(2S,4S,5R)-2-{[(3S,4R,6R)-6-(benzyloxy)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 161636
• Molecular Formular: C19H28O11
• Molecular Mass: 432.41902
• Monoisotopic Mass: 432.16316172
• SMILES: [C@H]1([C@@H](C([C@@H](OC1CO)O[C@H]1[C@@H](C([C@@H](OC1CO)OCc1ccccc1)O)O)O)O)O
• Canonical SMILES: OCC1O[C@@H](OCc2ccccc2)C([C@H]([C@@H]1O[C@@H]1OC(CO)[C@@H]([C@@H](C1O)O)O)O)O
• InChI: InChI=1S/C19H28O11/c20-6-10-12(22)13(23)15(25)19(28-10)30-17-11(7-21)29-18(16(26)14(17)24)27-8-9-4-2-1-3-5-9/h1-5,10-26H,6-8H2/t10?,11?,12-,13-,14+,15?,16?,17+,18+,19-/m0/s1
• InChIKey: UMOKGHPPSFCSDC-CSZNIZKZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R)-2-{[(3S,4R,6R)-6-(benzyloxy)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,4S,5R)-2-{[(3S,4R,6R)-6-(benzyloxy)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Phenylmethyl 4-O-β-D-Galactopyranosyl-β-D-glucopyranoside; Benzyl 4-O-β-D-Galactopyranosyl-β-D-glucopyranoside; Benzyl β-D-Lactoside

Database IDs

• CAS Number: 18404-72-3
• PubChem SID: 162255771
• PubChem CID: 71313852

CALCULATED PROPERTIES

• Acid pKa: 11.939712
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -2.3357754
• LogD (pH = 7.4): -2.3357878
• Log P: -2.3357751
• Molar Refractivity: 97.7005 cm^3
• Polarizability: 40.217133 Å^3
• Polar Surface Area: 178.53 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Warm Methanol; Water
• Apperance: White Solid
• Melting Point: 169-171°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B281625

A nonionic detergent for the solubilization of membrane bound protein.

REFERENCES

• Ly, H., et al.: Biochem., 41, 6572 (2002)
• Liu, Y., et al.: Chem. & Biol., 14, 847 (2002)
• Xia, C., et al.: J. Med. Chem., 50, 3489 (2002)