(3S,4S,6S)-2-(hydroxymethyl)-6-(naphthalen-2-yloxy)oxane-3,4,5-triol

• ChemBase ID: 174977
• Molecular Formular: C16H18O6
• Molecular Mass: 306.31052
• Monoisotopic Mass: 306.1103383
• SMILES: c1(ccc2c(c1)cccc2)O[C@@H]1OC([C@H]([C@@H](C1O)O)O)CO
• Canonical SMILES: OCC1O[C@@H](Oc2ccc3c(c2)cccc3)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H18O6/c17-8-12-13(18)14(19)15(20)16(22-12)21-11-6-5-9-3-1-2-4-10(9)7-11/h1-7,12-20H,8H2/t12?,13-,14+,15?,16-/m1/s1
• InChIKey: MWHKPYATGMFFPI-KVDYFSNESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S,6S)-2-(hydroxymethyl)-6-(naphthalen-2-yloxy)oxane-3,4,5-triol
• IUPAC Traditional name: (3S,4S,6S)-2-(hydroxymethyl)-6-(naphthalen-2-yloxy)oxane-3,4,5-triol
• Synonyms: 2-Naphthalenyl-β-D-glucopyranoside; 2-Naphthyl β-D-Glucopyranoside; β-Naphthyl-D-glucoside; β-Naphthyl β-D-Glucopyranoside

Database IDs

• CAS Number: 33993-25-8
• PubChem SID: 164230887
• PubChem CID: 45039992

CALCULATED PROPERTIES

• Acid pKa: 12.200141
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.39108908
• LogD (pH = 7.4): 0.3910823
• Log P: 0.39108917
• Molar Refractivity: 76.6335 cm^3
• Polarizability: 32.007286 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - N368505

Chemotherapeutic agent, especially cancerostatics.

REFERENCES

• Blumenfeld, M., et al.: J. Biol. Chem., 260, 11560 (1985)
• Alonso, M., et al.: J. Biol. Chem., 270, 15315 (1985)