clavulanic acid   Click here for help

GtoPdb Ligand ID: 11128

Synonyms: BRL-14151 | BRL-14151K | BRL14151 | clavulanate | MM 14151
Approved drug PDB Ligand
clavulanic acid is an approved drug
Compound class: Natural product
Comment: Clavulanic acid is a β-lactamase inhibitor that was isolated from Streptomyces clavuligerus [1]. It is used in combination with β-lactam antibacterials and does not have inherent antibacterial activity. Clavulanic acid can overcome antibacterial resistance in bacteria that secrete β-lactamase. Included in the WHO Essential Medicines list as the mixture of amoxicillin + clavulanic acid (co-amoxiclav).

clavulanic acid 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 2
Rotatable bonds 2
Topological polar surface area 87.07
Molecular weight 199.05
XLogP -1.52
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 OC(=O)[C@@H]1N2[C@H](O/C/1=C\CO)CC2=O
Isomeric SMILES OC(=O)[C@@H]1N2[C@H](O/C/1=C\CO)CC2=O
InChI InChI=1S/C8H9NO5/c10-2-1-4-7(8(12)13)9-5(11)3-6(9)14-4/h1,6-7,10H,2-3H2,(H,12,13)/b4-1-/t6-,7-/m1/s1
InChI Key HZZVJAQRINQKSD-PBFISZAISA-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/)
References
1. Brown AG, Butterworth D, Cole M, Hanscomb G, Hood JD, Reading C, Rolinson GN. (1976)
Naturally-occurring beta-lactamase inhibitors with antibacterial activity.
J Antibiot (Tokyo), 29 (6): 668-9. [PMID:950324]