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

• ChemBase ID: 169735
• Molecular Formular: C9H18O8
• Molecular Mass: 254.23442
• Monoisotopic Mass: 254.10016754
• SMILES: [C@H]1([C@@H](C([C@@H](OC1CO)OC[C@H](CO)O)O)O)O
• Canonical SMILES: OC[C@@H](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+/m0/s1
• InChIKey: NHJUPBDCSOGIKX-OIGFRMNVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5R)-2-[(2S)-2,3-dihydroxypropoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,4S,5R)-2-[(2S)-2,3-dihydroxypropoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: (2S)-2,3-Dihydroxypropyl β-D-Galactopyranoside; (S)-2,3-Dihydroxypropyl β-D-Galactopyranoside; 1-O-β-D-Galactopyranosyl-sn-glycerol; (2S)-Glycerol-O-β-D-galactopyranoside

Database IDs

• CAS Number: 38841-15-5
• PubChem SID: 162263867
• PubChem CID: 71317131

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

PROPERTIES

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - G601505

(2S)-Glycerol-O-β-D-galactopyranoside showed the highest inhibitory effect toward tumor promotion.

REFERENCES

• Colombo, D., et al.: Bioorg. Med. Chem. Lett., 6, 1187 (1996)