(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2-nitrophenyl)sulfanyl]oxane-3,4,5-triol

• ChemBase ID: 138546
• Molecular Formular: C12H15NO7S
• Molecular Mass: 317.315
• Monoisotopic Mass: 317.05692283
• SMILES: c1ccc(c(c1)[N+](=O)[O-])S[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Sc2ccccc2[N+](=O)[O-])[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C12H15NO7S/c14-5-7-9(15)10(16)11(17)12(20-7)21-8-4-2-1-3-6(8)13(18)19/h1-4,7,9-12,14-17H,5H2/t7-,9+,10+,11-,12+/m1/s1
• InChIKey: SZAOZNVCHHBUDZ-RUXWNWLUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2-nitrophenyl)sulfanyl]oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2-nitrophenyl)sulfanyl]oxane-3,4,5-triol
• Synonyms: 2-Nitrophenyl 1-thio-β-D-galactopyranoside; 2-Nitrophenyl β-D-thiogalactopyranoside; 2-Nitrophenyl 1-thio-β-D-galactopyranoside; 2-硝基苯基 1-硫代-β-D-吡喃半乳糖苷; 2-硝基苯基 β-D-硫代半乳糖吡喃糖苷; 2-硝基苯基 1-硫代-β-D-吡喃半乳糖苷

Database IDs

• CAS Number: 1158-17-4
• EC Number: 214-593-0
• MDL Number: MFCD00076099
• PubChem SID: 24897575; 162232800
• PubChem CID: 101992

CALCULATED PROPERTIES

• Acid pKa: 12.458429
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.2605539
• LogD (pH = 7.4): -0.26055765
• Log P: -0.26055387
• Molar Refractivity: 74.0447 cm^3
• Polarizability: 28.957787 Å^3
• Polar Surface Area: 135.97 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 201 °C (dec.)(lit.)
• Optical Rotation: [α]25/D -229.7°, c = 0.71 in methanol

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C12H15NO7S

DETAILS

Sigma Aldrich - N2509

Application
2-Nitrophenyl 1-thio-β-D-galactopyranoside is an enzyme substrate used in the election of lac- mutants.