OTB-658   Click here for help

GtoPdb Ligand ID: 13548

Synonyms: compound 19c [PMID: 32666789]
Compound class: Synthetic organic
Comment: OTB-658 is a prelinical candidate belonging to the oxazolidinone class of antibacterial compounds. It was discovered using a structure-activity aided strategy to identify novel oxazolidinones that retain activity against Mycobacterium tuberculosis but have reduced toxicity [4].
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 7
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 96.41
Molecular weight 381.42
XLogP 1.63
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 CC(=O)NC[C@H]1[C@]2([H])COC3=CC(=C(C=C3N2C(=O)O1)F)N4CCSCC4
Isomeric SMILES CC(NC[C@@H]1OC(N2C3=CC(F)=C(N4CCSCC4)C=C3OC[C@]21[H])=O)=O
InChI InChI=1S/C17H20FN3O4S/c1-10(22)19-8-16-14-9-24-15-7-12(20-2-4-26-5-3-20)11(18)6-13(15)21(14)17(23)25-16/h6-7,14,16H,2-5,8-9H2,1H3,(H,19,22)/t14-,16-/m0/s1
InChI Key WZAVWVAEARSISR-HOCLYGCPSA-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. Guo S, Wang B, Fu L, Chen X, Zhang W, Huang H, Lu Y. (2021)
In Vitro and In Vivo Activity of Oxazolidinone Candidate OTB-658 against Mycobacterium tuberculosis.
Antimicrob Agents Chemother, 65 (11): e0097421. [PMID:34398674]
2. Leach KL, Swaney SM, Colca JR, McDonald WG, Blinn JR, Thomasco LM, Gadwood RC, Shinabarger D, Xiong L, Mankin AS. (2007)
The site of action of oxazolidinone antibiotics in living bacteria and in human mitochondria.
Mol Cell, 26 (3): 393-402. [PMID:17499045]
3. Liu H, Zhu H, Fu L, Zhang W, Chen X, Wang B, Guo S, Ding Y, Wang N, Li D et al.. (2023)
Efficacy of Replacing Linezolid with OTB-658 in Anti-Tuberculosis Regimens in Murine Models.
Antimicrob Agents Chemother, 67 (2): e0139922. [PMID:36622240]
4. Zhao H, Wang B, Fu L, Li G, Lu H, Liu Y, Sheng L, Li Y, Zhang B, Lu Y et al.. (2020)
Discovery of a Conformationally Constrained Oxazolidinone with Improved Safety and Efficacy Profiles for the Treatment of Multidrug-Resistant Tuberculosis.
J Med Chem, 63 (17): 9316-9339. [PMID:32666789]