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

• ChemBase ID: 175742
• Molecular Formular: C13H19N3O3S
• Molecular Mass: 297.37326
• Monoisotopic Mass: 297.11471248
• SMILES: S1[C@H]2N(C(=C(C1)C[N+]1(CCCC1)C)C(=O)[O-])C(=O)[C@H]2N
• Canonical SMILES: O=C1[C@@H](N)[C@@H]2N1C(=C(CS2)C[N+]1(C)CCCC1)C(=O)[O-]
• InChI: InChI=1S/C13H19N3O3S/c1-16(4-2-3-5-16)6-8-7-20-12-9(14)11(17)15(12)10(8)13(18)19/h9,12H,2-7,14H2,1H3/t9-,12-/m1/s1
• InChIKey: IIVPIDBZUUAWTF-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}-1-methylpyrrolidin-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}-1-methylpyrrolidin-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]-1-methylpyrrolidinium Inner Salt; (6R-trans-NMP-ACA); 7-Amino-3-(1-methylpyrrolidino)methyl-3-cephem-4-carboxylate Inner Salt; NMP-ACA (Cefepime Impurity)

Database IDs

• CAS Number: 103296-32-8
• PubChem SID: 164231652
• PubChem CID: 9796244

CALCULATED PROPERTIES

• Acid pKa: 3.5609026
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -6.1334615
• LogD (pH = 7.4): -4.561636
• Log P: -6.580053
• Molar Refractivity: 99.6054 cm^3
• Polarizability: 29.972078 Å^3
• Polar Surface Area: 86.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N894200

Cefepime impurity. Cephalosporin intermediate synthesis.

REFERENCES

• Lee, Y., et al.: J. Antibiot., 47, 609 (1994)