(2R)-2-propanamido-3-sulfanylpropanoic acid

• ChemBase ID: 176948
• Molecular Formular: C6H11NO3S
• Molecular Mass: 177.22144
• Monoisotopic Mass: 177.04596422
• SMILES: SC[C@H](NC(=O)CC)C(=O)O
• Canonical SMILES: SC[C@@H](C(=O)O)NC(=O)CC
• InChI: InChI=1S/C6H11NO3S/c1-2-5(8)7-4(3-11)6(9)10/h4,11H,2-3H2,1H3,(H,7,8)(H,9,10)/t4-/m0/s1
• InChIKey: KBBJNRLWAGIQLW-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-propanamido-3-sulfanylpropanoic acid
• IUPAC Traditional name: (2R)-2-propanamido-3-sulfanylpropanoic acid
• Synonyms: N-(1-Oxopropyl)-L-cysteine; N-Propionyl-cysteine; N-Propionylcysteine; N-Propionyl-L-cysteine

Database IDs

• CAS Number: 2885-79-2
• PubChem SID: 164232858
• PubChem CID: 151048

CALCULATED PROPERTIES

• Acid pKa: 3.931257
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -1.5863732
• LogD (pH = 7.4): -3.2088332
• Log P: -0.010776895
• Molar Refractivity: 42.2943 cm^3
• Polarizability: 16.661419 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P786800

It is used as a reducing agent for hair in permanent waves. It does not damage the hair (as thioglycolic acid does); it is nontoxic, and does not harm the eyes or the mucous membranes.

REFERENCES

• Batterham, M., et al.: Eur. J. Clin. Nutrition, 55, 107 (2001)