(4R,5S)-5-[(1S,2R)-1-carboxy-2-hydroxypropyl]-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-4-methyl-4,5-dihydro-1H-pyrrole-2-carboxylic acid

• ChemBase ID: 178105
• Molecular Formular: C16H23N3O5S2
• Molecular Mass: 401.50092
• Monoisotopic Mass: 401.10791285
• SMILES: [C@H]1(NC(=C([C@@H]1C)SC1CN(C1)C1=NCCS1)C(=O)O)[C@H](C(=O)O)[C@H](O)C
• Canonical SMILES: C[C@H]([C@H]([C@@H]1NC(=C([C@@H]1C)SC1CN(C1)C1=NCCS1)C(=O)O)C(=O)O)O
• InChI: InChI=1S/C16H23N3O5S2/c1-7-11(10(8(2)20)14(21)22)18-12(15(23)24)13(7)26-9-5-19(6-9)16-17-3-4-25-16/h7-11,18,20H,3-6H2,1-2H3,(H,21,22)(H,23,24)/t7-,8-,10-,11-/m1/s1
• InChIKey: PLLIEDVYOCYIJX-YJFSRANCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S)-5-[(1S,2R)-1-carboxy-2-hydroxypropyl]-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-4-methyl-4,5-dihydro-1H-pyrrole-2-carboxylic acid
• IUPAC Traditional name: (4R,5S)-5-[(1S,2R)-1-carboxy-2-hydroxypropyl]-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-4-methyl-4,5-dihydro-1H-pyrrole-2-carboxylic acid
• Synonyms: Δ2,3(Δ3,4)-4,7-seco-Tebipenemoic Acid

Database IDs

• PubChem SID: 164234015
• PubChem CID: 71752336

CALCULATED PROPERTIES

• Acid pKa: 3.5228333
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.3160727
• LogD (pH = 7.4): -6.0558314
• Log P: -2.2593858
• Molar Refractivity: 101.7795 cm^3
• Polarizability: 38.732697 Å^3
• Polar Surface Area: 122.46 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T012850

Δ2,3(Δ3,4)-4,7-seco-Tebipenemoic Acid is an impurity of Tebipenem Pivoxil (T012900).