(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 166208
• Molecular Formular: C15H15N5O7S2
• Molecular Mass: 441.4389
• Monoisotopic Mass: 441.04128985
• SMILES: S1[C@H]2N(C(=C(C1)C)C(=O)O)C(=O)[C@H]2NC(=O)/C(=N\OCC(=O)O)/c1csc(n1)N
• Canonical SMILES: OC(=O)CO/N=C(\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C)/c1csc(n1)N
• InChI: InChI=1S/C15H15N5O7S2/c1-5-3-28-13-9(12(24)20(13)10(5)14(25)26)18-11(23)8(19-27-2-7(21)22)6-4-29-15(16)17-6/h4,9,13H,2-3H2,1H3,(H2,16,17)(H,18,23)(H,21,22)(H,25,26)/b19-8-/t9-,13-/m1/s1
• InChIKey: ZDMZWMRTKADQNC-HBWVYFAYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-[(carboxymethoxy)imino]acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; [6R-[6α,7β(Z)]]-7-[[(2-Amino-4-thiazolyl)[(carboxymethoxy)imino]acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 3-Desethenyl-3-methyl Cefixime (Cefixime EP Impurity E)

Database IDs

• CAS Number: 72701-01-0
• PubChem SID: 162260341
• PubChem CID: 71315623

CALCULATED PROPERTIES

• Acid pKa: 3.43961
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -4.689936
• LogD (pH = 7.4): -7.236493
• Log P: -1.7593769
• Molar Refractivity: 100.2667 cm^3
• Polarizability: 38.041485 Å^3
• Polar Surface Area: 184.51 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D289065

3-Desethenyl-3-methyl Cefixime is an impurity of the third generation cephalosporin antibiotic, Cefixime (C242800).

REFERENCES

• Yamanaka, H. et al.: J. Antibiot., 39, 101 (1986)