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

• ChemBase ID: 133308
• Molecular Formular: C12H15NO8
• Molecular Mass: 301.2494
• Monoisotopic Mass: 301.07976645
• SMILES: c1cc(ccc1[N+](=O)[O-])O[C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: OC[C@H]1O[C@H](Oc2ccc(cc2)[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)20-7-3-1-6(2-4-7)13(18)19/h1-4,8-12,14-17H,5H2/t8-,9+,10+,11-,12+/m1/s1
• InChIKey: IFBHRQDFSNCLOZ-IIRVCBMXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4,5-triol
• IUPAC Traditional name: p-nitrophenyl-α-D-galactoside
• Synonyms: p-Nitrophenyl α-D-galactopyranoside; 4-Nitrophenyl α-D-galactopyranoside; GAL1-α-PNP; 4-Nitrophenyl α-D-Galactopyranoside; NSC 89286; p-Nitrophenyl α-D-Galactopyranoside

Database IDs

• CAS Number: 7493-95-0
• EC Number: 231-343-6
• MDL Number: MFCD00065050
• Beilstein Number: 92214
• PubChem SID: 24897448; 162227585
• PubChem CID: 82000

CALCULATED PROPERTIES

• Acid pKa: 12.200142
• 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: 26.651247 Å^3
• Polar Surface Area: 145.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 165-167°C; 166-169 °C
• Optical Rotation: [α]20/D +243±5°, c = 1% in H2O

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥99.0% (HPLC)
• Empirical Formula (Hill Notation): C12H15NO8

DETAILS

Sigma Aldrich - 73653

Other Notes
Substrate for α-galactosidase1; Binds to the lactose carrier protein of E. coli2,3

REFERENCES

• Anisha, G., et al.: Proc. Biochem., 44, 327 (2009)
• Bergstroem, M., et al.: Chem. Biol. Drug Des., 73, 132 (2009)
• Liu, Q., et al.: J. Biol. Chem., 283, 8545 (2009)