clavulanic acid

Also known as clavulonic acid, (Z)-(2R,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, (2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Β-lactam molecule used as β-lactamase inhibitor to overcome antibiotic resistance in bacteria

Chemical data

Formula: C8H9NO5
Molecular weight: 199.16 g/mol
IUPAC name: (2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES: C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O
InChIKey: HZZVJAQRINQKSD-PBFISZAISA-N
XLogP: -1.2
Polar surface area: 87.1 Å²
H-bond donors: 2
H-bond acceptors: 5
Formal charge: 0

via PubChem

Research

10,059 papers

Clavulanic Acid and its Potential Therapeutic Effects on the Central Nervous System.Archives of medical research · 2024
Pharmacokinetics of Clavulanic Acid in the Pediatric Population: A Systematic Literature Review.Clinical pharmacokinetics · 2022
Clavulanic acid: a review.Biotechnology advances · 2008
How Clavulanic Acid Inhibits Serine β-Lactamases.Chembiochem : a European journal of chemical biology · 2024
Clavulanic acid biosynthesis and genetic manipulation for its overproduction.Applied microbiology and biotechnology · 2010

via PubMed

Wikidata facts

Mass: 199.048

Show 5 more facts

chemical formula: C₈H₉NO₅
isomeric SMILES: C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O
canonical SMILES: C1C2N(C1=O)C(C(=CCO)O2)C(=O)O
Commons category: Clavulanic acid
World Health Organisation international non-proprietary name: acidum clavulanicum

Sources (6)

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