vaborbactam   Click here for help

GtoPdb Ligand ID: 10871

Synonyms: compound 9f [PMID: 25782055] | RPX-7009 | RPX7009 | Vabomere (vaborbactam + meropenem)
Approved drug PDB Ligand
vaborbactam is an approved drug (FDA (2017), EMA (2018))
Compound class: Synthetic organic
Comment: Vaborbactam is a β-lactamase inhibitor [3]. Structurally it is based on a cyclic boronic acid pharmacophore.

vaborbactam is commercially available from our sponsors

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 6
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 124.1
Molecular weight 297.08
XLogP 0.33
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 O=C(Cc1cccs1)N[C@H]1CC[C@H](OB1O)CC(=O)O
Isomeric SMILES O=C(Cc1cccs1)N[C@H]1CC[C@H](OB1O)CC(=O)O
InChI InChI=1S/C12H16BNO5S/c15-11(7-9-2-1-5-20-9)14-10-4-3-8(6-12(16)17)19-13(10)18/h1-2,5,8,10,18H,3-4,6-7H2,(H,14,15)(H,16,17)/t8-,10-/m0/s1
InChI Key IOOWNWLVCOUUEX-WPRPVWTQSA-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
Approved drug? Yes. FDA (2017)  |  EMA (2018)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
2-[(3R,6S)-2-hydroxy-3-[(2-thiophen-2-ylacetyl)amino]oxaborinan-6-yl]acetic acid
International Nonproprietary Names Click here for help
INN number INN
10182 vaborbactam
Synonyms Click here for help
compound 9f [PMID: 25782055] | RPX-7009 | RPX7009 | Vabomere (vaborbactam + meropenem)
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Meropenem + Vaborbactam | Vaborbactam
Other databases
DrugCentral Ligand 5253
GtoPdb PubChem SID 405560312
PubChem CID 56649692
RCSB PDB Ligand 4D6
Search Google for chemical match using the InChIKey IOOWNWLVCOUUEX-WPRPVWTQSA-N
Search Google for chemicals with the same backbone IOOWNWLVCOUUEX
Search PubMed clinical trials vaborbactam
Search PubMed titles vaborbactam
Search PubMed titles/abstracts vaborbactam
UniChem Compound Search for chemical match using the InChIKey IOOWNWLVCOUUEX-WPRPVWTQSA-N
UniChem Connectivity Search for chemical match using the InChIKey IOOWNWLVCOUUEX-WPRPVWTQSA-N

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MedChemExpress
Vaborbactam (links to external site)
Cat. No. HY-19930