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

• ChemBase ID: 176555
• Molecular Formular: C14H20O6
• Molecular Mass: 284.305
• Monoisotopic Mass: 284.12598836
• SMILES: O([C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)CCc1ccccc1
• Canonical SMILES: OC[C@H]1O[C@@H](OCCc2ccccc2)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C14H20O6/c15-8-10-11(16)12(17)13(18)14(20-10)19-7-6-9-4-2-1-3-5-9/h1-5,10-18H,6-8H2/t10-,11-,12+,13-,14-/m1/s1
• InChIKey: MLRIJUWUQTVDQE-RKQHYHRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-phenylethoxy)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-phenylethoxy)oxane-3,4,5-triol
• Synonyms: 2-Phenylethyl-β-D-glucopyranoside; 2-Phenylethyl O-β-D-Glucopyranoside; 2-Phenylethyl β-D-Glucopyranoside; 2-Phenylethyl β-D-Glucoside; Phenethyl β-D-Glucopyranoside; Phenethyl β-D-Glucoside; Phenylethyl 2-Glucoside; Phenylethyl β-D-Glucopyranoside; β-Phenylethanol Glucoside; β-Phenylethyl β-D-Glucoside

Database IDs

• CAS Number: 18997-54-1
• PubChem SID: 164232465
• PubChem CID: 11289099

CALCULATED PROPERTIES

• Acid pKa: 12.210973
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.27627847
• LogD (pH = 7.4): -0.27628508
• Log P: -0.2762784
• Molar Refractivity: 70.0422 cm^3
• Polarizability: 28.20122 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P320865

One of the two new glycosides from Conyza bonariensis.

REFERENCES

• Cos, P., et al.: J. Nat. Prod., 61, 71 (1998)