Page last updated: 2024-11-12

cymserine

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Description

cymserine: butyrylcholinesterase inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9907847
CHEMBL ID129837
MeSH IDM0497364

Synonyms (15)

Synonym
4-isopropylphenserine
cymserine
cymserine.tartaric acid
(3as,8ar)-1,3a,8-trimethyl-1h,2h,3h,3ah,8h,8ah-pyrrolo[2,3-b]indol-5-yl n-[4-(propan-2-yl)phenyl]carbamate
bdbm10960
CHEMBL129837
(-)-cymserine
145209-39-8
DTXSID10432696
EOI96371PZ ,
carbamic acid, n-(4-(1-methylethyl)phenyl)-, (3as,8ar)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-yl ester
[(3ar,8bs)-3,4,8b-trimethyl-2,3a-dihydro-1h-pyrrolo[2,3-b]indol-7-yl] n-(4-propan-2-ylphenyl)carbamate
unii-eoi96371pz
carbamic acid, n-[4-(1-methylethyl)phenyl]-, (3as,8ar)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-yl ester
PD182241
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
CholinesteraseHomo sapiens (human)IC50 (µMol)0.25290.00001.559910.0000AID1164690; AID1796572; AID1796574; AID1820979; AID1916836
AcetylcholinesteraseMus musculus (house mouse)IC50 (µMol)8.40000.00071.11818.4000AID464986
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)0.48080.00000.933210.0000AID1164699; AID1796572; AID1796574; AID1820943; AID1916835; AID262754; AID31501; AID511766
CholinesteraseMus musculus (house mouse)IC50 (µMol)0.24000.00910.56021.9920AID464987
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (25)

Processvia Protein(s)Taxonomy
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (18)

Assay IDTitleYearJournalArticle
AID464987Inhibition of mouse serum BChE after 1 hr by modified Ellman's colorimetric method2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Design, synthesis, evaluation and QSAR analysis of N(1)-substituted norcymserine derivatives as selective butyrylcholinesterase inhibitors.
AID1916835Inhibition of AChE (unknown origin)2022European journal of medicinal chemistry, Oct-05, Volume: 240Recent advance on carbamate-based cholinesterase inhibitors as potential multifunctional agents against Alzheimer's disease.
AID1916836Inhibition of BChE (unknown origin)2022European journal of medicinal chemistry, Oct-05, Volume: 240Recent advance on carbamate-based cholinesterase inhibitors as potential multifunctional agents against Alzheimer's disease.
AID464988Selectivity ratio of IC50 for mouse serum BChE over IC50 for mouse brain AChE2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Design, synthesis, evaluation and QSAR analysis of N(1)-substituted norcymserine derivatives as selective butyrylcholinesterase inhibitors.
AID1164690Inhibition of recombinant human BChE by Ellman method2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Discovery, biological evaluation, and crystal structure of a novel nanomolar selective butyrylcholinesterase inhibitor.
AID511766Inhibition of human AChE by Ellmans test2010Journal of medicinal chemistry, Sep-09, Volume: 53, Issue:17
Novel carbamates as orally active acetylcholinesterase inhibitors found to improve scopolamine-induced cognition impairment: pharmacophore-based virtual screening, synthesis, and pharmacology.
AID262755Anticholinesterase activity against human plasma BChE2006Journal of medicinal chemistry, Apr-06, Volume: 49, Issue:7
Inhibition of human acetyl- and butyrylcholinesterase by novel carbamates of (-)- and (+)-tetrahydrofurobenzofuran and methanobenzodioxepine.
AID1820943Inhibition of AChE (unknown origin)2022European journal of medicinal chemistry, Feb-05, Volume: 229Design, synthesis, and biological evaluation of carbamate derivatives of N-salicyloyl tryptamine as multifunctional agents for the treatment of Alzheimer's disease.
AID1820979Inhibition of BuChE (unknown origin)2022European journal of medicinal chemistry, Feb-05, Volume: 229Design, synthesis, and biological evaluation of carbamate derivatives of N-salicyloyl tryptamine as multifunctional agents for the treatment of Alzheimer's disease.
AID464986Inhibition of mouse brain AChE after 1 hr by modified Ellman's colorimetric method2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Design, synthesis, evaluation and QSAR analysis of N(1)-substituted norcymserine derivatives as selective butyrylcholinesterase inhibitors.
AID1164699Inhibition of AChE (unknown origin)2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Discovery, biological evaluation, and crystal structure of a novel nanomolar selective butyrylcholinesterase inhibitor.
AID1916838Selectivity index, ratio of IC50 for AChE (unknown origin) to BChE (unknown origin)2022European journal of medicinal chemistry, Oct-05, Volume: 240Recent advance on carbamate-based cholinesterase inhibitors as potential multifunctional agents against Alzheimer's disease.
AID31501In vitro inhibition of human erythrocyte acetylcholinesterase.2001Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24
Methyl analogues of the experimental Alzheimer drug phenserine: synthesis and structure/activity relationships for acetyl- and butyrylcholinesterase inhibitory action.
AID262757Selectivity for BChE over AChE2006Journal of medicinal chemistry, Apr-06, Volume: 49, Issue:7
Inhibition of human acetyl- and butyrylcholinesterase by novel carbamates of (-)- and (+)-tetrahydrofurobenzofuran and methanobenzodioxepine.
AID262754Anticholinesterase activity against human erythrocyte AChE2006Journal of medicinal chemistry, Apr-06, Volume: 49, Issue:7
Inhibition of human acetyl- and butyrylcholinesterase by novel carbamates of (-)- and (+)-tetrahydrofurobenzofuran and methanobenzodioxepine.
AID44293In vitro inhibition of human plasma butyrylcholinesterase.2001Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24
Methyl analogues of the experimental Alzheimer drug phenserine: synthesis and structure/activity relationships for acetyl- and butyrylcholinesterase inhibitory action.
AID1796574Cholinesterase Inhibition Assay from Article 10.1021/jm010080x: \\Methyl analogues of the experimental Alzheimer drug phenserine: synthesis and structure/activity relationships for acetyl- and butyrylcholinesterase inhibitory action.\\2001Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24
Methyl analogues of the experimental Alzheimer drug phenserine: synthesis and structure/activity relationships for acetyl- and butyrylcholinesterase inhibitory action.
AID1796572Cholinesterase Inhibition Assay from Article 10.1021/jm010491d: \\Anticholinesterase activity of compounds related to geneserine tautomers. N-Oxides and 1,2-oxazines.\\2002Journal of medicinal chemistry, Aug-15, Volume: 45, Issue:17
Anticholinesterase activity of compounds related to geneserine tautomers. N-Oxides and 1,2-oxazines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's6 (50.00)29.6817
2010's4 (33.33)24.3611
2020's2 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.26

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 Index17.26 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.65 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (8.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (91.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]