2-({[4-amino-5-chloro-2-(2H5)ethoxyphenyl]formamido}methyl)-4-[(4-fluorophenyl)methyl]morpholin-4-ium-4-olate

• ChemBase ID: 174774
• Molecular Formular: C21H25ClFN3O4
• Molecular Mass: 437.8923032
• Monoisotopic Mass: 437.1517622
• SMILES: c1c(ccc(c1)C[N+]1(CC(OCC1)CNC(=O)c1cc(c(cc1OCC)N)Cl)[O-])F
• Canonical SMILES: CCOc1cc(N)c(cc1C(=O)NCC1OCC[N+](C1)([O-])Cc1ccc(cc1)F)Cl
• InChI: InChI=1S/C21H25ClFN3O4/c1-2-29-20-10-19(24)18(22)9-17(20)21(27)25-11-16-13-26(28,7-8-30-16)12-14-3-5-15(23)6-4-14/h3-6,9-10,16H,2,7-8,11-13,24H2,1H3,(H,25,27)
• InChIKey: IMJYXYWPAQJNFA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({[4-amino-5-chloro-2-(^2H₅)ethoxyphenyl]formamido}methyl)-4-[(4-fluorophenyl)methyl]morpholin-4-ium-4-olate
• IUPAC Traditional name: 2-({[4-amino-5-chloro-2-(^2H₅)ethoxyphenyl]formamido}methyl)-4-[(4-fluorophenyl)methyl]morpholin-4-ium-4-olate
• Synonyms: 4-Amino-5-chloro-2-(ethoxy-d5)-N-[[4-[(4-fluorophenyl)methyl]-4-oxido-2-morpholinyl]methyl]benzamide; Mosapride-d5 N-Oxide

Database IDs

• PubChem SID: 164230684
• PubChem CID: 71750823

CALCULATED PROPERTIES

• Acid pKa: 14.463725
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6244771
• LogD (pH = 7.4): 1.6245279
• Log P: 1.6245286
• Molar Refractivity: 114.3878 cm^3
• Polarizability: 42.570087 Å^3
• Polar Surface Area: 100.46 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M731017

A labelled metabolite of Mosapride (M731000).

REFERENCES

• Chen, H., et al.: J. Pharm. Biomed. Anal., 40, 142 (2006)
• Pedraglio, S., et al.: J. Pharm. Biomed. Anal., 44, 665 (2006)
• Christopher, L., et al.: Drug Metab. Dispos., 36, 1341 (2006)
• Curran, M., et al.: Drugs, 68, 981 (2006)