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

• ChemBase ID: 138657
• Molecular Formular: C14H15BrClNO6
• Molecular Mass: 408.629
• Monoisotopic Mass: 406.97712689
• SMILES: c1cc(c(c2c1[nH]cc2O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)Cl)Br
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2c[nH]c3c2c(Cl)c(cc3)Br)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C14H15BrClNO6/c15-5-1-2-6-9(10(5)16)7(3-17-6)22-14-13(21)12(20)11(19)8(4-18)23-14/h1-3,8,11-14,17-21H,4H2/t8-,11-,12+,13-,14-/m1/s1
• InChIKey: OPIFSICVWOWJMJ-LNNRFACYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,3R,4S,5S,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: X-glucoside; X-Glc; 5-Bromo-4-chloro-3-indolyl β-D-glucopyranoside; 5-溴-4-氯-3-吲哚基-β-D-吡喃葡萄糖苷

Database IDs

• CAS Number: 15548-60-4
• EC Number: 239-603-0
• MDL Number: MFCD00063690
• Beilstein Number: 1552603
• PubChem SID: 24891784; 162232908; 24850178
• PubChem CID: 84982

CALCULATED PROPERTIES

• Acid pKa: 12.199782
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 0.8731716
• LogD (pH = 7.4): 0.87316483
• Log P: 0.8731717
• Molar Refractivity: 83.6974 cm^3
• Polarizability: 34.64774 Å^3
• Polar Surface Area: 115.17 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble50 mg/mL, clear, colorless to very faintly yellow

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97%; ≥99.0% (TLC); 98%
• Empirical Formula (Hill Notation): C14H15BrClNO6

DETAILS

Sigma Aldrich - B4527

Substrates
A histochemical substrate for β-glucosidase.

Sigma Aldrich - 859036

Application
For the histochemical determination of β-glucosidase.1