3-amino-4-phenoxy-5-sulfamoylbenzoic acid

• ChemBase ID: 166144
• Molecular Formular: C13H12N2O5S
• Molecular Mass: 308.30978
• Monoisotopic Mass: 308.04669249
• SMILES: c1(cc(c(c(c1)S(=O)(=O)N)Oc1ccccc1)N)C(=O)O
• Canonical SMILES: OC(=O)c1cc(N)c(c(c1)S(=O)(=O)N)Oc1ccccc1
• InChI: InChI=1S/C13H12N2O5S/c14-10-6-8(13(16)17)7-11(21(15,18)19)12(10)20-9-4-2-1-3-5-9/h1-7H,14H2,(H,16,17)(H2,15,18,19)
• InChIKey: GVQZPZSQRCXSJI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-amino-4-phenoxy-5-sulfamoylbenzoic acid
• IUPAC Traditional name: 3-amino-4-phenoxy-5-sulfamoylbenzoic acid
• Synonyms: 3-Amino-5-(aminosulfonyl)-4-phenoxy-benzoic Acid; 3-Amino-4-phenoxy-5-sulfamoylbenzoic Acid; Desbutylbumetanide; PF 1578; Desbutyl Bumetanide

Database IDs

• CAS Number: 28328-54-3
• PubChem SID: 162260277
• PubChem CID: 119927

CALCULATED PROPERTIES

• Acid pKa: 4.684573
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.031716775
• LogD (pH = 7.4): -1.7480675
• Log P: 0.9082207
• Molar Refractivity: 76.4133 cm^3
• Polarizability: 29.49321 Å^3
• Polar Surface Area: 132.71 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D288780

A metabolite of Bumetanide (B689550).

REFERENCES

• Halladay, S.C., et al.: Life Sci., 17, 1003 (1975)
• Kolis, S.J., et al.: Drug Metab. Dispos., 4, 169 (1975)