brasiliquinone A

CHEBI:65516 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A carbopolycyclic compound that is (3S)-3-ethyl-6,8-dihydroxy-3,4-dihydrotetraphene-1,7,12(2H)-trione substituted at position 8 by a 3-amino-2,3,6-trideoxy-α-L-ribo-hexopyranosyl group. It is isolated from the culture broth of Nocardia brasiliensis and exhibits antibacterial activity against Gram-positive bacteria. It is also active against the multiple drug-resistant P388/ADR tumour cells. — 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:25830 CHEBI:25830
CHEBI:33853 CHEBI:33853
CHEBI:35294 CHEBI:35294
CHEBI:35315 CHEBI:35315
CHEBI:47779 CHEBI:47779

Chemical structure

Computed structure properties
Molecular formula	C26H27NO7
Charge	0
Average mass	465.502 Da
Monoisotopic mass	465.17875 Da
Source	ChEBI
InChIKey	GMELFDQPUZSJEE-XHBGPGOOSA-N

SMILES

CC[C@@H]1CC(=O)c2c(cc(O)c3c2C(=O)c2cccc(O[C@H]4C[C@@H](N)[C@@H](O)[C@H](C)O4)c2C3=O)C1

InChI

InChI=1S/C26H27NO7/c1-3-12-7-13-9-17(29)22-23(20(13)16(28)8-12)25(31)14-5-4-6-18(21(14)26(22)32)34-19-10-15(27)24(30)11(2)33-19/h4-6,9,11-12,15,19,24,29-30H,3,7-8,10,27H2,1-2H3/t11-,12-,15+,19-,24-/m0/s1

Also called

(3S)-3-ethyl-6-hydroxy-1,7,12-trioxo-1,2,3,4,7,12-hexahydrotetraphen-8-yl 3-amino-2,3,6-trideoxy-α-L-ribo-hexopyranoside (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

chemspider:8248720
reaxys:8176069

Activity roles

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

CHEBI:33281 CHEBI:33281
CHEBI:33282 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:65516`	brasiliquinone A	`antibioticmech:chebi-0769113f72`	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.