bedaquiline   Click here for help

GtoPdb Ligand ID: 11171

Synonyms: BDQ | compound 1a [PMID: 17496888] | R-207910 [1] | Sirturo® | TMC-207 | TMC207
Approved drug PDB Ligand
bedaquiline is an approved drug (FDA (2012), EMA (2014))
Compound class: Synthetic organic
Comment: Bedaquiline is a quinoline-based antimycobacterial drug that is used in the treatment of tuberculosis [1]. Functionally, it inhibits mycobacterial ATP synthase and enhances the antibacterial activity of second-line drug combinations.
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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 8
Topological polar surface area 45.59
Molecular weight 554.16
XLogP 7.38
No. Lipinski's rules broken 1
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Canonical SMILES COc1nc2ccc(cc2cc1[C@H]([C@](c1cccc2c1cccc2)(CCN(C)C)O)c1ccccc1)Br
Isomeric SMILES COc1nc2ccc(cc2cc1[C@H]([C@](c1cccc2c1cccc2)(CCN(C)C)O)c1ccccc1)Br
InChI InChI=1S/C32H31BrN2O2/c1-35(2)19-18-32(36,28-15-9-13-22-10-7-8-14-26(22)28)30(23-11-5-4-6-12-23)27-21-24-20-25(33)16-17-29(24)34-31(27)37-3/h4-17,20-21,30,36H,18-19H2,1-3H3/t30-,32-/m1/s1
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Molecular structure representations generated using Open Babel