(4S)-3-[(2S)-5-oxopyrrolidine-2-carbonyl]-1,3-thiazolidine-4-carboxylic acid

• ChemBase ID: 176723
• Molecular Formular: C9H12N2O4S
• Molecular Mass: 244.26758
• Monoisotopic Mass: 244.05177787
• SMILES: C1(=O)CC[C@H](N1)C(=O)N1[C@H](CSC1)C(=O)O
• Canonical SMILES: O=C1CC[C@H](N1)C(=O)N1CSC[C@@H]1C(=O)O
• InChI: InChI=1S/C9H12N2O4S/c12-7-2-1-5(10-7)8(13)11-4-16-3-6(11)9(14)15/h5-6H,1-4H2,(H,10,12)(H,14,15)/t5-,6+/m0/s1
• InChIKey: UUTKICFRNVKFRG-NTSWFWBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-3-[(2S)-5-oxopyrrolidine-2-carbonyl]-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: (4S)-3-[(2S)-5-oxopyrrolidine-2-carbonyl]-1,3-thiazolidine-4-carboxylic acid
• Synonyms: (4R)-3-[[(2S)-5-oxo-2-pyrrolidinyl]carbonyl]-4-thiazolidinecarboxylic Acid; Adimod; Axil; Onaka; Polimod; Pidotimod

Database IDs

• CAS Number: 121808-62-6
• PubChem SID: 164232633
• PubChem CID: 12150545

CALCULATED PROPERTIES

• Acid pKa: 3.565711
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.221541
• LogD (pH = 7.4): -4.647885
• Log P: -1.2931193
• Molar Refractivity: 55.8341 cm^3
• Polarizability: 22.043678 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 197-204°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P437650

Immunostimulant used in patients with cell-mediated immunodepression.

REFERENCES

• Gu, C., et al.: Pharm. Res., 25, 979 (2008)
• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2008)
• Giagulli, C., et al.: Int. Immunopharmacol., 9, 1366 (2008)