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

• ChemBase ID: 153252
• Molecular Formular: C15H14N4O6S2
• Molecular Mass: 410.42486
• Monoisotopic Mass: 410.03547619
• SMILES: c1c(nc(s1)N)/C(=C\CC(=O)O)/C(=O)N[C@H]1[C@@H]2N(C1=O)C(=CCS2)C(=O)O
• Canonical SMILES: OC(=O)C/C=C(/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC=C2C(=O)O)\c1csc(n1)N
• InChI: InChI=1S/C15H14N4O6S2/c16-15-17-7(5-27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-8(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)/t10-,13-/m1/s1
• InChIKey: UNJFKXSSGBWRBZ-ZWNOBZJWSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 97519-39-6(anhydrous)
• MDL Number: MFCD00864918
• PubChem SID: 162247391
• PubChem CID: 6398762

CALCULATED PROPERTIES

• Acid pKa: 2.9868503
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.8269622
• LogD (pH = 7.4): -6.7946153
• Log P: -1.4103966
• Molar Refractivity: 97.0238 cm^3
• Polarizability: 36.321697 Å^3
• Polar Surface Area: 162.92 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥50 mg/mL
• Apperance: white to tan powder

Safety Information

• Storage Condition: desiccated
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H14N4O6S2 · xH2O

DETAILS

Sigma Aldrich - SML0037

Biochem/physiol Actions
Ceftibuten is a third generation cephalosporin antibiotic