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

• ChemBase ID: 166682
• Molecular Formular: C13H12N2O5S2
• Molecular Mass: 340.37478
• Monoisotopic Mass: 340.01876349
• SMILES: [C@@H]12N(C(=C(CS1)CSC(=O)c1ccco1)C(=O)O)C(=O)[C@H]2N
• Canonical SMILES: N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSC(=O)c1ccco1
• InChI: InChI=1S/C13H12N2O5S2/c14-8-10(16)15-9(12(17)18)6(4-21-11(8)15)5-22-13(19)7-2-1-3-20-7/h1-3,8,11H,4-5,14H2,(H,17,18)/t8-,11-/m1/s1
• InChIKey: ZMPDMYFTSINIIZ-LDYMZIIASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-amino-3-[(furan-2-carbonylsulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-amino-3-[(furan-2-carbonylsulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-Amino-3-[[(2-furanylcarbonyl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Desthiazoximic Acid Ceftiofur

Database IDs

• CAS Number: 80370-59-8
• PubChem SID: 162260815
• PubChem CID: 11221491

CALCULATED PROPERTIES

• Acid pKa: 2.8901396
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -2.0507593
• LogD (pH = 7.4): -2.3293371
• Log P: -2.0490415
• Molar Refractivity: 82.1447 cm^3
• Polarizability: 31.707943 Å^3
• Polar Surface Area: 113.84 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Methanol
• Apperance: Light Brown Solid

DETAILS

Toronto Research Chemicals - D297455

Ceftiofur intermediate.