(2R)-5-methyl-2-[(1R)-2-oxo-1-[2-(thiophen-2-yl)acetamido]ethyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid

• ChemBase ID: 3754
• Molecular Formular: C14H16N2O4S2
• Molecular Mass: 340.41784
• Monoisotopic Mass: 340.055149
• SMILES: S1CC(=C(C(=O)O)N[C@H]1[C@@H](C=O)NC(=O)Cc1cccs1)C
• Canonical SMILES: O=C[C@H]([C@H]1SCC(=C(N1)C(=O)O)C)NC(=O)Cc1cccs1
• InChI: InChI=1S/C14H16N2O4S2/c1-8-7-22-13(16-12(8)14(19)20)10(6-17)15-11(18)5-9-3-2-4-21-9/h2-4,6,10,13,16H,5,7H2,1H3,(H,15,18)(H,19,20)/t10-,13-/m1/s1
• InChIKey: SFVACKBZMIZHCK-ZWNOBZJWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-5-methyl-2-[(1R)-2-oxo-1-[2-(thiophen-2-yl)acetamido]ethyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• IUPAC Traditional name: (2R)-5-methyl-2-[(1R)-2-oxo-1-[2-(thiophen-2-yl)acetamido]ethyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• Synonyms: Degraded Cephaloridine

Database IDs

• PubChem SID: 46507610; 160967192
• PubChem CID: 5287902

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.8889294
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.75244665
• LogD (pH = 7.4): -2.3553152
• Log P: 0.8640144
• Molar Refractivity: 85.0202 cm^3
• Polarizability: 32.547752 Å^3
• Polar Surface Area: 95.5 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.12
• LOG S: -3.92
• Solubility (Water): 4.11e-02 g/l

DETAILS

DrugBank - DB04133

Drug information: experimental