(2H5)benzyl 2-{2-[(acetylsulfanyl)methyl]-3-phenylpropanamido}acetate

• ChemBase ID: 177237
• Molecular Formular: C21H23NO4S
• Molecular Mass: 385.47662
• Monoisotopic Mass: 385.13477922
• SMILES: c1(CC(C(=O)NCC(=O)OCc2ccccc2)CSC(=O)C)ccccc1
• Canonical SMILES: O=C(CNC(=O)C(Cc1ccccc1)CSC(=O)C)OCc1ccccc1
• InChI: InChI=1S/C21H23NO4S/c1-16(23)27-15-19(12-17-8-4-2-5-9-17)21(25)22-13-20(24)26-14-18-10-6-3-7-11-18/h2-11,19H,12-15H2,1H3,(H,22,25)
• InChIKey: ODUOJXZPIYUATO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (^2H₅)benzyl 2-{2-[(acetylsulfanyl)methyl]-3-phenylpropanamido}acetate
• IUPAC Traditional name: (^2H₅)benzyl 2-{2-[(acetylsulfanyl)methyl]-3-phenylpropanamido}acetate
• Synonyms: N-[2-[(Acetylthio)methyl]-1-oxo-3-phenylpropyl]glycine (Phenyl-d5)methyl Ester; Acetorphan-d5; (+/-)-Racecadotril-d5; Redotil-d5; Tiorfan-d5; Racecadotril-d5

Database IDs

• PubChem SID: 164233147
• PubChem CID: 71751912

CALCULATED PROPERTIES

• Acid pKa: 12.602205
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.1748388
• LogD (pH = 7.4): 3.1748364
• Log P: 3.1748388
• Molar Refractivity: 105.9974 cm^3
• Polarizability: 41.66338 Å^3
• Polar Surface Area: 72.47 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R070602

Labelled Racecadotril (R070600). Antidiarrheal; enkephalinase inhibitor, reducing the amount of water and electrolytes into the intestine.

REFERENCES

• Cezard, J., et al.: Gastroenterol., 120, 799 (2001)
• Sato, T., et al.: J. Med. Chem., 51, 7705 (2001)
• Lakshmana, P., et al.: J. Pharm. Res., 8, 39 (2001)