2-[amino({[carboxy(phenyl)methyl]carbamoyl})methyl]-5-methyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid

• ChemBase ID: 163973
• Molecular Formular: C16H19N3O5S
• Molecular Mass: 365.40416
• Monoisotopic Mass: 365.10454172
• SMILES: c1ccc(cc1)C(NC(=O)C(N)C1NC(=C(CS1)C)C(=O)O)C(=O)O
• Canonical SMILES: NC(C1SCC(=C(N1)C(=O)O)C)C(=O)NC(c1ccccc1)C(=O)O
• InChI: InChI=1S/C16H19N3O5S/c1-8-7-25-14(19-11(8)15(21)22)10(17)13(20)18-12(16(23)24)9-5-3-2-4-6-9/h2-6,10,12,14,19H,7,17H2,1H3,(H,18,20)(H,21,22)(H,23,24)
• InChIKey: JJUQRQMFNIGCFS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[amino({[carboxy(phenyl)methyl]carbamoyl})methyl]-5-methyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• IUPAC Traditional name: 2-{amino[carboxy(phenyl)methylcarbamoyl]methyl}-5-methyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• Synonyms: 2-[1-Amino-2-[carboxy(phenyl)methylamino]-2-oxoethyl]-3,6-dihydro-5-methyl-2H-1,3-thiazine-4-carboxylic Acid; Cephalexin Diketopiperazine Monoacid(Mixture of Diastereomers)

Database IDs

• PubChem SID: 162258108
• PubChem CID: 71314640

CALCULATED PROPERTIES

• Acid pKa: 3.099178
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -3.4863298
• LogD (pH = 7.4): -5.4635906
• Log P: -2.2885697
• Molar Refractivity: 92.0514 cm^3
• Polarizability: 35.82811 Å^3
• Polar Surface Area: 141.75 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C256765

A hydrolysis product of Cephalexin Diketopiperazine (C256760). An impurity of Cephalexin (C256800) and Cephaloglycin.