NaturalProductMech

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F9775B

naturalproductmech:mibig-afdd774b74 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 InChIKeyZFYMCYAXXOXUHT-UHFFFAOYSA-N
SMILESCC1=CC2=C(C(=C1)O)OC3=C(O2)C(=O)C(=C4C3(C5C(=CC(=O)C5(C4=O)O)C)C)O
Stereochemistry undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers
Cross-referencespubchem:25235989

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.

TaxonBasisClusterEvidence
Aspergillus nidulans FGSC A4
NCBITaxon:227321		 BGC_CHARACTERIZED mibig:BGC0000057 PMID:20174687

Occurrences 0

None cited.

Biosynthetic gene clusters 1

AccessionHostLocus evidenceGenome
mibig:BGC0000057 Aspergillus nidulans FGSC A4
NCBITaxon:227321 		CLUSTER_DEMONSTRATED genbank:AACD01000135.1

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.

StepEnzymeReactionSubstrate → productEvidence
1 OrsA
UniProtKB:Q5AUX1		 RHEA:62973 ungrounded → CHEBI:16162 DOI:10.1039/b904541d
2 OrsB/OrsC F-9775 tailoring module ungrounded → naturalproductmech:mibig-afdd774b74 DOI:10.1039/b904541d

Step 1: This curates the Aspergillus nidulans FGSC A4 non-reducing polyketide synthase OrsA from the BGC0000057/AACD01000135.1 route; OrsA condenses acetyl-CoA with three malonyl-CoA units to form o-orsellinate, the branch precursor for F-9775 B biosynthesis.

Step 2: This curates the genetically supported OrsB/OrsC branch that diverts the OrsA orsellinic acid product toward F-9775 A and B. The exact isolated substrate, intermediates and individual OrsB and OrsC reactions remain unresolved, so this two-protein step is marked proposed and leaves enzyme_id empty.

Mechanism & Biosynthesis Overview

PRODUCERS & OCCURRENCE 1 producer (1 causal) 0 cited occurrences BIOSYNTHETIC LOCUS 1 gene cluster 2 curated pathway steps NATURAL PRODUCT F9775B naturalproductmech:mibig-afdd774b74 Polyketides TARGETS & BIOACTIVITY 0 molecular targets 0 bioactivities · 1 graph

Causal graph — biosynthesis 8 nodes, 7 edges

Partial Aspergillus nidulans F-9775 B biosynthesis graph for OrsA orsellinate formation and the OrsB/OrsC-dependent F-9775 branch.

SubjectPredicateObjectNotesEvidence
acetyl-CoA(4-) is condensed by OrsA RHEA:62973 selects acetyl-CoA as the starter unit in the OrsA o-orsellinate synthase reaction.
DOI:10.1039/b904541d
https://www.uniprot.org/uniprotkb/Q5AUX1
https://www.ncbi.nlm.nih.gov/protein/EAA59563.1
  • reference
    DOI:10.1039/b904541d
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    only two additional genes
    notes
    Sanchez et al. used targeted deletions in Aspergillus nidulans and found that OrsA is sufficient for orsellinic acid biosynthesis, while the adjacent AN7911.4/orsB and AN7912.4/orsC genes are additionally required for F-9775 A and B synthesis.
  • reference
    https://www.uniprot.org/uniprotkb/Q5AUX1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    notes
    Reviewed UniProtKB:Q5AUX1 is the Aspergillus nidulans FGSC A4 OrsA orsellinic acid synthase, length 2103 aa, annotates the left-to-right physiological RHEA:62973 reaction, and cross-references EMBL AACD01000135 protein EAA59563.1.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/EAA59563.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    notes
    NCBI GenPept EAA59563.1 is locus_tag AN7909.2 from the BGC0000057 AACD01000135.1 Aspergillus nidulans FGSC A4 locus and maps to reviewed UniProtKB:Q5AUX1.
malonyl-CoA(5-) is condensed by OrsA RHEA:62973 consumes three malonyl-CoA units per o-orsellinate formed by OrsA.
DOI:10.1039/b904541d
https://www.uniprot.org/uniprotkb/Q5AUX1
https://www.ncbi.nlm.nih.gov/protein/EAA59563.1
  • reference
    DOI:10.1039/b904541d
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    only two additional genes
    notes
    Sanchez et al. used targeted deletions in Aspergillus nidulans and found that OrsA is sufficient for orsellinic acid biosynthesis, while the adjacent AN7911.4/orsB and AN7912.4/orsC genes are additionally required for F-9775 A and B synthesis.
  • reference
    https://www.uniprot.org/uniprotkb/Q5AUX1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    notes
    Reviewed UniProtKB:Q5AUX1 is the Aspergillus nidulans FGSC A4 OrsA orsellinic acid synthase, length 2103 aa, annotates the left-to-right physiological RHEA:62973 reaction, and cross-references EMBL AACD01000135 protein EAA59563.1.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/EAA59563.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    notes
    NCBI GenPept EAA59563.1 is locus_tag AN7909.2 from the BGC0000057 AACD01000135.1 Aspergillus nidulans FGSC A4 locus and maps to reviewed UniProtKB:Q5AUX1.
OrsA forms o-orsellinate The curated Rhea reaction forms o-orsellinate, which enters the OrsB/OrsC-dependent F-9775 branch.
DOI:10.1039/b904541d
https://www.uniprot.org/uniprotkb/Q5AUX1
https://www.ncbi.nlm.nih.gov/protein/EAA59563.1
  • reference
    DOI:10.1039/b904541d
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    only two additional genes
    notes
    Sanchez et al. used targeted deletions in Aspergillus nidulans and found that OrsA is sufficient for orsellinic acid biosynthesis, while the adjacent AN7911.4/orsB and AN7912.4/orsC genes are additionally required for F-9775 A and B synthesis.
  • reference
    https://www.uniprot.org/uniprotkb/Q5AUX1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    notes
    Reviewed UniProtKB:Q5AUX1 is the Aspergillus nidulans FGSC A4 OrsA orsellinic acid synthase, length 2103 aa, annotates the left-to-right physiological RHEA:62973 reaction, and cross-references EMBL AACD01000135 protein EAA59563.1.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/EAA59563.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    notes
    NCBI GenPept EAA59563.1 is locus_tag AN7909.2 from the BGC0000057 AACD01000135.1 Aspergillus nidulans FGSC A4 locus and maps to reviewed UniProtKB:Q5AUX1.
o-orsellinate feeds OrsB/OrsC F-9775 tailoring AN7911.4 and AN7912.4 deletions still produced orsellinic acid but failed to produce F-9775 A and B, placing the genetically supported OrsB/OrsC branch downstream of the OrsA product.
DOI:10.1039/b904541d
https://www.uniprot.org/uniprotkb/Q5AUW9
https://www.ncbi.nlm.nih.gov/protein/EAA59565.1
https://www.uniprot.org/uniprotkb/Q5AUW8
https://www.ncbi.nlm.nih.gov/protein/EAA59566.1
  • reference
    DOI:10.1039/b904541d
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    only two additional genes
    notes
    Sanchez et al. used targeted deletions in Aspergillus nidulans and found that OrsA is sufficient for orsellinic acid biosynthesis, while the adjacent AN7911.4/orsB and AN7912.4/orsC genes are additionally required for F-9775 A and B synthesis.
  • reference
    https://www.uniprot.org/uniprotkb/Q5AUW9
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    notes
    Reviewed UniProtKB:Q5AUW9 is the Aspergillus nidulans FGSC A4 decarboxylase OrsB/F9775 biosynthesis cluster protein B, length 331 aa, gene orsB, and cross-references EMBL AACD01000135.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/EAA59565.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    snippet
    /protein_id="EAA59565.1"
    notes
    NCBI GenPept EAA59565.1 is the AACD01000135.1 locus_tag AN7911.2 coding sequence that maps to Aspergillus nidulans FGSC A4 OrsB.
  • reference
    https://www.uniprot.org/uniprotkb/Q5AUW8
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    notes
    Reviewed UniProtKB:Q5AUW8 is the Aspergillus nidulans FGSC A4 tyrosinase-like protein OrsC/F9775 biosynthesis cluster protein C, length 369 aa, gene orsC, and cross-references EMBL AACD01000135.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/EAA59566.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    snippet
    /protein_id="EAA59566.1"
    notes
    NCBI GenPept EAA59566.1 is the AACD01000135.1 locus_tag AN7912.2 coding sequence that maps to Aspergillus nidulans FGSC A4 OrsC.
OrsB is required for OrsB/OrsC F-9775 tailoring Deleting AN7911.4/orsB abolished F-9775 A and B production while leaving orsellinic acid production intact.
DOI:10.1039/b904541d
https://www.uniprot.org/uniprotkb/Q5AUW9
https://www.ncbi.nlm.nih.gov/protein/EAA59565.1
https://www.uniprot.org/uniprotkb/Q5AUW8
https://www.ncbi.nlm.nih.gov/protein/EAA59566.1
  • reference
    DOI:10.1039/b904541d
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    only two additional genes
    notes
    Sanchez et al. used targeted deletions in Aspergillus nidulans and found that OrsA is sufficient for orsellinic acid biosynthesis, while the adjacent AN7911.4/orsB and AN7912.4/orsC genes are additionally required for F-9775 A and B synthesis.
  • reference
    https://www.uniprot.org/uniprotkb/Q5AUW9
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    notes
    Reviewed UniProtKB:Q5AUW9 is the Aspergillus nidulans FGSC A4 decarboxylase OrsB/F9775 biosynthesis cluster protein B, length 331 aa, gene orsB, and cross-references EMBL AACD01000135.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/EAA59565.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    snippet
    /protein_id="EAA59565.1"
    notes
    NCBI GenPept EAA59565.1 is the AACD01000135.1 locus_tag AN7911.2 coding sequence that maps to Aspergillus nidulans FGSC A4 OrsB.
  • reference
    https://www.uniprot.org/uniprotkb/Q5AUW8
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    notes
    Reviewed UniProtKB:Q5AUW8 is the Aspergillus nidulans FGSC A4 tyrosinase-like protein OrsC/F9775 biosynthesis cluster protein C, length 369 aa, gene orsC, and cross-references EMBL AACD01000135.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/EAA59566.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    snippet
    /protein_id="EAA59566.1"
    notes
    NCBI GenPept EAA59566.1 is the AACD01000135.1 locus_tag AN7912.2 coding sequence that maps to Aspergillus nidulans FGSC A4 OrsC.
OrsC is required for OrsB/OrsC F-9775 tailoring Deleting AN7912.4/orsC abolished F-9775 A and B production while leaving orsellinic acid production intact.
DOI:10.1039/b904541d
https://www.uniprot.org/uniprotkb/Q5AUW9
https://www.ncbi.nlm.nih.gov/protein/EAA59565.1
https://www.uniprot.org/uniprotkb/Q5AUW8
https://www.ncbi.nlm.nih.gov/protein/EAA59566.1
  • reference
    DOI:10.1039/b904541d
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    only two additional genes
    notes
    Sanchez et al. used targeted deletions in Aspergillus nidulans and found that OrsA is sufficient for orsellinic acid biosynthesis, while the adjacent AN7911.4/orsB and AN7912.4/orsC genes are additionally required for F-9775 A and B synthesis.
  • reference
    https://www.uniprot.org/uniprotkb/Q5AUW9
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    notes
    Reviewed UniProtKB:Q5AUW9 is the Aspergillus nidulans FGSC A4 decarboxylase OrsB/F9775 biosynthesis cluster protein B, length 331 aa, gene orsB, and cross-references EMBL AACD01000135.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/EAA59565.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    snippet
    /protein_id="EAA59565.1"
    notes
    NCBI GenPept EAA59565.1 is the AACD01000135.1 locus_tag AN7911.2 coding sequence that maps to Aspergillus nidulans FGSC A4 OrsB.
  • reference
    https://www.uniprot.org/uniprotkb/Q5AUW8
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    notes
    Reviewed UniProtKB:Q5AUW8 is the Aspergillus nidulans FGSC A4 tyrosinase-like protein OrsC/F9775 biosynthesis cluster protein C, length 369 aa, gene orsC, and cross-references EMBL AACD01000135.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/EAA59566.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    snippet
    /protein_id="EAA59566.1"
    notes
    NCBI GenPept EAA59566.1 is the AACD01000135.1 locus_tag AN7912.2 coding sequence that maps to Aspergillus nidulans FGSC A4 OrsC.
OrsB/OrsC F-9775 tailoring forms F9775B Sanchez et al. genetically delimited the F-9775 A/B branch to OrsA plus OrsB and OrsC, but the exact F-9775 B-specific sequence of tailoring reactions remains unresolved.
DOI:10.1039/b904541d
https://www.uniprot.org/uniprotkb/Q5AUW9
https://www.ncbi.nlm.nih.gov/protein/EAA59565.1
https://www.uniprot.org/uniprotkb/Q5AUW8
https://www.ncbi.nlm.nih.gov/protein/EAA59566.1
  • reference
    DOI:10.1039/b904541d
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    only two additional genes
    notes
    Sanchez et al. used targeted deletions in Aspergillus nidulans and found that OrsA is sufficient for orsellinic acid biosynthesis, while the adjacent AN7911.4/orsB and AN7912.4/orsC genes are additionally required for F-9775 A and B synthesis.
  • reference
    https://www.uniprot.org/uniprotkb/Q5AUW9
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    notes
    Reviewed UniProtKB:Q5AUW9 is the Aspergillus nidulans FGSC A4 decarboxylase OrsB/F9775 biosynthesis cluster protein B, length 331 aa, gene orsB, and cross-references EMBL AACD01000135.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/EAA59565.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    snippet
    /protein_id="EAA59565.1"
    notes
    NCBI GenPept EAA59565.1 is the AACD01000135.1 locus_tag AN7911.2 coding sequence that maps to Aspergillus nidulans FGSC A4 OrsB.
  • reference
    https://www.uniprot.org/uniprotkb/Q5AUW8
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    notes
    Reviewed UniProtKB:Q5AUW8 is the Aspergillus nidulans FGSC A4 tyrosinase-like protein OrsC/F9775 biosynthesis cluster protein C, length 369 aa, gene orsC, and cross-references EMBL AACD01000135.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/EAA59566.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-28
    snippet
    /protein_id="EAA59566.1"
    notes
    NCBI GenPept EAA59566.1 is the AACD01000135.1 locus_tag AN7912.2 coding sequence that maps to Aspergillus nidulans FGSC A4 OrsC.

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

Explore across X-Mech

AntibioticMech (F9775B) ↗ MediaIngredientMech (naturalproductmech:mibig-afdd774b74) ↗ TaxonMech: Aspergillus nidulans FGSC A4 (NCBITaxon:227321) ↗ PathwayMech (mibig:BGC0000057) ↗

Provenance

Source conceptSourceVersion
BGC0000057MIBIG5

This page is generated from data/natural_products/polyketides/f9775b.yaml, which is generated from the committed inventories. Neither is edited by hand.