NTB-3119   Click here for help

GtoPdb Ligand ID: 13584

Synonyms: compound 6b [PMID: 30336450]
Compound class: Synthetic organic
Comment: NTB-3119 is a preclinical candidate for the treatment of tuberculosis (TB), identified from a novel series of benzothiopyranones and designed through scaffold morphing from the benzothiazinone class of antimycobacterial compounds [1]. It is an inhibitor of decaprenylphosphoryl-beta-D-ribose oxidase (DprE1), an essential mycobacterial cell wall biosynthesis enzyme.
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 3
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 91.99
Molecular weight 455.5
XLogP 4.58
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 C1CCC(CC1)CN2CCN(CC2)C3=CC(=O)C4=CC(=CC(=C4S3)[N+](=O)[O-])C(F)(F)F
Isomeric SMILES C1CCC(CC1)CN2CCN(CC2)C3=CC(=O)C4=C(S3)C(=CC(=C4)C(F)(F)F)[N+](=O)[O-]
InChI InChI=1S/C21H24F3N3O3S/c22-21(23,24)15-10-16-18(28)12-19(31-20(16)17(11-15)27(29)30)26-8-6-25(7-9-26)13-14-4-2-1-3-5-14/h10-12,14H,1-9,13H2
InChI Key LKTGKSLRRVEZFI-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. Li P, Wang B, Zhang X, Batt SM, Besra GS, Zhang T, Ma C, Zhang D, Lin Z, Li G et al.. (2018)
Identification of novel benzothiopyranone compounds against Mycobacterium tuberculosis through scaffold morphing from benzothiazinones.
Eur J Med Chem, 160: 157-170. [PMID:30336450]