(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(quinolin-8-yloxy)oxane-3,4,5-triol

• ChemBase ID: 154050
• Molecular Formular: C15H17NO6
• Molecular Mass: 307.29858
• Monoisotopic Mass: 307.10558727
• SMILES: c1cc2cccnc2c(c1)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](Oc2cccc3c2nccc3)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C15H17NO6/c17-7-10-12(18)13(19)14(20)15(22-10)21-9-5-1-3-8-4-2-6-16-11(8)9/h1-6,10,12-15,17-20H,7H2/t10-,12+,13+,14-,15-/m1/s1
• InChIKey: BWMXDESAZVPVGR-BGNCJLHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(quinolin-8-yloxy)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(quinolin-8-yloxy)oxane-3,4,5-triol
• Synonyms: 8-Quinolinyl-β-D-galactopyranoside; 8-Hydroxyquinoline β-D-galactopyranoside

Database IDs

• CAS Number: 113079-84-8
• MDL Number: MFCD00798398
• PubChem SID: 162248189
• PubChem CID: 9879604

CALCULATED PROPERTIES

• Acid pKa: 12.200038
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.44152862
• LogD (pH = 7.4): -0.44074985
• Log P: -0.44073296
• Molar Refractivity: 74.1046 cm^3
• Polarizability: 31.15124 Å^3
• Polar Surface Area: 112.27 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -86.0±4.0°, c = 1 in methanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPLC)
• Impurities: ≤10% water
• Empirical Formula (Hill Notation): C15H17NO6

DETAILS

Sigma Aldrich - 92326

Biochem/physiol Actions
Chromogenic substrate for β-D-galactosidase1