solanapyrone D

CHEBI:38240 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

Structure

Standard InChIKey	AWQLNKJBXASXDU-IPJQOSJUSA-N
SMILES	[H][C@@]12CCCC[C@@]1([H])[C@@H]([C@H](C)C=C2)C1=CC(OC)=C(C=O)C(=O)O1
Stereochemistry	fully defined
Cross-references	npatlas:NPA019901

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
Alternaria solani NCBITaxon:48100	SOURCE_ASSERTION	mibig:BGC0000146	PMID:20486243

Occurrences 3

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
Alternaria solani NCBITaxon:48100	LOTUS	DOI:10.1002/CBIC.201000173
Alternaria solani NCBITaxon:48100	LOTUS	DOI:10.1039/C39890001284
Alternaria solani NCBITaxon:48100	LOTUS	DOI:10.1271/BBB.62.2016

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000146	Alternaria solani NCBITaxon:48100	CLUSTER_UNSTATED	genbank:AB514562.1

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	Sol5 bifunctional solanapyrone synthase UniProtKB:D7UQ40	RHEA:75143	CHEBI:63164 → CHEBI:38240	DOI:10.1002/cbic.201000173

Step 1: Alternaria solani Sol5 catalyzes the cycloisomerization of prosolanapyrone III to solanapyrone D; UniProt and Rhea ground this half-reaction as RHEA:75143.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Alternaria solani Sol5-catalyzed conversion of prosolanapyrone III to solanapyrone D.

Subject	Predicate	Object	Notes	Evidence
prosolanapyrone III	is cyclized by	Sol5	RHEA:75143 places prosolanapyrone III on the substrate side of the Sol5-catalyzed cycloisomerase reaction.	DOI:10.1002/cbic.201000173 DOI:10.1016/s0167-4838(98)00040-5 DOI:10.1271/bbb.70600 https://mibig.secondarymetabolites.org/repository/BGC0000146.3/ https://www.uniprot.org/uniprotkb/D7UQ40 https://www.rhea-db.org/rhea/75143 reference DOI:10.1002/cbic.201000173 evidence type PRIMARY_EXPERIMENT snippet Sol5, encoding a flavin-dependent oxidase (solanapyrone synthase, SPS), was expressed in Pichia pastoris and purified notes Kasahara et al. cloned the Alternaria solani solanapyrone biosynthetic cluster AB514562, identified sol5 in the cluster, and expressed and purified Sol5 as solanapyrone synthase. reference DOI:10.1016/s0167-4838(98)00040-5 evidence type PRIMARY_EXPERIMENT snippet converting prosolanapyrone II to solanapyrones A and D via oxidation and subsequent Diels-Alder reaction notes Katayama et al. detected Alternaria solani solanapyrone synthase activity producing solanapyrone D in cell-free extracts and partially purified active fractions. reference DOI:10.1271/bbb.70600 evidence type PRIMARY_EXPERIMENT snippet identified as truncated solanapyrone synthase, and its N-terminal amino acid sequence was found to be QETQNLNNFLESNAINP notes Katayama et al. purified a truncated Alternaria solani solanapyrone synthase whose N terminus maps to the Sol5 sequence. reference https://mibig.secondarymetabolites.org/repository/BGC0000146.3/ evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes MIBiG entry version 3 links BGC0000146 to the Alternaria solani AB514562 solanapyrone biosynthetic gene cluster; the GenBank record contains sol5 / BAJ09785.1 annotated as oxidase/Diels-Alderase. reference https://www.uniprot.org/uniprotkb/D7UQ40 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes UniProtKB:D7UQ40 is the Alternaria solani sol5 / BAJ09785.1 bifunctional solanapyrone synthase from EMBL AB514562 and annotates the RHEA:75143 prosolanapyrone III to solanapyrone D cycloisomerase reaction. reference https://www.rhea-db.org/rhea/75143 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes RHEA:75143 is the prosolanapyrone III to solanapyrone D reaction; RHEA:75144 is its left-to-right direction.
Sol5	forms	solanapyrone D	RHEA:75143 places solanapyrone D on the product side of the Sol5-catalyzed cycloisomerase reaction.	DOI:10.1002/cbic.201000173 DOI:10.1016/s0167-4838(98)00040-5 DOI:10.1271/bbb.70600 https://mibig.secondarymetabolites.org/repository/BGC0000146.3/ https://www.uniprot.org/uniprotkb/D7UQ40 https://www.rhea-db.org/rhea/75143 reference DOI:10.1002/cbic.201000173 evidence type PRIMARY_EXPERIMENT snippet Sol5, encoding a flavin-dependent oxidase (solanapyrone synthase, SPS), was expressed in Pichia pastoris and purified notes Kasahara et al. cloned the Alternaria solani solanapyrone biosynthetic cluster AB514562, identified sol5 in the cluster, and expressed and purified Sol5 as solanapyrone synthase. reference DOI:10.1016/s0167-4838(98)00040-5 evidence type PRIMARY_EXPERIMENT snippet converting prosolanapyrone II to solanapyrones A and D via oxidation and subsequent Diels-Alder reaction notes Katayama et al. detected Alternaria solani solanapyrone synthase activity producing solanapyrone D in cell-free extracts and partially purified active fractions. reference DOI:10.1271/bbb.70600 evidence type PRIMARY_EXPERIMENT snippet identified as truncated solanapyrone synthase, and its N-terminal amino acid sequence was found to be QETQNLNNFLESNAINP notes Katayama et al. purified a truncated Alternaria solani solanapyrone synthase whose N terminus maps to the Sol5 sequence. reference https://mibig.secondarymetabolites.org/repository/BGC0000146.3/ evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes MIBiG entry version 3 links BGC0000146 to the Alternaria solani AB514562 solanapyrone biosynthetic gene cluster; the GenBank record contains sol5 / BAJ09785.1 annotated as oxidase/Diels-Alderase. reference https://www.uniprot.org/uniprotkb/D7UQ40 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes UniProtKB:D7UQ40 is the Alternaria solani sol5 / BAJ09785.1 bifunctional solanapyrone synthase from EMBL AB514562 and annotates the RHEA:75143 prosolanapyrone III to solanapyrone D cycloisomerase reaction. reference https://www.rhea-db.org/rhea/75143 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes RHEA:75143 is the prosolanapyrone III to solanapyrone D reaction; RHEA:75144 is its left-to-right direction.

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

Explore across X-Mech

AntibioticMech (solanapyrone D) ↗ MediaIngredientMech (CHEBI:38240) ↗ TaxonMech: Alternaria solani (NCBITaxon:48100) ↗ PathwayMech (mibig:BGC0000146) ↗

Provenance

Source concept	Source	Version
BGC0000146	MIBIG	3
CHEBI:38240	CHEBI	3-star

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