Page last updated: 2024-12-08

dimethyl 2-(2-nitrobenzylidene)malonate

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Description

dimethyl 2-(2-nitrobenzylidene)malonate: inhibits TLR4 signaling; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID277385
CHEMBL ID1569494
SCHEMBL ID7833049
MeSH IDM0581378

Synonyms (16)

Synonym
nsc126224
65974-52-9
mls000737573 ,
nsc-126224
smr000528564
dimethyl 2-[(2-nitrophenyl)methylidene]propanedioate
dimethyl 2-(2-nitrobenzylidene)malonate
HMS2882B21 ,
bdbm50391678
chembl1569494 ,
dimethyl 2-[(2-nitrophenyl)methylidene]malonate
LKLMASCOTOBEMT-UHFFFAOYSA-N
SCHEMBL7833049
DTXSID00298788
nci126224
EX-A8010
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (28)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency7.07950.003245.467312,589.2998AID2517
Chain A, Beta-lactamaseEscherichia coli K-12Potency0.63100.044717.8581100.0000AID485294
Nrf2Homo sapiens (human)Potency3.54810.09208.222223.1093AID624171
glp-1 receptor, partialHomo sapiens (human)Potency10.00000.01846.806014.1254AID624417
thioredoxin reductaseRattus norvegicus (Norway rat)Potency56.23410.100020.879379.4328AID588453
ATAD5 protein, partialHomo sapiens (human)Potency23.09990.004110.890331.5287AID504467
TDP1 proteinHomo sapiens (human)Potency9.89080.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency30.30010.180013.557439.8107AID1460; AID1468
thioredoxin glutathione reductaseSchistosoma mansoniPotency7.07950.100022.9075100.0000AID485364
Smad3Homo sapiens (human)Potency19.95260.00527.809829.0929AID588855
nonstructural protein 1Influenza A virus (A/WSN/1933(H1N1))Potency7.94330.28189.721235.4813AID2326
IDH1Homo sapiens (human)Potency18.35640.005210.865235.4813AID686970
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency79.43280.035520.977089.1251AID504332
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency56.23410.354828.065989.1251AID504847
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency29.09290.00419.984825.9290AID504444
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency31.62283.548119.542744.6684AID743266
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency22.38720.050127.073689.1251AID588590
urokinase-type plasminogen activator precursorMus musculus (house mouse)Potency2.23870.15855.287912.5893AID540303
plasminogen precursorMus musculus (house mouse)Potency2.23870.15855.287912.5893AID540303
urokinase plasminogen activator surface receptor precursorMus musculus (house mouse)Potency2.23870.15855.287912.5893AID540303
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency17.78280.00798.23321,122.0200AID2551
gemininHomo sapiens (human)Potency14.14140.004611.374133.4983AID624296; AID624297
DNA dC->dU-editing enzyme APOBEC-3G isoform 1Homo sapiens (human)Potency8.91250.058010.694926.6086AID602310
neuropeptide S receptor isoform AHomo sapiens (human)Potency7.94330.015812.3113615.5000AID1461
Glycoprotein hormones alpha chainHomo sapiens (human)Potency8.91254.46688.344810.0000AID624291
TAR DNA-binding protein 43Homo sapiens (human)Potency15.84891.778316.208135.4813AID652104
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Toll-like receptor 4 Mus musculus (house mouse)IC50 (µMol)0.75670.00570.56891.5400AID687252; AID687254; AID687256
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Potassium inwardly-rectifying channel, subfamily J, member 1Homo sapiens (human)EC50 (µMol)7.93870.64734.97119.3289AID2753
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Toll-like receptor 4 Mus musculus (house mouse)INH5.92005.92005.92005.9200AID687253
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (32)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell population proliferationGlycoprotein hormones alpha chainHomo sapiens (human)
hormone-mediated signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
regulation of signaling receptor activityGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of steroid biosynthetic processGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell migrationGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid gland developmentGlycoprotein hormones alpha chainHomo sapiens (human)
luteinizing hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIGlycoprotein hormones alpha chainHomo sapiens (human)
negative regulation of organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid hormone generationGlycoprotein hormones alpha chainHomo sapiens (human)
negative regulation of protein phosphorylationTAR DNA-binding protein 43Homo sapiens (human)
mRNA processingTAR DNA-binding protein 43Homo sapiens (human)
RNA splicingTAR DNA-binding protein 43Homo sapiens (human)
negative regulation of gene expressionTAR DNA-binding protein 43Homo sapiens (human)
regulation of protein stabilityTAR DNA-binding protein 43Homo sapiens (human)
positive regulation of insulin secretionTAR DNA-binding protein 43Homo sapiens (human)
response to endoplasmic reticulum stressTAR DNA-binding protein 43Homo sapiens (human)
positive regulation of protein import into nucleusTAR DNA-binding protein 43Homo sapiens (human)
regulation of circadian rhythmTAR DNA-binding protein 43Homo sapiens (human)
regulation of apoptotic processTAR DNA-binding protein 43Homo sapiens (human)
negative regulation by host of viral transcriptionTAR DNA-binding protein 43Homo sapiens (human)
rhythmic processTAR DNA-binding protein 43Homo sapiens (human)
regulation of cell cycleTAR DNA-binding protein 43Homo sapiens (human)
3'-UTR-mediated mRNA destabilizationTAR DNA-binding protein 43Homo sapiens (human)
3'-UTR-mediated mRNA stabilizationTAR DNA-binding protein 43Homo sapiens (human)
nuclear inner membrane organizationTAR DNA-binding protein 43Homo sapiens (human)
amyloid fibril formationTAR DNA-binding protein 43Homo sapiens (human)
regulation of gene expressionTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
protein bindingGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
double-stranded DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
RNA bindingTAR DNA-binding protein 43Homo sapiens (human)
mRNA 3'-UTR bindingTAR DNA-binding protein 43Homo sapiens (human)
protein bindingTAR DNA-binding protein 43Homo sapiens (human)
lipid bindingTAR DNA-binding protein 43Homo sapiens (human)
identical protein bindingTAR DNA-binding protein 43Homo sapiens (human)
pre-mRNA intronic bindingTAR DNA-binding protein 43Homo sapiens (human)
molecular condensate scaffold activityTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
extracellular regionGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
Golgi lumenGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone complexGlycoprotein hormones alpha chainHomo sapiens (human)
pituitary gonadotropin complexGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
intracellular non-membrane-bounded organelleTAR DNA-binding protein 43Homo sapiens (human)
nucleusTAR DNA-binding protein 43Homo sapiens (human)
nucleoplasmTAR DNA-binding protein 43Homo sapiens (human)
perichromatin fibrilsTAR DNA-binding protein 43Homo sapiens (human)
mitochondrionTAR DNA-binding protein 43Homo sapiens (human)
cytoplasmic stress granuleTAR DNA-binding protein 43Homo sapiens (human)
nuclear speckTAR DNA-binding protein 43Homo sapiens (human)
interchromatin granuleTAR DNA-binding protein 43Homo sapiens (human)
nucleoplasmTAR DNA-binding protein 43Homo sapiens (human)
chromatinTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
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.
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.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID687260Inhibition of TLR1/TLR2 in Pam3CSK4-stimulated mouse RAW264.7 cells at 0.6 uM after 24 hrs2012Bioorganic & medicinal chemistry, Oct-15, Volume: 20, Issue:20
Selection, synthesis, and anti-inflammatory evaluation of the arylidene malonate derivatives as TLR4 signaling inhibitors.
AID687262Inhibition of TLR3 in poly(I:C)-stimulated mouse RAW264.7 cells at 0.6 uM after 24 hrs2012Bioorganic & medicinal chemistry, Oct-15, Volume: 20, Issue:20
Selection, synthesis, and anti-inflammatory evaluation of the arylidene malonate derivatives as TLR4 signaling inhibitors.
AID687254Inhibition of TLR4 in LPS-stimulated mouse RAW264.7 cells assessed as reduction of NO production after 24 hrs2012Bioorganic & medicinal chemistry, Oct-15, Volume: 20, Issue:20
Selection, synthesis, and anti-inflammatory evaluation of the arylidene malonate derivatives as TLR4 signaling inhibitors.
AID687263Inhibition of TLR2/TLR6 in FSL1-stimulated mouse RAW264.7 cells at 0.6 uM after 24 hrs2012Bioorganic & medicinal chemistry, Oct-15, Volume: 20, Issue:20
Selection, synthesis, and anti-inflammatory evaluation of the arylidene malonate derivatives as TLR4 signaling inhibitors.
AID1446908Inhibition of human KDAC6 expressed in baculovirus expression system at 30 uM using FITC-Histone 4 acetylated peptide as substrate after 60 mins by microfluidic assay2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
Structural insights of SmKDAC8 inhibitors: Targeting Schistosoma epigenetics through a combined structure-based 3D QSAR, in vitro and synthesis strategy.
AID1446906Inhibition of full length human C-terminal FLAG/His-tagged KDAC1 expressed in baculovirus expression system at 30 uM using substrate A after 60 mins by microfluidic assay relative to control2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
Structural insights of SmKDAC8 inhibitors: Targeting Schistosoma epigenetics through a combined structure-based 3D QSAR, in vitro and synthesis strategy.
AID687256Inhibition of TLR4 in LPS-stimulated mouse RAW264.7 cells assessed as reduction of IL1-beta production after 24 hrs by ELISA2012Bioorganic & medicinal chemistry, Oct-15, Volume: 20, Issue:20
Selection, synthesis, and anti-inflammatory evaluation of the arylidene malonate derivatives as TLR4 signaling inhibitors.
AID687253Inhibition of TLR4 in LPS-stimulated mouse BV2 cells assessed as reduction of NF-kappaB activation after 24 hrs by Dual-GLO luciferase assay2012Bioorganic & medicinal chemistry, Oct-15, Volume: 20, Issue:20
Selection, synthesis, and anti-inflammatory evaluation of the arylidene malonate derivatives as TLR4 signaling inhibitors.
AID687252Inhibition of TLR4 in LPS-stimulated mouse RAW264.7 cells assessed as reduction of TNFalpha production after 24 hrs by ELISA2012Bioorganic & medicinal chemistry, Oct-15, Volume: 20, Issue:20
Selection, synthesis, and anti-inflammatory evaluation of the arylidene malonate derivatives as TLR4 signaling inhibitors.
AID1446910Inhibition of Schistosoma mansoni KDAC8 at 30 uM using (FAM)-labeled peptide as substrate after 60 mins by microfluidic assay2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
Structural insights of SmKDAC8 inhibitors: Targeting Schistosoma epigenetics through a combined structure-based 3D QSAR, in vitro and synthesis strategy.
AID687255Cytotoxicity against mouse RAW264.7 cells assessed as cell viability up to 10 uM after 24 hrs by WST-1 assay2012Bioorganic & medicinal chemistry, Oct-15, Volume: 20, Issue:20
Selection, synthesis, and anti-inflammatory evaluation of the arylidene malonate derivatives as TLR4 signaling inhibitors.
AID1446907Inhibition of full length human C-terminal His-tagged KDAC3/N-terminal GST-tagged human NCOR2 (395 to 489 residues) expressed in baculovirus expression system at 30 uM using FITC-p53 acetylated peptide as substrate after 60 mins by microfluidic assay2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
Structural insights of SmKDAC8 inhibitors: Targeting Schistosoma epigenetics through a combined structure-based 3D QSAR, in vitro and synthesis strategy.
AID1446909Inhibition of full length human C-terminal His-tagged KDAC8 expressed in baculovirus expression system at 30 uM using (FAM)-labeled peptide as substrate after 60 mins by microfluidic assay relative to control2017Bioorganic & medicinal chemistry, 04-01, Volume: 25, Issue:7
Structural insights of SmKDAC8 inhibitors: Targeting Schistosoma epigenetics through a combined structure-based 3D QSAR, in vitro and synthesis strategy.
AID687261Inhibition of TLR7/TLR8 in R848-stimulated mouse RAW264.7 cells at 0.6 uM after 24 hrs2012Bioorganic & medicinal chemistry, Oct-15, Volume: 20, Issue:20
Selection, synthesis, and anti-inflammatory evaluation of the arylidene malonate derivatives as TLR4 signaling inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (14.29)29.6817
2010's5 (71.43)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.29

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.29 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.29)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]