(2R,4R,5Z)-2-(carboxymethyl)-5-(2-hydroxyethylidene)-3-[(2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carbonyl]-1,3-oxazolidine-4-carboxylic acid

• ChemBase ID: 164816
• Molecular Formular: C16H18N2O10
• Molecular Mass: 398.32152
• Monoisotopic Mass: 398.09614479
• SMILES: C1(=O)N2[C@@H](C1)O/C(=C\CO)/[C@@H]2C(=O)N1[C@H](/C(=C/CO)/O[C@@H]1CC(=O)O)C(=O)O
• Canonical SMILES: OC/C=C/1\O[C@H]2N([C@H]1C(=O)N1[C@@H](CC(=O)O)O/C(=C\CO)/[C@@H]1C(=O)O)C(=O)C2
• InChI: InChI=1S/C16H18N2O10/c19-3-1-7-13(17-9(21)5-10(17)27-7)15(24)18-11(6-12(22)23)28-8(2-4-20)14(18)16(25)26/h1-2,10-11,13-14,19-20H,3-6H2,(H,22,23)(H,25,26)/b7-1-,8-2-/t10-,11-,13-,14-/m1/s1
• InChIKey: WDFKSRMFLRKPLO-BJBUEPEESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5Z)-2-(carboxymethyl)-5-(2-hydroxyethylidene)-3-[(2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carbonyl]-1,3-oxazolidine-4-carboxylic acid
• IUPAC Traditional name: (2R,4R,5Z)-2-(carboxymethyl)-5-(2-hydroxyethylidene)-3-[(2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carbonyl]-1,3-oxazolidine-4-carboxylic acid
• Synonyms: (2R,4R,5Z)-4-Carboxy-5-(2-hydroxyethylidene)-3-[[(2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]hept-2-yl]carbonyl]-2-oxazolidineacetic Acid; Potassium Clavunate Impurity E; Clavulanic Acid Dimer Impurity

Database IDs

• CAS Number: 1260617-10-4
• PubChem SID: 162258950
• PubChem CID: 71314884

CALCULATED PROPERTIES

• Acid pKa: 3.1317828
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -6.974123
• LogD (pH = 7.4): -9.735892
• Log P: -3.0424151
• Molar Refractivity: 88.505 cm^3
• Polarizability: 34.10424 Å^3
• Polar Surface Area: 174.14 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C563760

An impurity of Clavulanic Acid (C563750).