2-{2-[(2H5)phenyl(2H2)methyl]-3-sulfanylpropanamido}acetic acid

• ChemBase ID: 178576
• Molecular Formular: C12H15NO3S
• Molecular Mass: 253.3174
• Monoisotopic Mass: 253.07726435
• SMILES: c1ccccc1CC(C(=O)NCC(=O)O)CS
• Canonical SMILES: SCC(C(=O)NCC(=O)O)Cc1ccccc1
• InChI: InChI=1S/C12H15NO3S/c14-11(15)7-13-12(16)10(8-17)6-9-4-2-1-3-5-9/h1-5,10,17H,6-8H2,(H,13,16)(H,14,15)
• InChIKey: LJJKNPQAGWVLDQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[(^2H₅)phenyl(^2H₂)methyl]-3-sulfanylpropanamido}acetic acid
• IUPAC Traditional name: {2-[(^2H₅)phenyl(^2H₂)methyl]-3-sulfanylpropanamido}acetic acid
• Synonyms: N-[2-(Mercaptomethyl)-1-oxo-3-phenylpropyl]glycine-d7; 2-Mercaptomethyl-3-phenylpropionylaminoacetic Acid-d7; D,L-3-Mercapto-2-benzylpropanoylglycine-d7; (+/-)-Thiorphan-d7; Thiorphan-d7

Database IDs

• PubChem SID: 164234486
• PubChem CID: 71752536

CALCULATED PROPERTIES

• Acid pKa: 4.017452
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.028880706
• LogD (pH = 7.4): -1.6859314
• Log P: 1.4638641
• Molar Refractivity: 67.1479 cm^3
• Polarizability: 26.193842 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T369502

The active metabolite of Racecadotril (R070600).

REFERENCES

• Roques, B.P., et al.: Nature, 288, 286 (1980)
• Tiraboschi, G., et al.: Protein Engineering, 12, 2, 141 (1999)