YWA1

CHEBI:133763 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 heptaketide that is 2,3-dihydro-4H-benzo[g]chromen-4-one bearing a methyl substituent at position 2 and four hydroxy substituents at positions 2, 5, 6 and 8.

Structure

Standard InChIKey	RTYDQIKVNMHQMZ-UHFFFAOYSA-N
SMILES	CC1(O)CC(=O)C2=C(O)C3=C(O)C=C(O)C=C3C=C2O1
Stereochemistry	undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers
Cross-references	pubchem:100923872, npatlas:NPA033448

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 oryzae RIB40 NCBITaxon:510516	SOURCE_ASSERTION	mibig:BGC0002175	PMID:31655589

Occurrences 4

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
Aspergillus nidulans NCBITaxon:162425	LOTUS	DOI:10.1016/S0040-4039(98)80027-0
Aspergillus nidulans NCBITaxon:162425	CHEBI	PMID:11251292
Aspergillus flavus NCBITaxon:5059	LOTUS	DOI:10.1186/S12896-019-0567-X
Aspergillus fumigatus NCBITaxon:746128	CHEBI	PMID:23557488

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0002175	Aspergillus oryzae RIB40 NCBITaxon:510516	CLUSTER_UNSTATED	genbank:BA000052.1

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	wA naphthopyrone polyketide synthase UniProtKB:Q2UA48	RHEA:62652	CHEBI:57288 + CHEBI:57384 → CHEBI:133763	DOI:10.1186/s12896-019-0567-x

Step 1: The A. oryzae wA promoter-replacement experiment supports AO090102000545 as the exact YWA1-forming gene. The full acetyl-CoA and malonyl-CoA stoichiometry is grounded by RHEA:62652 rather than by purified Q2UA48 biochemistry.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 4 nodes, 3 edges

Aspergillus oryzae RIB40 wA encodes a non-reducing polyketide synthase that forms the naphthopyrone YWA1.

Subject	Predicate	Object	Notes	Evidence
acetyl-CoA	is accepted by	wA polyketide synthase	RHEA:62652 supplies acetyl-CoA as the starter in the curated naphthopyrone YWA1 synthase reaction; applying that stoichiometry to Q2UA48 is proposed from the database reaction annotation.	DOI:10.1186/s12896-019-0567-x https://mibig.secondarymetabolites.org/repository/BGC0002175.3/BGC0002175.gbk https://www.uniprot.org/uniprotkb/Q2UA48 https://www.rhea-db.org/rhea/62652 reference DOI:10.1186/s12896-019-0567-x evidence type PRIMARY_EXPERIMENT snippet production of the polyketide derived from A. oryzae wA notes Tamano et al. replaced the native wA promoter in an A. oryzae kojA disruptant with the kojA promoter, confirmed recombination at the targeted wA locus, and matched the accumulated compound to a YWA1 standard by UV-Vis and UPLC-MS. reference https://mibig.secondarymetabolites.org/repository/BGC0002175.3/BGC0002175.gbk evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG BGC0002175.3 maps the Aspergillus oryzae RIB40 YWA1 cluster CDS AO090102000545 to GenPept BAE61567.1. reference https://www.uniprot.org/uniprotkb/Q2UA48 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes Unreviewed UniProtKB:Q2UA48 is the 2,141 aa Aspergillus oryzae RIB40 AO090102000545 entry; its canonical sequence is identical to the MIBiG BAE61567.1 translation, and its RHEA:62652/RHEA:62653 annotation is computational. reference https://www.rhea-db.org/rhea/62652 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes RHEA:62652 is the acetyl-CoA plus six malonyl-CoA naphthopyrone YWA1 synthase master reaction, mapped to left-to-right direction RHEA:62653 through homologous Swiss-Prot fungal naphthopyrone synthases.
malonyl-CoA	is iteratively condensed by	wA polyketide synthase	RHEA:62652 supplies six malonyl-CoA extender units in the curated naphthopyrone YWA1 synthase reaction; applying that stoichiometry to Q2UA48 is proposed from the database reaction annotation.	DOI:10.1186/s12896-019-0567-x https://mibig.secondarymetabolites.org/repository/BGC0002175.3/BGC0002175.gbk https://www.uniprot.org/uniprotkb/Q2UA48 https://www.rhea-db.org/rhea/62652 reference DOI:10.1186/s12896-019-0567-x evidence type PRIMARY_EXPERIMENT snippet production of the polyketide derived from A. oryzae wA notes Tamano et al. replaced the native wA promoter in an A. oryzae kojA disruptant with the kojA promoter, confirmed recombination at the targeted wA locus, and matched the accumulated compound to a YWA1 standard by UV-Vis and UPLC-MS. reference https://mibig.secondarymetabolites.org/repository/BGC0002175.3/BGC0002175.gbk evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG BGC0002175.3 maps the Aspergillus oryzae RIB40 YWA1 cluster CDS AO090102000545 to GenPept BAE61567.1. reference https://www.uniprot.org/uniprotkb/Q2UA48 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes Unreviewed UniProtKB:Q2UA48 is the 2,141 aa Aspergillus oryzae RIB40 AO090102000545 entry; its canonical sequence is identical to the MIBiG BAE61567.1 translation, and its RHEA:62652/RHEA:62653 annotation is computational. reference https://www.rhea-db.org/rhea/62652 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes RHEA:62652 is the acetyl-CoA plus six malonyl-CoA naphthopyrone YWA1 synthase master reaction, mapped to left-to-right direction RHEA:62653 through homologous Swiss-Prot fungal naphthopyrone synthases.
wA polyketide synthase	forms	YWA1	wA promoter replacement in A. oryzae produced YWA1-matching yellow pigment in the kojA-disruptant PkojA::wA strain.	DOI:10.1186/s12896-019-0567-x https://mibig.secondarymetabolites.org/repository/BGC0002175.3/BGC0002175.gbk https://www.uniprot.org/uniprotkb/Q2UA48 https://www.rhea-db.org/rhea/62652 reference DOI:10.1186/s12896-019-0567-x evidence type PRIMARY_EXPERIMENT snippet production of the polyketide derived from A. oryzae wA notes Tamano et al. replaced the native wA promoter in an A. oryzae kojA disruptant with the kojA promoter, confirmed recombination at the targeted wA locus, and matched the accumulated compound to a YWA1 standard by UV-Vis and UPLC-MS. reference https://mibig.secondarymetabolites.org/repository/BGC0002175.3/BGC0002175.gbk evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG BGC0002175.3 maps the Aspergillus oryzae RIB40 YWA1 cluster CDS AO090102000545 to GenPept BAE61567.1. reference https://www.uniprot.org/uniprotkb/Q2UA48 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes Unreviewed UniProtKB:Q2UA48 is the 2,141 aa Aspergillus oryzae RIB40 AO090102000545 entry; its canonical sequence is identical to the MIBiG BAE61567.1 translation, and its RHEA:62652/RHEA:62653 annotation is computational. reference https://www.rhea-db.org/rhea/62652 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes RHEA:62652 is the acetyl-CoA plus six malonyl-CoA naphthopyrone YWA1 synthase master reaction, mapped to left-to-right direction RHEA:62653 through homologous Swiss-Prot fungal naphthopyrone synthases.

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

Explore across X-Mech

AntibioticMech (YWA1) ↗ MediaIngredientMech (CHEBI:133763) ↗ TaxonMech: Aspergillus oryzae RIB40 (NCBITaxon:510516) ↗ PathwayMech (mibig:BGC0002175) ↗

Provenance

Source concept	Source	Version
BGC0002175	MIBIG	3
CHEBI:133763	CHEBI	3-star

This page is generated from data/natural_products/polyketides/ywa1.yaml, which is generated from the committed inventories. Neither is edited by hand.