5-bromo-4-chloro-3-indolyl beta-D-galactoside (CHEBI:75055)

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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

Average Mass

408.62900

Monoisotopic Mass

406.97713

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.

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
BCIG	ChEBI
Indoxyl-Gal	ChEBI
X-gal	ChEBI
X-Gal	ChEBI

Last Modified

02 September 2013