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).
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2D Structure
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Physico-chemical Properties
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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
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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
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)
DrugCentral Ligand 669
GtoPdb PubChem SID 434122188
PubChem CID 5280980
RCSB PDB Ligand J01
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UniChem Compound Search for chemical match using the InChIKey HZZVJAQRINQKSD-PBFISZAISA-N
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