Page last updated: 2024-11-10

pinosylvin

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

Description

pinosylvin: phytoalexin found in pine and eucalyptus [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
EucalyptusgenusA genus of trees of the Myrtaceae family, native to Australia, that yields gums, oils, and resins which are used as flavoring agents, astringents, and aromatics.[MeSH]MyrtaceaeThe myrtle plant family of the order Myrtales. It includes several aromatic medicinal plants such as EUCALYPTUS.[MeSH]

Cross-References

ID SourceID
PubMed CID5280457
CHEMBL ID101506
CHEBI ID36011
CHEBI ID17323
SCHEMBL ID454262
MeSH IDM0140732

Synonyms (63)

Synonym
AC-7928
CHEBI:36011
5-(2-phenylethenyl)-1,3-benzenediol
5-(2-phenylvinyl)benzene-1,3-diol
stilbene, 1f
bdbm50045924
BRD-K94645280-001-02-1
(e)-5-(2-phenylethenyl)-1,3-benzenediol
5-[(1e)-2-phenylethenyl]benzene-1,3-diol
(e)-pinosylvin
(e)-3,5-stilbenediol
trans-3,5-dihydroxystilbene
5-[(e)-2-phenylvinyl]benzene-1,3-diol
pinosylvine
CHEBI:17323 ,
trans-pinosylvin
SDCCGMLS-0066433.P001
BSPBIO_001753
nsc362430
nsc-362430
22139-77-1
NCGC00179033-01
5-[(e)-styryl]benzene-1,3-diol
(trans)-3,5-stilbenediol
SPECTRUM5_000307
3,5-stilbenediol
pinosylvin
C01745 ,
102-61-4
nsc 362430
brn 1870942
3,5-stilbenediol, (e)-
1,3-benzenediol, 5-(2-phenylethenyl)-, (e)-
LMPK13090001
D33B05BD-8441-4288-A247-D461C3D1F1CA
stilbene, 3,5-dihydroxy-, trans-
AKOS000276828
CHEMBL101506 ,
5-[(e)-2-phenylethenyl]benzene-1,3-diol
A815968
881r434aib ,
3,5-dihydroxy-trans-stilbene
unii-881r434aib
3-06-00-05577 (beilstein handbook reference)
5-((1e)-2-phenylethenyl)-1,3-benzenediol
1,3-benzenediol, 5-(2-phenylethenyl)-
CCG-38399
SCHEMBL454262
pinosylvin [mi]
1,3-benzenediol, 5-((1e)-2-phenylethenyl)-
(e)-5-styrylbenzene-1,3-diol
1,3-benzenediol, 5-[(1e)-2-phenylethenyl]-
5-[(e)-2-phenylethenyl]-1,3-benzenediol
pinosylvin, >=97.0% (hplc)
BCP18617
DTXSID00895857
5-[(1e)-2-phenylethenyl]-1,3-benzenediol
mfcd00210544
Q7196412
EX-A3505
HY-N2387
CS-0022590
AS-76520

Research Excerpts

Overview

Pinosylvin is a phenolic compound mainly found in the Pinus species. It is an effective inhibitor of neutrophil activity, and is potentially useful as a complementary medicine in states associated with persistent inflammation.

ExcerptReferenceRelevance
"Pinosylvin is a natural stilbenoid found particularly in Scots pine. "( Pinosylvin Shifts Macrophage Polarization to Support Resolution of Inflammation.
Hämäläinen, M; Kivimäki, K; Leppänen, T; Moilanen, E; Vuolteenaho, K, 2021
)
3.51
"Pinosylvin is a known functional compound of the Pinus species. "( Pinosylvin at a high concentration induces AMPK-mediated autophagy for preventing necrosis in bovine aortic endothelial cells.
Park, H; Park, J; Pyee, J, 2014
)
3.29
"Pinosylvin is a natural stilbenoid known to exhibit antibacterial bioactivity against foodborne bacteria. "( Pinosylvin-Based Polymers: Biodegradable Poly(Anhydride-Esters) for Extended Release of Antibacterial Pinosylvin.
Bien-Aime, S; Uhrich, KE; Yu, W, 2016
)
3.32
"Pinosylvin is a phenolic compound mainly found in the Pinus species. "( Pinosylvin induces cell survival, migration and anti-adhesiveness of endothelial cells via nitric oxide production.
Jeong, E; Lee, HR; Park, H; Pyee, J, 2013
)
3.28
"Pinosylvin is an effective inhibitor of neutrophil activity, and is potentially useful as a complementary medicine in states associated with persistent inflammation."( The natural stilbenoid pinosylvin and activated neutrophils: effects on oxidative burst, protein kinase C, apoptosis and efficiency in adjuvant arthritis.
Drábiková, K; Harmatha, J; Jančinová, V; Nosáľ, R; Perečko, T; Smidrkal, J, 2012
)
2.13
"Pinosylvin was shown to be a potent inhibitor of PDCHSX (K(i) = 6 microM) as well as PDSTS2 (K(i) = 13 microM), which presumably maintains the balance between the stilbenoid and flavonoid biosyntheses."( A stilbene synthase from Japanese red pine (Pinus densiflora): implications for phytoalexin accumulation and down-regulation of flavonoid biosynthesis.
Kodan, A; Kuroda, H; Sakai, F, 2002
)
1.04

Pharmacokinetics

ExcerptReferenceRelevance
" The pharmacokinetic profiles of pinosylvin were subsequently assessed in Sprague-Dawley rats."( Quantification of pinosylvin in rat plasma by liquid chromatography-tandem mass spectrometry: application to a pre-clinical pharmacokinetic study.
Ho, PC; Lin, HS; Luo, W; Wu, J; Yeo, SC, 2013
)
1

Bioavailability

pinosylvin could not be quantified in plasma at 15mg/kg. Dose-escalation to 50mg/ kg led to a low and erratic plasma exposure with very poor estimated oral bioavailability (F<1%)

ExcerptReferenceRelevance
" The estimates of oral bioavailability characterize these stilbenes as poorly bioavailable compounds."( Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats.
Davies, NM; Roupe, KA; Teng, XW; Yáñez, JA, 2006
)
0.57
" These results serve to highlight the contrasting effects on different activities brought about by methoxylation, which is widely employed as a structural modification approach to improve potency and bioavailability of resveratrol."( Methoxylation of resveratrol: effects on induction of NAD(P)H quinone-oxidoreductase 1 (NQO1) activity and growth inhibitory properties.
Go, ML; Zhang, W, 2011
)
0.37
" Upon oral administration at 15mg/kg, pinosylvin could not be quantified in plasma (<1ng/mL) while dose-escalation to 50mg/kg led to a low and erratic plasma exposure with very poor estimated oral bioavailability (F<1%)."( Quantification of pinosylvin in rat plasma by liquid chromatography-tandem mass spectrometry: application to a pre-clinical pharmacokinetic study.
Ho, PC; Lin, HS; Luo, W; Wu, J; Yeo, SC, 2013
)
0.99
" Methyl pinosylvin, pinosylvin, matairesinol, nortrachelogenin, as well as resveratrol, a metabolite of pinosylvin, were detected in serum at total concentration of 7-73 μM, confirming the bioavailability of pine knot extract derived lignans and stilbenoids."( Novel Lignan and stilbenoid mixture shows anticarcinogenic efficacy in preclinical PC-3M-luc2 prostate cancer model.
Aittokallio, T; Eckerman, C; Holmbom, B; Laajala, TD; Mäkelä, SI; Polari, L; Saarinen, NM; Smeds, A; Yatkin, E, 2014
)
0.84

Dosage Studied

ExcerptRelevanceReference
" From this active fraction, seven compounds have been isolated and four compounds (pinosylvin, galangin, quercetin and methyl gallate) have been examined for their dose-response effect on the viability of A549 cells and on TNF-α inhibitory activity."( Bioactivity guided isolation of anticancer constituents from leaves of Alnus sieboldiana (Betulaceae).
Asakawa, Y; Kuzuhara, T; Ludwiczuk, A; Saha, A, 2011
)
0.59
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pinosylvin
[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]

Pathways (2)

PathwayProteinsCompounds
pinosylvin metabolism211
pinobanksin biosynthesis115
pinobanksin biosynthesis215

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Tyrosine-protein kinase LckHomo sapiens (human)IC50 (µMol)193.00000.00021.317310.0000AID164858
Cytochrome P450 1B1Homo sapiens (human)Ki0.07430.00300.97417.4600AID1799522
Transient receptor potential cation channel subfamily A member 1Rattus norvegicus (Norway rat)IC50 (µMol)12.10000.45003.42437.5000AID1272522
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]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (115)

Processvia Protein(s)Taxonomy
protein phosphorylationTyrosine-protein kinase LckHomo sapiens (human)
intracellular zinc ion homeostasisTyrosine-protein kinase LckHomo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic processTyrosine-protein kinase LckHomo sapiens (human)
response to xenobiotic stimulusTyrosine-protein kinase LckHomo sapiens (human)
peptidyl-tyrosine phosphorylationTyrosine-protein kinase LckHomo sapiens (human)
hemopoiesisTyrosine-protein kinase LckHomo sapiens (human)
platelet activationTyrosine-protein kinase LckHomo sapiens (human)
T cell differentiationTyrosine-protein kinase LckHomo sapiens (human)
T cell costimulationTyrosine-protein kinase LckHomo sapiens (human)
positive regulation of heterotypic cell-cell adhesionTyrosine-protein kinase LckHomo sapiens (human)
intracellular signal transductionTyrosine-protein kinase LckHomo sapiens (human)
peptidyl-tyrosine autophosphorylationTyrosine-protein kinase LckHomo sapiens (human)
Fc-gamma receptor signaling pathwayTyrosine-protein kinase LckHomo sapiens (human)
T cell receptor signaling pathwayTyrosine-protein kinase LckHomo sapiens (human)
positive regulation of T cell receptor signaling pathwayTyrosine-protein kinase LckHomo sapiens (human)
positive regulation of T cell activationTyrosine-protein kinase LckHomo sapiens (human)
leukocyte migrationTyrosine-protein kinase LckHomo sapiens (human)
release of sequestered calcium ion into cytosolTyrosine-protein kinase LckHomo sapiens (human)
regulation of lymphocyte activationTyrosine-protein kinase LckHomo sapiens (human)
positive regulation of leukocyte cell-cell adhesionTyrosine-protein kinase LckHomo sapiens (human)
positive regulation of intrinsic apoptotic signaling pathwayTyrosine-protein kinase LckHomo sapiens (human)
innate immune responseTyrosine-protein kinase LckHomo sapiens (human)
cell surface receptor protein tyrosine kinase signaling pathwayTyrosine-protein kinase LckHomo sapiens (human)
B cell receptor signaling pathwayTyrosine-protein kinase LckHomo sapiens (human)
cellular response to organic cyclic compoundCytochrome P450 1B1Homo sapiens (human)
angiogenesisCytochrome P450 1B1Homo sapiens (human)
trabecular meshwork developmentCytochrome P450 1B1Homo sapiens (human)
DNA modificationCytochrome P450 1B1Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 1B1Homo sapiens (human)
nitric oxide biosynthetic processCytochrome P450 1B1Homo sapiens (human)
cell adhesionCytochrome P450 1B1Homo sapiens (human)
response to nutrientCytochrome P450 1B1Homo sapiens (human)
steroid metabolic processCytochrome P450 1B1Homo sapiens (human)
estrogen metabolic processCytochrome P450 1B1Homo sapiens (human)
negative regulation of cell population proliferationCytochrome P450 1B1Homo sapiens (human)
male gonad developmentCytochrome P450 1B1Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to oxidative stressCytochrome P450 1B1Homo sapiens (human)
toxin metabolic processCytochrome P450 1B1Homo sapiens (human)
positive regulation of vascular endothelial growth factor productionCytochrome P450 1B1Homo sapiens (human)
positive regulation of smooth muscle cell migrationCytochrome P450 1B1Homo sapiens (human)
sterol metabolic processCytochrome P450 1B1Homo sapiens (human)
arachidonic acid metabolic processCytochrome P450 1B1Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 1B1Homo sapiens (human)
collagen fibril organizationCytochrome P450 1B1Homo sapiens (human)
adrenal gland developmentCytochrome P450 1B1Homo sapiens (human)
negative regulation of cell migrationCytochrome P450 1B1Homo sapiens (human)
negative regulation of NF-kappaB transcription factor activityCytochrome P450 1B1Homo sapiens (human)
response to follicle-stimulating hormoneCytochrome P450 1B1Homo sapiens (human)
response to estradiolCytochrome P450 1B1Homo sapiens (human)
negative regulation of cell adhesion mediated by integrinCytochrome P450 1B1Homo sapiens (human)
benzene-containing compound metabolic processCytochrome P450 1B1Homo sapiens (human)
retinol metabolic processCytochrome P450 1B1Homo sapiens (human)
retinal metabolic processCytochrome P450 1B1Homo sapiens (human)
positive regulation of apoptotic processCytochrome P450 1B1Homo sapiens (human)
blood vessel endothelial cell migrationCytochrome P450 1B1Homo sapiens (human)
endothelial cell migrationCytochrome P450 1B1Homo sapiens (human)
estrous cycleCytochrome P450 1B1Homo sapiens (human)
positive regulation of translationCytochrome P450 1B1Homo sapiens (human)
positive regulation of angiogenesisCytochrome P450 1B1Homo sapiens (human)
positive regulation of receptor signaling pathway via JAK-STATCytochrome P450 1B1Homo sapiens (human)
membrane lipid catabolic processCytochrome P450 1B1Homo sapiens (human)
response to arsenic-containing substanceCytochrome P450 1B1Homo sapiens (human)
blood vessel morphogenesisCytochrome P450 1B1Homo sapiens (human)
retinal blood vessel morphogenesisCytochrome P450 1B1Homo sapiens (human)
ganglion developmentCytochrome P450 1B1Homo sapiens (human)
cellular response to hydrogen peroxideCytochrome P450 1B1Homo sapiens (human)
cellular response to cAMPCytochrome P450 1B1Homo sapiens (human)
cellular response to tumor necrosis factorCytochrome P450 1B1Homo sapiens (human)
cellular response to luteinizing hormone stimulusCytochrome P450 1B1Homo sapiens (human)
cellular response to cortisol stimulusCytochrome P450 1B1Homo sapiens (human)
cellular response to progesterone stimulusCytochrome P450 1B1Homo sapiens (human)
response to dexamethasoneCytochrome P450 1B1Homo sapiens (human)
endothelial cell-cell adhesionCytochrome P450 1B1Homo sapiens (human)
response to indole-3-methanolCytochrome P450 1B1Homo sapiens (human)
cellular response to toxic substanceCytochrome P450 1B1Homo sapiens (human)
omega-hydroxylase P450 pathwayCytochrome P450 1B1Homo sapiens (human)
response to 3-methylcholanthreneCytochrome P450 1B1Homo sapiens (human)
regulation of reactive oxygen species metabolic processCytochrome P450 1B1Homo sapiens (human)
positive regulation of reactive oxygen species metabolic processCytochrome P450 1B1Homo sapiens (human)
positive regulation of DNA biosynthetic processCytochrome P450 1B1Homo 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 (38)

Processvia Protein(s)Taxonomy
phosphotyrosine residue bindingTyrosine-protein kinase LckHomo sapiens (human)
protein tyrosine kinase activityTyrosine-protein kinase LckHomo sapiens (human)
non-membrane spanning protein tyrosine kinase activityTyrosine-protein kinase LckHomo sapiens (human)
protein serine/threonine phosphatase activityTyrosine-protein kinase LckHomo sapiens (human)
protein bindingTyrosine-protein kinase LckHomo sapiens (human)
ATP bindingTyrosine-protein kinase LckHomo sapiens (human)
phospholipase activator activityTyrosine-protein kinase LckHomo sapiens (human)
protein kinase bindingTyrosine-protein kinase LckHomo sapiens (human)
protein phosphatase bindingTyrosine-protein kinase LckHomo sapiens (human)
SH2 domain bindingTyrosine-protein kinase LckHomo sapiens (human)
T cell receptor bindingTyrosine-protein kinase LckHomo sapiens (human)
CD4 receptor bindingTyrosine-protein kinase LckHomo sapiens (human)
CD8 receptor bindingTyrosine-protein kinase LckHomo sapiens (human)
identical protein bindingTyrosine-protein kinase LckHomo sapiens (human)
phospholipase bindingTyrosine-protein kinase LckHomo sapiens (human)
phosphatidylinositol 3-kinase bindingTyrosine-protein kinase LckHomo sapiens (human)
ATPase bindingTyrosine-protein kinase LckHomo sapiens (human)
signaling receptor bindingTyrosine-protein kinase LckHomo sapiens (human)
monooxygenase activityCytochrome P450 1B1Homo sapiens (human)
iron ion bindingCytochrome P450 1B1Homo sapiens (human)
protein bindingCytochrome P450 1B1Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 1B1Homo sapiens (human)
heme bindingCytochrome P450 1B1Homo sapiens (human)
aromatase activityCytochrome P450 1B1Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 1B1Homo sapiens (human)
hydroperoxy icosatetraenoate dehydratase activityCytochrome P450 1B1Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, NAD(P)H as one donor, and incorporation of one atom of oxygenCytochrome P450 1B1Homo 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 (14)

Processvia Protein(s)Taxonomy
pericentriolar materialTyrosine-protein kinase LckHomo sapiens (human)
immunological synapseTyrosine-protein kinase LckHomo sapiens (human)
cytosolTyrosine-protein kinase LckHomo sapiens (human)
plasma membraneTyrosine-protein kinase LckHomo sapiens (human)
membrane raftTyrosine-protein kinase LckHomo sapiens (human)
extracellular exosomeTyrosine-protein kinase LckHomo sapiens (human)
plasma membraneTyrosine-protein kinase LckHomo sapiens (human)
mitochondrionCytochrome P450 1B1Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 1B1Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 1B1Homo 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 (52)

Assay IDTitleYearJournalArticle
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.
AID568508Cytotoxicity against mouse Hepa-1c1c7 cells after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Feb-01, Volume: 21, Issue:3
Methoxylation of resveratrol: effects on induction of NAD(P)H quinone-oxidoreductase 1 (NQO1) activity and growth inhibitory properties.
AID1354540Antiinflammatory activity in mouse J774 cells assessed as reduction in LPS-induced nitric oxide production after 24 hrs by Griess assay2018Journal of natural products, 05-25, Volume: 81, Issue:5
Natural Stilbenoids Have Anti-Inflammatory Properties in Vivo and Down-Regulate the Production of Inflammatory Mediators NO, IL6, and MCP1 Possibly in a PI3K/Akt-Dependent Manner.
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.
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.
AID1081917Antifungal activity against Diaporthe ampelina assessed as growth inhibition after 120 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.
AID334606Growth inhibition of Cladosporium herbarum VIAM MA1511 at 10 ug by bioautography test2002Journal of natural products, Jun, Volume: 65, Issue:6
Antifungal stilbenoids from Stemona collinsae.
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.
AID402928Antimicrobial activity against methicillin-resistant Staphylococcus aureus 1 after 24 hrs2004Journal of natural products, Jun, Volume: 67, Issue:6
New stilbene derivatives from Calligonum leucocladum.
AID568507Induction of NQO1 activity in mouse Hepa1c1c7 cells assessed as concentration required to twofold increase of NQO1 activity at IC50 concentration relative to control2011Bioorganic & medicinal chemistry letters, Feb-01, Volume: 21, Issue:3
Methoxylation of resveratrol: effects on induction of NAD(P)H quinone-oxidoreductase 1 (NQO1) activity and growth inhibitory properties.
AID1354550Antiinflammatory activity in carrageenan induced C57BL/6 mouse model of inflammation assessed as reduction in MCP1 expression in hind paw at 30 mg/kg, ip pretreated for 1 to 2 hrs followed by carrageenan challenge measured after 6 hrs by ELISA2018Journal of natural products, 05-25, Volume: 81, Issue:5
Natural Stilbenoids Have Anti-Inflammatory Properties in Vivo and Down-Regulate the Production of Inflammatory Mediators NO, IL6, and MCP1 Possibly in a PI3K/Akt-Dependent Manner.
AID402929Antimicrobial activity against methicillin-resistant Staphylococcus aureus 5 after 24 hrs2004Journal of natural products, Jun, Volume: 67, Issue:6
New stilbene derivatives from Calligonum leucocladum.
AID377036Ex vivo inhibition of leukotriene formation in calcium ionophore activated human neutrophilic granulocyte by ELISA2005Journal of natural products, Jan, Volume: 68, Issue:1
Inhibition of leukotriene biosynthesis by stilbenoids from Stemona species.
AID416976Induction of DNA fragmentation in human HL60 cells at 200 uM after 48 hrs by ethidium bromide based gel electrophoresis2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Antioxidant-based lead discovery for cancer chemoprevention: the case of resveratrol.
AID416969Prooxidant activity assessed as induction calf thymus DNA damage in presence of 250 uM Cu(II) by ethidium bromide binding based fluorimetric assay2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Antioxidant-based lead discovery for cancer chemoprevention: the case of resveratrol.
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.
AID1081911Antifungal activity against Botryotinia fuckeliana assessed as growth inhibition after 72 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.
AID1354549Antiinflammatory activity in carrageenan induced C57BL/6 mouse model of inflammation assessed as reduction in IL6 expression in hind paw at 30 mg/kg, ip pretreated for 1 to 2 hrs followed by carrageenan challenge measured after 6 hrs by ELISA2018Journal of natural products, 05-25, Volume: 81, Issue:5
Natural Stilbenoids Have Anti-Inflammatory Properties in Vivo and Down-Regulate the Production of Inflammatory Mediators NO, IL6, and MCP1 Possibly in a PI3K/Akt-Dependent Manner.
AID402931Antimicrobial activity against methicillin-resistant Staphylococcus aureus 12 after 24 hrs2004Journal of natural products, Jun, Volume: 67, Issue:6
New stilbene derivatives from Calligonum leucocladum.
AID1354541Antiinflammatory activity in mouse J774 cells assessed as reduction in LPS-induced IL6 expression after 24 hrs by ELISA2018Journal of natural products, 05-25, Volume: 81, Issue:5
Natural Stilbenoids Have Anti-Inflammatory Properties in Vivo and Down-Regulate the Production of Inflammatory Mediators NO, IL6, and MCP1 Possibly in a PI3K/Akt-Dependent Manner.
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.
AID416965Inhibition of hydrogen peroxide-induced cell death of BALB/c mouse thymocytes preincubated for 30 mins before hydrogen peroxide challenge measured after 24 hrs by MTT assay2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Antioxidant-based lead discovery for cancer chemoprevention: the case of resveratrol.
AID402932Antimicrobial activity against methicillin-resistant Staphylococcus aureus COL after 24 hrs2004Journal of natural products, Jun, Volume: 67, Issue:6
New stilbene derivatives from Calligonum leucocladum.
AID402926Antimicrobial activity against methicillin-resistant Staphylococcus aureus 2 after 24 hrs2004Journal of natural products, Jun, Volume: 67, Issue:6
New stilbene derivatives from Calligonum leucocladum.
AID402930Antimicrobial activity against methicillin-resistant Staphylococcus aureus 8 after 24 hrs2004Journal of natural products, Jun, Volume: 67, Issue:6
New stilbene derivatives from Calligonum leucocladum.
AID1354546Antiinflammatory activity in carrageenan induced C57BL/6 mouse model of inflammation assessed as reduction in paw edema at 30 mg/kg, ip pretreated for 1 to 2 hrs followed by carrageenan challenge measured after 3 to 6 hrs by plethysmometer2018Journal of natural products, 05-25, Volume: 81, Issue:5
Natural Stilbenoids Have Anti-Inflammatory Properties in Vivo and Down-Regulate the Production of Inflammatory Mediators NO, IL6, and MCP1 Possibly in a PI3K/Akt-Dependent Manner.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID416980Induction of apoptosis in human HL60 cells assessed as cell accumulation at sub-G1 phase at 200 uM after 48 hrs by propidium iodide staining based flow cytometry2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Antioxidant-based lead discovery for cancer chemoprevention: the case of resveratrol.
AID416970Antiproliferative activity against human HL60 cells after 48 hrs by MTT assay2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Antioxidant-based lead discovery for cancer chemoprevention: the case of resveratrol.
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.
AID294468ABTS radical scavenging activity assessed as trolox equivalent antioxidant capacity2007European journal of medicinal chemistry, Jun, Volume: 42, Issue:6
Quinone reductase induction activity of methoxylated analogues of resveratrol.
AID716916Cytotoxicity against mouse B16F10 cells assessed as suppression of cell viability at 12.5 to 200 uM after 72 hrs2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Resveratrol as a kcat type inhibitor for tyrosinase: potentiated melanogenesis inhibitor.
AID164858Tested in vitro for the inhibition of protein-tyrosine kinase p56lck using angiotensin I (1.2 mM) and [gamma-32P]-ATP (50 pM)1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Synthesis and protein-tyrosine kinase inhibitory activity of polyhydroxylated stilbene analogues of piceatannol.
AID1354538Inhibition of PI3K/Akt in mouse J774 cells assessed as reduction in LPS-induced Akt phosphorylation at Ser473 after 4 hrs by Western blot analysis2018Journal of natural products, 05-25, Volume: 81, Issue:5
Natural Stilbenoids Have Anti-Inflammatory Properties in Vivo and Down-Regulate the Production of Inflammatory Mediators NO, IL6, and MCP1 Possibly in a PI3K/Akt-Dependent Manner.
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.
AID294469Cytotoxicity against mouse Hepa 1c1c7 cells assessed as cell viability at 12.5 uM after 24 hrs by MTT assay2007European journal of medicinal chemistry, Jun, Volume: 42, Issue:6
Quinone reductase induction activity of methoxylated analogues of resveratrol.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID716920Cytotoxicity against mouse B16F10 cells assessed as suppression of cell viability at 400 uM after 72 hrs2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Resveratrol as a kcat type inhibitor for tyrosinase: potentiated melanogenesis inhibitor.
AID294474Induction of quinone reductase activity in mouse Hepa 1c1c7 cells at 12.5 uM after 24 hrs relative to control2007European journal of medicinal chemistry, Jun, Volume: 42, Issue:6
Quinone reductase induction activity of methoxylated analogues of resveratrol.
AID402925Antimicrobial activity against methicillin-resistant Staphylococcus aureus 4 after 24 hrs2004Journal of natural products, Jun, Volume: 67, Issue:6
New stilbene derivatives from Calligonum leucocladum.
AID416968Inhibition of hydrogen peroxide-induced DNA damage in human PBL cells at 12.5 uM by Comet assay2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Antioxidant-based lead discovery for cancer chemoprevention: the case of resveratrol.
AID1081912Antifungal activity against Botryotinia fuckeliana assessed as growth inhibition after 48 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.
AID416964Antioxidant effect assessed as inhibition of AAPH-induced oxidative pBR322 plasmid DNA strand breakage at 10 uM by gel electrophoresis2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Antioxidant-based lead discovery for cancer chemoprevention: the case of resveratrol.
AID294477Induction of quinone reductase in mouse mutant Hepa 1c1c7c1 cells at 12.5 uM after 24 hrs relative to control2007European journal of medicinal chemistry, Jun, Volume: 42, Issue:6
Quinone reductase induction activity of methoxylated analogues of resveratrol.
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.
AID402927DPPH radical scavenging activity assessed as ratio of absorbance at 20 uM relative to L-cysteine2004Journal of natural products, Jun, Volume: 67, Issue:6
New stilbene derivatives from Calligonum leucocladum.
AID1354542Antiinflammatory activity in mouse J774 cells assessed as reduction in LPS-induced MCP1 expression after 24 hrs by ELISA2018Journal of natural products, 05-25, Volume: 81, Issue:5
Natural Stilbenoids Have Anti-Inflammatory Properties in Vivo and Down-Regulate the Production of Inflammatory Mediators NO, IL6, and MCP1 Possibly in a PI3K/Akt-Dependent Manner.
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.
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.
AID1799522EROD Assay from Article 10.1016/j.chembiol.2007.05.004: \\Synthesis of unnatural flavonoids and stilbenes by exploiting the plant biosynthetic pathway in Escherichia coli.\\2007Chemistry & biology, Jun, Volume: 14, Issue:6
Synthesis of unnatural flavonoids and stilbenes by exploiting the plant biosynthetic pathway in Escherichia coli.
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.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (87)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (1.15)18.7374
1990's3 (3.45)18.2507
2000's26 (29.89)29.6817
2010's45 (51.72)24.3611
2020's12 (13.79)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.08

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 Index32.08 (24.57)
Research Supply Index4.48 (2.92)
Research Growth Index5.52 (4.65)
Search Engine Demand Index42.09 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (32.08)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (2.30%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other85 (97.70%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]