Page last updated: 2024-12-11

3,5-dimethoxy-trans-stilbene

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Description

3,5-dimethoxystilbene: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5316874
CHEMBL ID188181
CHEBI ID173733
SCHEMBL ID918727
SCHEMBL ID918726
MeSH IDM0561223

Synonyms (44)

Synonym
(e)-3,5-dimethoxystilbene
CHEBI:173733
21956-56-9
1,3-dimethoxy-5-[(e)-2-phenylethenyl]benzene
mls002608528 ,
78916-49-1
nsc43313
nsc-43313
3,5-dimethoxy-trans-stilbene
AKOS000277656
trans-3,5-dimethoxystilbene
CHEMBL188181 ,
smr001527275
3,5-dimethoxystilbene
D2592
HMS3087I14
1,3-dimethoxy-5-styryl-benzene
A815783
bdbm50394654
SCHEMBL918727
SCHEMBL918726
(e)-1,3-dimethoxy-5-styrylbenzene
trans-pinosylvin dimethyl ether
(e)-1-(3,5-dimethoxyphenyl)-2-phenylethene
benzene, 1,3-dimethoxy-5-[(1e)-2-phenylethenyl]-
pinosylvin, dimethyl ether
benzene, 1,3-dimethoxy-5-(2-phenylethenyl)-, (e)-
AC-24222
DWA4D52V24 ,
stilbene, 3,5-dimethoxy-, (e)-
pinosylvin dimethyl ether
benzene, 1,3-dimethoxy-5-((1e)-2-phenylethenyl)-
unii-dwa4d52v24
3,5-dimethoxystilbene, aldrichcpr
mfcd00210545
AS-58979
1,3-dimethoxy-5-[(1e)-2-phenylethenyl]benzene
1,3-dimethoxy-5-styrylbenzene
DTXSID301016205
Q27276649
D90087
CS-0323981
3,5-dimethoxy trans-stilbene
Z3245416406
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
stilbenoidAny olefinic compound characterised by a 1,2-diphenylethylene backbone.
[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 (13)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency79.43280.631035.7641100.0000AID504339
Nrf2Homo sapiens (human)Potency15.84890.09208.222223.1093AID624171
thioredoxin reductaseRattus norvegicus (Norway rat)Potency71.77220.100020.879379.4328AID588453; AID588456
PINK1Homo sapiens (human)Potency39.81072.818418.895944.6684AID624263
ParkinHomo sapiens (human)Potency39.81070.819914.830644.6684AID624263
chromobox protein homolog 1Homo sapiens (human)Potency56.23410.006026.168889.1251AID540317
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency23.10930.00419.984825.9290AID504444
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency100.00000.050127.073689.1251AID588590
gemininHomo sapiens (human)Potency23.72460.004611.374133.4983AID624296; AID624297
Guanine nucleotide-binding protein GHomo sapiens (human)Potency2.81841.995325.532750.1187AID624287
[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)
AcetylcholinesteraseElectrophorus electricus (electric eel)IC50 (µMol)9.00000.00000.94539.9400AID696908
Transient receptor potential cation channel subfamily A member 1Rattus norvegicus (Norway rat)IC50 (µMol)3.40000.45003.42437.5000AID1272522
Transient receptor potential cation channel subfamily V member 1Homo sapiens (human)IC50 (µMol)10.00000.00020.606010.0000AID1272526
[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)
Transient receptor potential cation channel subfamily A member 1Rattus norvegicus (Norway rat)EC50 (µMol)1.70000.06002.22238.4000AID1272523
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (42)

Processvia Protein(s)Taxonomy
negative regulation of inflammatory response to antigenic stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
renal water homeostasisGuanine nucleotide-binding protein GHomo sapiens (human)
G protein-coupled receptor signaling pathwayGuanine nucleotide-binding protein GHomo sapiens (human)
regulation of insulin secretionGuanine nucleotide-binding protein GHomo sapiens (human)
cellular response to glucagon stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
thermoceptionTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
negative regulation of transcription by RNA polymerase IITransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
fever generationTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
microglial cell activationTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
diet induced thermogenesisTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
peptide secretionTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
negative regulation of systemic arterial blood pressureTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
lipid metabolic processTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cell surface receptor signaling pathwayTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
chemosensory behaviorTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
negative regulation of heart rateTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
negative regulation of mitochondrial membrane potentialTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
glutamate secretionTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
calcium-mediated signalingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to heatTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
positive regulation of apoptotic processTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
response to peptide hormoneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
positive regulation of nitric oxide biosynthetic processTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
behavioral response to painTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
sensory perception of mechanical stimulusTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
detection of temperature stimulus involved in thermoceptionTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
detection of temperature stimulus involved in sensory perception of painTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
detection of chemical stimulus involved in sensory perception of painTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
protein homotetramerizationTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
excitatory postsynaptic potentialTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
smooth muscle contraction involved in micturitionTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
calcium ion transmembrane transportTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to alkaloidTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to ATPTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to tumor necrosis factorTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to acidic pHTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to temperature stimulusTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
negative regulation of establishment of blood-brain barrierTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
calcium ion import across plasma membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
response to capsazepineTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to nerve growth factor stimulusTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (17)

Processvia Protein(s)Taxonomy
G protein activityGuanine nucleotide-binding protein GHomo sapiens (human)
adenylate cyclase activator activityGuanine nucleotide-binding protein GHomo sapiens (human)
transmembrane signaling receptor activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
extracellular ligand-gated monoatomic ion channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
voltage-gated calcium channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
calcium channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
protein bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
calmodulin bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
ATP bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
intracellularly gated calcium channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
chloride channel regulator activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
phosphatidylinositol bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
identical protein bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
metal ion bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
phosphoprotein bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
temperature-gated ion channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
plasma membraneGuanine nucleotide-binding protein GHomo sapiens (human)
plasma membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
external side of plasma membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
dendritic spine membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
neuronal cell bodyTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
postsynaptic membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
plasma membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (35)

Assay IDTitleYearJournalArticle
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
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.
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.
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1081919Octanol-water partition coefficient, log P of the compound by HPLC analysis2011Journal of agricultural and food chemistry, Mar-09, Volume: 59, Issue:5
Biological activity of peanut (Arachis hypogaea) phytoalexins and selected natural and synthetic Stilbenoids.
AID1272524Agonist activity at rat TRPA1 expressed in HEK293 cells assessed as induction of intracellular calcium level relative to allyl isothiocyanate2016Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3
TRPA1 channels as targets for resveratrol and related stilbenoids.
AID696905Cytotoxicity against human KB cells at 20 uM after 72 hrs by neutral red staining2012Journal of natural products, Nov-26, Volume: 75, Issue:11
Acetylcholinesterase inhibitors from the leaves of Macaranga kurzii.
AID349224Antimicrobial activity against methicillin-resistant Staphylococcus aureus MC1 by NCCLS M7-A6 method2008Bioorganic & medicinal chemistry letters, Nov-01, Volume: 18, Issue:21
New classes of Gram-positive selective antibacterials: inhibitors of MRSA and surrogates of the causative agents of anthrax and tuberculosis.
AID1272523Agonist activity at rat TRPA1 expressed in HEK293 cells assessed as induction of intracellular calcium level2016Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3
TRPA1 channels as targets for resveratrol and related stilbenoids.
AID1272525Agonist activity at human TRPV1 expressed in HEK293 cells assessed as induction of intracellular calcium level relative to allyl isothiocyanate2016Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3
TRPA1 channels as targets for resveratrol and related stilbenoids.
AID1081915Antifungal activity against Phomopsis obscurans assessed as growth inhibition at 30 uM after 144 hr by NCCLS M27-A broth microdilution method2011Journal of agricultural and food chemistry, Mar-09, Volume: 59, Issue:5
Biological activity of peanut (Arachis hypogaea) phytoalexins and selected natural and synthetic Stilbenoids.
AID360867Antifungal activity against Cladosporium cucumerinum after 24 hrs by agar-dilution assay2001Journal of natural products, Jun, Volume: 64, Issue:6
Five new prenylated stilbenes from the root bark of Lonchocarpus chiricanus.
AID349238Antimicrobial activity against Escherichia coli by NCCLS M7-A6 method2008Bioorganic & medicinal chemistry letters, Nov-01, Volume: 18, Issue:21
New classes of Gram-positive selective antibacterials: inhibitors of MRSA and surrogates of the causative agents of anthrax and tuberculosis.
AID349233Antimicrobial activity against Bacillus cereus by NCCLS M7-A6 method2008Bioorganic & medicinal chemistry letters, Nov-01, Volume: 18, Issue:21
New classes of Gram-positive selective antibacterials: inhibitors of MRSA and surrogates of the causative agents of anthrax and tuberculosis.
AID349241Antimicrobial activity against Mycobacterium smegmatis by NCCLS M7-A6 method2008Bioorganic & medicinal chemistry letters, Nov-01, Volume: 18, Issue:21
New classes of Gram-positive selective antibacterials: inhibitors of MRSA and surrogates of the causative agents of anthrax and tuberculosis.
AID696908Inhibition of Electrophorus electricus C2888 AChE using acetylthiocholine iodide as substrate by Ellman's spectroscopic method2012Journal of natural products, Nov-26, Volume: 75, Issue:11
Acetylcholinesterase inhibitors from the leaves of Macaranga kurzii.
AID360868Antifungal activity against Cladosporium cucumerinum at 100 ug after 2 to 3 days by bioautographic TLC assay2001Journal of natural products, Jun, Volume: 64, Issue:6
Five new prenylated stilbenes from the root bark of Lonchocarpus chiricanus.
AID360869Larvicidal activity against Aedes aegypti larvae assessed as minimum concentration required to kill all larvae after 24 hrs by dilution test2001Journal of natural products, Jun, Volume: 64, Issue:6
Five new prenylated stilbenes from the root bark of Lonchocarpus chiricanus.
AID1467689Inhibition of human TRPA1 expressed in HEK293 cells assessed as decrease in AITC-induced calcium influx at 30 uM preincubated for 6 mins followed by AITC addition measured for 1 min by Fluo-4 dye-based assay relative to resveratrol2017Bioorganic & medicinal chemistry letters, 07-15, Volume: 27, Issue:14
Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor.
AID1272526Antagonist activity at human TRPV1 expressed in HEK293 cells assessed as inhibition of allyl isothiocyanate-induced increase of intracellular calcium level2016Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3
TRPA1 channels as targets for resveratrol and related stilbenoids.
AID248171inhibitory concentration against PGE-2 production in LPS-stimulated RAW264.7 cells2004Bioorganic & medicinal chemistry letters, Dec-06, Volume: 14, Issue:23
Synthesis and inhibitory effects of pinosylvin derivatives on prostaglandin E2 production in lipopolysaccharide-induced mouse macrophage cells.
AID1272522Antagonist activity at rat TRPA1 expressed in HEK293 cells assessed as inhibition of allyl isothiocyanate-induced increase of intracellular calcium level2016Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3
TRPA1 channels as targets for resveratrol and related stilbenoids.
AID1314129Stability of the compound2016Bioorganic & medicinal chemistry letters, 08-15, Volume: 26, Issue:16
A facile and rapid access to resveratrol derivatives and their radioprotective activity.
AID1467690Agonist activity at human TRPA1 expressed in HEK293 cells assessed as induction of calcium influx at 30 uM after 6 mins by Fluo-4 dye-based assay relative to AITC2017Bioorganic & medicinal chemistry letters, 07-15, Volume: 27, Issue:14
Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor.
AID349222Antimicrobial activity against Staphylococcus aureus ATCC 29213 by NCCLS M7-A6 method2008Bioorganic & medicinal chemistry letters, Nov-01, Volume: 18, Issue:21
New classes of Gram-positive selective antibacterials: inhibitors of MRSA and surrogates of the causative agents of anthrax and tuberculosis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (28.57)29.6817
2010's8 (57.14)24.3611
2020's2 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]