(6R,7R)-3-[(acetyloxy)methyl]-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(2H3)methoxyimino]acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 163919
• Molecular Formular: C16H17N5O7S2
• Molecular Mass: 455.46548
• Monoisotopic Mass: 455.05693991
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)C)NC(=O)/C(=N\OC)/c1csc(n1)N
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)C
• InChI: InChI=1S/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9-/t10-,14-/m1/s1
• InChIKey: GPRBEKHLDVQUJE-QSWIMTSFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-3-[(acetyloxy)methyl]-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(^2H₃)methoxyimino]acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-3-[(acetyloxy)methyl]-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(^2H₃)methoxyimino]acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-3-[(Acetyloxy)methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid-d3; Cefotax-d3; HR 756-d3; Pretor-d3; Tolycar-d3; Cefotaxime-d3

Database IDs

• PubChem SID: 162258054
• PubChem CID: 71314613

CALCULATED PROPERTIES

• Acid pKa: 3.1773155
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -2.9842594
• LogD (pH = 7.4): -4.1677856
• Log P: -1.9052299
• Molar Refractivity: 105.1083 cm^3
• Polarizability: 40.078888 Å^3
• Polar Surface Area: 173.51 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: >300°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C242952

Broad spectrum third generation cephalosporin antibiotic.

REFERENCES

• Wise, R., et al.: Antimicrob. Agents Chemother., 14, 807 (1978)
• Muhtadi, F.J., et al.: Anal. Profiles Drug Subs., 11, 139 (1978)