1-[(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2E)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]ethyl acetate

• ChemBase ID: 163952
• Molecular Formular: C20H22N4O10S
• Molecular Mass: 510.47448
• Monoisotopic Mass: 510.10566392
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)OC(C)OC(=O)C)COC(=O)N)NC(=O)/C(=N/OC)/c1ccco1
• Canonical SMILES: CO/N=C(\c1ccco1)/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)OC(OC(=O)C)C)COC(=O)N
• InChI: InChI=1S/C20H22N4O10S/c1-9(25)33-10(2)34-19(28)15-11(7-32-20(21)29)8-35-18-14(17(27)24(15)18)22-16(26)13(23-30-3)12-5-4-6-31-12/h4-6,10,14,18H,7-8H2,1-3H3,(H2,21,29)(H,22,26)/b23-13+/t10?,14-,18-/m1/s1
• InChIKey: KEJCWVGMRLCZQQ-DJMWJSSGSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162258087
• PubChem CID: 5361467

CALCULATED PROPERTIES

• Acid pKa: 10.924807
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.43309042
• LogD (pH = 7.4): -0.43320468
• Log P: -0.43308887
• Molar Refractivity: 117.0305 cm^3
• Polarizability: 45.71133 Å^3
• Polar Surface Area: 189.06 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C248075

A trans-isomeric impurity of the antibacterial Cefuroxime Axetil (C248065).