(3R,4S,6S)-2-(hydroxymethyl)-6-(methylsulfanyl)oxane-3,4,5-triol

• ChemBase ID: 174361
• Molecular Formular: C7H14O5S
• Molecular Mass: 210.24806
• Monoisotopic Mass: 210.05619455
• SMILES: [C@H]1(OC([C@@H]([C@@H](C1O)O)O)CO)SC
• Canonical SMILES: CS[C@@H]1OC(CO)[C@@H]([C@@H](C1O)O)O
• InChI: InChI=1S/C7H14O5S/c1-13-7-6(11)5(10)4(9)3(2-8)12-7/h3-11H,2H2,1H3/t3?,4-,5-,6?,7-/m0/s1
• InChIKey: LZFNFLTVAMOOPJ-VBBXJRDUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,6S)-2-(hydroxymethyl)-6-(methylsulfanyl)oxane-3,4,5-triol
• IUPAC Traditional name: (3R,4S,6S)-2-(hydroxymethyl)-6-(methylsulfanyl)oxane-3,4,5-triol
• Synonyms: Methyl-β-D-thiogalactoside; 2-Hydroxymethyl-6-methylsulfanyl-tetrahydro-pyran-3,4,5-triol; Methyl-1-thio-β-D-galactopyranoside

Database IDs

• CAS Number: 155-30-6
• PubChem SID: 164230271
• PubChem CID: 45039903

CALCULATED PROPERTIES

• Acid pKa: 12.483309
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.5784216
• LogD (pH = 7.4): -1.578425
• Log P: -1.5784215
• Molar Refractivity: 46.7948 cm^3
• Polarizability: 19.30825 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 115-117°C

DETAILS

Toronto Research Chemicals - M330753

Inhibition of β-glucosidase.

REFERENCES

• Barkley, M.D., et al.: Biochemistry, 14, 1700 (1975)
• Gonzalez, J.B., Biotechnol. Lett., 4, 369 (1982)