clavulanic acid   Click here for help

GtoPdb Ligand ID: 11128

Synonyms: BRL-14151 | BRL-14151K | BRL14151 | clavulanate
Approved drug PDB Ligand
clavulanic acid is an approved drug
Compound class: Synthetic organic
Comment: Clavulanic acid is a β-lactamase inhibitor that was isolated from Streptomyces clavuligerusi. It is used in combination with β-lactam antibiotics and does not have inherent antibiotic activity. Clavulanic acid can overcome antibiotic resistance in bacteria that secrete β-lactamase. 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
SMILES / InChI / InChIKey
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
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
Database Links Click here for help
CAS Registry No. 58001-44-8 (source: PubChem)
ChEBI CHEBI:48947
ChEMBL Ligand CHEMBL777
GtoPdb PubChem SID 434122188
PubChem CID 5280980
RCSB PDB Ligand J01
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