(2R)-2-[(R)-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido](carboxy)methyl]-5-ethenyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid

• ChemBase ID: 163911
• Molecular Formular: C16H17N5O8S2
• Molecular Mass: 471.46488
• Monoisotopic Mass: 471.05185453
• SMILES: S1[C@@H](NC(=C(C1)C=C)C(=O)O)[C@@H](C(=O)O)NC(=O)/C(=N\OCC(=O)O)/c1csc(n1)N
• Canonical SMILES: C=CC1=C(N[C@H](SC1)[C@@H](C(=O)O)NC(=O)/C(=N\OCC(=O)O)/c1csc(n1)N)C(=O)O
• InChI: InChI=1S/C16H17N5O8S2/c1-2-6-4-30-13(20-9(6)14(25)26)11(15(27)28)19-12(24)10(21-29-3-8(22)23)7-5-31-16(17)18-7/h2,5,11,13,20H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,25,26)(H,27,28)/b21-10-/t11-,13+/m0/s1
• InChIKey: YHASEJDNUZDWSN-OSUSRSLZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(R)-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido](carboxy)methyl]-5-ethenyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• IUPAC Traditional name: (2R)-2-[(R)-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido](carboxy)methyl]-5-ethenyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• Synonyms: α-[[(Z)-2-(2-amino-4-thiazolyl)-2-[(carboxymethoxy)imino]acetyl]amino]-2-[(2R)-5-methyl-7-oxo-1,2,5,7-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl]acetic Acid; Cefixime EP Impurity A

Database IDs

• PubChem SID: 162258046
• PubChem CID: 71314609

CALCULATED PROPERTIES

• Acid pKa: -0.2885341
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -6.098358
• LogD (pH = 7.4): -10.189732
• Log P: -1.5306077
• Molar Refractivity: 107.9896 cm^3
• Polarizability: 40.829075 Å^3
• Polar Surface Area: 213.53 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C242805

Cefixime EP Impurity A is an impurity of the third generation cephalosporin antibiotic, Cefixime (C242800).

REFERENCES

• Namiki, Y. et al.: J. Pharmac. Sci., 76, 208 (1987)