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

• ChemBase ID: 166047
• Molecular Formular: C14H15N5O6S2
• Molecular Mass: 413.4288
• Monoisotopic Mass: 413.04637523
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)O)CO)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]1SCC(=C2C(=O)O)CO
• InChI: InChI=1S/C14H15N5O6S2/c1-25-18-7(6-4-27-14(15)16-6)10(21)17-8-11(22)19-9(13(23)24)5(2-20)3-26-12(8)19/h4,8,12,20H,2-3H2,1H3,(H2,15,16)(H,17,21)(H,23,24)/b18-7-/t8-,12-/m1/s1
• InChIKey: FHYWAOQGXIZAAF-GHXIOONMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-(hydroxymethyl)-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-(methoxyimino)acetamido]-3-(hydroxymethyl)-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-(methoxyimino)acetyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Deacetylcefotaxime; Desacetylcefotaxime; 3-Desacetyl Cefotaxime

Database IDs

• CAS Number: 66340-28-1
• PubChem SID: 162260180
• PubChem CID: 9576239

CALCULATED PROPERTIES

• Acid pKa: 3.1435397
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -3.4593241
• LogD (pH = 7.4): -4.6155467
• Log P: -2.377021
• Molar Refractivity: 95.9568 cm^3
• Polarizability: 36.222645 Å^3
• Polar Surface Area: 167.44 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Pale Yellow Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D288405

An impurity of Cefotaxime sodium (C242950).

REFERENCES

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