bromotopsentin

CHEBI:144088 ·resolve ·ANTIVIRAL ·EXACT SEEDED

An aromatic ketone that is imidazole that is substituted at positions 2 and 5 by (6-hydroxy-1H-indol-3-yl)carbonyl and 6-bromo-1H-indol-3-yl groups respectively. Isolated from Mediterranean shallow-water sponges Topsentia genetrix, and from Caribbean deep-sea sponges of the Halichondriidae family, it has antitumour and antiviral properties. Toxic to fish. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:24780 CHEBI:24780
CHEBI:38958 CHEBI:38958
CHEBI:52514 CHEBI:52514
CHEBI:76224 CHEBI:76224
CHEBI:84729 CHEBI:84729

Chemical structure

Computed structure properties
Molecular formula	C20H13BrN4O2
Charge	0
Average mass	421.254 Da
Monoisotopic mass	420.02219 Da
Source	ChEBI
InChIKey	YHGQVXFIJGWOFP-UHFFFAOYSA-N

SMILES

O=C(c1ncc(-c2cnc3cc(Br)ccc23)n1)c1cnc2cc(O)ccc12

InChI

InChI=1S/C20H13BrN4O2/c21-10-1-3-12-14(7-22-16(12)5-10)18-9-24-20(25-18)19(27)15-8-23-17-6-11(26)2-4-13(15)17/h1-9,22-23,26H,(H,24,25)

Also called

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

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:112515-44-3
knapsack:C00026969

Activity roles

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

CHEBI:22587 CHEBI:22587

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:144088`	bromotopsentin	`antibioticmech:chebi-65a680b98e`	2026-08-30

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

Provenance

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