(1R,2R,3R)-1-[(4R)-4-hydroxy-1,3-thiazolidin-2-yl]butane-1,2,3,4-tetrol

• ChemBase ID: 177527
• Molecular Formular: C7H15NO5S
• Molecular Mass: 225.2627
• Monoisotopic Mass: 225.06709359
• SMILES: C1SC(N[C@@H]1O)[C@@H]([C@@H]([C@@H](CO)O)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@H](C1SC[C@H](N1)O)O)O)O
• InChI: InChI=1S/C7H15NO5S/c9-1-3(10)5(12)6(13)7-8-4(11)2-14-7/h3-13H,1-2H2/t3-,4-,5-,6-,7?/m1/s1
• InChIKey: MTQJDFBYTNFYRA-YDEIVXIUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,3R)-1-[(4R)-4-hydroxy-1,3-thiazolidin-2-yl]butane-1,2,3,4-tetrol
• IUPAC Traditional name: (1R,2R,3R)-1-[(4R)-4-hydroxy-1,3-thiazolidin-2-yl]butane-1,2,3,4-tetrol
• Synonyms: RibCys; D-Ribose-L-cysteine(Mixture of Diastereomers)

Database IDs

• CAS Number: 232617-15-1
• PubChem SID: 164233437
• PubChem CID: 71752074

CALCULATED PROPERTIES

• Acid pKa: 12.656717
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): -3.8527977
• LogD (pH = 7.4): -2.8604014
• Log P: -2.8082273
• Molar Refractivity: 50.149 cm^3
• Polarizability: 20.766127 Å^3
• Polar Surface Area: 113.18 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R417550

D-Ribose-L-cysteine is a prodrug of L-cysteine that has potential therapeutic advantage in the inhibition of astrocytoma cell proliferation. D-Ribose-L-cysteine has been shown to protect against acetaminophen-induced hepatic and renal toxicity.

REFERENCES

• Jurkowska, H. et al.: Amino Acids, 41, 131 (2011)
• Roberts, J. et al.: J. Lab. Comp. Radiopharm., 42, 485 (2011)
• Slitt, A. et al.: Basic Clin. Pharm. Toxicol., 96, 487 (2011)