Page last updated: 2024-12-11

2,4,3',5'-tetramethoxystilbene

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Description

2,4,3',5'-tetramethoxystilbene: potent inhibitor of human cytochrome P450 1B1; an antihypertensive agent; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5354004
CHEMBL ID46909
CHEBI ID92804
SCHEMBL ID4366766
MeSH IDM0407170

Synonyms (46)

Synonym
BRD-K45988865-001-01-0
TMS ,
2,4,3',5'-tetramethoxystilbene
3,5,2',4'-tetramethoxy-trans-stilbene
2,3',4,5'-tetramethoxystilbene
(e)-2,3',4,5'-tetramethoxystilbene
CHEMBL46909 ,
trans-2,4,3',5'-tetramethoxystilbene
1-[(e)-2-(3,5-dimethoxyphenyl)vinyl]-2,4-dimethoxybenzene
trans-2,4,3'',5''-tetramethoxystilbene
bdbm50108052
1-[(e)-2-(2,4-dimethoxyphenyl)ethenyl]-3,5-dimethoxybenzene
AKOS015967529
20578-92-1
24144-92-1
(e)-1-(3,5-dimethoxystyryl)-2,4-dimethoxybenzene
SCHEMBL4366766
1-[2,(3,5-dimethoxyphenyl)ethenyl]-2,4-dimethoxybenzene
AC-35369
JDBCWSHYEQUBLW-AATRIKPKSA-N
oxyresveratrol tetramethyl ether
HMS3648A21
(e)-4,5'-(ethene-1,2-diyl)bis(1,3-dimethoxybenzene)
trans-2,3',4,5'-tetramethoxystilbene
HY-19340
EX-A1015
SR-01000597603-1
sr-01000597603
CS-5626
CHEBI:92804
AS-71536
1-[(1e)-2-(3,5-dimethoxyphenyl)ethenyl]-2,4-dimethoxybenzene
2,4,3',5'-tetramethoxystilbene, >=98% (hplc)
J-015362
BCP21292
mfcd03428621
HMS3676F17
stilbene, 2,3',4,5'-tetramethoxy-
SR-01000597603-2
HMS3412F17
3,5,2',4'-tetramethoxystilbene
benzene, 1-[(1e)-2-(3,5-dimethoxyphenyl)ethenyl]-2,4-dimethoxy-
A912947
1-[(1e)-2-(3,5-dimethoxyphenyl)ethenyl]-2,4-dimethoxy-benzene
3,5,2 inverted exclamation mark ,4 inverted exclamation mark -tetramethoxystilbene
DTXSID101186212

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" After intravenous administration, OTE possessed a long terminal elimination half-life (t(1/2) (λz) = 481 ± 137 min) and slow clearance (Cl = 29."( Quantification of oxyresveratrol analog trans-2,4,3',5'-tetramethoxystilbene in rat plasma by a rapid HPLC method: application in a pre-clinical pharmacokinetic study.
Choo, QY; Ho, PC; Lin, HS, 2010
)
0.62

Bioavailability

ExcerptReferenceRelevance
" The bioavailability of TMS is low."( Tetramethoxystilbene-Loaded Liposomes Restore Reactive-Oxygen-Species-Mediated Attenuation of Dilator Responses in Rat Aortic Vessels Ex vivo.
Alexander, Y; Astley, C; Azzawi, M; Beards, F; Degens, H; Harris, LK; Lightfoot, AP; Renshall, L; Whitehead, D; Zaabalawi, A, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" The pharmacokinetics of OTE was assessed in rats using 2-hydroxypropyl-β-cyclodextrin as a dosing vehicle."( Quantification of oxyresveratrol analog trans-2,4,3',5'-tetramethoxystilbene in rat plasma by a rapid HPLC method: application in a pre-clinical pharmacokinetic study.
Choo, QY; Ho, PC; Lin, HS, 2010
)
0.62
[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)
Cytochrome P450 1A1Homo sapiens (human)IC50 (µMol)0.30000.00791.24789.9000AID1453035; AID1533283; AID54202
Cytochrome P450 1A2Homo sapiens (human)IC50 (µMol)3.06670.00011.774010.0000AID1453036; AID1533284; AID54221
TyrosinaseHomo sapiens (human)IC50 (µMol)100.00000.02304.459310.0000AID276018
Cytochrome P450 1B1Homo sapiens (human)IC50 (µMol)0.00600.00130.86969.9000AID1306443; AID1453034; AID1533285; AID54233
Cytochrome P450 1B1Homo sapiens (human)Ki0.00300.00300.97417.4600AID1533725
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (115)

Processvia Protein(s)Taxonomy
cellular response to organic cyclic compoundCytochrome P450 1A1Homo sapiens (human)
response to hypoxiaCytochrome P450 1A1Homo sapiens (human)
long-chain fatty acid metabolic processCytochrome P450 1A1Homo sapiens (human)
lipid hydroxylationCytochrome P450 1A1Homo sapiens (human)
fatty acid metabolic processCytochrome P450 1A1Homo sapiens (human)
steroid biosynthetic processCytochrome P450 1A1Homo sapiens (human)
porphyrin-containing compound metabolic processCytochrome P450 1A1Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 1A1Homo sapiens (human)
steroid metabolic processCytochrome P450 1A1Homo sapiens (human)
estrogen metabolic processCytochrome P450 1A1Homo sapiens (human)
amine metabolic processCytochrome P450 1A1Homo sapiens (human)
response to nematodeCytochrome P450 1A1Homo sapiens (human)
response to herbicideCytochrome P450 1A1Homo sapiens (human)
ethylene metabolic processCytochrome P450 1A1Homo sapiens (human)
coumarin metabolic processCytochrome P450 1A1Homo sapiens (human)
flavonoid metabolic processCytochrome P450 1A1Homo sapiens (human)
response to iron(III) ionCytochrome P450 1A1Homo sapiens (human)
insecticide metabolic processCytochrome P450 1A1Homo sapiens (human)
dibenzo-p-dioxin catabolic processCytochrome P450 1A1Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 1A1Homo sapiens (human)
response to foodCytochrome P450 1A1Homo sapiens (human)
response to lipopolysaccharideCytochrome P450 1A1Homo sapiens (human)
response to vitamin ACytochrome P450 1A1Homo sapiens (human)
response to immobilization stressCytochrome P450 1A1Homo sapiens (human)
vitamin D metabolic processCytochrome P450 1A1Homo sapiens (human)
retinol metabolic processCytochrome P450 1A1Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 1A1Homo sapiens (human)
9-cis-retinoic acid biosynthetic processCytochrome P450 1A1Homo sapiens (human)
camera-type eye developmentCytochrome P450 1A1Homo sapiens (human)
nitric oxide metabolic processCytochrome P450 1A1Homo sapiens (human)
response to arsenic-containing substanceCytochrome P450 1A1Homo sapiens (human)
digestive tract developmentCytochrome P450 1A1Homo sapiens (human)
tissue remodelingCytochrome P450 1A1Homo sapiens (human)
hydrogen peroxide biosynthetic processCytochrome P450 1A1Homo sapiens (human)
response to hyperoxiaCytochrome P450 1A1Homo sapiens (human)
maternal process involved in parturitionCytochrome P450 1A1Homo sapiens (human)
hepatocyte differentiationCytochrome P450 1A1Homo sapiens (human)
cellular response to copper ionCytochrome P450 1A1Homo sapiens (human)
omega-hydroxylase P450 pathwayCytochrome P450 1A1Homo sapiens (human)
positive regulation of G1/S transition of mitotic cell cycleCytochrome P450 1A1Homo sapiens (human)
response to 3-methylcholanthreneCytochrome P450 1A1Homo sapiens (human)
steroid catabolic processCytochrome P450 1A2Homo sapiens (human)
porphyrin-containing compound metabolic processCytochrome P450 1A2Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 1A2Homo sapiens (human)
cholesterol metabolic processCytochrome P450 1A2Homo sapiens (human)
estrogen metabolic processCytochrome P450 1A2Homo sapiens (human)
toxin biosynthetic processCytochrome P450 1A2Homo sapiens (human)
post-embryonic developmentCytochrome P450 1A2Homo sapiens (human)
alkaloid metabolic processCytochrome P450 1A2Homo sapiens (human)
regulation of gene expressionCytochrome P450 1A2Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 1A2Homo sapiens (human)
dibenzo-p-dioxin metabolic processCytochrome P450 1A2Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 1A2Homo sapiens (human)
lung developmentCytochrome P450 1A2Homo sapiens (human)
methylationCytochrome P450 1A2Homo sapiens (human)
monocarboxylic acid metabolic processCytochrome P450 1A2Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 1A2Homo sapiens (human)
retinol metabolic processCytochrome P450 1A2Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 1A2Homo sapiens (human)
cellular respirationCytochrome P450 1A2Homo sapiens (human)
aflatoxin metabolic processCytochrome P450 1A2Homo sapiens (human)
hydrogen peroxide biosynthetic processCytochrome P450 1A2Homo sapiens (human)
oxidative demethylationCytochrome P450 1A2Homo sapiens (human)
cellular response to cadmium ionCytochrome P450 1A2Homo sapiens (human)
omega-hydroxylase P450 pathwayCytochrome P450 1A2Homo sapiens (human)
melanin biosynthetic process from tyrosineTyrosinaseHomo sapiens (human)
eye pigment biosynthetic processTyrosinaseHomo sapiens (human)
visual perceptionTyrosinaseHomo sapiens (human)
cell population proliferationTyrosinaseHomo sapiens (human)
response to UVTyrosinaseHomo sapiens (human)
response to blue lightTyrosinaseHomo sapiens (human)
response to vitamin DTyrosinaseHomo sapiens (human)
melanin biosynthetic processTyrosinaseHomo sapiens (human)
thymus developmentTyrosinaseHomo sapiens (human)
response to cAMPTyrosinaseHomo sapiens (human)
pigmentationTyrosinaseHomo 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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (28)

Processvia Protein(s)Taxonomy
monooxygenase activityCytochrome P450 1A1Homo sapiens (human)
iron ion bindingCytochrome P450 1A1Homo sapiens (human)
protein bindingCytochrome P450 1A1Homo sapiens (human)
arachidonic acid monooxygenase activityCytochrome P450 1A1Homo sapiens (human)
oxidoreductase activityCytochrome P450 1A1Homo sapiens (human)
oxidoreductase activity, acting on diphenols and related substances as donorsCytochrome P450 1A1Homo sapiens (human)
flavonoid 3'-monooxygenase activityCytochrome P450 1A1Homo sapiens (human)
oxygen bindingCytochrome P450 1A1Homo sapiens (human)
enzyme bindingCytochrome P450 1A1Homo sapiens (human)
heme bindingCytochrome P450 1A1Homo sapiens (human)
Hsp70 protein bindingCytochrome P450 1A1Homo sapiens (human)
demethylase activityCytochrome P450 1A1Homo sapiens (human)
Hsp90 protein bindingCytochrome P450 1A1Homo sapiens (human)
aromatase activityCytochrome P450 1A1Homo sapiens (human)
vitamin D 24-hydroxylase activityCytochrome P450 1A1Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 1A1Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 1A1Homo sapiens (human)
long-chain fatty acid omega-hydroxylase activityCytochrome P450 1A1Homo sapiens (human)
hydroperoxy icosatetraenoate dehydratase activityCytochrome P450 1A1Homo sapiens (human)
long-chain fatty acid omega-1 hydroxylase activityCytochrome P450 1A1Homo sapiens (human)
monooxygenase activityCytochrome P450 1A2Homo sapiens (human)
iron ion bindingCytochrome P450 1A2Homo sapiens (human)
protein bindingCytochrome P450 1A2Homo sapiens (human)
electron transfer activityCytochrome P450 1A2Homo sapiens (human)
oxidoreductase activityCytochrome P450 1A2Homo 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 1A2Homo sapiens (human)
enzyme bindingCytochrome P450 1A2Homo sapiens (human)
heme bindingCytochrome P450 1A2Homo sapiens (human)
demethylase activityCytochrome P450 1A2Homo sapiens (human)
caffeine oxidase activityCytochrome P450 1A2Homo sapiens (human)
aromatase activityCytochrome P450 1A2Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 1A2Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 1A2Homo sapiens (human)
hydroperoxy icosatetraenoate dehydratase activityCytochrome P450 1A2Homo sapiens (human)
tyrosinase activityTyrosinaseHomo sapiens (human)
copper ion bindingTyrosinaseHomo sapiens (human)
protein bindingTyrosinaseHomo sapiens (human)
identical protein bindingTyrosinaseHomo sapiens (human)
protein homodimerization activityTyrosinaseHomo 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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
mitochondrial inner membraneCytochrome P450 1A1Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 1A1Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 1A1Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 1A2Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 1A2Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 1A2Homo sapiens (human)
cytoplasmTyrosinaseHomo sapiens (human)
lysosomeTyrosinaseHomo sapiens (human)
Golgi-associated vesicleTyrosinaseHomo sapiens (human)
melanosome membraneTyrosinaseHomo sapiens (human)
melanosomeTyrosinaseHomo sapiens (human)
intracellular membrane-bounded organelleTyrosinaseHomo sapiens (human)
perinuclear region of cytoplasmTyrosinaseHomo sapiens (human)
mitochondrionCytochrome P450 1B1Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 1B1Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 1B1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID276025Cytotoxicity against human NCI-H187 cells2006Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21
Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent.
AID1453034Inhibition of recombinant human CYP1B1 expressed in Escherichia coli DH5alpha using ethoxyresorufin as substrate preincubated for 3 mins followed by NADPH addition measured after 10 mins by spectrofluorometric assay2017European journal of medicinal chemistry, Jul-28, Volume: 135Inhibitors of cytochrome P450 (CYP) 1B1.
AID54225Selectivity ratio for Cytochrome P450 1B1 compared to Cytochrome P450 1A22002Journal of medicinal chemistry, Jan-03, Volume: 45, Issue:1
Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors.
AID276018Inhibition of tyrosinase2006Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21
Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent.
AID54233Inhibition of ethoxyresorufin O-deethylation (EROD) in bicistronic bacterial membranes expressing human cytochrome P450 1B12002Journal of medicinal chemistry, Jan-03, Volume: 45, Issue:1
Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors.
AID1453035Inhibition of recombinant human CYP1A1 expressed in Escherichia coli DH5alpha using ethoxyresorufin as substrate preincubated for 3 mins followed by NADPH addition measured after 10 mins by spectrofluorometric assay2017European journal of medicinal chemistry, Jul-28, Volume: 135Inhibitors of cytochrome P450 (CYP) 1B1.
AID1533287Selectivity ratio of IC50 for recombinant human CYP1A1 expressed in Escherichia coli membranes to IC50 for recombinant human CYP1A2 expressed in Escherichia coli membranes2018ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12
Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity.
AID54202Inhibition of ethoxyresorufin O-deethylation (EROD) in bicistronic bacterial membranes epressing human cytochrome P450 1A12002Journal of medicinal chemistry, Jan-03, Volume: 45, Issue:1
Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors.
AID54221Inhibition of ethoxyresorufin O-deethylation (EROD) in bicistronic bacterial membranes expressing human cytochrome P450 1A22002Journal of medicinal chemistry, Jan-03, Volume: 45, Issue:1
Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors.
AID1533285Inhibition of recombinant human CYP1B1 expressed in Escherichia coli membranes co-expressing NADPH-P450 reductase assessed as reduction in ethoxyresorufin O-de-ethylation preincubated for 3 mins followed by NADPH addition and measured after 10 mins by flu2018ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12
Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity.
AID276024Cytotoxicity against human BC cells2006Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21
Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent.
AID54204Selectivity ratio for Cytochrome P450 1B1 compared to Cytochrome P450 1A12002Journal of medicinal chemistry, Jan-03, Volume: 45, Issue:1
Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors.
AID1306443Inhibition of recombinant human CYP1B1 expressed in Escherichia coli DH5aplha cells assessed as O-deethylation of ethoxyresorufin in presence of NADPH measured after 2 mins by spectrofluorometric method2016Bioorganic & medicinal chemistry letters, 07-15, Volume: 26, Issue:14
Aryl morpholino triazenes inhibit cytochrome P450 1A1 and 1B1.
AID1533283Inhibition of recombinant human CYP1A1 expressed in Escherichia coli membranes co-expressing NADPH-P450 reductase assessed as reduction in ethoxyresorufin O-de-ethylation preincubated for 3 mins followed by NADPH addition and measured after 10 mins by flu2018ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12
Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity.
AID1533286Selectivity ratio of IC50 for recombinant human CYP1A1 expressed in Escherichia coli membranes to IC50 for recombinant human CYP1B1 expressed in Escherichia coli membranes2018ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12
Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity.
AID1533288Selectivity ratio of IC50 for recombinant human CYP1A2 expressed in Escherichia coli membranes to IC50 for recombinant human CYP1B1 expressed in Escherichia coli membranes2018ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12
Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity.
AID1533725Inhibition of human CYP1B1 using ethoxyresorufin as substrate preincubated for 3 mins followed by NADPH addition measured after 10 mins by EROD assay2019European journal of medicinal chemistry, Feb-01, Volume: 163Phytoestrogens and their synthetic analogues as substrate mimic inhibitors of CYP1B1.
AID1453036Inhibition of recombinant human CYP1A2 expressed in Escherichia coli DH5alpha using ethoxyresorufin as substrate preincubated for 3 mins followed by NADPH addition measured after 10 mins by spectrofluorometric assay2017European journal of medicinal chemistry, Jul-28, Volume: 135Inhibitors of cytochrome P450 (CYP) 1B1.
AID1533284Inhibition of recombinant human CYP1A2 expressed in Escherichia coli membranes co-expressing NADPH-P450 reductase assessed as reduction in ethoxyresorufin O-de-ethylation preincubated for 3 mins followed by NADPH addition and measured after 10 mins by flu2018ACS medicinal chemistry letters, Dec-13, Volume: 9, Issue:12
Adaptable Small Ligand of CYP1 Enzymes for Use in Understanding the Structural Features Determining Isoform Selectivity.
AID276017Inhibition of tyrosinase at 100 uM2006Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21
Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent.
AID276023Cytotoxicity against human KB cells2006Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21
Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's8 (29.63)29.6817
2010's19 (70.37)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.24

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 Index11.24 (24.57)
Research Supply Index3.33 (2.92)
Research Growth Index4.57 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.24)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (7.41%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other25 (92.59%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]