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

• ChemBase ID: 176565
• Molecular Formular: C12H16O6
• Molecular Mass: 256.25184
• Monoisotopic Mass: 256.09468823
• SMILES: [C@@H]1([C@@H](C([C@H](OC1CO)Oc1ccccc1)O)O)O
• Canonical SMILES: OCC1O[C@H](Oc2ccccc2)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H16O6/c13-6-8-9(14)10(15)11(16)12(18-8)17-7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8?,9-,10+,11?,12+/m1/s1
• InChIKey: NEZJDVYDSZTRFS-ZVCXTHFISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S,6R)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol
• IUPAC Traditional name: (3S,4S,6R)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol
• Synonyms: Phenyl α-D-Glucoside; Phenyl α-D-Glucopyranoside

Database IDs

• CAS Number: 4630-62-0
• PubChem SID: 164232475
• PubChem CID: 46782738

CALCULATED PROPERTIES

• Acid pKa: 12.200142
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.59838766
• LogD (pH = 7.4): -0.59839445
• Log P: -0.5983876
• Molar Refractivity: 60.1833 cm^3
• Polarizability: 24.608507 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: 168-170°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P324000

Inhibits sucrose transport into plant cells

REFERENCES

• Nishimoto, M., et al.: Biosci., Biotechnol., Biochem., 71, 1703 (2007)
• Nakai, H., et al.: J. Biochem., 142, 491 (2007)
• Reinders, A., et al.: Plant Mol. Biol., 68, 289 (2007)