(6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-5-yl)-4-carboxy(,3,4-13C3)but-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 163874
• Molecular Formular: C15H14N4O6S2
• Molecular Mass: 413.40282451
• Monoisotopic Mass: 413.0455407
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC=C2C(=O)O)NC(=O)/C(=[13CH]\[13CH2][13C](=O)O)/c1sc(nc1)N
• Canonical SMILES: O[13C](=O)[13CH2]/[13CH]=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/i1+1,2+1,9+1
• InChIKey: RTEIAVXUFXNVQE-DBCHFAKXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-5-yl)-4-carboxy(,3,4-^1^3C₃)but-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-5-yl)-4-carboxy(,3,4-^1^3C₃)but-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: [6R-[6α,7β(Z)]]-7-[[2-(2-Amino-4-thiazolyl)-4-carboxy-1-oxo-2-(butenyl-13C3)]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Sch-39720; Cephalosporin 7432-S-13C3; S 7432-13C3; Cedax-13C3; Ceftibuten-13C3

Database IDs

• PubChem SID: 162258009
• PubChem CID: 71314584

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 - C244507

A labelled third-generation cephalosporin antibiotic used in the treatment of respiratory tract infection, urinary tract infection, enteritis and gastroenteritis

REFERENCES

• Guest, N. et al.: Int. J. Antimicrob. Agents, 10, 49 (1998)
• Hamashima, Y., et al.: J. Antibiot., 40, 1468 (1998)
• Nakashima, M., et al.: J. Clin. Pharmacol., 28, 246 (1998)