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).
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/)
Classification Click here for help
Compound class Natural product
Approved drug? Yes
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
(2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
4948 clavulanic acid
Synonyms Click here for help
BRL-14151 | BRL-14151K | BRL14151 | clavulanate | MM 14151
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Clavulanic acid
Other databases
CAS Registry No. 58001-44-8 (source: PubChem)
ChEBI CHEBI:48947
ChEMBL Ligand CHEMBL777
DrugCentral Ligand 669
GtoPdb PubChem SID 434122188
PubChem CID 5280980
RCSB PDB Ligand J01
Search Google for chemical match using the InChIKey HZZVJAQRINQKSD-PBFISZAISA-N
Search Google for chemicals with the same backbone HZZVJAQRINQKSD
Search PubMed clinical trials clavulanic acid
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Search PubMed titles/abstracts clavulanic acid
UniChem Compound Search for chemical match using the InChIKey HZZVJAQRINQKSD-PBFISZAISA-N
UniChem Connectivity Search for chemical match using the InChIKey HZZVJAQRINQKSD-PBFISZAISA-N