bromodeoxytopsentin

CHEBI:144087 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

An aromatic ketone that is imidazole which is substituted by a 1H-indole-3-carbonyl group and a 6-bromo-1H-indol-3-yl group at positions 2 and 4, respectively. Isolated from the Mediterranean shallow-water sponge, Topsentia genetrix. It is a potent inhibitor of MRSA pyruvate kinase and exhibits antibacterial properties. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:24780
Label unavailable CHEBI:38958
Label unavailable CHEBI:52514
Label unavailable CHEBI:76224

Chemical structure

Computed structure properties
Molecular formula	C20H13BrN4O
Charge	0
Average mass	405.255 Da
Monoisotopic mass	404.02727 Da
Source	ChEBI
InChIKey	RMAWSNVDVKZXDX-UHFFFAOYSA-N

SMILES

O=C(c1ncc(-c2cnc3cc(Br)ccc23)n1)c1cnc2ccccc12

InChI

InChI=1S/C20H13BrN4O/c21-11-5-6-13-14(8-23-17(13)7-11)18-10-24-20(25-18)19(26)15-9-22-16-4-2-1-3-12(15)16/h1-10,22-23H,(H,24,25)

Also called

[4-(6-bromo-1H-indol-3-yl)-1H-imidazol-2-yl](1H-indol-3-yl)methanone (EXACT_SYNONYM)— chebi
[5-(6-bromo-1H-indol-3-yl)-1H-imidazol-2-yl](1H-indol-3-yl)methanone (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antibacterial agent CHEBI:33282

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:144087`	bromodeoxytopsentin	`antibioticmech:chebi-9c37550b0a`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

pyruvate kinase PROTEIN MEASURED_TARGET_ASSOCIATION

Purified-enzyme assays measured 16-60 nM inhibition for the most active bis-indoles and compared human isoforms; the exact-compound cocrystal was not reported. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2011-10 (retrieved 2026-09-02).

Staphylococcus aureus NCBITaxon:1280

PMID:22030393 (Primary MRSA pyruvate-kinase inhibition and antibacterial study (DOI:10.1074/jbc.M111.289033).)

Mechanism summary

Mode of action: ENERGY_METABOLISM_INHIBITION microbial target — CURATOR: PMID:22030393 measured nanomolar inhibition of methicillin-resistant Staphylococcus aureus pyruvate kinase by bromodeoxytopsentin, at least 166-fold selectivity over human pyruvate-kinase isoforms, and antibacterial activity against S. aureus. The reported cocrystal used a related bis-indole compound, so bromodeoxytopsentin is not classified as a direct-binding target here.

Record-level evidence

PMID:22030393 (Primary bromodeoxytopsentin MRSA pyruvate-kinase and antibacterial study.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI identity, structure, role, and antibacterial class; added energy-metabolism inhibition and a measured MRSA pyruvate-kinase association without transferring the related-compound cocrystal claim.

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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