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

• ChemBase ID: 153139
• Molecular Formular: C8H8KNO5
• Molecular Mass: 237.25112
• Monoisotopic Mass: 237.00395404
• SMILES: C1[C@@H]2N(C1=O)[C@H](/C(=C\CO)/O2)C(=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/t6-,7-;/m1./s1
• InChIKey: ABVRVIZBZKUTMK-ZJLYAJKPSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium (2R,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: potassium (2R,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate
• Synonyms: Clavulanate potassium; Potassium clavulanate; 棒酸钾; 克拉维酸钾

Database IDs

• CAS Number: 61177-45-5
• EC Number: 262-640-9
• MDL Number: MFCD01710901
• PubChem SID: 24860237; 24898415; 162247279
• PubChem CID: 57502524

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

Safety Information

• RTECS: RN6802700
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 11-14-36; 11-36
• Safety Statements: 8-16-26-43
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H228-H252-H319
• GHS Precautionary statements: P210-P235 + P410-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Grade: VETRANAL™, analytical standard
• Biological Source: from Streptomyces clavuligerus
• Empirical Formula (Hill Notation): C8H8NO5K

DETAILS

Sigma Aldrich - P3494

Biochem/physiol Actions
β-lactamase inhibitor, typically added to amoxicillin to increase its effectiveness.
In combination with penicillin group antibiotics to inhibit specific (group 2) β-penicillinases and cephalosporinases.

Sigma Aldrich - 33454

Biochem/physiol Actions
β-lactamase inhibitor, typically added to amoxicillin to increase its effectiveness.
Legal Information
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