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

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CHEBI:75424 - 5-bromo-4-chloro-3-indolyl β-D-glucoside

ChEBI ID	CHEBI:75424
ChEBI Name	5-bromo-4-chloro-3-indolyl β-D-glucoside
Stars
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.
Last Modified	6 September 2013
Submitter	Gareth Owen
Downloads	Molfile

Formula	C14H15BrClNO6
Net Charge	0
Average Mass	408.632
Monoisotopic Mass	406.97713
SMILES	[H][C@@]1(Oc2cnc3ccc(Br)c(Cl)c23)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
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

Roles Classification

Application:

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 Relation(s)
	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 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)
	5-bromo-4-chloro-3-indolyl β-D-glucoside (CHEBI:75424) is a β-D-glucoside (CHEBI:22798)

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

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

Registry Numbers	Sources
Reaxys:1552603	Reaxys
CAS:15548-60-4	ChemIDplus

Citations