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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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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 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

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=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

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-[[(3S)-3-(aminomethyl)-4-chloro-1-hydroxy-3H-2,1-benzoxaborol-7-yl]oxy]ethanol
International Nonproprietary Names Click here for help
INN number INN
12456 ganfeborole
Synonyms Click here for help
GSK3036656 | GSK656
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo GSK3036656
Other databases
CAS Registry No. 2131798-12-2 (source: Scifinder)
ChEMBL Ligand CHEMBL4116378
GtoPdb PubChem SID 483123344
PubChem CID 133080621
Search Google for chemical match using the InChIKey DJUOWOXTPXUHDQ-MRVPVSSYSA-N
Search Google for chemicals with the same backbone DJUOWOXTPXUHDQ
Search PubMed clinical trials ganfeborole
Search PubMed titles ganfeborole
Search PubMed titles/abstracts ganfeborole
UniChem Compound Search for chemical match using the InChIKey DJUOWOXTPXUHDQ-MRVPVSSYSA-N
UniChem Connectivity Search for chemical match using the InChIKey DJUOWOXTPXUHDQ-MRVPVSSYSA-N