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

• ChemBase ID: 160431
• Molecular Formular: C21H25NO9
• Molecular Mass: 435.4245
• Monoisotopic Mass: 435.15293139
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1CO)Oc1c(c(cc(c1)O)O)C(=O)CCc1ccc(cc1)N)O)O)O
• Canonical SMILES: OCC1O[C@@H](Oc2cc(O)cc(c2C(=O)CCc2ccc(cc2)N)O)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H25NO9/c22-11-4-1-10(2-5-11)3-6-13(25)17-14(26)7-12(24)8-15(17)30-21-20(29)19(28)18(27)16(9-23)31-21/h1-2,4-5,7-8,16,18-21,23-24,26-29H,3,6,9,22H2/t16?,18-,19+,20?,21-/m1/s1
• InChIKey: ZOUNSRHGQVWZJN-NFRVFMFJSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 82628-89-5
• PubChem SID: 162254566
• PubChem CID: 46780350

CALCULATED PROPERTIES

• Acid pKa: 7.9020057
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): 0.43595982
• LogD (pH = 7.4): 0.33405435
• Log P: 0.4521118
• Molar Refractivity: 108.5712 cm^3
• Polarizability: 42.17576 Å^3
• Polar Surface Area: 182.93 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Yellowish Brown Solid
• Melting Point: >80°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A627515

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)