3-{3-[bis(propan-2-yl)amino]-1-phenylpropyl}-4-hydroxybenzoic acid

• ChemBase ID: 163802
• Molecular Formular: C22H29NO3
• Molecular Mass: 355.47056
• Monoisotopic Mass: 355.21474379
• SMILES: c1cc(cc(c1O)C(CCN(C(C)C)C(C)C)c1ccccc1)C(=O)O
• Canonical SMILES: CC(N(C(C)C)CCC(c1cc(ccc1O)C(=O)O)c1ccccc1)C
• InChI: InChI=1S/C22H29NO3/c1-15(2)23(16(3)4)13-12-19(17-8-6-5-7-9-17)20-14-18(22(25)26)10-11-21(20)24/h5-11,14-16,19,24H,12-13H2,1-4H3,(H,25,26)
• InChIKey: NKTNTJFTBRPQIZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{3-[bis(propan-2-yl)amino]-1-phenylpropyl}-4-hydroxybenzoic acid
• IUPAC Traditional name: 3-[3-(diisopropylamino)-1-phenylpropyl]-4-hydroxybenzoic acid
• Synonyms: 3-[3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-hydroxybenzoic Acid; rac 5-Carboxy Tolterodine

Database IDs

• CAS Number: 1076199-77-3
• PubChem SID: 162257937
• PubChem CID: 10089561

CALCULATED PROPERTIES

• Acid pKa: 4.31941
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.2161977
• LogD (pH = 7.4): 2.2370007
• Log P: 2.2376564
• Molar Refractivity: 106.1722 cm^3
• Polarizability: 40.87762 Å^3
• Polar Surface Area: 60.77 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C183210

A metabolite of Tolterodine (T535800). Also, a degradation product of Fesoterodine (F321300) formed under stress conditions in tablet dosage forms.

REFERENCES

• Nilvebrant, L., et al.: Eur. J. Pharmacol., 327, 195 (1997)
• Palmer, L., et al.: J. Pharm. Biomed. Anal., 16, 155 (1997)
• Postlind, H., et al.: Drug Metab. Dispos., 26, 289 (1997)
• Rentzhog, L., et al.: Br. J. Urol., 81, 42 (1997)
• Pahlman, I., et al.: Bi