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

• ChemBase ID: 175409
• Molecular Formular: C11H13NO7
• Molecular Mass: 271.22342
• Monoisotopic Mass: 271.06920176
• SMILES: c1c(ccc(c1)O[C@@H]1[C@H]([C@H]([C@@H](CO1)O)O)O)[N+](=O)[O-]
• Canonical SMILES: O[C@@H]1[C@H](OC[C@H]([C@@H]1O)O)Oc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C11H13NO7/c13-8-5-18-11(10(15)9(8)14)19-7-3-1-6(2-4-7)12(16)17/h1-4,8-11,13-15H,5H2/t8-,9+,10-,11-/m1/s1
• InChIKey: MLJYKRYCCUGBBV-LMLFDSFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(4-nitrophenoxy)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5R)-2-(4-nitrophenoxy)oxane-3,4,5-triol
• Synonyms: XYL1-α-PNP; p-Nitrophenyl α-D-Xylopyranoside

Database IDs

• CAS Number: 10238-28-5
• PubChem SID: 164231319
• PubChem CID: 82482

CALCULATED PROPERTIES

• Acid pKa: 12.235022
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.028068548
• LogD (pH = 7.4): -0.02807481
• Log P: -0.028068468
• Molar Refractivity: 61.5455 cm^3
• Polarizability: 24.139444 Å^3
• Polar Surface Area: 124.97 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 170-172°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N509000

A chromogenic substrate for α-xylosidase.

REFERENCES

• Falkoski, D., et al.: J. Agric. Food Chem., 54, 10184 (2006)
• Nakai, H., et al.: J. Biochem., 142, 491 (2006)
• Kang, M., et al.: Biocatal. Biotransform., 26, 96 (2006)