ganfeborole   Click here for help

GtoPdb Ligand ID: 12796

Synonyms: GSK3036656 | GSK656
Compound class: Synthetic organic
Comment: Ganfeborole (GSK3036656) is a first-in-class boron-containing antitubercular agent. It is the lead from a series of 3-aminomethylbenzoxaboroles that are potent inhibitors of Mycobacterium tuberculosis leucyl-tRNA synthetase (LeuRS) [2]. We show the (S) enantiomer, which is the most active form.
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 CDK toolkit. 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 3
Rotatable bonds 4
Topological polar surface area 84.94
Molecular weight 257.48
XLogP -0.61
No. Lipinski's rules broken 0
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.

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Canonical SMILES C1=C(C2=C(C(=C1)OCCO)B(O)O[C@@H]2CN)Cl
Isomeric SMILES O(CCO)C1=C2C([C@@H](CN)OB2O)=C(Cl)C=C1
InChI InChI=1S/C10H13BClNO4/c12-6-1-2-7(16-4-3-14)10-9(6)8(5-13)17-11(10)15/h1-2,8,14-15H,3-5,13H2/t8-/m1/s1
InChI Key DJUOWOXTPXUHDQ-MRVPVSSYSA-N
References
1. Dong W, Li S, Wen S, Jing W, Shi J, Ma Y, Huo F, Gao F, Pang Y, Lu J. (2020)
In Vitro Susceptibility Testing of GSK656 against Mycobacterium Species.
Antimicrob Agents Chemother, 64 (2). [PMID:31791947]
2. Li X, Hernandez V, Rock FL, Choi W, Mak YSL, Mohan M, Mao W, Zhou Y, Easom EE, Plattner JJ et al.. (2017)
Discovery of a Potent and Specific M. tuberculosis Leucyl-tRNA Synthetase Inhibitor: (S)-3-(Aminomethyl)-4-chloro-7-(2-hydroxyethoxy)benzo[c][1,2]oxaborol-1(3H)-ol (GSK656).
J Med Chem, 60 (19): 8011-8026. [PMID:28953378]
3. Tenero D, Derimanov G, Carlton A, Tonkyn J, Davies M, Cozens S, Gresham S, Gaudion A, Puri A, Muliaditan M et al.. (2019)
First-Time-in-Human Study and Prediction of Early Bactericidal Activity for GSK3036656, a Potent Leucyl-tRNA Synthetase Inhibitor for Tuberculosis Treatment.
Antimicrob Agents Chemother, 63 (8). [PMID:31182528]