2-(2H5)phenyl(phenyl)methanesulfinylacetic acid

• ChemBase ID: 174676
• Molecular Formular: C15H14O3S
• Molecular Mass: 274.33486
• Monoisotopic Mass: 274.06636531
• SMILES: c1ccccc1C(S(=O)CC(=O)O)c1ccccc1
• Canonical SMILES: OC(=O)CS(=O)C(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C15H14O3S/c16-14(17)11-19(18)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H,16,17)
• InChIKey: QARQPIWTMBRJFX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(^2H₅)phenyl(phenyl)methanesulfinylacetic acid
• IUPAC Traditional name: (^2H₅)phenyl(phenyl)methanesulfinylacetic acid
• Synonyms: 2-[Di-(phenyl-d5)-methylsulfinyl]acetic Acid; Modafinil-d5 Acid; Modafinic Acid-d5; Modafinil Carboxylate-d5 (Mixture of Diastereomers)

Database IDs

• PubChem SID: 164230586
• PubChem CID: 45039949

CALCULATED PROPERTIES

• Acid pKa: 4.0638003
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.89144456
• LogD (pH = 7.4): -0.7815634
• Log P: 2.339777
• Molar Refractivity: 75.5664 cm^3
• Polarizability: 29.587725 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M482512

A metabolite of Modafinil, a central nervous system vigilance promoting agent, which possesses neuroprotective properties.

REFERENCES

• Duteil, J., et al.: Eur. J. Pharmacol., 180, 49 (1990)
• Wong, Y., et al.: J. Clin. Pharmacol., 317, 30 (1990)
• Robertson, P., et al.: Drug Disp., 42, 123 (2003)