(6R,7R)-3-ethenyl-7-(4-hydroxy-1,2-oxazole-3-amido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 170604
• Molecular Formular: C13H11N3O6S
• Molecular Mass: 337.30794
• Monoisotopic Mass: 337.03685609
• SMILES: [C@@H]12N(C(=C(CS1)C=C)C(=O)O)C(=O)[C@H]2NC(=O)c1nocc1O
• Canonical SMILES: C=CC1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)NC(=O)c1nocc1O
• InChI: InChI=1S/C13H11N3O6S/c1-2-5-4-23-12-8(11(19)16(12)9(5)13(20)21)14-10(18)7-6(17)3-22-15-7/h2-3,8,12,17H,1,4H2,(H,14,18)(H,20,21)/t8-,12-/m1/s1
• InChIKey: FDZFCJHOKSKSPM-PRHODGIISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-3-ethenyl-7-(4-hydroxy-1,2-oxazole-3-amido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-3-ethenyl-7-(4-hydroxy-1,2-oxazole-3-amido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-(4-Hydroxyisoxazole-3-carboxamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

Database IDs

• PubChem SID: 164226514
• PubChem CID: 57435809

CALCULATED PROPERTIES

• Acid pKa: 2.8921733
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -3.002183
• LogD (pH = 7.4): -4.4129624
• Log P: 0.20028298
• Molar Refractivity: 79.6225 cm^3
• Polarizability: 29.499641 Å^3
• Polar Surface Area: 132.97 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H943595

Cefdinir (C242670) impurity.