(2R)-2-amino-3-(2H3)methyl-3-sulfanyl(4,4,4-2H3)butanoic acid

• ChemBase ID: 176263
• Molecular Formular: C5H11NO2S
• Molecular Mass: 149.21134
• Monoisotopic Mass: 149.0510496
• SMILES: SC([C@H](N)C(=O)O)(C)C
• Canonical SMILES: N[C@@H](C(S)(C)C)C(=O)O
• InChI: InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m1/s1
• InChIKey: VVNCNSJFMMFHPL-GSVOUGTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-(^2H₃)methyl-3-sulfanyl(4,4,4-^2H₃)butanoic acid
• IUPAC Traditional name: (2R)-2-amino-3-(^2H₃)methyl-3-sulfanyl(4,4,4-^2H₃)butanoic acid
• Synonyms: 3-Mercapto-L-valine-d6; (+)-Penicillamine-d6; (R)-Penicillamine-d6; L-Penicillamine-d6; NSC 241261-d6; L-Penicillamine-d6

Database IDs

• PubChem SID: 164232173
• PubChem CID: 71751484

CALCULATED PROPERTIES

• Acid pKa: 2.555553
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -2.1465738
• LogD (pH = 7.4): -2.1542492
• Log P: -2.1465182
• Molar Refractivity: 37.225 cm^3
• Polarizability: 15.066766 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P223007

Labelled L-Penicillamine, a metabolite of penicillin. L-Penicillamine is used in the treatment of Wilson’s disease, Cystinuria, Scleroderma and arsenic poisoning.

REFERENCES

• Marti-Prats, L., et al.: Neurosci. Lett., 483, 143 (2010)
• Singh, A., et al.: J. Pharm. Sci., 99, 3931 (2010)
• Everette, J., et al.: J. Agric. Food Chem., 58, 8139 (2010)