brequinar   Click here for help

GtoPdb Ligand ID: 7406

Synonyms: DUP-785 | DUP785 | NSC 368390 | NSC-368390 | NSC368390
PDB Ligand
Compound class: Synthetic organic
Comment: Brequinar inhibits dihydroorotate dehydrogenase (DHODH), the fourth enzyme in the de novo pyrimidine biosynthesis pathway [2], and it depletes cells of the precursors that are critical for RNA and DNA synthesis [3]. It was developed for potential anti-neoplastic activity. The drug exhibits anti-neoplastic activity against refractory solid tumours in preclinical models, with continuous treatment being necessary to effectively deplete pyrimidine pools in the cancer cells and cause tumour inhibition [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 50.19
Molecular weight 375.11
XLogP 6.26
No. Lipinski's rules broken 1
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Canonical SMILES Fc1ccc2c(c1)c(C(=O)O)c(c(n2)c1ccc(cc1)c1ccccc1F)C
Isomeric SMILES Fc1ccc2c(c1)c(C(=O)O)c(c(n2)c1ccc(cc1)c1ccccc1F)C
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)
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
dihydroorotate dehydrogenase (quinone) Hs Inhibitor Inhibition 7.0 pKi - 3
pKi 7.0 (Ki 1x10-7 M) [3]