(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid

• ChemBase ID: 163948
• Molecular Formular: C16H16N4O8S
• Molecular Mass: 424.38524
• Monoisotopic Mass: 424.06888449
• SMILES: [C@H]1(C(=O)N2[C@@H]1SC=C(C2C(=O)O)COC(=O)N)NC(=O)/C(=N\OC)/c1ccco1
• Canonical SMILES: CO/N=C(\C(=O)N[C@@H]1C(=O)N2[C@@H]1SC=C(C2C(=O)O)COC(=O)N)/c1ccco1
• InChI: InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,6,10-11,14H,5H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,11?,14-/m1/s1
• InChIKey: AIEMBSSBMKFDGU-YNZZGVKBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid
• Synonyms: (6R,7R)-3-[[(Aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-furanyl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic Acid; Δ2-Cefuroxime

Database IDs

• CAS Number: 229499-08-5
• PubChem SID: 162258083
• PubChem CID: 23659637

CALCULATED PROPERTIES

• Acid pKa: 3.5037751
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.9832423
• LogD (pH = 7.4): -4.369544
• Log P: -0.99518794
• Molar Refractivity: 95.8822 cm^3
• Polarizability: 37.307236 Å^3
• Polar Surface Area: 173.76 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C248060

A potentially related compound in cephalosporin antibacterial compounds. An isomer of Cefuroxime (C248050).

REFERENCES

• Chavette, R., et al.: J. Med. Chem., 9, 741 (1966)
• Miyouchi, M., et al.: J. Chem. Pharm. Bull., 38, 1906 (1966)
• Sugioka, T., et al.: Chem. Pharm. Bull., 38, 1998 (1966)