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KSP-1007   Click here for help

GtoPdb Ligand ID: 13547

Compound class: Synthetic organic
Comment: KSP-1007 is a bicyclic boronic acid β-lactamase inhibitor (BLI), with broad-spectrum activity against both serine and metallo-β-lactamases, discovered through a collaboration between the Kitasato Institute (Tokyo, Japan) and Sumitomo Pharma (Osaka, Japan) [1]. KSP-1007, in combination with meropenem, is under clinical development for the treatment of infections caused by carbapenem-resistant bacterial infections.
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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Click here for structure editor
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 10
Hydrogen bond donors 4
Rotatable bonds 6
Topological polar surface area 146.71
Molecular weight 386.17
XLogP -1.14
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=C2CCB(O)OC2=C(C(=C1)OC3CN(C3)C(=O)[C@@H](C4=CNC=N4)N)C(=O)O
Isomeric SMILES C1=CC(=C(C2=C1CCB(O)O2)C(=O)O)OC3CN(C3)C(=O)[C@@H](C4=CNC=N4)N
InChI InChI=1S/C17H19BN4O6/c19-14(11-5-20-8-21-11)16(23)22-6-10(7-22)27-12-2-1-9-3-4-18(26)28-15(9)13(12)17(24)25/h1-2,5,8,10,14,26H,3-4,6-7,19H2,(H,20,21)(H,24,25)/t14-/m1/s1
InChI Key CAHUDGVGUAJGGS-CQSZACIVSA-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
7-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo KSP-1007+meropenem
Other databases
CAS Registry No. 2380240-20-8 (source: Scifinder)
GtoPdb PubChem SID 500839957
PubChem CID 149866877
Search Google for chemical match using the InChIKey CAHUDGVGUAJGGS-CQSZACIVSA-N
Search Google for chemicals with the same backbone CAHUDGVGUAJGGS
UniChem Compound Search for chemical match using the InChIKey CAHUDGVGUAJGGS-CQSZACIVSA-N
UniChem Connectivity Search for chemical match using the InChIKey CAHUDGVGUAJGGS-CQSZACIVSA-N