(2S)-2-acetamido-3-methyl-3-sulfanylbutanoic acid

• ChemBase ID: 131586
• Molecular Formular: C7H13NO3S
• Molecular Mass: 191.24802
• Monoisotopic Mass: 191.06161428
• SMILES: CC(=O)N[C@@H](C(=O)O)C(C)(C)S
• Canonical SMILES: CC(=O)N[C@H](C(S)(C)C)C(=O)O
• InChI: InChI=1S/C7H13NO3S/c1-4(9)8-5(6(10)11)7(2,3)12/h5,12H,1-3H3,(H,8,9)(H,10,11)/t5-/m0/s1
• InChIKey: MNNBCKASUFBXCO-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-acetamido-3-methyl-3-sulfanylbutanoic acid
• IUPAC Traditional name: N-acetylpenicillamine
• Synonyms: N-Acetyl-3-mercapto-D-valine; N-Acetyl-D-penicillamine; N-Acetylpenicillamine; N-Acetyl-3-mercaptovaline; N-Acetyl-D-penicillamine

Database IDs

• CAS Number: 15537-71-0
• EC Number: 239-585-4
• MDL Number: MFCD00078887
• Beilstein Number: 1724742
• PubChem SID: 162225864
• PubChem CID: 65532

CALCULATED PROPERTIES

• Acid pKa: 4.0109563
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -1.5647984
• LogD (pH = 7.4): -3.2200093
• Log P: -0.06580952
• Molar Refractivity: 46.6688 cm^3
• Polarizability: 18.48424 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - A5678

Application
Chiral reagent for precolumn derivatization of enantiomeric amino acids or amino alcohols

Toronto Research Chemicals - A187365

Protected Penicillamin.

REFERENCES

• Klingstroem, J., et al.: Eur. J. Immunol., 36, 2649 (2006)
• Atyabi, F., et al.: J. Nanosci. Nanotechnol., 9, 4593 (2006)
• Yip, K., et al.: Brit. J. Pharmacol., 156, 1279 (2006)