1-{[(6R,7R)-7-amino-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium

• ChemBase ID: 160541
• Molecular Formular: C13H13N3O3S
• Molecular Mass: 291.32562
• Monoisotopic Mass: 291.06776229
• SMILES: [C@@H]12N(C(=C(CS1)C[n+]1ccccc1)C(=O)[O-])C(=O)[C@H]2N
• Canonical SMILES: N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[n+]1ccccc1
• InChI: InChI=1S/C13H13N3O3S/c14-9-11(17)16-10(13(18)19)8(7-20-12(9)16)6-15-4-2-1-3-5-15/h1-5,9,12H,6-7,14H2/t9-,12-/m1/s1
• InChIKey: ACIOXMJZEFKYHZ-BXKDBHETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(6R,7R)-7-amino-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium
• IUPAC Traditional name: 1-{[(6R,7R)-7-amino-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium
• Synonyms: 1-[[(6R,7R)-7-Amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-pyridinium Inner Salt; (6R-trans)-1-[(7-Amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl]pyridinium Inner Salt; N-(7-Aminoceph-3-em-3-ylmethyl)pyridinium-4-carboxylate; N-(7-Aminocephem-3-em-3-ylmethyl)pyridinium-4-carboxylate; [7-Amino-3-(1-pyridylmethyl)-3-cephem-4-carboxylic Acid; 7-Amino-3-(1-pyridylmethyl)-3-cephem-4-carboxylic Acid

Database IDs

• CAS Number: 3432-88-0
• PubChem SID: 162254676
• PubChem CID: 11055417

CALCULATED PROPERTIES

• Acid pKa: 2.963607
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -6.5471396
• LogD (pH = 7.4): -5.1795297
• Log P: -6.766269
• Molar Refractivity: 86.2192 cm^3
• Polarizability: 28.951643 Å^3
• Polar Surface Area: 90.34 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A632580

7-Amino-3-(1-pyridylmethyl)-3-cephem-4-carboxylic acid is an impurity of Ceftazidime (C244100). Ceftazidime impurity B.

REFERENCES

• Miyake, A., et al.: Antimicrob. Agents Chemother., 486, 182 (1989)
• Seibert, G., et al.: Arzneim.-Forsch., 33, 1084 (1989)