2-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-2-{5-methyl-7-oxo-1H,2H,4H,5H,7H-furo[3,4-d][1,3]thiazin-2-yl}acetic acid

• ChemBase ID: 160504
• Molecular Formular: C14H15N5O6S2
• Molecular Mass: 413.4288
• Monoisotopic Mass: 413.04637523
• SMILES: C1(NC2=C(CS1)C(OC2=O)C)C(NC(=O)/C(=N\O)/c1csc(n1)N)C(=O)O
• Canonical SMILES: O/N=C(/c1csc(n1)N)\C(=O)NC(C1SCC2=C(N1)C(=O)OC2C)C(=O)O
• InChI: InChI=1S/C14H15N5O6S2/c1-4-5-2-26-11(18-7(5)13(23)25-4)9(12(21)22)17-10(20)8(19-24)6-3-27-14(15)16-6/h3-4,9,11,18,24H,2H2,1H3,(H2,15,16)(H,17,20)(H,21,22)/b19-8-
• InChIKey: DKFLDACXFQGVEO-UWVJOHFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-2-{5-methyl-7-oxo-1H,2H,4H,5H,7H-furo[3,4-d][1,3]thiazin-2-yl}acetic acid
• IUPAC Traditional name: [(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]({5-methyl-7-oxo-1H,2H,4H,5H-furo[3,4-d][1,3]thiazin-2-yl})acetic acid
• Synonyms: [2RS-[2α[RS*(Z)],5β]]-α-[[(2-Amino-4-thiazolyl)(hydroxyimino)acetyl]amino]-1,2,5,7-tetrahydro-5-methyl-7-oxo-4H-furo[3,4-d][1,3]thiazine-2-acetic Acid; 2(R)-2-[(Z)-2-(Aminothiazol-4-yl)-2-(hydroxyimino)acetamido)]-2-[(2RS,5RS)-5-methyl-7-oxo-2,4,5,7-tetrahydro-1H-furo[3,4-d][1,3]thiazin-2-yl]acetic Acid(Mixture of 4 Diastereomers)

Database IDs

• CAS Number: 178422-45-2
• PubChem SID: 162254639
• PubChem CID: 71313360

CALCULATED PROPERTIES

• Acid pKa: 1.7627053
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -3.582024
• LogD (pH = 7.4): -4.3750005
• Log P: -1.7087411
• Molar Refractivity: 95.4789 cm^3
• Polarizability: 36.2883 Å^3
• Polar Surface Area: 176.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A630385

Cefdinir (C242670) impurity formed by hydrolytic degradation pathway β-lactam ring opened lactones.

REFERENCES

• Inamoto, Y., et al.: J. Antibiot., 41, 828 (1988)
• Ternansky, R., et al.: J. Antibiot., 46, 1897 (1988)