(6R,7R)-7-(2,2-dimethylpropanamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 159543
• Molecular Formular: C13H18N2O4S
• Molecular Mass: 298.35802
• Monoisotopic Mass: 298.09872807
• SMILES: C(C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C)(C)(C)C
• Canonical SMILES: O=C1[C@@H](NC(=O)C(C)(C)C)[C@@H]2N1C(=C(CS2)C)C(=O)O
• InChI: InChI=1S/C13H18N2O4S/c1-6-5-20-10-7(14-12(19)13(2,3)4)9(16)15(10)8(6)11(17)18/h7,10H,5H2,1-4H3,(H,14,19)(H,17,18)/t7-,10-/m1/s1
• InChIKey: JLNXDMISSHNIAD-GMSGAONNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-(2,2-dimethylpropanamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-(2,2-dimethylpropanamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-[(2,2-dimethyl-1-oxopropyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Cephalexin Impurity E; (6R-trans)-7-[(2,2-dimethyl-1-oxopropyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 7-Aminodeacetoxycephalosporanic Acid Pivalamide; 7-ADCA Pivalamide

Database IDs

• CAS Number: 146794-70-9
• PubChem SID: 162253678
• PubChem CID: 14949331

CALCULATED PROPERTIES

• Acid pKa: 4.0593634
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.544349
• LogD (pH = 7.4): -2.2158136
• Log P: 0.9082339
• Molar Refractivity: 74.9584 cm^3
• Polarizability: 29.074654 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A235000

7-ADCA Pivalamide is an impurity of the semi-synthetic antibiotic Cephalexin (C256800) as well as its hydroxy analogue Cefadroxil (C235750).

REFERENCES

• Hendrix, C. et al.: J. Liq. Chrom., 16, 421 (1993)
• Hendrix, C. et al.: J. Chrom., 634, 257 (1993)