(2S,3R,4S,5R,6R)-2-[(6-chloro-1H-indol-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 153746
• Molecular Formular: C14H16ClNO6
• Molecular Mass: 329.73294
• Monoisotopic Mass: 329.06661492
• SMILES: c1cc(cc2c1ccn2O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)Cl
• Canonical SMILES: OC[C@H]1O[C@@H](On2ccc3c2cc(Cl)cc3)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C14H16ClNO6/c15-8-2-1-7-3-4-16(9(7)5-8)22-14-13(20)12(19)11(18)10(6-17)21-14/h1-5,10-14,17-20H,6H2/t10-,11+,12+,13-,14+/m1/s1
• InChIKey: CCSMDIRWROWGMP-HTOAHKCRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5R,6R)-2-[(6-chloro-1H-indol-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,3R,4S,5R,6R)-2-[(6-chloroindol-1-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Salmon Glu; 6-Chloro-3-indolyl β-D-glucopyranoside; Rose-Gal; Salmon-Gal; 6-Chloro-3-indolyl-β-D-galactopyranoside

Database IDs

• CAS Number: 138182-21-5; 159954-28-6
• MDL Number: MFCD00467206
• PubChem SID: 24889906; 162247885; 24854972
• PubChem CID: 10336708

CALCULATED PROPERTIES

• Acid pKa: 12.158559
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.03225408
• LogD (pH = 7.4): -0.03226155
• Log P: -0.032253984
• Molar Refractivity: 77.269 cm^3
• Polarizability: 31.676823 Å^3
• Polar Surface Area: 104.31 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D -45.5±2°, c = 1% in methanol

Safety Information

• 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: ≥98.0% (HPLC); ≥99.0% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C14H16ClNO6

DETAILS

Sigma Aldrich - 93546

Other Notes
Substrate employed in chromogenic medium for the detection of yeasts with β-glucosidase activity.1

Sigma Aldrich - 24904

Other Notes
Sales restrictions may apply