(2S)-3-hydroxy-2-(2-sulfanylpropanamido)propanoic acid

• ChemBase ID: 172683
• Molecular Formular: C6H11NO4S
• Molecular Mass: 193.22084
• Monoisotopic Mass: 193.04087884
• SMILES: C(C(=O)N[C@H](C(=O)O)CO)(S)C
• Canonical SMILES: OC[C@@H](C(=O)O)NC(=O)C(S)C
• InChI: InChI=1S/C6H11NO4S/c1-3(12)5(9)7-4(2-8)6(10)11/h3-4,8,12H,2H2,1H3,(H,7,9)(H,10,11)/t3?,4-/m0/s1
• InChIKey: NGCWQOJBMCFVRB-BKLSDQPFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-hydroxy-2-(2-sulfanylpropanamido)propanoic acid
• IUPAC Traditional name: (2S)-3-hydroxy-2-(2-sulfanylpropanamido)propanoic acid
• Synonyms: N-(2-Mercapto-1-oxopropyl)-L-serine

Database IDs

• CAS Number: 1313496-17-1
• PubChem SID: 164228593
• PubChem CID: 53388515

CALCULATED PROPERTIES

• Acid pKa: 3.7027745
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -2.8076277
• LogD (pH = 7.4): -4.320318
• Log P: -1.011445
• Molar Refractivity: 43.8079 cm^3
• Polarizability: 17.358849 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M225400

N-(2-Mercapto-1-oxopropyl)-L-serine is a serine analog of Tiopronin (T444780).

REFERENCES

• Aleman, C., et al.: Cancer Res., 63, 3084 (2003)
• Ludwig, J., et al.: Cancer Res., 66, 4808 (2003)
• Hall, M., et al.: J. Med. Chem., 52, 3191 (2003)