telacebec   Click here for help

GtoPdb Ligand ID: 12953

Synonyms: MMV687696 | Q203
PDB Ligand
Compound class: Synthetic organic
Comment: Telacebec is a first-in-class imidazopyridine amide that inhibits the mycobacterial cytochrome bc1 complex [3]. It is being clinically evaluated as a treatment for tuberculosis (TB).
Telacebec was one of the compounds with activity against Mycobacterium tuberculosis included in the Medicines for Malaria Venture (MMV) Pathogen Box (see MMVOpen for futher details).

telacebec is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 6
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 57.17
Molecular weight 557.01
XLogP 5.29
No. Lipinski's rules broken 2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCC1=C(C(=O)NCC2=CC=C(C=C2)N3CCC(CC3)C4=CC=C(C=C4)OC(F)(F)F)N5C=C(C=CC5=N1)Cl
Isomeric SMILES CCC1=C(N2C=C(C=CC2=N1)Cl)C(=O)NCC3=CC=C(C=C3)N4CCC(CC4)C5=CC=C(C=C5)OC(F)(F)F
InChI InChI=1S/C29H28ClF3N4O2/c1-2-25-27(37-18-22(30)7-12-26(37)35-25)28(38)34-17-19-3-8-23(9-4-19)36-15-13-21(14-16-36)20-5-10-24(11-6-20)39-29(31,32)33/h3-12,18,21H,2,13-17H2,1H3,(H,34,38)
InChI Key OJICYBSWSZGRFB-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
6-chloro-2-ethyl-N-[[4-[4-[4-(trifluoromethoxy)phenyl]piperidin-1-yl]phenyl]methyl]imidazo[1,2-a]pyridine-3-carboxamide
International Nonproprietary Names Click here for help
INN number INN
10573 telacebec
Synonyms Click here for help
MMV687696 | Q203
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Telacebec
Other databases
BindingDB Ligand 50022086
CAS Registry No. 1334719-95-7 (source: Scifinder)
ChEMBL Ligand CHEMBL3298910
DrugBank Ligand DB17754
GtoPdb PubChem SID 485206074
PubChem CID 68234908
RCSB PDB Ligand HUU
Search Google for chemical match using the InChIKey OJICYBSWSZGRFB-UHFFFAOYSA-N
Search Google for chemicals with the same backbone OJICYBSWSZGRFB
Search PubMed clinical trials telacebec
Search PubMed titles telacebec
Search PubMed titles/abstracts telacebec
UniChem Compound Search for chemical match using the InChIKey OJICYBSWSZGRFB-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey OJICYBSWSZGRFB-UHFFFAOYSA-N

Product suppliers

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MedChemExpress
Telacebec (links to external site)
Cat. No. HY-101040