pentabromopseudilin

naturalproductmech:mibig-005498ea51 MINTED SEEDED enzyme inhibitor

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	LXMNWKJHYOZUQL-UHFFFAOYSA-N
SMILES	C1=C(C=C(C(=C1Br)O)C2=C(C(=C(N2)Br)Br)Br)Br
Stereochemistry	fully defined
Cross-references	pubchem:324093

Filing pathway

Shikimates and phenylpropanoids — 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 other, from MIBiG.

Producer organisms 3

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
Pseudoalteromonas luteoviolacea 2ta16 NCBITaxon:1353533	BGC_CORRELATED	mibig:BGC0000891	PMID:24974229
Pseudoalteromonas phenolica O-BC30 NCBITaxon:1315281	SOURCE_ASSERTION	mibig:BGC0000890	PMID:24974229
Marinomonas mediterranea MMB-1 NCBITaxon:717774	SOURCE_ASSERTION	mibig:BGC0001465	PMID:24974229

Occurrences 2

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
Pseudoalteromonas luteoviolacea NCBITaxon:43657	LOTUS	DOI:10.1021/JO00092A020
Pseudoalteromonas luteoviolacea NCBITaxon:43657	LOTUS	DOI:10.1021/NP100506Z

Biosynthetic gene clusters 3

Accession	Host	Locus evidence	Genome
mibig:BGC0000891	Pseudoalteromonas luteoviolacea 2ta16 NCBITaxon:1353533	CLUSTER_DEMONSTRATED	genbank:AUSV01000133.1
mibig:BGC0000890	Pseudoalteromonas phenolica O-BC30 NCBITaxon:1315281	CLUSTER_DEMONSTRATED	genbank:KF540211.1
mibig:BGC0001465	Marinomonas mediterranea MMB-1 NCBITaxon:717774	CLUSTER_UNSTATED	genbank:NC_015276.1

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	Bmp7 UniProtKB:V4HJ73		ungrounded → naturalproductmech:mibig-005498ea51	DOI:10.1038/nchembio.1564

Step 1: Bmp7 is the Pseudoalteromonas luteoviolacea 2ta16 cytochrome P450 that catalyzes oxidative heterocoupling of a bromophenol and bromopyrrole to pentabromopseudilin. The exact local record product is captured here; the substrates 2,4-dibromophenol and 2,3,4-tribromopyrrole are left in the graph because the PathwayStep slot accepts one substrate CURIE and 2,3,4-tribromopyrrole has no local curated CURIE.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 5 nodes, 4 edges

Bmp7 catalyzes oxidative heterocoupling of 2,4-dibromophenol and 2,3,4-tribromopyrrole to pentabromopseudilin.

Subject	Predicate	Object	Evidence
2,4-dibromophenol	participates in	bromophenol-bromopyrrole oxidative heterocoupling	DOI:10.1038/nchembio.1564 reference DOI:10.1038/nchembio.1564 evidence type PRIMARY_EXPERIMENT snippet heterodimerization of 4 and 6 notes Agarwal et al. defined compounds 4 and 6 as 2,4-dibromophenol and 2,3,4-tribromopyrrole, then used an in vitro Bmp7 reaction to heterodimerize them.
2,3,4-tribromopyrrole	participates in	bromophenol-bromopyrrole oxidative heterocoupling	DOI:10.1038/nchembio.1564 reference DOI:10.1038/nchembio.1564 evidence type PRIMARY_EXPERIMENT snippet heterodimerization of 4 and 6 notes Agarwal et al. defined compounds 4 and 6 as 2,4-dibromophenol and 2,3,4-tribromopyrrole, then used an in vitro Bmp7 reaction to heterodimerize them.
Bmp7	catalyzes	bromophenol-bromopyrrole oxidative heterocoupling	DOI:10.1038/nchembio.1564 UniProtKB:V4HJ73 NCBI_Nuccore:AUSV01000133.1 NCBI_Protein:ESP90850.1 reference DOI:10.1038/nchembio.1564 evidence type PRIMARY_EXPERIMENT snippet We confirmed the enzymatic synthesis of 3 notes Agarwal et al. assayed purified Pseudoalteromonas luteoviolacea 2ta16 Bmp7 with 2,4-dibromophenol, 2,3,4-tribromopyrrole, Bmp9, Bmp10 and NADH, then confirmed enzymatic synthesis of pentabromopseudilin by comparison to an authentic standard. reference UniProtKB:V4HJ73 evidence type DATABASE_ASSERTION snippet DR EMBL; AUSV01000133; ESP90850.1; -; Genomic_DNA. notes UniProtKB:V4HJ73 is reviewed Pseudoalteromonas luteoviolacea 2ta16 Bmp7/PL2TA16_01241 and cites DOI:10.1038/nchembio.1564. reference NCBI_Nuccore:AUSV01000133.1 evidence type DATABASE_ASSERTION snippet /locus_tag="PL2TA16_01241" notes GenBank places cytochrome P450 GenPept ESP90850.1 at AUSV01000133.1:42270..43745 inside the BGC0000891 interval. reference NCBI_Protein:ESP90850.1 evidence type DATABASE_ASSERTION snippet /product="cytochrome P450" notes ESP90850.1 is encoded by PL2TA16_01241, the GenBank CDS that maps to UniProtKB:V4HJ73.
bromophenol-bromopyrrole oxidative heterocoupling	produces	pentabromopseudilin	DOI:10.1038/nchembio.1564 mibig:BGC0000891 reference DOI:10.1038/nchembio.1564 evidence type PRIMARY_EXPERIMENT snippet We confirmed the enzymatic synthesis of 3 notes Agarwal et al. assayed purified Pseudoalteromonas luteoviolacea 2ta16 Bmp7 with 2,4-dibromophenol, 2,3,4-tribromopyrrole, Bmp9, Bmp10 and NADH, then confirmed enzymatic synthesis of pentabromopseudilin by comparison to an authentic standard. reference mibig:BGC0000891 evidence type DATABASE_ASSERTION notes MIBiG BGC0000891 records pentabromopseudilin for the AUSV01000133.1:32483..43745 locus.

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

Bioactivities 1

Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.

Assay	Result	Target enzyme	Source detail
Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB	IC50 1.4 uM; ACTIVE	Not recorded	PMID:24446431 assay Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB evidence reference PMID:24446431 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 977608, deposited by Shanghai Institute of Organic Chemistry; assay type Other. call ACTIVE measurement type IC50 value 1.4 units uM activity class ENZYME_INHIBITOR

Explore across X-Mech

AntibioticMech (pentabromopseudilin) ↗ MediaIngredientMech (naturalproductmech:mibig-005498ea51) ↗ TaxonMech: Pseudoalteromonas luteoviolacea 2ta16 (NCBITaxon:1353533) ↗ TaxonMech: Pseudoalteromonas phenolica O-BC30 (NCBITaxon:1315281) ↗ TaxonMech: Marinomonas mediterranea MMB-1 (NCBITaxon:717774) ↗ PathwayMech (mibig:BGC0000891) ↗ PathwayMech (mibig:BGC0000890) ↗ PathwayMech (mibig:BGC0001465) ↗

Open questions 1

shared-structure — This structure is reported by more than one MIBiG entry: BGC0000890, BGC0000891, BGC0001465. Confirm they describe the same compound rather than an upstream cross-reference error.

Provenance

Source concept	Source	Version
BGC0000891	MIBIG	4
BGC0000890	MIBIG	5
BGC0001465	MIBIG	5

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