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

• ChemBase ID: 105748
• Molecular Formular: C14H15BrClNO6
• Molecular Mass: 408.629
• Monoisotopic Mass: 406.97712689
• SMILES: Brc1ccc2c(c(O[C@H]3O[C@@H]([C@H](O)[C@H](O)[C@H]3O)CO)c[nH]2)c1Cl
• 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-YGEXGZRRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5R,6R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: X-α-Gal; 5-Bromo-4-chloro-3-indolyl α-D-galactopyranoside; 5-Bromo-4-chloro-3-indolyl-α-D-galactoside; X-α-D-Galactoside; 5-BROMO-4-CHLORO-3-INDOLYL-α-D-GALACTOPYRANOSIDE

Database IDs

• CAS Number: 107021-38-5
• MDL Number: MFCD00063780
• PubChem SID: 162092397
• PubChem CID: 10173103

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 135.0±5.0°, c = 1 in DMF/H2O 1:1

Safety Information

• Storage Condition: -20°C, Desiccate, Protect from light
• 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%; ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C14H15BrClNO6

DETAILS

MP Biomedicals - 02193921

Purity: >98% An α-galactoside substrate which differentiates α-galactosidase positive yeast strains or bacteria. Protect from light and humidity.

Sigma Aldrich - 16555

Application
suitable as substrate for α-galactosidase; employed in the yeast two-hybrid screen1; for differentiating α-galactosidase-positive strains of yeast2