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

• ChemBase ID: 92579
• Molecular Formular: C21H23N3O9
• Molecular Mass: 461.42202
• Monoisotopic Mass: 461.14342933
• SMILES: OC[C@H]1O[C@@H](Oc2c(C(=O)CCc3ccc(cc3)N=[N+]=[N-])c(O)cc(O)c2)[C@H](O)[C@@H](O)[C@@H]1O
• Canonical SMILES: [N-]=[N+]=Nc1ccc(cc1)CCC(=O)c1c(O)cc(cc1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O
• InChI: InChI=1S/C21H23N3O9/c22-24-23-11-4-1-10(2-5-11)3-6-13(27)17-14(28)7-12(26)8-15(17)32-21-20(31)19(30)18(29)16(9-25)33-21/h1-2,4-5,7-8,16,18-21,25-26,28-31H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1
• InChIKey: AXCDEMZKQHNYNE-QNDFHXLGSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 79541-46-1
• MDL Number: MFCD00269920
• PubChem SID: 162079277
• PubChem CID: 133219

CALCULATED PROPERTIES

• Acid pKa: 7.901947
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): 1.5856563
• LogD (pH = 7.4): 1.4694418
• Log P: 1.7014073
• Molar Refractivity: 114.1584 cm^3
• Polarizability: 43.342953 Å^3
• Polar Surface Area: 186.34 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Orange Solid
• Melting Point: 168-170°C dec.

DETAILS

Apollo Scientific Ltd - OR9251T

High affinity probe & photoaffinity label for the glucosetransport system in brush border membranes.

Toronto Research Chemicals - A925000

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)