(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-5-yl)-4-carboxybut-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 163872
• Molecular Formular: C15H14N4O6S2
• Molecular Mass: 410.42486
• Monoisotopic Mass: 410.03547619
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC=C2C(=O)O)NC(=O)/C(=C/CC(=O)O)/c1sc(nc1)N
• Canonical SMILES: OC(=O)C/C=C(/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC=C2C(=O)O)\c1cnc(s1)N
• InChI: InChI=1S/C15H14N4O6S2/c16-15-17-5-8(27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-7(14(24)25)3-4-26-13(10)19/h1,3,5,10,13H,2,4H2,(H2,16,17)(H,18,22)(H,20,21)(H,24,25)/b6-1+/t10-,13-/m1/s1
• InChIKey: RTEIAVXUFXNVQE-VTSZRNMSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-5-yl)-4-carboxybut-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-5-yl)-4-carboxybut-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: [6R-[6α,7β(E)]]-7-[[2-(2-Amino-4-thiazolyl)-4-carboxy-1-oxo-2-butenyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Dihydrate; (E)-Ceftibuten Dihydrate

Database IDs

• PubChem SID: 162258007
• PubChem CID: 71314582

CALCULATED PROPERTIES

• Acid pKa: 2.8825364
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.878987
• LogD (pH = 7.4): -6.871945
• Log P: -1.6925397
• Molar Refractivity: 97.1799 cm^3
• Polarizability: 36.32478 Å^3
• Polar Surface Area: 162.92 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C244490

The E-isomer of Ceftibuten (C244500).

REFERENCES

• Hamashima, Y., et al.: J. Antibiot., 40, 1468 (1987)
• Nakashima, M., et al.: J. Clin. Pharmacol., 28, 246 (1988)