber CBS 135680 cytochrome P450 protein encoded by six exons on WGS scaffold KK088422.1.
FogE cytochrome P450 monooxygenase	forms	C-3-hydroxylated salicyl alcohol intermediate	The FogE product is a hydroxylated salicyl alcohol intermediate; subsequent FogH prenylation and FogF oxidation to flavoglaucin are outside this single-step graph.	DOI:10.1021/acs.orglett.0c00440 https://mite.lisc.univie.ac.at/repository/MITE0000457 https://mibig.secondarymetabolites.org/repository/BGC0002234.3/BGC0002234.gbk https://www.uniprot.org/uniprotkb/A0A017SFB8 https://www.ncbi.nlm.nih.gov/protein/EYE95339.1 reference DOI:10.1021/acs.orglett.0c00440 evidence type PRIMARY_EXPERIMENT snippet heterologous expression, precursor feeding, and biochemical characterization notes Nies et al. elucidated the Aspergillus ruber flavoglaucin and congener pathway; MITE and UniProtKB curate the FogE-specific C-3 aromatic hydroxylation from this same primary article. reference https://mite.lisc.univie.ac.at/repository/MITE0000457 evidence type DATABASE_ASSERTION snippet aromatic hydroxylation of flavoglaucin biosynthetic intermediate retrieved on 2026-10-01 notes MITE0000457 is an active FogE cytochrome P450 entry for hydroxylation of a flavoglaucin-pathway salicyl alcohol intermediate; it links UniProtKB:A0A017SFB8, GenPept EYE95339.1, MIBiG BGC0002234 and the Nies et al. DOI. reference https://mibig.secondarymetabolites.org/repository/BGC0002234.3/BGC0002234.gbk evidence type DATABASE_ASSERTION snippet locus_tag="EURHEDRAFT_455792" retrieved on 2026-10-01 notes MIBiG BGC0002234.3 places EYE95339.1 inside the active Aspergillus ruber CBS 135680 flavoglaucin cluster as the EURHEDRAFT_455792 cytochrome P450 CDS. reference https://www.uniprot.org/uniprotkb/A0A017SFB8 evidence type DATABASE_ASSERTION snippet Cytochrome P450 monooxygenase fogE retrieved on 2026-10-01 notes Reviewed UniProtKB:A0A017SFB8 resolves as Aspergillus ruber CBS 135680 FogE/FOGE_ASPRC, a 538 aa cytochrome P450 monooxygenase, and cross-references EMBL KK088422 protein EYE95339.1. reference https://www.ncbi.nlm.nih.gov/protein/EYE95339.1 evidence type DATABASE_ASSERTION snippet cytochrome P450 [Aspergillus ruber CBS 135680] retrieved on 2026-10-01 notes GenPept EYE95339.1 is the 538 aa Aspergillus ruber CBS 135680 cytochrome P450 protein encoded by six exons on WGS scaffold KK088422.1.

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

Explore across X-Mech

AntibioticMech (flavoglaucin) ↗ MediaIngredientMech (naturalproductmech:mibig-be4adf1947) ↗ TaxonMech: Aspergillus ruber CBS 135680 (NCBITaxon:1388766) ↗ PathwayMech (mibig:BGC0002234) ↗

Provenance

Source concept	Source	Version
BGC0002234	MIBIG	3

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