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
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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 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
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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 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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-nitro-6-(trifluoromethyl)thiochromen-4-one
Synonyms Click here for help
compound 6b [PMID: 30336450]
Database Links Click here for help
BindingDB Ligand 50520740
CAS Registry No. 2252473-48-4 (source: Scifinder)
ChEMBL Ligand CHEMBL4586075
GtoPdb PubChem SID 504705403
PubChem CID 141730928
Search Google for chemical match using the InChIKey LKTGKSLRRVEZFI-UHFFFAOYSA-N
Search Google for chemicals with the same backbone LKTGKSLRRVEZFI
UniChem Compound Search for chemical match using the InChIKey LKTGKSLRRVEZFI-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey LKTGKSLRRVEZFI-UHFFFAOYSA-N