(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitrophenoxy)oxane-2-carboxylic acid

• ChemBase ID: 133390
• Molecular Formular: C12H13NO9
• Molecular Mass: 315.23292
• Monoisotopic Mass: 315.059031
• SMILES: c1cc(ccc1[N+](=O)[O-])O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)O)O)O)O
• Canonical SMILES: OC(=O)[C@H]1O[C@@H](Oc2ccc(cc2)[N+](=O)[O-])[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H13NO9/c14-7-8(15)10(11(17)18)22-12(9(7)16)21-6-3-1-5(2-4-6)13(19)20/h1-4,7-10,12,14-16H,(H,17,18)/t7-,8-,9+,10-,12+/m0/s1
• InChIKey: QSUILVWOWLUOEU-GOVZDWNOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitrophenoxy)oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitrophenoxy)oxane-2-carboxylic acid
• Synonyms: 4-Nitrophenyl-β-D-glucopyranosiduronic acid; PNPG; 4-Nitrophenyl β-D-glucuronide; p-Nitrophenyl β-Glucuronic Acid; 4-Nitrophenyl β-D-Glucopyranosiduronic Acid; p-Nitrophenyl β-D-Glucuronide

Database IDs

• CAS Number: 10344-94-2
• EC Number: 233-753-0
• MDL Number: MFCD00036210
• Beilstein Number: 1438576
• PubChem SID: 24886595; 162227667; 24897507
• PubChem CID: 82565

CALCULATED PROPERTIES

• Acid pKa: 2.7867358
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -2.9905224
• LogD (pH = 7.4): -3.833205
• Log P: -0.33812886
• Molar Refractivity: 67.3754 cm^3
• Polarizability: 26.670088 Å^3
• Polar Surface Area: 162.27 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, faintly yellow; Methanol
• Apperance: Crystalline Solid
• Melting Point: 150-153°C
• Optical Rotation: [α]20/D -102±3°, c = 1% in ethanol

Safety Information

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

Product Information

• Purity: ≥98% (TLC); ≥99.0% (TLC)
• Suitability: suitable as substrate for β-glucuronidase test
• Impurities: ≤0.05% free 4-nitrophenol; ≤7% water
• Empirical Formula (Hill Notation): C12H13NO9

DETAILS

Sigma Aldrich - N1627

Substrates
Chromogenic substrate for β-glucuronidase (GUS) gene detection.
Application
4-Nitrophenyl β-D-glucuronide is a chromogenic substrate for β-glucuronidase (GUS) gene detection. 98% (TLC)

Sigma Aldrich - 73677

Substrates
Chromogenic substrate for β-glucuronidase (GUS) gene detection.

REFERENCES

• Muraoka, M., et al.: J. Biol. Chem., 282, 24615 (2007)
• De Angelis, M., et al.: Vet. Microbiol., 123, 133 (2007)
• Geddie, M., et al.: J. Mol. Biol., 369, 1052 (2007)
• Ball, A., et al.: J. Enz. Inhib. Med. Chem., 23, 131 (2007)