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

• ChemBase ID: 102657
• Molecular Formular: C12H15NO8
• Molecular Mass: 301.2494
• Monoisotopic Mass: 301.07976645
• SMILES: [O-][N+](=O)c1c(O[C@@H]2O[C@@H]([C@H](O)[C@H](O)[C@H]2O)CO)cccc1
• 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-YBXAARCKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(2-nitrophenoxy)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(2-nitrophenoxy)oxane-3,4,5-triol
• Synonyms: o-Nitrophenyl-β-D-galactoside; 2-Nitrophenyl β-D-galactopyranoside; o-NITROPHENYL-β-D-GALACTOPYRANOSIDE; 2-Nitrophenyl β-D-Galactopyranoside; o-Nitrophenyl β-D-Galactopyranoside; 2-Nitrophenylgalactoside; Ortho-Nitrophenyl-β-galactoside; o-Nitrophenyl β-D-galactopyranoside; ONPG; 2-Nitrophenyl β-D-galactopyranoside

Database IDs

• CAS Number: 369-07-3
• EC Number: 206-716-1
• MDL Number: MFCD00063255
• Beilstein Number: 92207
• PubChem SID: 24886478; 24897461; 162089966
• PubChem CID: 96647; 123646
• MeSH Name: 2-nitrophenylgalactoside
• Wikipedia Title: Ortho-Nitrophenyl-β-galactoside

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

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Crystalline Solid
• Melting Point: 195°C; 198-200°C
• Optical Rotation: [α]20/D -70±1°, c = 1% in H2O

Safety Information

• Storage Condition: 2-8°C
• 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: ≥98% (enzymatic); ≥99.0% (HPLC)
• Empirical Formula (Hill Notation): C12H15NO8

DETAILS

MP Biomedicals - 02194030

Molecular Biology Reagent
Crystalline
Cell culture component for molecular genetics. Substrate for β-galactosidase

MP Biomedicals - 02102473

Crystalline
Substrate for β-galactosidase

Sigma Aldrich - N1127

包装
1 g in poly tube
250 mg in poly bottle
5, 25 g in poly bottle
500 mg in poly tube
Substrates
Chromogenic substrate for β-galactosidase
Application
2-Nitrophenyl β-D-galactopyranoside is an enzyme substrate used to detect lacZ activity and hence the presence of β-galactosidase.
Biochem/physiol Actions
β-galactosidase, breaks down lactose into galactose and glucose. β-Galactosidase is not lactose specific and can act on simple galactosides. 2-Nitrophenyl β-D-galactopyranoside hydrolysis results in the release of galactose and a yellow chromogenic compound. The test substrate does not depend on an induced or constitutive permease enzyme to enter the cell, therefore reactions are rapid and occur within a 24-hour period.

Sigma Aldrich - 73660

Other Notes
Substrate for the determination of β-galactosidases1