CHEBI:75055 - 5-bromo-4-chloro-3-indolyl β-D-galactoside

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ChEBI Name 5-bromo-4-chloro-3-indolyl β-D-galactoside
ChEBI ID CHEBI:75055
ChEBI ASCII Name 5-bromo-4-chloro-3-indolyl beta-D-galactoside
Definition An indolyl carbohydrate that is the β-D-galactoside of 3-hydroxy-1H-indole in which the indole moiety is substituted at positions 4 and 5 by chlorine and bromine, respectively. It is used to test for the presence of an enzyme, β-galactosidase, which cleaved the glycosidic bond to give 5-bromo-4-chloro-3-hydroxy-1H-indole, which immediately dimerises to give an intensely blue product.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C14H15BrClNO6
Net Charge 0
Average Mass 408.62900
Monoisotopic Mass 406.977
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-AEOCFKNESA-N
SMILES [H][C@]1(O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)Oc1c[nH]c2ccc(Br)c(Cl)c12
Roles Classification
Application(s): chromogenic compound
Colourless, endogenous or exogenous pigment precursors that may be transformed by biological mechanisms into coloured compounds. They are used in biochemical assays and in diagnosis as indicators, particularly in the form of enzyme substrates.
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ChEBI Ontology
Outgoing 5-bromo-4-chloro-3-indolyl β-D-galactoside (CHEBI:75055) has role chromogenic compound (CHEBI:75050)
5-bromo-4-chloro-3-indolyl β-D-galactoside (CHEBI:75055) is a β-D-galactoside (CHEBI:28034)
5-bromo-4-chloro-3-indolyl β-D-galactoside (CHEBI:75055) is a D-aldohexose derivative (CHEBI:63387)
5-bromo-4-chloro-3-indolyl β-D-galactoside (CHEBI:75055) is a indolyl carbohydrate (CHEBI:24821)
5-bromo-4-chloro-3-indolyl β-D-galactoside (CHEBI:75055) is a organobromine compound (CHEBI:37141)
5-bromo-4-chloro-3-indolyl β-D-galactoside (CHEBI:75055) is a organochlorine compound (CHEBI:36683)
IUPAC Name
5-bromo-4-chloro-1H-indol-3-yl β-D-galactopyranoside
Synonyms Sources
5-bromo-4-chloro-3-indolyl β-galactoside ChemIDplus
5-bromo-4-chloroindol-3-yl-β-D-galactopyranoside ChemIDplus
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Registry Numbers Types Sources
1552604 Reaxys Registry Number Reaxys
7240-90-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
02 September 2013