BNPS-skatole (CHEBI:85968)

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ChEBI Name	BNPS-skatole

ChEBI ID	CHEBI:85968

Definition	A bromoindole that is 3H-indole in which the hydrogen at position 2 has been replaced by an (o-nitrophenyl)sulfanyl group and in which the hydrogens at position 3 have been replaced by a bromine and a methyl group. It is used particularly for the selective cleavage of tryptophanyl peptide bonds (cleavage occurs at peptide bonds after amino acids with available C^γ=C^δ double bonds such as tryptophan, tyrosine, and histidine).

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Margaret Duesbury

Supplier Information

Download	Molfile XML SDF

Formula

C15H11BrN2O2S

Net Charge

Average Mass

363.22900

Monoisotopic Mass

361.97246

InChI

InChI=1S/C15H11BrN2O2S/c1-15(16)10-6-2-3-7-11(10)17-14(15)21-13-9-5-4-8-12(13)18(19)20/h2-9H,1H3

InChIKey

BXTVQNYQYUTQAZ-UHFFFAOYSA-N

SMILES

CC1(Br)C(Sc2ccccc2[N+]([O-])=O)=Nc2ccccc12

Roles Classification
Application(s):	reagent A substance used in a chemical reaction to detect, measure, examine, or produce other substances.

ChEBI Ontology
Outgoing	BNPS-skatole (CHEBI:85968) has role reagent (CHEBI:33893) BNPS-skatole (CHEBI:85968) is a C-nitro compound (CHEBI:35716) BNPS-skatole (CHEBI:85968) is a aryl sulfide (CHEBI:35683) BNPS-skatole (CHEBI:85968) is a bromoindole (CHEBI:52514)

IUPAC Name

3-bromo-3-methyl-2-[(2-nitrophenyl)sulfanyl]-3H-indole

Synonyms	Sources
2-(2-nitrophenyl)-3-methyl-3-bromoindolenine	ChEBI
3-bromo-3-methyl-2-(2-nitrophenyl)sulfanylindole	IUPAC
3-bromo-3-methyl-2-(2-nitrophenylthio)-3H-indole	ChEBI
Bnps-skatole	ChemIDplus

Last Modified

10 June 2015