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

• ChemBase ID: 166151
• Molecular Formular: C15H15N3O7S
• Molecular Mass: 381.3605
• Monoisotopic Mass: 381.06307084
• SMILES: [C@@H]12N(C(=C(CS1)CO)C(=O)O)C(=O)[C@H]2NC(=O)/C(=N\OC)/c1occc1
• Canonical SMILES: CO/N=C(/c1ccco1)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CO
• InChI: InChI=1S/C15H15N3O7S/c1-24-17-9(8-3-2-4-25-8)12(20)16-10-13(21)18-11(15(22)23)7(5-19)6-26-14(10)18/h2-4,10,14,19H,5-6H2,1H3,(H,16,20)(H,22,23)/b17-9-/t10-,14-/m1/s1
• InChIKey: OUSLHGWWWMRAIG-FBCAJUAOSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 56271-94-4
• PubChem SID: 162260284
• PubChem CID: 9800056

CALCULATED PROPERTIES

• Acid pKa: 3.1392334
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -3.3447337
• LogD (pH = 7.4): -4.466192
• Log P: -1.0105534
• Molar Refractivity: 89.3376 cm^3
• Polarizability: 34.086296 Å^3
• Polar Surface Area: 141.67 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethylformamide; DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 218-221°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D288830

A degradation product of Cefuroxime, and an intermediate for the synthesis of Cephalosporin antibiotics

REFERENCES

• Nomura, H., et al.: J. Med. Chem., 17, 12 (1974)
• Takaya, T., et al.: J. Antibiotics, 34, 1300 (1974)
• Wang, D., et al.: J. Pharm. Sci., 83, 577 (1974)
• Okamoto, Y., et al.: J. Pharm. Sci., 85, 985 (1974)