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

• ChemBase ID: 162801
• Molecular Formular: C14H15BrClNO6
• Molecular Mass: 408.629
• Monoisotopic Mass: 406.97712689
• SMILES: [C@H]1([C@@H](C([C@@H](OC1CO)Oc1c2c(ccc(c2Cl)Br)[nH]c1)O)O)O
• Canonical SMILES: OCC1O[C@@H](Oc2c[nH]c3c2c(Cl)c(cc3)Br)C([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+/m0/s1
• InChIKey: OPIFSICVWOWJMJ-DDMYNCDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,4S,5R)-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 5-Bromo-4-chloro-1H-indol-3-yl β-D-Galactopyranoside; 5-Bromo-4-chloroindol-3-yl β-D-galactoside; X-GAL; 5-Bromo-4-chloro-3-indolyl β-D-Galactopyranoside

Database IDs

• CAS Number: 7240-90-6
• PubChem SID: 162256936
• PubChem CID: 46780889

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; DMSO; Methanol
• Apperance: White Solid
• Melting Point: >180°C dec.

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B682350

A substrate for β-Galactosidase that is converted by the enzyme into an intense indigo-blue chromophore (615 nm).

REFERENCES

• Horwitz, J., et al.: J. Med. Chem., 7, 514 (1964)
• Lojda, Z., et al.: Histochemie, 34, 361 (1973)