methyl 4-hydroxy-3-{1-phenyl-3-[(propan-2-yl)amino]propyl}benzoate

• ChemBase ID: 163727
• Molecular Formular: C20H25NO3
• Molecular Mass: 327.4174
• Monoisotopic Mass: 327.18344367
• SMILES: c1cc(cc(c1O)C(CCNC(C)C)c1ccccc1)C(=O)OC
• Canonical SMILES: COC(=O)c1ccc(c(c1)C(c1ccccc1)CCNC(C)C)O
• InChI: InChI=1S/C20H25NO3/c1-14(2)21-12-11-17(15-7-5-4-6-8-15)18-13-16(20(23)24-3)9-10-19(18)22/h4-10,13-14,17,21-22H,11-12H2,1-3H3
• InChIKey: BXVUSHZWMYUKKK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 4-hydroxy-3-{1-phenyl-3-[(propan-2-yl)amino]propyl}benzoate
• IUPAC Traditional name: methyl 4-hydroxy-3-[3-(isopropylamino)-1-phenylpropyl]benzoate
• Synonyms: 4-Hydroxy-3-[3-[(1-methylethyl)amino]-1-phenylpropyl]-benzoic Acid Methyl Ester; rac 5-Carboxy Desisopropyl Tolterodine Methyl Ester

Database IDs

• PubChem SID: 162257862
• PubChem CID: 71314533

CALCULATED PROPERTIES

• Acid pKa: 8.699114
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.96098787
• LogD (pH = 7.4): 1.8751305
• Log P: 3.0100996
• Molar Refractivity: 96.4792 cm^3
• Polarizability: 37.447548 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Dimethyl Sulfoxide; Methanol
• Apperance: White Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C177935

A protected metabolite of Tolterodine (T535800).

REFERENCES

• Lowry, O., et al.: J. Biol. Chem., 193, 265 (1951)
• Andersson, K., et al.: Drugs, 35, 477 (1951)
• Chiu, S., et al.: J. Pharmacol. Toxicol. Methods, 29, 77 (1951)
• Shimada, T., et al.: J. Pharmacol. Exp. Ther., 270, 414 (1951)
• Postlind, H., et al.: Drug M