Page last updated: 2024-12-07

bnps-skatole

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

BNPS-skatole (N-bromosuccinimide-activated skatole) is a chemical reagent used to cleave proteins at tryptophan residues. It works by reacting with the indole ring of tryptophan, forming a stable derivative that can be cleaved under mild conditions. This reagent has been used in a variety of research applications, including protein sequencing, mapping protein domains, and studying protein-protein interactions. It is particularly useful for studying the structure and function of proteins that contain tryptophan residues.'

BNPS-skatole : A bromoindole that is 3H-indole in which the hydrogen at position 2 has been replaced by an (o-nitrophenyl)sulfanyl group and in which the hydrogens at position 3 have been replaced by a bromine and a methyl group.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(gamma)=C(delta) double bonds such as tryptophan, tyrosine, and histidine). [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID94388
CHEMBL ID2144631
CHEBI ID85968
SCHEMBL ID168417
MeSH IDM0047765

Synonyms (30)

Synonym
nsc-240875
mls003389455 ,
27933-36-4
nsc240875
3-bromo-3-methyl-2-(2-nitrophenylthio)-3h-indole, >=85%
bnps-skatole
28805-72-3
3-bromo-3-methyl-2-((2-nitrophenyl)thio)-3h-indole
3-bromo-3-methyl-2-(2-nitrophenyl)sulfanylindole
smr002049108
3h-indole, 3-bromo-3-methyl-2-((2-nitrophenyl)thio)-
nsc 240875
2-(2-nitrophenylsulfenyl)-3-methyl-3-bromoindolenine
einecs 248-737-9
FT-0608506
3h-indole,3-bromo-3-methyl-2-[(2-nitrophenyl)thio]-
3-bromo-3-methyl-2-(2-nitrophenylthio)-3h-indole
SCHEMBL168417
CHEMBL2144631
chebi:85968 ,
AKOS024373600
3-bromo-3-methyl-2-[(2-nitrophenyl)sulfanyl]-3h-indole
2-(2-nitrophenyl)-3-methyl-3-bromoindolenine
J-016926
3-bromo-3-methyl-2-(2-nitrophenyl-mercapto)-3h-indole
2-(2'-nitrophenylsulphanyl)-3-methyl-3-bromoindolenine
3h-indole, 3-bromo-3-methyl-2-[(2-nitrophenyl)thio]-
Q27158821
DTXSID00951447
bnps skatole

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" As a result of an antibacterial assay using a paper disk, actinokineosin showed antibacterial activity against Micrococcus luteus at a dosage of 50 μg per disk."( Isolation of a new antibacterial peptide actinokineosin from Actinokineospora spheciospongiae based on genome mining.
Kaweewan, I; Kodani, S; Ohnishi-Kameyama, M; Takasaka, N, 2017
)
0.46
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
reagentA substance used in a chemical reaction to detect, measure, examine, or produce other substances.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
aryl sulfideAny organic sulfide in which the sulfur is attached to at least one aromatic group.
C-nitro compoundA nitro compound having the nitro group (-NO2) attached to a carbon atom.
bromoindoleAn organobromine compound that is a compound based on an indole skeleton, containing one or more bromine atoms.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (9)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
glp-1 receptor, partialHomo sapiens (human)Potency7.07950.01846.806014.1254AID624417
TDP1 proteinHomo sapiens (human)Potency21.85280.000811.382244.6684AID686978; AID686979
apical membrane antigen 1, AMA1Plasmodium falciparum 3D7Potency14.12540.707912.194339.8107AID720542
IDH1Homo sapiens (human)Potency6.51310.005210.865235.4813AID686970
serine/threonine-protein kinase PLK1Homo sapiens (human)Potency10.62130.168316.404067.0158AID720504
eyes absent homolog 2 isoform aHomo sapiens (human)Potency19.01481.199814.641950.1187AID720540
VprHuman immunodeficiency virus 1Potency56.23411.584919.626463.0957AID651644
Alpha-synucleinHomo sapiens (human)Potency5.62340.56239.398525.1189AID652106
C-terminal-binding protein 1Homo sapiens (human)Potency13.46140.30149.321019.0148AID720541
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (86)

Processvia Protein(s)Taxonomy
calcium ion homeostasisAlpha-synucleinHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIAlpha-synucleinHomo sapiens (human)
microglial cell activationAlpha-synucleinHomo sapiens (human)
positive regulation of receptor recyclingAlpha-synucleinHomo sapiens (human)
positive regulation of neurotransmitter secretionAlpha-synucleinHomo sapiens (human)
negative regulation of protein kinase activityAlpha-synucleinHomo sapiens (human)
fatty acid metabolic processAlpha-synucleinHomo sapiens (human)
neutral lipid metabolic processAlpha-synucleinHomo sapiens (human)
phospholipid metabolic processAlpha-synucleinHomo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic processAlpha-synucleinHomo sapiens (human)
mitochondrial membrane organizationAlpha-synucleinHomo sapiens (human)
adult locomotory behaviorAlpha-synucleinHomo sapiens (human)
response to xenobiotic stimulusAlpha-synucleinHomo sapiens (human)
response to iron(II) ionAlpha-synucleinHomo sapiens (human)
regulation of phospholipase activityAlpha-synucleinHomo sapiens (human)
negative regulation of platelet-derived growth factor receptor signaling pathwayAlpha-synucleinHomo sapiens (human)
regulation of glutamate secretionAlpha-synucleinHomo sapiens (human)
regulation of dopamine secretionAlpha-synucleinHomo sapiens (human)
synaptic vesicle exocytosisAlpha-synucleinHomo sapiens (human)
synaptic vesicle primingAlpha-synucleinHomo sapiens (human)
regulation of transmembrane transporter activityAlpha-synucleinHomo sapiens (human)
negative regulation of microtubule polymerizationAlpha-synucleinHomo sapiens (human)
receptor internalizationAlpha-synucleinHomo sapiens (human)
protein destabilizationAlpha-synucleinHomo sapiens (human)
response to magnesium ionAlpha-synucleinHomo sapiens (human)
negative regulation of transporter activityAlpha-synucleinHomo sapiens (human)
response to lipopolysaccharideAlpha-synucleinHomo sapiens (human)
negative regulation of monooxygenase activityAlpha-synucleinHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylationAlpha-synucleinHomo sapiens (human)
response to type II interferonAlpha-synucleinHomo sapiens (human)
cellular response to oxidative stressAlpha-synucleinHomo sapiens (human)
SNARE complex assemblyAlpha-synucleinHomo sapiens (human)
positive regulation of SNARE complex assemblyAlpha-synucleinHomo sapiens (human)
regulation of locomotionAlpha-synucleinHomo sapiens (human)
dopamine biosynthetic processAlpha-synucleinHomo sapiens (human)
mitochondrial ATP synthesis coupled electron transportAlpha-synucleinHomo sapiens (human)
regulation of macrophage activationAlpha-synucleinHomo sapiens (human)
positive regulation of apoptotic processAlpha-synucleinHomo sapiens (human)
negative regulation of apoptotic processAlpha-synucleinHomo sapiens (human)
negative regulation of cysteine-type endopeptidase activity involved in apoptotic processAlpha-synucleinHomo sapiens (human)
negative regulation of neuron apoptotic processAlpha-synucleinHomo sapiens (human)
positive regulation of endocytosisAlpha-synucleinHomo sapiens (human)
negative regulation of exocytosisAlpha-synucleinHomo sapiens (human)
positive regulation of exocytosisAlpha-synucleinHomo sapiens (human)
regulation of long-term neuronal synaptic plasticityAlpha-synucleinHomo sapiens (human)
synaptic vesicle endocytosisAlpha-synucleinHomo sapiens (human)
synaptic vesicle transportAlpha-synucleinHomo sapiens (human)
positive regulation of inflammatory responseAlpha-synucleinHomo sapiens (human)
regulation of acyl-CoA biosynthetic processAlpha-synucleinHomo sapiens (human)
protein tetramerizationAlpha-synucleinHomo sapiens (human)
positive regulation of release of sequestered calcium ion into cytosolAlpha-synucleinHomo sapiens (human)
neuron apoptotic processAlpha-synucleinHomo sapiens (human)
dopamine uptake involved in synaptic transmissionAlpha-synucleinHomo sapiens (human)
negative regulation of dopamine uptake involved in synaptic transmissionAlpha-synucleinHomo sapiens (human)
negative regulation of serotonin uptakeAlpha-synucleinHomo sapiens (human)
regulation of norepinephrine uptakeAlpha-synucleinHomo sapiens (human)
negative regulation of norepinephrine uptakeAlpha-synucleinHomo sapiens (human)
excitatory postsynaptic potentialAlpha-synucleinHomo sapiens (human)
long-term synaptic potentiationAlpha-synucleinHomo sapiens (human)
positive regulation of inositol phosphate biosynthetic processAlpha-synucleinHomo sapiens (human)
negative regulation of thrombin-activated receptor signaling pathwayAlpha-synucleinHomo sapiens (human)
response to interleukin-1Alpha-synucleinHomo sapiens (human)
cellular response to copper ionAlpha-synucleinHomo sapiens (human)
cellular response to epinephrine stimulusAlpha-synucleinHomo sapiens (human)
positive regulation of protein serine/threonine kinase activityAlpha-synucleinHomo sapiens (human)
supramolecular fiber organizationAlpha-synucleinHomo sapiens (human)
negative regulation of mitochondrial electron transport, NADH to ubiquinoneAlpha-synucleinHomo sapiens (human)
positive regulation of glutathione peroxidase activityAlpha-synucleinHomo sapiens (human)
positive regulation of hydrogen peroxide catabolic processAlpha-synucleinHomo sapiens (human)
regulation of synaptic vesicle recyclingAlpha-synucleinHomo sapiens (human)
regulation of reactive oxygen species biosynthetic processAlpha-synucleinHomo sapiens (human)
positive regulation of protein localization to cell peripheryAlpha-synucleinHomo sapiens (human)
negative regulation of chaperone-mediated autophagyAlpha-synucleinHomo sapiens (human)
regulation of presynapse assemblyAlpha-synucleinHomo sapiens (human)
amyloid fibril formationAlpha-synucleinHomo sapiens (human)
synapse organizationAlpha-synucleinHomo sapiens (human)
chemical synaptic transmissionAlpha-synucleinHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIC-terminal-binding protein 1Homo sapiens (human)
protein phosphorylationC-terminal-binding protein 1Homo sapiens (human)
negative regulation of cell population proliferationC-terminal-binding protein 1Homo sapiens (human)
viral genome replicationC-terminal-binding protein 1Homo sapiens (human)
negative regulation of DNA-templated transcriptionC-terminal-binding protein 1Homo sapiens (human)
positive regulation of DNA-templated transcriptionC-terminal-binding protein 1Homo sapiens (human)
synaptic vesicle endocytosisC-terminal-binding protein 1Homo sapiens (human)
white fat cell differentiationC-terminal-binding protein 1Homo sapiens (human)
regulation of cell cycleC-terminal-binding protein 1Homo sapiens (human)
synaptic vesicle clusteringC-terminal-binding protein 1Homo sapiens (human)
regulation of transcription by RNA polymerase IIC-terminal-binding protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (36)

Processvia Protein(s)Taxonomy
fatty acid bindingAlpha-synucleinHomo sapiens (human)
phospholipase D inhibitor activityAlpha-synucleinHomo sapiens (human)
SNARE bindingAlpha-synucleinHomo sapiens (human)
magnesium ion bindingAlpha-synucleinHomo sapiens (human)
transcription cis-regulatory region bindingAlpha-synucleinHomo sapiens (human)
actin bindingAlpha-synucleinHomo sapiens (human)
protein kinase inhibitor activityAlpha-synucleinHomo sapiens (human)
copper ion bindingAlpha-synucleinHomo sapiens (human)
calcium ion bindingAlpha-synucleinHomo sapiens (human)
protein bindingAlpha-synucleinHomo sapiens (human)
phospholipid bindingAlpha-synucleinHomo sapiens (human)
ferrous iron bindingAlpha-synucleinHomo sapiens (human)
zinc ion bindingAlpha-synucleinHomo sapiens (human)
lipid bindingAlpha-synucleinHomo sapiens (human)
oxidoreductase activityAlpha-synucleinHomo sapiens (human)
kinesin bindingAlpha-synucleinHomo sapiens (human)
Hsp70 protein bindingAlpha-synucleinHomo sapiens (human)
histone bindingAlpha-synucleinHomo sapiens (human)
identical protein bindingAlpha-synucleinHomo sapiens (human)
alpha-tubulin bindingAlpha-synucleinHomo sapiens (human)
cysteine-type endopeptidase inhibitor activity involved in apoptotic processAlpha-synucleinHomo sapiens (human)
tau protein bindingAlpha-synucleinHomo sapiens (human)
phosphoprotein bindingAlpha-synucleinHomo sapiens (human)
molecular adaptor activityAlpha-synucleinHomo sapiens (human)
dynein complex bindingAlpha-synucleinHomo sapiens (human)
cuprous ion bindingAlpha-synucleinHomo sapiens (human)
transcription corepressor bindingC-terminal-binding protein 1Homo sapiens (human)
chromatin bindingC-terminal-binding protein 1Homo sapiens (human)
transcription corepressor activityC-terminal-binding protein 1Homo sapiens (human)
protein bindingC-terminal-binding protein 1Homo sapiens (human)
oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptorC-terminal-binding protein 1Homo sapiens (human)
protein domain specific bindingC-terminal-binding protein 1Homo sapiens (human)
identical protein bindingC-terminal-binding protein 1Homo sapiens (human)
NAD bindingC-terminal-binding protein 1Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingC-terminal-binding protein 1Homo sapiens (human)
DNA-binding transcription factor bindingC-terminal-binding protein 1Homo sapiens (human)
transcription coactivator activityC-terminal-binding protein 1Homo sapiens (human)
transcription coregulator bindingC-terminal-binding protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (27)

Processvia Protein(s)Taxonomy
platelet alpha granule membraneAlpha-synucleinHomo sapiens (human)
extracellular regionAlpha-synucleinHomo sapiens (human)
extracellular spaceAlpha-synucleinHomo sapiens (human)
nucleusAlpha-synucleinHomo sapiens (human)
cytoplasmAlpha-synucleinHomo sapiens (human)
mitochondrionAlpha-synucleinHomo sapiens (human)
lysosomeAlpha-synucleinHomo sapiens (human)
cytosolAlpha-synucleinHomo sapiens (human)
plasma membraneAlpha-synucleinHomo sapiens (human)
cell cortexAlpha-synucleinHomo sapiens (human)
actin cytoskeletonAlpha-synucleinHomo sapiens (human)
membraneAlpha-synucleinHomo sapiens (human)
inclusion bodyAlpha-synucleinHomo sapiens (human)
axonAlpha-synucleinHomo sapiens (human)
growth coneAlpha-synucleinHomo sapiens (human)
synaptic vesicle membraneAlpha-synucleinHomo sapiens (human)
perinuclear region of cytoplasmAlpha-synucleinHomo sapiens (human)
postsynapseAlpha-synucleinHomo sapiens (human)
supramolecular fiberAlpha-synucleinHomo sapiens (human)
protein-containing complexAlpha-synucleinHomo sapiens (human)
cytoplasmAlpha-synucleinHomo sapiens (human)
axon terminusAlpha-synucleinHomo sapiens (human)
neuronal cell bodyAlpha-synucleinHomo sapiens (human)
nucleusC-terminal-binding protein 1Homo sapiens (human)
nucleoplasmC-terminal-binding protein 1Homo sapiens (human)
presynaptic active zone cytoplasmic componentC-terminal-binding protein 1Homo sapiens (human)
glutamatergic synapseC-terminal-binding protein 1Homo sapiens (human)
GABA-ergic synapseC-terminal-binding protein 1Homo sapiens (human)
transcription repressor complexC-terminal-binding protein 1Homo sapiens (human)
nucleusC-terminal-binding protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (43)

TimeframeStudies, This Drug (%)All Drugs %
pre-199021 (48.84)18.7374
1990's12 (27.91)18.2507
2000's6 (13.95)29.6817
2010's3 (6.98)24.3611
2020's1 (2.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.85

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index20.85 (24.57)
Research Supply Index3.78 (2.92)
Research Growth Index4.05 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.85)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other43 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]