potassium (2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate

• ChemBase ID: 164815
• Molecular Formular: C8H8KNO5
• Molecular Mass: 237.25112
• Monoisotopic Mass: 237.00395404
• SMILES: C1C(=O)N2[C@@H]1O/C(=C\CO)/[C@@H]2C(=O)[O-].[K+]
• Canonical SMILES: [O-]C(=O)[C@@H]1N2[C@H](O/C/1=C\CO)CC2=O.[K+]
• InChI: InChI=1S/C8H9NO5.K/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);/q;+1/p-1/b4-1-;/t6-,7-;/m1./s1
• InChIKey: ABVRVIZBZKUTMK-JSYANWSFSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium (2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: potassium clavulanic acid anion
• Synonyms: MM 1415; Potassium Clavulanate; Clavulanic Acid Potassium Salt

Database IDs

• CAS Number: 61177-45-5
• PubChem SID: 162258949
• PubChem CID: 23665591

CALCULATED PROPERTIES

• Acid pKa: 3.3169081
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -3.6880052
• LogD (pH = 7.4): -4.943672
• Log P: -1.5212076
• Molar Refractivity: 55.0896 cm^3
• Polarizability: 16.934288 Å^3
• Polar Surface Area: 89.9 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Yellow Solid
• Melting Point: >170°C (dec)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C563750

Clavulanic Acid is a β-lactamase inhibitor, typically added to amoxicillin to increase its effectiveness.

REFERENCES

• Reading, C. and Cole, M.: Antimicrob. Ag. Chemother., 11, 852 (1977)
• Ball, A.P., et al.: Lancet, 1, 620 (1977)
• Brogden, R.N., et al. Drugs, 22, 337 (1981)