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 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 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
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=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
References
1. Hecker SJ, Reddy KR, Lomovskaya O, Griffith DC, Rubio-Aparicio D, Nelson K, Tsivkovski R, Sun D, Sabet M, Tarazi Z et al.. (2020)
Discovery of Cyclic Boronic Acid QPX7728, an Ultrabroad-Spectrum Inhibitor of Serine and Metallo-β-lactamases.
J Med Chem, 63 (14): 7491-7507. [PMID:32150407]
2. Lomovskaya O, Tsivkovski R, Nelson K, Rubio-Aparicio D, Sun D, Totrov M, Dudley MN. (2020)
Spectrum of Beta-Lactamase Inhibition by the Cyclic Boronate QPX7728, an Ultrabroad-Spectrum Beta-Lactamase Inhibitor of Serine and Metallo-Beta-Lactamases: Enhancement of Activity of Multiple Antibiotics against Isogenic Strains Expressing Single Beta-Lactamases.
Antimicrob Agents Chemother, 64 (6). [PMID:32229489]
3. Nelson K, Rubio-Aparicio D, Sun D, Dudley M, Lomovskaya O. (2020)
In Vitro Activity of the Ultrabroad-Spectrum-Beta-Lactamase Inhibitor QPX7728 against Carbapenem-Resistant Enterobacterales with Varying Intrinsic and Acquired Resistance Mechanisms.
Antimicrob Agents Chemother, 64 (8). [PMID:32482673]
4. Sun D, Tsivkovski R, Pogliano J, Tsunemoto H, Nelson K, Rubio-Aparicio D, Lomovskaya O. (2022)
Intrinsic Antibacterial Activity of Xeruborbactam In Vitro: Assessing Spectrum and Mode of Action.
Antimicrob Agents Chemother, 66 (10): e0087922. [PMID:36102663]