xeruborbactam   Click here for help

GtoPdb Ligand ID: 13131

Synonyms: QPX7728
PDB Ligand
Compound class: Synthetic organic
Comment: Xeruborbactam is a bicyclic boronate β-lactamase inhibitor (BLI) with a broad-spectrum of activity against both serine and metallo-β-lactamases [1]. Xeruborbactam is under clinical evaluation and was developed as a continuation of the program that discovered vaborbactam, with the aim of expanding the spectrum of activity to allow treatment of infections caused by a wider range of pathogens.
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 4
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 66.76
Molecular weight 221.98
XLogP 0.43
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=C2[C@H]3C[C@H]3B(O)OC2=C(C(=C1)F)C(=O)O
Isomeric SMILES B1([C@@H]2C[C@@H]2C3=C(O1)C(=C(C=C3)F)C(=O)O)O
InChI InChI=1S/C10H8BFO4/c12-7-2-1-4-5-3-6(5)11(15)16-9(4)8(7)10(13)14/h1-2,5-6,15H,3H2,(H,13,14)/t5-,6-/m1/s1
InChI Key KOHUFVUIYUCFNG-PHDIDXHHSA-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
Prodrug xeruborbactam isoboxil
IUPAC Name Click here for help
(1aR,7bS)-5-fluoro-2-hydroxy-1a,7b-dihydro-1H-cyclopropa[c][1,2]benzoxaborinine-4-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
11785 xeruborbactam
Synonyms Click here for help
QPX7728
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Xeruborbactam
Other databases
BindingDB Ligand 50541448
CAS Registry No. 2170834-63-4 (source: Scifinder)
ChEMBL Ligand CHEMBL4633785
GtoPdb PubChem SID 491299913
PubChem CID 140830474
RCSB PDB Ligand RM9
Search Google for chemical match using the InChIKey KOHUFVUIYUCFNG-PHDIDXHHSA-N
Search Google for chemicals with the same backbone KOHUFVUIYUCFNG
Search PubMed clinical trials xeruborbactam
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UniChem Compound Search for chemical match using the InChIKey KOHUFVUIYUCFNG-PHDIDXHHSA-N
UniChem Connectivity Search for chemical match using the InChIKey KOHUFVUIYUCFNG-PHDIDXHHSA-N