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
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
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
Click here for help

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/)

✖
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/)
Bioactivity Comments
The MIC for in vitro antimycobacterial activity is 0.080-0.115 μg/ml against M. tuberculosis H37Rv and <0.016-0.167 μg/ml against multidrug-resistant M. tuberculosis clinical isolates [1]. In vivo, OTB-658 reduces colony-forming unit (CFU) counts in the lungs and spleen in acute and chronic murine tuberculosis (TB) infection models [1]. It also shows promising efficacy when used in TB murine models as a replacement for linezolid [3].