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

• ChemBase ID: 155974
• Molecular Formular: C15H19NO6
• Molecular Mass: 309.31446
• Monoisotopic Mass: 309.12123733
• SMILES: Cn1cc(c2c1cccc2)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](Oc2cn(c3c2cccc3)C)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C15H19NO6/c1-16-6-10(8-4-2-3-5-9(8)16)21-15-14(20)13(19)12(18)11(7-17)22-15/h2-6,11-15,17-20H,7H2,1H3/t11-,12+,13+,14-,15-/m1/s1
• InChIKey: FDECOIVNOJUVCV-GZBLMMOJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(1-methyl-1H-indol-3-yl)oxy]oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(1-methylindol-3-yl)oxy]oxane-3,4,5-triol
• Synonyms: Green-β-D-gal; N-Methylindolyl-β-D-galactopyranoside; 1-Methyl-3-indolyl-β-D-galactopyranoside

Database IDs

• CAS Number: 207598-26-3
• MDL Number: MFCD00467869
• PubChem SID: 24884837; 162250112
• PubChem CID: 16218184

CALCULATED PROPERTIES

• Acid pKa: 12.200049
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.27594963
• LogD (pH = 7.4): -0.27595642
• Log P: -0.27594954
• Molar Refractivity: 76.1665 cm^3
• Polarizability: 31.501795 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 -41.5±2°, c = 1% in DMF/H2O 1:1

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C15H19NO6

DETAILS

Sigma Aldrich - 67610

Application
Chromogenic substrate for β-galactosidase producing a green insoluble product.