2,3,4,5-tetrabromopyrrole

naturalproductmech:mibig-dcee736e16 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	MIIWISWSCMVZHG-UHFFFAOYSA-N
SMILES	C1(=C(NC(=C1Br)Br)Br)Br
Stereochemistry	fully defined
Cross-references	pubchem:4605890

Filing pathway

Alkaloids — 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 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
Pseudoalteromonas piscicida NCBITaxon:43662	SOURCE_ASSERTION	mibig:BGC0001463	DOI:10.1073/pnas.1519695113
Pseudoalteromonas sp. PS5 NCBITaxon:1437473	SOURCE_ASSERTION	mibig:BGC0001464	DOI:10.1016/j.ijantimicag.2022.106523

Occurrences 0

None cited.

Biosynthetic gene clusters 2

Accession	Host	Locus evidence	Genome
mibig:BGC0001463	Pseudoalteromonas piscicida NCBITaxon:43662	CLUSTER_DEMONSTRATED	genbank:KT808878.1
mibig:BGC0001464	Pseudoalteromonas sp. PS5 NCBITaxon:1437473	CLUSTER_UNSTATED	genbank:KR011923.1

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 5 nodes, 4 edges

PS5 bmp2 in-frame deletion and loss of detected tetrabromopyrrole production, with a separately grounded native reference protein. A genetic-production context, not direct Bmp2 catalysis. Reference correspondence is not proof of experimental-stock sequence identity. Only extracted main text was inspected; no successful visual figure or supplementary-method review, rescue, quantitative yield or pathway-finality claim.

Subject	Predicate	Object	Notes	Evidence
bmp2 gene, PS5 reference locus	encodes_reference_protein	Bmp2, native PS5 reference protein	Reference-locus mapping only. Native PS5 Bmp2 is not O-BC30 A0A0S2JXW2 (43-aa difference) or the PDB-linked 409-aa GSH construct A0A140UHM3 with conflicting Streptomyces taxonomy. Neither selected as a PS5 UniProt example. UniParc UPI00078B3448 links active EMBL AKJ75108.1 and inactive UniProtKB/TrEMBL A0A139ZY81 (bmp2, taxon 1437473) with zero active UniProtKB entries.	https://www.ncbi.nlm.nih.gov/protein/AKJ75108.1 https://www.ncbi.nlm.nih.gov/nuccore/KR011923.1 DOI:10.1038/s43705-023-00309-6 https://rest.uniprot.org/uniparc/UPI00078B3448.json reference https://www.ncbi.nlm.nih.gov/protein/AKJ75108.1 evidence type DATABASE_ASSERTION notes Native PS5/taxon1437473 Bmp2 conceptual translation, 406aa; gene bmp2 and coded_by KR011923.1:2810..4030, table11. Not an independent protein assay. retrieved on 2026-10-07 reference https://www.ncbi.nlm.nih.gov/nuccore/KR011923.1 evidence type CURATOR_INFERENCE notes Complete1221-nt plus-CDS2810..4030, codon1/table11, equals annotation and independent GenPept, all406aa; coded_by coordinates/DNA and PS5/taxon agree. KR011923.1 is a6705-bp cluster, not a complete genome. retrieved on 2026-10-07 reference DOI:10.1038/s43705-023-00309-6 evidence type CURATOR_INFERENCE notes Fig1B caption cites PS5 cluster KR011923. Mapping its named bmp2 reference to the native CDS is curator inference; the experimental stock and mutant sequence were not independently verified. retrieved on 2026-10-07 reference https://rest.uniprot.org/uniparc/UPI00078B3448.json evidence type DATABASE_ASSERTION notes UniParc UPI00078B3448 (406 aa) links active EMBL AKJ75108.1 (Pseudoalteromonas sp. PS5, taxon 1437473, gene bmp2) and inactive UniProtKB/TrEMBL A0A139ZY81, with zero active UniProtKB cross-references. retrieved on 2026-10-30
PS5 bmp2 in-frame deletion	targets	bmp2 gene, PS5 reference locus	Reported in-frame deletion in PS5. No exact deletion junctions, off-target exclusion or complementation/rescue adopted.	DOI:10.1038/s43705-023-00309-6 reference DOI:10.1038/s43705-023-00309-6 evidence type PRIMARY_EXPERIMENT notes Main text page1 describes the bmp2 deletion; Fig1B caption identifies the PS5 reference cluster. Supplementary construction methods were not inspected. retrieved on 2026-10-07
PS5 bmp2 in-frame deletion	eliminates_detected_production	Detected TBP production in PS5 under tested conditions	Qualitative mutant-versus-wild-type production readout under tested conditions only. Not proof of absence under every condition or Bmp2-alone catalytic sufficiency. No quantitative concentrations or normalization adopted without supplementary methods.	DOI:10.1038/s43705-023-00309-6 reference DOI:10.1038/s43705-023-00309-6 evidence type PRIMARY_EXPERIMENT notes Main text page1 production-loss paragraph and Fig1D caption, page2. LC-MS/MS of three replicate5-mL culture extractions per treatment. Full extracted main text inspected; subsequent figure-render retrieval timed out, so no visual figure or supplementary-method verification. retrieved on 2026-10-07 snippet resulted in the complete loss of TBP production
Detected TBP production in PS5 under tested conditions	has_measured_product	2,3,4,5-tetrabromopyrrole	Reported TBP identity in culture extracts, not a new structural determination, purified-enzyme conversion or pure-compound bioactivity assay.	DOI:10.1038/s43705-023-00309-6 reference DOI:10.1038/s43705-023-00309-6 evidence type PRIMARY_EXPERIMENT notes Main text page1 identifies TBP as tetrabromopyrrole; Fig1D caption names the LC-MS/MS production readout. No carrier-bound substrate or pathway order inferred. retrieved on 2026-10-07

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

Explore across X-Mech

AntibioticMech (2,3,4,5-tetrabromopyrrole) ↗ MediaIngredientMech (naturalproductmech:mibig-dcee736e16) ↗ TaxonMech: Pseudoalteromonas piscicida (NCBITaxon:43662) ↗ TaxonMech: Pseudoalteromonas sp. PS5 (NCBITaxon:1437473) ↗ PathwayMech (mibig:BGC0001463) ↗ PathwayMech (mibig:BGC0001464) ↗

Open questions 1

shared-structure — This structure is reported by more than one MIBiG entry: BGC0001463, BGC0001464. Confirm they describe the same compound rather than an upstream cross-reference error.

Provenance

Source concept	Source	Version
BGC0001463	MIBIG	4
BGC0001464	MIBIG	3

This page is generated from data/natural_products/alkaloids/2-3-4-5-tetrabromopyrrole.yaml, which is generated from the committed inventories. Neither is edited by hand.