3-[(2-ethylhexyl)amino]-4-phenoxy-5-sulfamoylbenzoic acid

• ChemBase ID: 166207
• Molecular Formular: C21H28N2O5S
• Molecular Mass: 420.52242
• Monoisotopic Mass: 420.17189301
• SMILES: c1(cc(c(c(c1)S(=O)(=O)N)Oc1ccccc1)NCC(CC)CCCC)C(=O)O
• Canonical SMILES: CCCCC(CNc1cc(cc(c1Oc1ccccc1)S(=O)(=O)N)C(=O)O)CC
• InChI: InChI=1S/C21H28N2O5S/c1-3-5-9-15(4-2)14-23-18-12-16(21(24)25)13-19(29(22,26)27)20(18)28-17-10-7-6-8-11-17/h6-8,10-13,15,23H,3-5,9,14H2,1-2H3,(H,24,25)(H2,22,26,27)
• InChIKey: MDNHIMFOFVKGQA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2-ethylhexyl)amino]-4-phenoxy-5-sulfamoylbenzoic acid
• IUPAC Traditional name: 3-[(2-ethylhexyl)amino]-4-phenoxy-5-sulfamoylbenzoic acid
• Synonyms: 3-(Aminosulfonyl)-5-[(2-ethylhexyl)amino]-4-phenoxybenzoic Acid; PF 2825; N-Desbutyl-N-(2-ethylhexyl) Bumetanide

Database IDs

• CAS Number: 153012-65-8
• PubChem SID: 162260340
• PubChem CID: 71315622

CALCULATED PROPERTIES

• Acid pKa: 4.693841
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.3503184
• LogD (pH = 7.4): 1.5723875
• Log P: 4.1197596
• Molar Refractivity: 114.0549 cm^3
• Polarizability: 44.149055 Å^3
• Polar Surface Area: 118.72 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D289060

N-Desbutyl-N-(2-ethylhexyl) Bumetanide is an analogue of the diuretic, Bumetanide (B689550).

REFERENCES

• Petzinger, E. et al.: Am. J. Physiol., 265, G942 (1993)