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

• ChemBase ID: 153863
• 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-HRNXZZBMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5S,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: X-α-Glc; X-α-glucoside; 5-Bromo-4-chloro-3-indolyl α-D-glucopyranoside; 5-Bromo-4-chloro-3-indolyl α-D-galactopyranoside

Database IDs

• CAS Number: 108789-36-2
• MDL Number: MFCD00155606
• PubChem SID: 162248002
• PubChem CID: 2733916

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

• Optical Rotation: [α]/D 105.0±5.0°, 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: -20°C

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C14H15BrClNO6

DETAILS

Sigma Aldrich - 73837

Application
suitable as substrate for α-glucosidase1; substrate used in the Druggan-Forsythe-Iversen medium (DFI agar) for the selective detection of Enterobacter sakazakii in infant milk2