5-bromo-4-chloro-3-indolyl beta-D-glucoside (CHEBI:75424)

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ChEBI Name	5-bromo-4-chloro-3-indolyl β-D-glucoside

ChEBI ID	CHEBI:75424

ChEBI ASCII Name	5-bromo-4-chloro-3-indolyl beta-D-glucoside

Definition	An indolyl carbohydrate that is the β-D-glucoside 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-glucosidase, which cleaves 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.

Supplier Information

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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-LNNRFACYSA-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-glucoside (CHEBI:75424) has functional parent indoxyl (CHEBI:17840) 5-bromo-4-chloro-3-indolyl β-D-glucoside (CHEBI:75424) has role chromogenic compound (CHEBI:75050) 5-bromo-4-chloro-3-indolyl β-D-glucoside (CHEBI:75424) is a β-D-glucoside (CHEBI:22798) 5-bromo-4-chloro-3-indolyl β-D-glucoside (CHEBI:75424) is a D-aldohexose derivative (CHEBI:63387) 5-bromo-4-chloro-3-indolyl β-D-glucoside (CHEBI:75424) is a indolyl carbohydrate (CHEBI:24821) 5-bromo-4-chloro-3-indolyl β-D-glucoside (CHEBI:75424) is a organobromine compound (CHEBI:37141) 5-bromo-4-chloro-3-indolyl β-D-glucoside (CHEBI:75424) is a organochlorine compound (CHEBI:36683)

IUPAC Name

5-bromo-4-chloro-1H-indol-3-yl β-D-glucopyranoside

Synonyms	Sources
(−)-5-bromo-4-chloro-3-indolyl-β-D-glucoside	ChEBI
5-bromo-4-chloro-3-indolyl β-glucoside	ChEBI
5-bromo-4-chloroindol-3-yl-β-D-glucopyranoside	ChemIDplus
EINECS 239-603-0	ChemIDplus
Indoxyl-Glucoside	ChEBI
X-Glc	ChEBI
X-glucoside	ChEBI

Citation	Type	Source
1725950	PubMed citation	Europe PMC

Last Modified

06 September 2013