(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(2-nitrophenoxy)oxane-3,4,5-triol

• ChemBase ID: 175176
• Molecular Formular: C12H15NO8
• Molecular Mass: 301.2494
• Monoisotopic Mass: 301.07976645
• SMILES: [C@H]1([C@@H]([C@@H]([C@H](O[C@H]1CO)Oc1ccccc1[N+](=O)[O-])O)O)O
• Canonical SMILES: OC[C@@H]1O[C@H](Oc2ccccc2[N+](=O)[O-])[C@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C12H15NO8/c14-5-8-9(15)10(16)11(17)12(21-8)20-7-4-2-1-3-6(7)13(18)19/h1-4,8-12,14-17H,5H2/t8-,9+,10+,11-,12+/m1/s1
• InChIKey: KUWPCJHYPSUOFW-IIRVCBMXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(2-nitrophenoxy)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(2-nitrophenoxy)oxane-3,4,5-triol
• Synonyms: 2-Nitrophenyl-α-D-galactopyranoside; o-Nitrophenyl α-D-Galactoside; o-Nitrophenyl α-D-Galactopyranoside

Database IDs

• CAS Number: 19887-85-5
• PubChem SID: 164231086
• PubChem CID: 22850352

CALCULATED PROPERTIES

• Acid pKa: 12.200035
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.6584035
• LogD (pH = 7.4): -0.6584103
• Log P: -0.6584034
• Molar Refractivity: 67.508 cm^3
• Polarizability: 26.654507 Å^3
• Polar Surface Area: 145.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N503575

It is a specific substrate for α-D-Galactosidase.

REFERENCES

• Ahmed, H., et al.: J. Biol. Chem., 264, 9365 (1989)