(2Z)-2-(2-amino-1,3-thiazol-4-yl)-N-[(4R,5R)-3,11-dioxo-10-oxa-6-thia-2-azatricyclo[6.3.0.02,5]undec-1(8)-en-4-yl]-2-(methoxyimino)acetamide

• ChemBase ID: 165846
• Molecular Formular: C14H13N5O5S2
• Molecular Mass: 395.41352
• Monoisotopic Mass: 395.03581054
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC1=C2C(=O)OC1)NC(=O)/C(=N\OC)/c1csc(n1)N
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC1=C2C(=O)OC1
• InChI: InChI=1S/C14H13N5O5S2/c1-23-18-7(6-4-26-14(15)16-6)10(20)17-8-11(21)19-9-5(2-24-13(9)22)3-25-12(8)19/h4,8,12H,2-3H2,1H3,(H2,15,16)(H,17,20)/b18-7-/t8-,12-/m1/s1
• InChIKey: MCSWUKXFFGUOQE-GHXIOONMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-2-(2-amino-1,3-thiazol-4-yl)-N-[(4R,5R)-3,11-dioxo-10-oxa-6-thia-2-azatricyclo[6.3.0.0^2,^5]undec-1(8)-en-4-yl]-2-(methoxyimino)acetamide
• IUPAC Traditional name: (2Z)-2-(2-amino-1,3-thiazol-4-yl)-N-[(4R,5R)-3,11-dioxo-10-oxa-6-thia-2-azatricyclo[6.3.0.0^2,^5]undec-1(8)-en-4-yl]-2-(methoxyimino)acetamide
• Synonyms: [5aR-[5aα,6β(Z)]]-2-Amino-α-(methoxyimino)-N-(1,4,5a,6-tetrahydro-1,7-dioxo-3H,7H-azeto[2,1-b]furo[3,4-d][1,3]thiazin-6-yl)-4-thiazoleacetamide; 3-Desacetyl Cefotaxime Lactone

Database IDs

• CAS Number: 66340-33-8
• PubChem SID: 162259979
• PubChem CID: 13080558

CALCULATED PROPERTIES

• Acid pKa: 10.926156
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.2902701
• LogD (pH = 7.4): -0.27336532
• Log P: -0.27302837
• Molar Refractivity: 92.4646 cm^3
• Polarizability: 35.057114 Å^3
• Polar Surface Area: 136.21 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D288390

3-Desacetyl Cefotaxime Lactone is an impurity of Cefotaxime sodium (C242950). 3-Desacetyl Cefotaxime Lactone is also a degradation product for other cephalosporin antibiotics such as: Ceftriaxone (C245000), Cefodizime and Ceftiofur (C244700).

REFERENCES

• Amaker, R., et al.: Antimicrob. Agents Chemother., 40, 1139 (1996)
• Taylor, P., et al.: Clin. Biochem., 38, 328 (1996)