taniborbactam   Click here for help

GtoPdb Ligand ID: 10774

Synonyms: VNRX-5133 | VNRX5133
PDB Ligand
Compound class: Synthetic organic
Comment: Taniborbactam (VNRX-5133) is a clinical stage, injectable, broad-spectrum β-lactamase inhibitor [1,3]. It has activity against both serine- and metallo-β-lactamases (e.g. oxacillinase, Klebsiella pneumoniae carbapenemase, New Delhi metallo-beta-lactamase, Verona integron-encoded metallo-beta-lactamase and extended spectrum beta-lactamase) [4]. Taniborbactam will be administered alongside the cephalosporin antibacterial cefepime. It is being developed by Venatorx Pharmaceuticals in partnership with the Global Antibiotic Research & Development Partnership (GARDP).
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 7
Hydrogen bond donors 5
Rotatable bonds 8
Topological polar surface area 133.91
Molecular weight 389.21
XLogP 1.19
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 NCCNC1CCC(CC1)CC(=O)N[C@H]1Cc2cccc(c2OB1O)C(=O)O
Isomeric SMILES NCCNC1CCC(CC1)CC(=O)N[C@H]1Cc2cccc(c2OB1O)C(=O)O
InChI InChI=1S/C19H28BN3O5/c21-8-9-22-14-6-4-12(5-7-14)10-17(24)23-16-11-13-2-1-3-15(19(25)26)18(13)28-20(16)27/h1-3,12,14,16,22,27H,4-11,21H2,(H,23,24)(H,25,26)/t12?,14?,16-/m0/s1
InChI Key PFZUWUXKQPRWAL-PXCJXSSVSA-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
(3R)-3-[[2-[4-(2-aminoethylamino)cyclohexyl]acetyl]amino]-2-hydroxy-3,4-dihydro-1,2-benzoxaborinine-8-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
10817 taniborbactam
Synonyms Click here for help
VNRX-5133 | VNRX5133
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefepime + Taniborbactam
Other databases
CAS Registry No. 1613267-49-4 (source: WHO INN record)
GtoPdb PubChem SID 405560215
PubChem CID 76902493
RCSB PDB Ligand KJK
Search Google for chemical match using the InChIKey PFZUWUXKQPRWAL-PXCJXSSVSA-N
Search Google for chemicals with the same backbone PFZUWUXKQPRWAL
Search PubMed clinical trials taniborbactam
Search PubMed titles taniborbactam
Search PubMed titles/abstracts taniborbactam
UniChem Compound Search for chemical match using the InChIKey PFZUWUXKQPRWAL-PXCJXSSVSA-N
UniChem Connectivity Search for chemical match using the InChIKey PFZUWUXKQPRWAL-PXCJXSSVSA-N