CHEBI:177387 - brequinar

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ChEBI Name brequinar
ChEBI ID CHEBI:177387
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Stan Laulederkind
Secondary ChEBI IDs CHEBI:41224
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Formula C23H15F2NO2
Net Charge 0
Average Mass 375.375
Monoisotopic Mass 375.10709
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)
InChIKey PHEZJEYUWHETKO-UHFFFAOYSA-N
SMILES CC1=C(C(O)=O)C2=C(C=CC(F)=C2)N=C1C1=CC=C(C=C1)C1=CC=CC=C1F
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor
An EC 1.3.5.* (oxidoreductase acting on CH-CH of donor with a quinone or related compound as acceptor) inhibitor that interferes with the action of dihydroorotate dehydrogenase (quinone), EC 1.3.5.2.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
antiviral agent
A substance that destroys or inhibits replication of viruses.
pyrimidine synthesis inhibitor
A pathway inhibitor that inhibits the synthesis of pyrimidine.
anticoronaviral agent
Any antiviral agent which inhibits the activity of coronaviruses.
antimetabolite
A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
Application(s): immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing brequinar (CHEBI:177387) has role anticoronaviral agent (CHEBI:149553)
brequinar (CHEBI:177387) has role antimetabolite (CHEBI:35221)
brequinar (CHEBI:177387) has role antineoplastic agent (CHEBI:35610)
brequinar (CHEBI:177387) has role antiviral agent (CHEBI:22587)
brequinar (CHEBI:177387) has role EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor (CHEBI:77103)
brequinar (CHEBI:177387) has role immunosuppressive agent (CHEBI:35705)
brequinar (CHEBI:177387) has role pyrimidine synthesis inhibitor (CHEBI:68543)
brequinar (CHEBI:177387) is a biphenyls (CHEBI:22888)
brequinar (CHEBI:177387) is a monocarboxylic acid (CHEBI:25384)
brequinar (CHEBI:177387) is a monofluorobenzenes (CHEBI:83575)
brequinar (CHEBI:177387) is a quinolinemonocarboxylic acid (CHEBI:26512)
brequinar (CHEBI:177387) is conjugate acid of brequinar(1−) (CHEBI:177870)
Incoming brequinar(1−) (CHEBI:177870) is conjugate base of brequinar (CHEBI:177387)
IUPAC Name
6-fluoro-2-(2'-fluoro[biphenyl]-4-yl)-3-methylquinoline-4-carboxylic acid
INNs Sources
brequinar WHO MedNet
bréquinar WHO MedNet
brequinar WHO MedNet
brequinarum WHO MedNet
Synonyms Sources
6-fluoro-2-(2'-fluoro-1,1'-biphenyl-4-yl)-3-methylquinoline-4-carboxylic acid PDBeChem
6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-methylquinoline-4-carboxylic acid IUPAC
6-fluoro-2-(2'-fluorobiphenyl-4-yl)-3-methylquinoline-4-carboxylic acid PDBeChem
6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methyl-quinoline-4-carboxylic acid PDBeChem
6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methylquinoline-4-carboxylic acid SUBMITTER
biphenquinate SUBMITTER
Manual Xrefs Databases
51422 ChemSpider
Brequinar Wikipedia
BRF PDBeChem
DB03523 DrugBank
LSM-45952 LINCS
WO9742953 Patent
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Registry Numbers Types Sources
8354757 Reaxys Registry Number Reaxys
96187-53-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
18 August 2021