brequinar

CHEBI:177387 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A quinolinemonocarboxylic acid that is quinoline substituted by 2'-fluoro[1,1'-biphenyl]-4-yl, methyl, carboxy and fluoro groups at positions 2, 3, 4, and 6, respectively. It is an inhibitor of dihydroorotate dehydrogenase, an enzyme that is required for de novo pyrimidine biosynthesis. The compound exhibits antineoplastic and antiviral properties. — 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:22888 CHEBI:22888
CHEBI:25384 CHEBI:25384
CHEBI:26512 CHEBI:26512
CHEBI:83575 CHEBI:83575

Chemical structure

Computed structure properties
Molecular formula	C23H15F2NO2
Charge	0
Average mass	375.374 Da
Monoisotopic mass	375.10709 Da
Source	ChEBI
InChIKey	PHEZJEYUWHETKO-UHFFFAOYSA-N

SMILES

Cc1c(-c2ccc(-c3ccccc3F)cc2)nc2ccc(F)cc2c1C(=O)O

InChI

InChI=1S/C23H15F2NO2/c1-13-21(23(27)28)18-12-16(24)10-11-20(18)26-22(13)15-8-6-14(7-9-15)17-4-2-3-5-19(17)25/h2-12H,1H3,(H,27,28)

Also called

brequinarum (INN)— chebi
bréquinar (INN)— chebi
6-fluoro-2-(2'-fluoro[biphenyl]-4-yl)-3-methylquinoline-4-carboxylic acid (EXACT_SYNONYM)— chebi
6-fluoro-2-(2'-fluoro-1,1'-biphenyl-4-yl)-3-methylquinoline-4-carboxylic acid (EXACT_SYNONYM)— chebi
6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-methylquinoline-4-carboxylic acid (EXACT_SYNONYM)— chebi
6-fluoro-2-(2'-fluorobiphenyl-4-yl)-3-methylquinoline-4-carboxylic acid (EXACT_SYNONYM)— chebi
6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methyl-quinoline-4-carboxylic acid (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:96187-53-0
chemspider:51422
drugbank:DB03523
lincs.smallmolecule:LSM-45952
patent:WO9742953
pdb-ccd:BRF
reaxys:8354757
wikipedia.en:Brequinar

Activity roles

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

CHEBI:149553 CHEBI:149553
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:177387`	brequinar	`antibioticmech:chebi-7267826d4a`	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.