bolagladin B

naturalproductmech:mibig-f9aa045875 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	BPAWMVDVEWZKAP-GQZVVMBSSA-N
SMILES	CC[C@@H](C)[C@H]1NC(=O)[C@@H](NC(=O)/C=C/NC(=O)/C=C\CCCCCCC/C=C\CCCCC(CC(=O)O)(OC)C(=O)O)COC(=O)[C@H](CO)NC(=O)[C@H](CCO)NC1=O
Stereochemistry	undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers
Cross-references	npatlas:NPA033056

Filing pathway

Unclassified — 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 nrps, from MIBiG.

Producer organisms 2

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
Burkholderia gladioli NCBITaxon:28095	BGC_CHARACTERIZED	mibig:BGC0002327	PMID:32780428
Burkholderia gladioli NCBITaxon:28095	BGC_CHARACTERIZED	mibig:BGC0002336	DOI:10.1002/ange.202009110

Occurrences 1

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
Burkholderia gladioli NCBITaxon:28095	LOTUS	DOI:10.1002/ANGE.202009110

Biosynthetic gene clusters 2

Accession	Host	Locus evidence	Genome
mibig:BGC0002327	Burkholderia gladioli NCBITaxon:28095	CLUSTER_DEMONSTRATED	genbank:MT844061.1
mibig:BGC0002336	Burkholderia gladioli NCBITaxon:28095	CLUSTER_DEMONSTRATED	genbank:NZ_CADEQC010000001.1

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	BolR UniProtKB:A0A7G7XYE0		ungrounded → ungrounded	DOI:10.1002/anie.202009107

Step 1: This curates the Burkholderia gladioli HKI0521 BGC0002327/MT844061.1 BolR citrate synthase required for the citrate-derived tricarboxylic fatty-acid tail in bolagladin A/B. Native oxaloacetyl- or citryl-CoA activation timing remains unresolved, so no exact substrate or product is asserted.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Partial Burkholderia gladioli HKI0521 bolagladin B biosynthesis graph for BolR involvement in the citrate-derived tricarboxylic fatty-acid tail.

Subject	Predicate	Object	Notes	Evidence
BolR	is required for	citrate-derived tricarboxylic fatty-acid tail assembly	HKI0521 bolR deletion abolished bolagladin A/B production and yielded tail-shortened shunt metabolites, while a B. gladioli BolR homolog showed citrate synthase activity in vitro.	DOI:10.1002/anie.202009107 DOI:10.1002/anie.202009110 https://www.uniprot.org/uniprotkb/A0A7G7XYE0 https://www.ncbi.nlm.nih.gov/protein/QNH85850.1 reference DOI:10.1002/anie.202009107 evidence type PRIMARY_EXPERIMENT snippet the production of 1 and 2 was fully abrogated notes Dose et al. constructed a Burkholderia gladioli HKI0521 bolR null mutant and showed that normal bolagladin A and B production was abolished, with tail-shortened shunt metabolites detected instead. reference DOI:10.1002/anie.202009110 evidence type PRIMARY_EXPERIMENT snippet resulted in complete conversion to products with molecular formulae corresponding to citric acid notes Dashti et al. purified a Burkholderia gladioli BolR homolog and showed citrate synthase activity from oxaloacetate and acetyl-CoA to citrate and CoA, corroborating the citrate synthase role assigned to HKI0521 BolR. reference https://www.uniprot.org/uniprotkb/A0A7G7XYE0 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes Unreviewed UniProtKB:A0A7G7XYE0 is the Burkholderia gladioli bolR 459 aa citrate synthase and cross-references EMBL MT844061 protein QNH85850.1. reference https://www.ncbi.nlm.nih.gov/protein/QNH85850.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept QNH85850.1 is the MT844061.1 BGC0002327 Burkholderia gladioli HKI0521 bolR citrate synthase CDS and is sequence-identical to UniProtKB:A0A7G7XYE0.
citrate-derived tricarboxylic fatty-acid tail assembly	contributes to	bolagladin B	Bolagladin B contains the tricarboxylic fatty-acid tail whose normal assembly requires BolR.	DOI:10.1002/anie.202009107 DOI:10.1002/anie.202009110 https://www.uniprot.org/uniprotkb/A0A7G7XYE0 https://www.ncbi.nlm.nih.gov/protein/QNH85850.1 reference DOI:10.1002/anie.202009107 evidence type PRIMARY_EXPERIMENT snippet the production of 1 and 2 was fully abrogated notes Dose et al. constructed a Burkholderia gladioli HKI0521 bolR null mutant and showed that normal bolagladin A and B production was abolished, with tail-shortened shunt metabolites detected instead. reference DOI:10.1002/anie.202009110 evidence type PRIMARY_EXPERIMENT snippet resulted in complete conversion to products with molecular formulae corresponding to citric acid notes Dashti et al. purified a Burkholderia gladioli BolR homolog and showed citrate synthase activity from oxaloacetate and acetyl-CoA to citrate and CoA, corroborating the citrate synthase role assigned to HKI0521 BolR. reference https://www.uniprot.org/uniprotkb/A0A7G7XYE0 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes Unreviewed UniProtKB:A0A7G7XYE0 is the Burkholderia gladioli bolR 459 aa citrate synthase and cross-references EMBL MT844061 protein QNH85850.1. reference https://www.ncbi.nlm.nih.gov/protein/QNH85850.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept QNH85850.1 is the MT844061.1 BGC0002327 Burkholderia gladioli HKI0521 bolR citrate synthase CDS and is sequence-identical to UniProtKB:A0A7G7XYE0.

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

Explore across X-Mech

AntibioticMech (bolagladin B) ↗ MediaIngredientMech (naturalproductmech:mibig-f9aa045875) ↗ TaxonMech: Burkholderia gladioli (NCBITaxon:28095) ↗ TaxonMech: Burkholderia gladioli (NCBITaxon:28095) ↗ PathwayMech (mibig:BGC0002327) ↗ PathwayMech (mibig:BGC0002336) ↗

Open questions 1

shared-structure — This structure is reported by more than one MIBiG entry: BGC0002327, BGC0002336. Confirm they describe the same compound rather than an upstream cross-reference error.

Provenance

Source concept	Source	Version
BGC0002327	MIBIG	3
BGC0002336	MIBIG	2

This page is generated from data/natural_products/unclassified/bolagladin-b.yaml, which is generated from the committed inventories. Neither is edited by hand.