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GSK839   Click here for help

GtoPdb Ligand ID: 13955

Compound class: Synthetic organic
Comment: GSK839 is a selective inhibitor of Mycobacterium tuberculosis tryptophan synthase (TrpAB) that is in preclinical evaluation for the treatment of tuberculosis. It is one of the compounds claimed by GlaxoSmithKline in patent WO2019034729A1 [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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Click here for structure editor
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 9
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 127.46
Molecular weight 378.38
XLogP -1.26
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 C1=CC(=CC=C1C2=NN(CC3=CC=C(C=N3)F)N=N2)S(=O)(=O)NCCO
Isomeric SMILES C1=CC(=CC=C1C2=NN(N=N2)CC3=NC=C(C=C3)F)S(=O)(=O)NCCO
InChI InChI=1S/C15H15FN6O3S/c16-12-3-4-13(17-9-12)10-22-20-15(19-21-22)11-1-5-14(6-2-11)26(24,25)18-7-8-23/h1-6,9,18,23H,7-8,10H2
InChI Key ZADGDPAVPJLDBU-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. Alemparte-Gallardo C, Encinas L, Esquivias Provencio J. (2019)
Novel tetrazole compounds and their use in the treatment of tuberculosis.
Patent number: WO2019034729A1. Assignee: GlaxoSmithKline. Priority date: 17/08/2017. Publication date: 21/02/2019.
2. Fernandes GFS, Thompson AM, Castagnolo D, Denny WA, Dos Santos JL. (2022)
Tuberculosis Drug Discovery: Challenges and New Horizons.
J Med Chem, 65 (11): 7489-7531. [PMID:35612311]