2-(3,6-dioxo-5-phenylpiperazin-2-yl)-5-methyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid

• ChemBase ID: 163972
• Molecular Formular: C16H17N3O4S
• Molecular Mass: 347.38888
• Monoisotopic Mass: 347.09397704
• SMILES: c1ccc(cc1)C1NC(=O)C(NC1=O)C1NC(=C(CS1)C)C(=O)O
• Canonical SMILES: O=C1NC(C(=O)NC1C1SCC(=C(N1)C(=O)O)C)c1ccccc1
• InChI: InChI=1S/C16H17N3O4S/c1-8-7-24-15(19-10(8)16(22)23)12-14(21)17-11(13(20)18-12)9-5-3-2-4-6-9/h2-6,11-12,15,19H,7H2,1H3,(H,17,21)(H,18,20)(H,22,23)
• InChIKey: BGVLRSBBXLRVEG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,6-dioxo-5-phenylpiperazin-2-yl)-5-methyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• IUPAC Traditional name: 2-(3,6-dioxo-5-phenylpiperazin-2-yl)-5-methyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• Synonyms: 2-(3,6-Dioxo-5-phenyl-2-piperazinyl)-3,6-dihydro-5-methyl-2H-1,3-thiazine-4-carboxylic Acid; Cephalexin Diketopiperazine

Database IDs

• CAS Number: 59865-11-1
• PubChem SID: 162258107
• PubChem CID: 71314639

CALCULATED PROPERTIES

• Acid pKa: 3.789849
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.3821906
• LogD (pH = 7.4): -2.9375064
• Log P: 0.32990134
• Molar Refractivity: 88.8515 cm^3
• Polarizability: 34.251198 Å^3
• Polar Surface Area: 107.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C256760

A degradation product of Cephalosporins (Cephalexin (C256800) and Cephaloglycin impurity).

REFERENCES

• Li, Q., et al.: Analytica Chimica Acta, 282, 145 (1993)