1-(2-hydroxy-6-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one

• ChemBase ID: 165999
• Molecular Formular: C21H24O9
• Molecular Mass: 420.40986
• Monoisotopic Mass: 420.14203235
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1CO)Oc1cccc(c1C(=O)CCc1ccc(cc1)O)O)O)O)O
• Canonical SMILES: OCC1O[C@@H](Oc2cccc(c2C(=O)CCc2ccc(cc2)O)O)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H24O9/c22-10-16-18(26)19(27)20(28)21(30-16)29-15-3-1-2-13(24)17(15)14(25)9-6-11-4-7-12(23)8-5-11/h1-5,7-8,16,18-24,26-28H,6,9-10H2/t16?,18-,19+,20?,21-/m1/s1
• InChIKey: KOTXSQPZNZHNFC-NFRVFMFJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2-hydroxy-6-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one
• IUPAC Traditional name: 1-(2-hydroxy-6-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one
• Synonyms: 1-[2-(β-D-Glucopyranosyloxy)-6-hydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone; 4'-Deoxyphlorizin

Database IDs

• CAS Number: 4319-68-0
• PubChem SID: 162260132
• PubChem CID: 71315503

CALCULATED PROPERTIES

• Acid pKa: 9.416
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): 1.2809854
• LogD (pH = 7.4): 1.2768915
• Log P: 1.2810378
• Molar Refractivity: 103.8708 cm^3
• Polarizability: 41.010998 Å^3
• Polar Surface Area: 156.91 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water(hot)
• Apperance: Off White to Pale Yellow Solid
• Melting Point: 132-134°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D248000

Inhibitor of glucose transport system.

REFERENCES

• Biochim. Biophys. Acta., 134-149, 290 (1972)