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

• ChemBase ID: 175410
• Molecular Formular: C21H23NO11
• Molecular Mass: 465.40742
• Monoisotopic Mass: 465.12711056
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)Oc1c(c(cc(c1)O)O)C(=O)CCc1ccc(cc1)[N+](=O)[O-])O)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2cc(O)cc(c2C(=O)CCc2ccc(cc2)[N+](=O)[O-])O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H23NO11/c23-9-16-18(27)19(28)20(29)21(33-16)32-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(5-2-10)22(30)31/h1-2,4-5,7-8,16,18-21,23-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1
• InChIKey: UZMKMTNQYIJXTD-QNDFHXLGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2,4-dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-nitrophenyl)propan-1-one
• IUPAC Traditional name: 1-(2,4-dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-nitrophenyl)propan-1-one
• Synonyms: 1-[2-(β-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-nitrophenyl)-1-propanone; 4-Nitrophlorizin

Database IDs

• CAS Number: 82628-84-0
• PubChem SID: 164231320
• PubChem CID: 71751108

CALCULATED PROPERTIES

• Acid pKa: 7.901947
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): 1.2193165
• LogD (pH = 7.4): 1.1031021
• Log P: 1.221022
• Molar Refractivity: 111.1955 cm^3
• Polarizability: 43.02326 Å^3
• Polar Surface Area: 202.73 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Brown Syrup

DETAILS

Toronto Research Chemicals - N513250

A high affinity probe and photoaffinity label for the glucose transport system in brush border membranes.

REFERENCES

• Hosang, M., et al.: FEBS Lett., 130, 244-248 (1981)