1-[(4-{[3-(hydroxymethyl)phenyl]amino}pyridin-3-yl)sulfonyl]-3-(propan-2-yl)urea

• ChemBase ID: 171386
• Molecular Formular: C16H20N4O4S
• Molecular Mass: 364.4194
• Monoisotopic Mass: 364.12052614
• SMILES: c1(cnccc1Nc1cccc(c1)CO)S(=O)(=O)NC(=O)NC(C)C
• Canonical SMILES: OCc1cccc(c1)Nc1ccncc1S(=O)(=O)NC(=O)NC(C)C
• InChI: InChI=1S/C16H20N4O4S/c1-11(2)18-16(22)20-25(23,24)15-9-17-7-6-14(15)19-13-5-3-4-12(8-13)10-21/h3-9,11,21H,10H2,1-2H3,(H,17,19)(H2,18,20,22)
• InChIKey: WCYVLAMJCQZUCR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(4-{[3-(hydroxymethyl)phenyl]amino}pyridin-3-yl)sulfonyl]-3-(propan-2-yl)urea
• IUPAC Traditional name: 1-(4-{[3-(hydroxymethyl)phenyl]amino}pyridin-3-ylsulfonyl)-3-isopropylurea
• Synonyms: 4-[[3-(Hydroxymethyl)phenyl]amino]-N-[[(1-methylethyl)amino]carbonyl]-3-pyridinesulfonamide; AC 3534; Hydroxy Torsemide

Database IDs

• CAS Number: 99300-68-2
• PubChem SID: 164227296
• PubChem CID: 14475217

CALCULATED PROPERTIES

• Acid pKa: 5.9225187
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.5425841
• LogD (pH = 7.4): -0.1618316
• Log P: 0.5832332
• Molar Refractivity: 93.6678 cm^3
• Polarizability: 36.525806 Å^3
• Polar Surface Area: 120.42 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 159-161°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H969980

A metabolite of Torsemide (T548750).

REFERENCES

• Besenfelder, E., et al.: J. Pharm. Biomed. Anal., 5, 259 (1987)
• Vormfelde, S., et al.: Clin. Pharmacol. Ther., 76, 557 (1987)