N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}acetamide

• ChemBase ID: 159465
• Molecular Formular: C12H13N3O4S
• Molecular Mass: 295.31432
• Monoisotopic Mass: 295.06267691
• SMILES: c1(ccc(cc1)NC(=O)C)S(=O)(=O)Nc1noc(c1)C
• Canonical SMILES: CC(=O)Nc1ccc(cc1)S(=O)(=O)Nc1noc(c1)C
• InChI: InChI=1S/C12H13N3O4S/c1-8-7-12(14-19-8)15-20(17,18)11-5-3-10(4-6-11)13-9(2)16/h3-7H,1-2H3,(H,13,16)(H,14,15)
• InChIKey: GXPIUNZCALHVBA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}acetamide
• IUPAC Traditional name: acetylsulfamethoxazole
• Synonyms: N-[4-[[(5-Methyl-3-isoxazolyl)amino]sulfonyl]phenyl]acetamide; 4’-Acetyl-3-sulfa-5-methylisoxazole; N4-Acetylsulfamethoxazole; N4-Acetylsulfisomezole; STX 606; Sulfisomezole-N4-acetate; N-Acetyl Sulfamethoxazole

Database IDs

• CAS Number: 21312-10-7
• PubChem SID: 162253600
• PubChem CID: 65280

CALCULATED PROPERTIES

• Acid pKa: 5.878687
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.7256879
• LogD (pH = 7.4): 0.0031090446
• Log P: 0.8571857
• Molar Refractivity: 74.6584 cm^3
• Polarizability: 27.933126 Å^3
• Polar Surface Area: 101.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 232-234°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A187885

A metabolite of Sulfamethoxazole.

REFERENCES

• Ciolino, H., et al.: Cancer Res., 58 , 2754 (1998)
• Larsen, T., et al.: Environ. Sci. Technol., 35, 192 (1998)
• Heberer, T., et al.: Toxicol. Lett., 131, 5 (1998)
• Larsen, T., et al.: J. Biotechnol., 113, 295 (1998)