(2S,3R)-2-[(2S,3R)-4-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-5-({[(2,2-dimethylpropanoyl)oxy]methoxy}carbonyl)-3-methyl-2,3-dihydro-1H-pyrrol-2-yl]-3-hydroxybutanoic acid

• ChemBase ID: 178107
• Molecular Formular: C22H33N3O7S2
• Molecular Mass: 515.64332
• Monoisotopic Mass: 515.17599241
• SMILES: [C@H]1(NC(=C([C@@H]1C)SC1CN(C1)C1=NCCS1)C(=O)OCOC(=O)C(C)(C)C)[C@@H]([C@H](O)C)C(=O)O
• Canonical SMILES: C[C@H]([C@H]([C@@H]1NC(=C([C@@H]1C)SC1CN(C1)C1=NCCS1)C(=O)OCOC(=O)C(C)(C)C)C(=O)O)O
• InChI: InChI=1S/C22H33N3O7S2/c1-11-15(14(12(2)26)18(27)28)24-16(19(29)31-10-32-20(30)22(3,4)5)17(11)34-13-8-25(9-13)21-23-6-7-33-21/h11-15,24,26H,6-10H2,1-5H3,(H,27,28)/t11-,12-,14-,15-/m1/s1
• InChIKey: XRCZSPQKQSSDGX-QHSBEEBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-[(2S,3R)-4-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-5-({[(2,2-dimethylpropanoyl)oxy]methoxy}carbonyl)-3-methyl-2,3-dihydro-1H-pyrrol-2-yl]-3-hydroxybutanoic acid
• IUPAC Traditional name: (2S,3R)-2-[(2S,3R)-4-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-5-({[(2,2-dimethylpropanoyl)oxy]methoxy}carbonyl)-3-methyl-2,3-dihydro-1H-pyrrol-2-yl]-3-hydroxybutanoic acid
• Synonyms: 4,7-seco-Tebipenemoic Acid Pivoxil

Database IDs

• PubChem SID: 164234017
• PubChem CID: 71483908

CALCULATED PROPERTIES

• Acid pKa: 3.72111
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 0.09159503
• LogD (pH = 7.4): -0.9354678
• Log P: 0.123949915
• Molar Refractivity: 130.5043 cm^3
• Polarizability: 50.804096 Å^3
• Polar Surface Area: 137.76 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T012870

4,7-seco-Tebipenemoic Acid Pivoxil is an impurity of Tebipenem Pivoxil (T012900).