Page last updated: 2024-11-05

5-methylisatin

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Description

5-Methylisatin is a derivative of isatin, an indole-2,3-dione, and is a key intermediate in the synthesis of various biologically active compounds. It can be synthesized through various methods, including the Sandmeyer reaction and the Fischer indole synthesis. 5-Methylisatin exhibits a range of pharmacological activities, including antioxidant, anti-inflammatory, and anticancer properties. Notably, it has shown potential as an inhibitor of the enzyme monoamine oxidase (MAO), which is implicated in neurodegenerative diseases such as Parkinson's disease. The compound's biological activity has led to its investigation as a potential therapeutic agent. Researchers are interested in exploring its potential for treating a variety of conditions, including cancer, Alzheimer's disease, and epilepsy.'

5-methylisatin: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11840
CHEMBL ID118883
SCHEMBL ID281743
MeSH IDM0286813

Synonyms (58)

Synonym
unii-ak8xab7ps8
5-21-11-00179 (beilstein handbook reference)
ak8xab7ps8 ,
UPCMLD0ENAT5609752:001
1h-indole-2,3-dione, 5-methyl-
indole-2,3-dione, 5-methyl-
5-methylindoline-2,3-dione
5-methyl-1h-indole-2,3-dione
5-methyl-indole-2,3-dione
brn 0123738
einecs 210-152-1
isatin, 5-methyl-
5-methylindole-2,3(1h)-dione
nsc 9398
bdbm22810
5-methyl-2,3-dihydro-1h-indole-2,3-dione
isatin-based compound, 30
1h-indole-2, 5-methyl-
indole-2, 5-methyl-
nsc-9398
nsc9398
608-05-9
5-methylisatin
EU-0035352
5-methylisatin, 95%
STK151660
AC-11497
M1703
5-methyl-2,3-indolinedione
inchi=1/c9h7no2/c1-5-2-3-7-6(4-5)8(11)9(12)10-7/h2-4h,1h3,(h,10,11,12)
vajcspzkmvqiap-uhfffaoysa-
AKOS000200894
5-methylindole-2,3-dione
CHEMBL118883
F0266-0774
A832893
5-methylindoline-2,3-dione;5-methylisatin
FS-3425
FT-0620659
SCHEMBL281743
SY007230
mfcd00005721
5-methyl isatin
2,3-dihydro-5-methylindole-2,3-dione
5-methyl-1h-indole-2,3-dione #
cambridge id 5100729
AM85842
W-105228
STR03374
DTXSID00209637
sr-01000403974
SR-01000403974-1
Z56899023
CS-W010873
BCP05738
5-methyl-2,3-dihydro-2,3-dioxoindole
O11477
EN300-12135
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Coagulation factor XIIHomo sapiens (human)Ki85.24000.00251.86697.2500AID1798240
CholinesteraseHomo sapiens (human)Ki87.70000.00001.51739.7300AID1798240; AID281481
Liver carboxylesterase 1Oryctolagus cuniculus (rabbit)Ki85.24000.01361.70257.2500AID1798240
AcetylcholinesteraseHomo sapiens (human)Ki87.70000.00001.27869.7300AID1798240; AID281480
Liver carboxylesterase 1Homo sapiens (human)Ki87.70000.00252.01368.4800AID1798240; AID281478
CruzipainTrypanosoma cruziIC50 (µMol)10.00000.00022.04508.0000AID213673
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (54)

Processvia Protein(s)Taxonomy
plasma kallikrein-kinin cascadeCoagulation factor XIIHomo sapiens (human)
Factor XII activationCoagulation factor XIIHomo sapiens (human)
blood coagulation, intrinsic pathwayCoagulation factor XIIHomo sapiens (human)
positive regulation of plasminogen activationCoagulation factor XIIHomo sapiens (human)
protein processingCoagulation factor XIIHomo sapiens (human)
protein autoprocessingCoagulation factor XIIHomo sapiens (human)
positive regulation of blood coagulationCoagulation factor XIIHomo sapiens (human)
zymogen activationCoagulation factor XIIHomo sapiens (human)
fibrinolysisCoagulation factor XIIHomo sapiens (human)
innate immune responseCoagulation factor XIIHomo sapiens (human)
response to misfolded proteinCoagulation factor XIIHomo sapiens (human)
positive regulation of fibrinolysisCoagulation factor XIIHomo sapiens (human)
blood coagulationCoagulation factor XIIHomo sapiens (human)
xenobiotic metabolic processCholinesteraseHomo sapiens (human)
learningCholinesteraseHomo sapiens (human)
negative regulation of cell population proliferationCholinesteraseHomo sapiens (human)
neuroblast differentiationCholinesteraseHomo sapiens (human)
peptide hormone processingCholinesteraseHomo sapiens (human)
response to alkaloidCholinesteraseHomo sapiens (human)
cocaine metabolic processCholinesteraseHomo sapiens (human)
negative regulation of synaptic transmissionCholinesteraseHomo sapiens (human)
response to glucocorticoidCholinesteraseHomo sapiens (human)
response to folic acidCholinesteraseHomo sapiens (human)
choline metabolic processCholinesteraseHomo sapiens (human)
acetylcholine catabolic processCholinesteraseHomo sapiens (human)
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo sapiens (human)
cholesterol biosynthetic processLiver carboxylesterase 1Homo sapiens (human)
cholesterol metabolic processLiver carboxylesterase 1Homo sapiens (human)
response to toxic substanceLiver carboxylesterase 1Homo sapiens (human)
positive regulation of cholesterol effluxLiver carboxylesterase 1Homo sapiens (human)
negative regulation of cholesterol storageLiver carboxylesterase 1Homo sapiens (human)
epithelial cell differentiationLiver carboxylesterase 1Homo sapiens (human)
cholesterol homeostasisLiver carboxylesterase 1Homo sapiens (human)
reverse cholesterol transportLiver carboxylesterase 1Homo sapiens (human)
medium-chain fatty acid metabolic processLiver carboxylesterase 1Homo sapiens (human)
regulation of bile acid biosynthetic processLiver carboxylesterase 1Homo sapiens (human)
cellular response to cholesterolLiver carboxylesterase 1Homo sapiens (human)
cellular response to low-density lipoprotein particle stimulusLiver carboxylesterase 1Homo sapiens (human)
cholesterol ester hydrolysis involved in cholesterol transportLiver carboxylesterase 1Homo sapiens (human)
positive regulation of cholesterol metabolic processLiver carboxylesterase 1Homo sapiens (human)
regulation of bile acid secretionLiver carboxylesterase 1Homo sapiens (human)
lipid catabolic processLiver carboxylesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (22)

Processvia Protein(s)Taxonomy
serine-type endopeptidase activityCoagulation factor XIIHomo sapiens (human)
calcium ion bindingCoagulation factor XIIHomo sapiens (human)
protein bindingCoagulation factor XIIHomo sapiens (human)
misfolded protein bindingCoagulation factor XIIHomo sapiens (human)
amyloid-beta bindingCholinesteraseHomo sapiens (human)
catalytic activityCholinesteraseHomo sapiens (human)
acetylcholinesterase activityCholinesteraseHomo sapiens (human)
cholinesterase activityCholinesteraseHomo sapiens (human)
protein bindingCholinesteraseHomo sapiens (human)
hydrolase activity, acting on ester bondsCholinesteraseHomo sapiens (human)
enzyme bindingCholinesteraseHomo sapiens (human)
choline bindingCholinesteraseHomo sapiens (human)
identical protein bindingCholinesteraseHomo sapiens (human)
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo sapiens (human)
sterol esterase activityLiver carboxylesterase 1Homo sapiens (human)
methylumbelliferyl-acetate deacetylase activityLiver carboxylesterase 1Homo sapiens (human)
carboxylesterase activityLiver carboxylesterase 1Homo sapiens (human)
carboxylic ester hydrolase activityLiver carboxylesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (23)

Processvia Protein(s)Taxonomy
extracellular regionCoagulation factor XIIHomo sapiens (human)
extracellular spaceCoagulation factor XIIHomo sapiens (human)
plasma membraneCoagulation factor XIIHomo sapiens (human)
collagen-containing extracellular matrixCoagulation factor XIIHomo sapiens (human)
extracellular exosomeCoagulation factor XIIHomo sapiens (human)
extracellular spaceCoagulation factor XIIHomo sapiens (human)
rough endoplasmic reticulumCoagulation factor XIIHomo sapiens (human)
extracellular regionCholinesteraseHomo sapiens (human)
nuclear envelope lumenCholinesteraseHomo sapiens (human)
endoplasmic reticulum lumenCholinesteraseHomo sapiens (human)
blood microparticleCholinesteraseHomo sapiens (human)
plasma membraneCholinesteraseHomo sapiens (human)
extracellular spaceCholinesteraseHomo sapiens (human)
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo sapiens (human)
cytoplasmLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulumLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulum lumenLiver carboxylesterase 1Homo sapiens (human)
lipid dropletLiver carboxylesterase 1Homo sapiens (human)
cytosolLiver carboxylesterase 1Homo sapiens (human)
lipid dropletLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulumLiver carboxylesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (27)

Assay IDTitleYearJournalArticle
AID1082384Inhibition of Brassica rapa subsp. oleifera at 100 mg/L2011Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18
Chemical synthesis, in vitro acetohydroxyacid synthase (AHAS) inhibition, herbicidal activity, and computational studies of isatin derivatives.
AID1063518Cytotoxicity against human K562 cells after 48 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2
Design, synthesis and in vitro cytotoxicity evaluation of 5-(2-carboxyethenyl)isatin derivatives as anticancer agents.
AID1284106Anticancer activity against human Jurkat cells after 48 hrs by MTT assay2016European journal of medicinal chemistry, Apr-13, Volume: 112Synthesis and anti-cancer activity evaluation of 5-(2-carboxyethenyl)-isatin derivatives.
AID281479Inhibition of rabbit liver carboxylesterase expressed in sf21 cells2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID1055716Antiproliferative activity against human MCF7 cells after 48 hrs by SRB assay2013European journal of medicinal chemistry, , Volume: 70Novel isatin-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents.
AID213673Inhibitory activity against the Trypanosoma cruzi cysteine protease cruzain2003Bioorganic & medicinal chemistry letters, Oct-20, Volume: 13, Issue:20
Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain.
AID1406678Antiproliferative activity against human K562 cells after 48 hrs by MTT assay
AID1055715Antiproliferative activity against human AsPC1 cells after 48 hrs by SRB assay2013European journal of medicinal chemistry, , Volume: 70Novel isatin-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents.
AID281481Inhibition of human BChE2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID281478Inhibition of human liver CE1 expressed in sf21 cells2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID281480Inhibition of human AChE2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID1082385Inhibition of Arabidopsis thaliana AHAS at 100 mg/L colorimetric assay2011Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18
Chemical synthesis, in vitro acetohydroxyacid synthase (AHAS) inhibition, herbicidal activity, and computational studies of isatin derivatives.
AID72521Inhibitory activity against Falcipain-2; No effect2003Bioorganic & medicinal chemistry letters, Oct-20, Volume: 13, Issue:20
Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain.
AID1063517Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2
Design, synthesis and in vitro cytotoxicity evaluation of 5-(2-carboxyethenyl)isatin derivatives as anticancer agents.
AID1406679Antiproliferative activity against human HepG2 cells after 48 hrs by MTT assay
AID1082383Inhibition of Brassica rapa subsp. oleifera root growth at 10 mg/L2011Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18
Chemical synthesis, in vitro acetohydroxyacid synthase (AHAS) inhibition, herbicidal activity, and computational studies of isatin derivatives.
AID1055714Antiproliferative activity against human PC3 cells after 48 hrs by SRB assay2013European journal of medicinal chemistry, , Volume: 70Novel isatin-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents.
AID197810Inhibitory activity against Rhodesain cysteine protease from Trypanosoma brucei rhodesiense; Not determined2003Bioorganic & medicinal chemistry letters, Oct-20, Volume: 13, Issue:20
Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain.
AID1063516Cytotoxicity against human HT-29 cells after 48 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2
Design, synthesis and in vitro cytotoxicity evaluation of 5-(2-carboxyethenyl)isatin derivatives as anticancer agents.
AID1055717Antiproliferative activity against human SW620 cells after 48 hrs by SRB assay2013European journal of medicinal chemistry, , Volume: 70Novel isatin-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents.
AID281477Inhibition of human intestinal carboxylesterase expressed in sf21 cells2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID1055713Antiproliferative activity against human NCI-H460 cells after 48 hrs by SRB assay2013European journal of medicinal chemistry, , Volume: 70Novel isatin-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
AID1798240Enzyme Inhibition Assay from Article 10.1021/jm061471k: \\Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.\\2007Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8
Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1159537qHTS screening for TAG (triacylglycerol) accumulators in algae2017Plant physiology, Aug, Volume: 174, Issue:4
Identification and Metabolite Profiling of Chemical Activators of Lipid Accumulation in Green Algae.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (18.18)29.6817
2010's8 (72.73)24.3611
2020's1 (9.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.05

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 Index28.05 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index5.00 (4.65)
Search Engine Demand Index24.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.05)

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%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]