botrydial

CHEBI:3159 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 cytotoxic fungal metabolite isolated from plant tissues infected by phytopathogen Botrytis cinerea.

Structure

Standard InChIKey	SJFIYVCSGNWVPJ-GKKOWQTJSA-N
SMILES	C[C@@H]1C[C@@H]([C@@H]2[C@]([C@H]1C=O)([C@@](CC2(C)C)(C)C=O)O)OC(=O)C
Stereochemistry	fully defined
Cross-references	npatlas:NPA003924

Filing pathway

Terpenoids — 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 terpene, 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
Botrytis cinerea B05.10 NCBITaxon:332648	BGC_CHARACTERIZED	mibig:BGC0000631	DOI:10.1021/cb800225v

Occurrences 6

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
Botrytis cinerea NCBITaxon:40559	LOTUS	DOI:10.1002/CBER.19741070530
Botrytis cinerea NCBITaxon:40559	LOTUS	DOI:10.1016/0031-9422(95)00643-5
Botrytis cinerea NCBITaxon:40559	LOTUS	DOI:10.1016/J.TETASY.2011.09.010
Botrytis cinerea NCBITaxon:40559	LOTUS	DOI:10.1016/S0040-4020(99)00032-0
Botrytis cinerea NCBITaxon:40559	LOTUS	DOI:10.1021/CB800225V
Botrytis cinerea NCBITaxon:40559	LOTUS	DOI:10.1021/NP980104B

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000631	Botrytis cinerea B05.10 NCBITaxon:332648	CLUSTER_DEMONSTRATED	genbank:CP009816.1

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.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 11 nodes, 10 edges

Process-level Botrytis cinerea B05.10 graph for BcBOT2 cyclization of farnesyl diphosphate followed by BcBOT4, BcBOT5, BcBOT3 and BcBOT1 tailoring to botrydial.

Subject	Predicate	Object	Evidence
(2E,6E)-farnesyl diphosphate	is cyclized by	BcBOT2	DOI:10.1021/cb800225v https://www.uniprot.org/uniprotkb/A0A384K0Q0 https://www.ncbi.nlm.nih.gov/protein/ATZ56107.1 reference DOI:10.1021/cb800225v evidence type PRIMARY_EXPERIMENT snippet Recombinant BcBOT2 protein converted farnesyl diphosphate to the parent sesquiterpene notes Pinedo et al. inactivated BcBOT2 in Botrytis cinerea and showed that the recombinant terpene synthase converts farnesyl diphosphate into the first committed botrydial intermediate, presilphiperfolan-8beta-ol. reference https://www.uniprot.org/uniprotkb/A0A384K0Q0 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes UniProtKB:A0A384K0Q0 resolves to unreviewed Botrytis cinerea strain B05.10 Bcbot2/BCIN_12g06390, length 399 aa, and cross-references EMBL CP009816. reference https://www.ncbi.nlm.nih.gov/protein/ATZ56107.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes NCBI GenPept ATZ56107.1 is the CP009816.1 Bcbot2/BCIN_12g06390 coding sequence from Botrytis cinerea strain B05.10.
BcBOT2	forms	presilphiperfolan-8beta-ol	DOI:10.1021/cb800225v https://www.uniprot.org/uniprotkb/A0A384K0Q0 https://www.ncbi.nlm.nih.gov/protein/ATZ56107.1 reference DOI:10.1021/cb800225v evidence type PRIMARY_EXPERIMENT snippet Recombinant BcBOT2 protein converted farnesyl diphosphate to the parent sesquiterpene notes Pinedo et al. inactivated BcBOT2 in Botrytis cinerea and showed that the recombinant terpene synthase converts farnesyl diphosphate into the first committed botrydial intermediate, presilphiperfolan-8beta-ol. reference https://www.uniprot.org/uniprotkb/A0A384K0Q0 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes UniProtKB:A0A384K0Q0 resolves to unreviewed Botrytis cinerea strain B05.10 Bcbot2/BCIN_12g06390, length 399 aa, and cross-references EMBL CP009816. reference https://www.ncbi.nlm.nih.gov/protein/ATZ56107.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes NCBI GenPept ATZ56107.1 is the CP009816.1 Bcbot2/BCIN_12g06390 coding sequence from Botrytis cinerea strain B05.10.
presilphiperfolan-8beta-ol	is hydroxylated in	C-4 hydroxylation	DOI:10.1021/acschembio.6b00581 https://www.uniprot.org/uniprotkb/A0A384JZV1 https://www.ncbi.nlm.nih.gov/protein/ATZ56105.1 reference DOI:10.1021/acschembio.6b00581 evidence type PRIMARY_EXPERIMENT snippet hydroxylations at the carbons C-10 and C-4 notes Moraga et al. inactivated BcBOT3 and BcBOT4 by homologous recombination and assigned their regio- and stereospecific hydroxylations; BcBOT4 catalyzes C-4 hydroxylation of the presilphiperfolan-8beta-ol skeleton. reference https://www.uniprot.org/uniprotkb/A0A384JZV1 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes UniProtKB:A0A384JZV1 resolves to unreviewed Botrytis cinerea strain B05.10 Bcbot4/BCIN_12g06370, length 526 aa, and cross-references EMBL CP009816. reference https://www.ncbi.nlm.nih.gov/protein/ATZ56105.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes NCBI GenPept ATZ56105.1 is the CP009816.1 Bcbot4/BCIN_12g06370 coding sequence from Botrytis cinerea strain B05.10.
BcBOT4	catalyzes	C-4 hydroxylation	DOI:10.1021/acschembio.6b00581 https://www.uniprot.org/uniprotkb/A0A384JZV1 https://www.ncbi.nlm.nih.gov/protein/ATZ56105.1 reference DOI:10.1021/acschembio.6b00581 evidence type PRIMARY_EXPERIMENT snippet hydroxylations at the carbons C-10 and C-4 notes Moraga et al. inactivated BcBOT3 and BcBOT4 by homologous recombination and assigned their regio- and stereospecific hydroxylations; BcBOT4 catalyzes C-4 hydroxylation of the presilphiperfolan-8beta-ol skeleton. reference https://www.uniprot.org/uniprotkb/A0A384JZV1 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes UniProtKB:A0A384JZV1 resolves to unreviewed Botrytis cinerea strain B05.10 Bcbot4/BCIN_12g06370, length 526 aa, and cross-references EMBL CP009816. reference https://www.ncbi.nlm.nih.gov/protein/ATZ56105.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes NCBI GenPept ATZ56105.1 is the CP009816.1 Bcbot4/BCIN_12g06370 coding sequence from Botrytis cinerea strain B05.10.
C-4 hydroxylation	precedes	C-4 acetylation	https://mibig.secondarymetabolites.org/repository/BGC0000631.5/index.html reference https://mibig.secondarymetabolites.org/repository/BGC0000631.5/index.html evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes MIBiG BGC0000631.5 records botrydial for the Botrytis cinerea B05.10 CP009816.1 locus and curates the biosynthetic path as BcBOT2 > BcBOT4 > BcBOT5 > BcBOT3\|BcBOT1.
BcBOT5	catalyzes	C-4 acetylation	https://mibig.secondarymetabolites.org/repository/BGC0000631.5/index.html https://www.uniprot.org/uniprotkb/A0A384JZT4 https://www.ncbi.nlm.nih.gov/protein/ATZ56109.1 reference https://mibig.secondarymetabolites.org/repository/BGC0000631.5/index.html evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes MIBiG BGC0000631.5 records botrydial for the Botrytis cinerea B05.10 CP009816.1 locus and curates the biosynthetic path as BcBOT2 > BcBOT4 > BcBOT5 > BcBOT3\|BcBOT1. reference https://www.uniprot.org/uniprotkb/A0A384JZT4 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes UniProtKB:A0A384JZT4 resolves to unreviewed Botrytis cinerea strain B05.10 Bcbot5/BCIN_12g06410, length 545 aa, and cross-references EMBL CP009816. reference https://www.ncbi.nlm.nih.gov/protein/ATZ56109.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes NCBI GenPept ATZ56109.1 is the CP009816.1 Bcbot5/BCIN_12g06410 coding sequence from Botrytis cinerea strain B05.10.
C-4 acetylation	precedes	BcBOT3/BcBOT1 P450 tailoring	https://mibig.secondarymetabolites.org/repository/BGC0000631.5/index.html reference https://mibig.secondarymetabolites.org/repository/BGC0000631.5/index.html evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes MIBiG BGC0000631.5 records botrydial for the Botrytis cinerea B05.10 CP009816.1 locus and curates the biosynthetic path as BcBOT2 > BcBOT4 > BcBOT5 > BcBOT3\|BcBOT1.
BcBOT3	catalyzes	BcBOT3/BcBOT1 P450 tailoring	DOI:10.1021/acschembio.6b00581 DOI:10.1021/cb800225v https://mibig.secondarymetabolites.org/repository/BGC0000631.5/index.html https://www.uniprot.org/uniprotkb/A0A384JZZ2 https://www.ncbi.nlm.nih.gov/protein/ATZ56108.1 reference DOI:10.1021/acschembio.6b00581 evidence type PRIMARY_EXPERIMENT snippet the function of the five genes notes Moraga et al. connected BcBOT3 and BcBOT4 to biosynthetic intermediates and established the five-gene genetic and molecular basis of botrydial biosynthesis. reference DOI:10.1021/cb800225v evidence type PRIMARY_EXPERIMENT snippet Five genes including BcBOT1 and BcBOT2 notes Pinedo et al. identified BcBOT1 and BcBOT2 in the Botrytis cinerea botrydial biosynthetic gene cluster. reference https://mibig.secondarymetabolites.org/repository/BGC0000631.5/index.html evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes MIBiG BGC0000631.5 records botrydial for the Botrytis cinerea B05.10 CP009816.1 locus and curates the biosynthetic path as BcBOT2 > BcBOT4 > BcBOT5 > BcBOT3\|BcBOT1. reference https://www.uniprot.org/uniprotkb/A0A384JZZ2 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes UniProtKB:A0A384JZZ2 resolves to unreviewed Botrytis cinerea strain B05.10 Bcbot3/BCIN_12g06400, length 567 aa, and cross-references EMBL CP009816. reference https://www.ncbi.nlm.nih.gov/protein/ATZ56108.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes NCBI GenPept ATZ56108.1 is the CP009816.1 Bcbot3/BCIN_12g06400 coding sequence from Botrytis cinerea strain B05.10.
BcBOT1	catalyzes	BcBOT3/BcBOT1 P450 tailoring	DOI:10.1021/acschembio.6b00581 DOI:10.1021/cb800225v https://mibig.secondarymetabolites.org/repository/BGC0000631.5/index.html https://www.uniprot.org/uniprotkb/A0A384JZT1 https://www.ncbi.nlm.nih.gov/protein/ATZ56106.1 reference DOI:10.1021/acschembio.6b00581 evidence type PRIMARY_EXPERIMENT snippet the function of the five genes notes Moraga et al. connected BcBOT3 and BcBOT4 to biosynthetic intermediates and established the five-gene genetic and molecular basis of botrydial biosynthesis. reference DOI:10.1021/cb800225v evidence type PRIMARY_EXPERIMENT snippet Five genes including BcBOT1 and BcBOT2 notes Pinedo et al. identified BcBOT1 and BcBOT2 in the Botrytis cinerea botrydial biosynthetic gene cluster. reference https://mibig.secondarymetabolites.org/repository/BGC0000631.5/index.html evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes MIBiG BGC0000631.5 records botrydial for the Botrytis cinerea B05.10 CP009816.1 locus and curates the biosynthetic path as BcBOT2 > BcBOT4 > BcBOT5 > BcBOT3\|BcBOT1. reference https://www.uniprot.org/uniprotkb/A0A384JZT1 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes UniProtKB:A0A384JZT1 resolves to unreviewed Botrytis cinerea strain B05.10 Bcbot1/BCIN_12g06380, length 510 aa, and cross-references EMBL CP009816. reference https://www.ncbi.nlm.nih.gov/protein/ATZ56106.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes NCBI GenPept ATZ56106.1 is the CP009816.1 Bcbot1/BCIN_12g06380 coding sequence from Botrytis cinerea strain B05.10.
BcBOT3/BcBOT1 P450 tailoring	produces	botrydial	DOI:10.1021/acschembio.6b00581 DOI:10.1021/cb800225v https://mibig.secondarymetabolites.org/repository/BGC0000631.5/index.html reference DOI:10.1021/acschembio.6b00581 evidence type PRIMARY_EXPERIMENT snippet the function of the five genes notes Moraga et al. connected BcBOT3 and BcBOT4 to biosynthetic intermediates and established the five-gene genetic and molecular basis of botrydial biosynthesis. reference DOI:10.1021/cb800225v evidence type PRIMARY_EXPERIMENT snippet Five genes including BcBOT1 and BcBOT2 notes Pinedo et al. identified BcBOT1 and BcBOT2 in the Botrytis cinerea botrydial biosynthetic gene cluster. reference https://mibig.secondarymetabolites.org/repository/BGC0000631.5/index.html evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes MIBiG BGC0000631.5 records botrydial for the Botrytis cinerea B05.10 CP009816.1 locus and curates the biosynthetic path as BcBOT2 > BcBOT4 > BcBOT5 > BcBOT3\|BcBOT1.

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

Explore across X-Mech

AntibioticMech (botrydial) ↗ MediaIngredientMech (CHEBI:3159) ↗ TaxonMech: Botrytis cinerea B05.10 (NCBITaxon:332648) ↗ PathwayMech (mibig:BGC0000631) ↗

Provenance

Source concept	Source	Version
BGC0000631	MIBIG	5
CHEBI:3159	CHEBI	3-star

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