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CRS0393   Click here for help

GtoPdb Ligand ID: 14410

Synonyms: CRS400393
Compound class: Synthetic organic
Comment: CRS0393 is the lead from a series of benzothiazole amide compounds with antimycobacterial activity [1-2]. Functionally, it inhibits Mycobacterial membrane protein large 3 (MmpL3), an inner membrane transporter essential for cell wall biosynthesis in mycobacteria [3]. CRS0393 is in preclinical development by Crestone Inc. as a treatment for tuberculosis (TB) or infections caused by nontuberculous mycobacteria (NTM).
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 3
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 66.76
Molecular weight 383.34
XLogP 4.87
No. Lipinski's rules broken 0

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 CC12CCCC(CCC1)(C2)C(=O)NC3=NC4=C(C(=CC(=C4)Cl)Cl)S3
Isomeric SMILES CC12CCCC(C1)(CCC2)C(=O)NC3=NC4=C(S3)C(=CC(=C4)Cl)Cl
InChI InChI=1S/C18H20Cl2N2OS/c1-17-4-2-6-18(10-17,7-3-5-17)15(23)22-16-21-13-9-11(19)8-12(20)14(13)24-16/h8-9H,2-7,10H2,1H3,(H,21,22,23)
InChI Key KHJLLQYNCQNVKV-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/)
References
1. De Groote MA, Jarvis TC, Wong C, Graham J, Hoang T, Young CL, Ribble W, Day J, Li W, Jackson M et al.. (2018)
Optimization and Lead Selection of Benzothiazole Amide Analogs Toward a Novel Antimycobacterial Agent.
Front Microbiol, 9: 2231. [PMID:30294313]
2. Graham J, Wong CE, Day J, McFaddin E, Ochsner U, Hoang T, Young CL, Ribble W, DeGroote MA, Jarvis T et al.. (2018)
Discovery of benzothiazole amides as potent antimycobacterial agents.
Bioorg Med Chem Lett, 28 (19): 3177-3181. [PMID:30172617]
3. Ochsner UA, De Groote MA, Jarvis TC, Liu H, Youmans T, Hoang T, Ribble W, Day J, Li W, Pearce C et al.. (2023)
Microbiological profile, preclinical pharmacokinetics and efficacy of CRS0393, a novel antimycobacterial agent targeting MmpL3.
Tuberculosis (Edinb), 138: 102288. [PMID:36470124]