(2S,3R,4R,5S)-2-[(1R)-1,2-dihydroxyethyl]-5-(4-nitrophenoxy)oxolane-3,4-diol

• ChemBase ID: 175175
• Molecular Formular: C12H15NO8
• Molecular Mass: 301.2494
• Monoisotopic Mass: 301.07976645
• SMILES: [C@H]1([C@@H](O[C@H]([C@@H]1O)Oc1ccc(cc1)[N+](=O)[O-])[C@@H](O)CO)O
• Canonical SMILES: OC[C@@H]([C@@H]1O[C@H]([C@@H]([C@@H]1O)O)Oc1ccc(cc1)[N+](=O)[O-])O
• InChI: InChI=1S/C12H15NO8/c14-5-8(15)11-9(16)10(17)12(21-11)20-7-3-1-6(2-4-7)13(18)19/h1-4,8-12,14-17H,5H2/t8?,9-,10-,11+,12-/m1/s1
• InChIKey: RMQNVZDXEMOJCW-IPDPYQKTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R,5S)-2-[(1R)-1,2-dihydroxyethyl]-5-(4-nitrophenoxy)oxolane-3,4-diol
• IUPAC Traditional name: (2S,3R,4R,5S)-2-[(1R)-1,2-dihydroxyethyl]-5-(4-nitrophenoxy)oxolane-3,4-diol
• Synonyms: pNP-β-D-Galf; 4-Nitrophenyl β-D-Galactofuranoside

Database IDs

• CAS Number: 100645-45-2
• PubChem SID: 164231085
• PubChem CID: 71751036

CALCULATED PROPERTIES

• Acid pKa: 12.226931
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.6584035
• LogD (pH = 7.4): -0.6584099
• Log P: -0.6584034
• Molar Refractivity: 67.508 cm^3
• Polarizability: 26.651247 Å^3
• Polar Surface Area: 145.2 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 150-153°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N503570

Galactofuranose is a widespread component of cell wall polysaccharides in bacteria, protozoa and fungi, but is totally absent in mammals. pNP-β-D-Galf is a convenient substrate for β-Galactofuranosidase.

REFERENCES

• Notermans, S., et al.: Mol. Immunol., 25, 975 (1988)
• Henrissat, B., et al.: Biochem. J., 280, 309 (1988)
• Pathak, A., et al.: Bioorg. Med. Chem., 9, 3129 (1988)