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

• ChemBase ID: 169677
• Molecular Formular: C9H18O8
• Molecular Mass: 254.23442
• Monoisotopic Mass: 254.10016754
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1CO)OCC(CO)O)O)O)O
• Canonical SMILES: OCC(CO[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O)O
• InChI: InChI=1S/C9H18O8/c10-1-4(12)3-16-9-8(15)7(14)6(13)5(2-11)17-9/h4-15H,1-3H2/t4?,5?,6-,7+,8?,9-/m1/s1
• InChIKey: NHJUPBDCSOGIKX-UEHOPBKBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5S)-2-(2,3-dihydroxypropoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,4S,5S)-2-(2,3-dihydroxypropoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 2,3-Dihydroxypropyl β-D-Glucopyranoside; Lilioside C; 1-(β-Glucosyl)glycerol(Mixture of Diastereomers)

Database IDs

• PubChem SID: 162263809
• PubChem CID: 68256528

CALCULATED PROPERTIES

• Acid pKa: 12.19484
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -3.6098497
• LogD (pH = 7.4): -3.6098566
• Log P: -3.6098497
• Molar Refractivity: 52.9294 cm^3
• Polarizability: 22.045732 Å^3
• Polar Surface Area: 139.84 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G596820

A component contained in cosmetic formulation. Diesters of glycosylglycerols are active in cancer chemo-prevention.

REFERENCES

• Joyard, J., et al.: Eur. J. Biochem., 199, 489 (1991)
• Colombo, D., et al.: Bioorg. Med. Chem. Lett., 6, 1187 (1991)
• Colombo, D., et al.: Bioorg. Med. Chem., 7, 1867 (1991)
• Colombo, D., et al.: Cancer Lett., 161, 201 (1991)