epetraborole   Click here for help

GtoPdb Ligand ID: 13079

Synonyms: AN3365 | BRII-658 | GSK2251052
Compound class: Synthetic organic
Comment: Epetraborole (GSK2251052) is an aminomethylbenzoxaborole antibacterial compound that is an inhibitor of bacterial leucyl-tRNA synthetase (LeuRS) [2]. It is being developed for the treatment of non-tuberculous mycobacterial pulmonary disease (NTM-PD).
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 3
Rotatable bonds 5
Topological polar surface area 84.94
Molecular weight 237.06
XLogP -0.83
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(=C2C(=C1)[C@@H](CN)OB2O)OCCCO
Isomeric SMILES B1(C2=C(C=CC=C2OCCCO)[C@H](O1)CN)O
InChI InChI=1S/C11H16BNO4/c13-7-10-8-3-1-4-9(16-6-2-5-14)11(8)12(15)17-10/h1,3-4,10,14-15H,2,5-7,13H2/t10-/m1/s1
InChI Key FXQIIDINBDJDKL-SNVBAGLBSA-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
3-[[(3S)-3-(aminomethyl)-1-hydroxy-3H-2,1-benzoxaborol-7-yl]oxy]propan-1-ol
International Nonproprietary Names Click here for help
INN number INN
10025 epetraborole
Synonyms Click here for help
AN3365 | BRII-658 | GSK2251052
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Epetraborole
Other databases
CAS Registry No. 1093643-37-8 (source: Scifinder)
ChEMBL Ligand CHEMBL3549142
DrugBank Ligand DB11744
GtoPdb PubChem SID 491299861
PubChem CID 46836890
Search Google for chemical match using the InChIKey FXQIIDINBDJDKL-SNVBAGLBSA-N
Search Google for chemicals with the same backbone FXQIIDINBDJDKL
Search PubMed clinical trials epetraborole
Search PubMed titles epetraborole
Search PubMed titles/abstracts epetraborole
UniChem Compound Search for chemical match using the InChIKey FXQIIDINBDJDKL-SNVBAGLBSA-N
UniChem Connectivity Search for chemical match using the InChIKey FXQIIDINBDJDKL-SNVBAGLBSA-N