4-phenoxy-3-(propylamino)-5-sulfamoylbenzoic acid

• ChemBase ID: 166177
• Molecular Formular: C16H18N2O5S
• Molecular Mass: 350.38952
• Monoisotopic Mass: 350.09364269
• SMILES: c1(cc(c(c(c1)S(=O)(=O)N)Oc1ccccc1)NCCC)C(=O)O
• Canonical SMILES: CCCNc1cc(cc(c1Oc1ccccc1)S(=O)(=O)N)C(=O)O
• InChI: InChI=1S/C16H18N2O5S/c1-2-8-18-13-9-11(16(19)20)10-14(24(17,21)22)15(13)23-12-6-4-3-5-7-12/h3-7,9-10,18H,2,8H2,1H3,(H,19,20)(H2,17,21,22)
• InChIKey: YZACFNSGLDGBNP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-phenoxy-3-(propylamino)-5-sulfamoylbenzoic acid
• IUPAC Traditional name: 4-phenoxy-3-(propylamino)-5-sulfamoylbenzoic acid
• Synonyms: 3-(Aminosulfonyl)-4-phenoxy-5-(propylamino)benzoic Acid; 4-Phenoxy-3-(propylamino)-5-sulfamoylbenzoic Acid; 4-Phenoxy-3-propylamino-5-sulfamoylbenzoic Acid; N-Desbutyl-N-propyl Bumetanide

Database IDs

• CAS Number: 28395-28-0
• PubChem SID: 162260310
• PubChem CID: 21506078

CALCULATED PROPERTIES

• Acid pKa: 4.689212
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.207703
• LogD (pH = 7.4): -0.57087123
• Log P: 2.089255
• Molar Refractivity: 91.1793 cm^3
• Polarizability: 34.9789 Å^3
• Polar Surface Area: 118.72 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D288925

Bumetanide (B689550) analogue as diuretic and antihypertensive. Bumetanide impurity.

REFERENCES

• Feit, P.W., et al.: J. Med. Chem., 14, 432 (1971)