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

• ChemBase ID: 168772
• Molecular Formular: C8H16O5S
• Molecular Mass: 224.27464
• Monoisotopic Mass: 224.07184461
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1CO)SCC)O)O)O
• Canonical SMILES: CCS[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O
• InChI: InChI=1S/C8H16O5S/c1-2-14-8-7(12)6(11)5(10)4(3-9)13-8/h4-12H,2-3H2,1H3/t4?,5-,6+,7?,8+/m1/s1
• InChIKey: CHAHFVCHPSPXOE-CXRKCYIZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5S)-2-(ethylsulfanyl)-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,4S,5S)-2-(ethylsulfanyl)-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Ethyl 1-Thio-β-D-glucopyranoside; NSC 400275; Ethyl β-Thioglucopyranoside

Database IDs

• CAS Number: 7473-36-1
• PubChem SID: 162262904
• PubChem CID: 71316672

CALCULATED PROPERTIES

• Acid pKa: 12.482076
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.3253915
• LogD (pH = 7.4): -1.3253951
• Log P: -1.3253915
• Molar Refractivity: 51.5926 cm^3
• Polarizability: 21.124384 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: White Solid
• Melting Point: 87-89°C

DETAILS

Toronto Research Chemicals - E926995

Α thioglucoside with antitumor potential.

REFERENCES

• Komba, S., et al.: Bioorg. Med. Chem., 4, 1833 (1996)
• Bertozzi, C., et al.: Science, 291, 2357 (1996)
• Davis, B., et al.: Chem. Rev., 102, 579 (1996)