1-{[(6R,7R)-7-[(2Z)-2-{2-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-1,3-thiazol-4-yl}-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium

• ChemBase ID: 160108
• Molecular Formular: C25H29N9O7S3
• Molecular Mass: 663.74886
• Monoisotopic Mass: 663.13520731
• SMILES: S1[C@H]2N(C(=C(C1)C[N+]1(CCCC1)C)C(=O)[O-])C(=O)[C@H]2NC(=O)/C(=N\OC)/c1csc(n1)NC(=O)/C(=N\OC)/c1csc(n1)N
• Canonical SMILES: CO/N=C(/c1csc(n1)NC(=O)/C(=N\OC)/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[N+]1(C)CCCC1
• InChI: InChI=1S/C25H29N9O7S3/c1-34(6-4-5-7-34)8-12-9-42-22-17(21(37)33(22)18(12)23(38)39)29-19(35)16(32-41-3)14-11-44-25(28-14)30-20(36)15(31-40-2)13-10-43-24(26)27-13/h10-11,17,22H,4-9H2,1-3H3,(H4-,26,27,28,29,30,35,36,38,39)/b31-15-,32-16-/t17-,22-/m1/s1
• InChIKey: KMTSWFKAQYRTIV-LANNWKMSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(6R,7R)-7-[(2Z)-2-{2-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-1,3-thiazol-4-yl}-2-(methoxyimino)acetamido]-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-[(2Z)-2-{2-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-1,3-thiazol-4-yl}-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium
• Synonyms: (6R,7R)-7-[[(2Z)-2-[2-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-4-thiazolyl]-2-(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-1-methylpyrrolidinium; Cefipime Impurity B; N-[2-Amino-α-(methoxyimino)-4-thiazoleacetyl] Cefepime(Cefepime Impurity B)DISCONTINUED

Database IDs

• PubChem SID: 162254243
• PubChem CID: 71313230

CALCULATED PROPERTIES

• Acid pKa: 3.6642659
• H Acceptors: 12
• H Donor: 3
• LogD (pH = 5.5): -2.3859859
• LogD (pH = 7.4): -2.381025
• Log P: -3.263675
• Molar Refractivity: 185.064 cm^3
• Polarizability: 60.975716 Å^3
• Polar Surface Area: 213.62 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A611985

A Cefepime (C242750) Impurity.

REFERENCES

• Naito, T., et al.: J. Antibiot., 39, 1092 (1986)