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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key QUIJNHUBAXPXFS-XLJNKUFUSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2012), EMA (2014))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-naphthalen-1-yl-1-phenylbutan-2-ol
International Nonproprietary Names Click here for help
INN number INN
9316 bedaquiline
Synonyms Click here for help
BDQ | compound 1a [PMID: 17496888] | R-207910 [1] | Sirturo® | TMC-207 | TMC207
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Bedaquiline (Sirturo), R207910
Other databases
ChEBI CHEBI:72292
ChEMBL Ligand CHEMBL376488
DrugBank Ligand DB08903
DrugCentral Ligand 4741
GtoPdb PubChem SID 434122231
PubChem CID 5388906
RCSB PDB Ligand BQ1
Search Google for chemical match using the InChIKey QUIJNHUBAXPXFS-XLJNKUFUSA-N
Search Google for chemicals with the same backbone QUIJNHUBAXPXFS
Search PubMed clinical trials bedaquiline
Search PubMed titles bedaquiline
Search PubMed titles/abstracts bedaquiline
UniChem Compound Search for chemical match using the InChIKey QUIJNHUBAXPXFS-XLJNKUFUSA-N
UniChem Connectivity Search for chemical match using the InChIKey QUIJNHUBAXPXFS-XLJNKUFUSA-N