JSF-3285   Click here for help

GtoPdb Ligand ID: 13585

PDB Ligand
Compound class: Synthetic organic
Comment: JSF-3285 is an indazole antibacterial compound discovered using a structure-based approach to optimize DG167 (PubChem CID 70689295), a known inhibitor of Mycobacterium tuberculosis 3-oxoacyl-[acyl-carrier-protein] synthase 1 (also known as β-ketoacyl-ACP synthase, KasA) [2]. JSF-3285 is being investigated as a preclinical candidate for the treatment of tuberculosis (TB). The structure is claimed in patent WO2019046467A1 filed by Rutgers University [1].
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 5
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 78.94
Molecular weight 285.34
XLogP 2.17
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 CC1=C2C=C(C=CC2=NN1)NS(=O)(=O)CCCCF
Isomeric SMILES CC1=C2C=C(C=CC2=NN1)NS(=O)(=O)CCCCF
InChI InChI=1S/C12H16FN3O2S/c1-9-11-8-10(4-5-12(11)15-14-9)16-19(17,18)7-3-2-6-13/h4-5,8,16H,2-3,6-7H2,1H3,(H,14,15)
InChI Key AHVAAGWAEHSRBU-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. Freundlich JS, Alland D, Neiditch,MB, Kumar P, Capodagli G, Awasthi D, Ekins S. (2019)
Therapeutic indazoles.
Patent number: WO2019046467A1. Assignee: Rutgers. Priority date: 29/08/2017. Publication date: 07/03/2019.
2. Inoyama D, Awasthi D, Capodagli GC, Tsotetsi K, Sukheja P, Zimmerman M, Li SG, Jadhav R, Russo R, Wang X et al.. (2020)
A Preclinical Candidate Targeting Mycobacterium tuberculosis KasA.
Cell Chem Biol, 27 (5): 560-570.e10. [PMID:32197094]