Page last updated: 2024-12-10

3,7-dimethoxy-5,3',4'-trihydroxyflavone

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Description

3,7-dimethoxy-5,3',4'-trihydroxyflavone: isolated from Veronia eremophila; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3',4',5-trihydroxy-3,7-dimethoxyflavone : A dimethoxyflavone that the 3,7-di-O-methyl derivative of quercetin. [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]

Cross-References

ID SourceID
PubMed CID5280417
CHEMBL ID164861
CHEBI ID18010
SCHEMBL ID828941
MeSH IDM0180084

Synonyms (36)

Synonym
2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4-benzopyrone
CHEBI:18010 ,
3,7-o-dimethylquercetin
3',4',5-trihydroxy-3,7-dimethoxyflavone
C01265 ,
2068-02-2
3,7-di-o-methylquercetin
2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4h-chromen-4-one
2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-chromen-4-one
3,7-dimethylquercetin
quercetin-3,7-dimethylether
bdbm50240897
3'',4'',5-trihydroxy-3,7-dimethoxyflavone
CHEMBL164861 ,
5,3',4'-trihydroxy-3,7-dimethoxyflavone
quercetin 3,7-dimethyl ether
LMPK12112731
2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxychromen-4-one
3,7-dimethoxy-5,3',4'-trihydroxyflavone
unii-v8r92xsr1m
einecs 218-187-4
v8r92xsr1m ,
SCHEMBL828941
fenofibricacidethylester
quercetin 3,7-di-o-methyl ether
AKOS025288164
flavone, 3',4',5-trihydroxy-3,7-dimethoxy-
2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4h-chromen-4-one #
4h-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-
LUJAXSNNYBCFEE-UHFFFAOYSA-N
DTXSID40174734
FS-8747
Q27102757
HY-N1798
CS-0017651
PD119377
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitorAn EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone.
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role 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]

Drug Classes (2)

ClassDescription
dimethoxyflavoneAny methoxyflavone with two methoxy substituents.
trihydroxyflavoneAny hydroxyflavone carrying three hydroxy groups at unspecified positions.
[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 (4)

PathwayProteinsCompounds
polymethylated quercetin biosynthesis210
polymethylated quercetin glucoside biosynthesis I - quercetin series (Chrysosplenium)226
polymethylated quercetin glucoside biosynthesis II - quercetagetin series (Chrysosplenium)231
superpathway of polymethylated quercetin/quercetagetin glucoside biosynthesis (Chrysosplenium)234
polymethylated quercetin glucoside biosynthesis I - quercetin series (Chrysosplenium)231
polymethylated quercetin glucoside biosynthesis II - quercetagetin series (Chrysosplenium)238
polymethylated quercetin biosynthesis211
superpathway of polymethylated quercetin/quercetagetin glucoside biosynthesis (Chrysosplenium)246

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
PlasminogenHomo sapiens (human)IC50 (µMol)1.50000.02503.628010.0000AID378554
Mitogen-activated protein kinase 10Homo sapiens (human)IC50 (µMol)10.00000.00201.703510.0000AID1799639
Mitogen-activated protein kinase 14Homo sapiens (human)IC50 (µMol)10.00000.00010.72667.8000AID1799639
NADPH oxidase 4Homo sapiens (human)IC50 (µMol)1.02000.07080.87881.3400AID510244
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (105)

Processvia Protein(s)Taxonomy
proteolysisPlasminogenHomo sapiens (human)
blood coagulationPlasminogenHomo sapiens (human)
negative regulation of cell population proliferationPlasminogenHomo sapiens (human)
negative regulation of cell-substrate adhesionPlasminogenHomo sapiens (human)
extracellular matrix disassemblyPlasminogenHomo sapiens (human)
tissue regenerationPlasminogenHomo sapiens (human)
fibrinolysisPlasminogenHomo sapiens (human)
positive regulation of blood vessel endothelial cell migrationPlasminogenHomo sapiens (human)
myoblast differentiationPlasminogenHomo sapiens (human)
muscle cell cellular homeostasisPlasminogenHomo sapiens (human)
tissue remodelingPlasminogenHomo sapiens (human)
biological process involved in interaction with symbiontPlasminogenHomo sapiens (human)
negative regulation of fibrinolysisPlasminogenHomo sapiens (human)
positive regulation of fibrinolysisPlasminogenHomo sapiens (human)
trophoblast giant cell differentiationPlasminogenHomo sapiens (human)
labyrinthine layer blood vessel developmentPlasminogenHomo sapiens (human)
mononuclear cell migrationPlasminogenHomo sapiens (human)
trans-synaptic signaling by BDNF, modulating synaptic transmissionPlasminogenHomo sapiens (human)
negative regulation of cell-cell adhesion mediated by cadherinPlasminogenHomo sapiens (human)
protein phosphorylationMitogen-activated protein kinase 10Homo sapiens (human)
signal transductionMitogen-activated protein kinase 10Homo sapiens (human)
JNK cascadeMitogen-activated protein kinase 10Homo sapiens (human)
response to light stimulusMitogen-activated protein kinase 10Homo sapiens (human)
Fc-epsilon receptor signaling pathwayMitogen-activated protein kinase 10Homo sapiens (human)
regulation of circadian rhythmMitogen-activated protein kinase 10Homo sapiens (human)
rhythmic processMitogen-activated protein kinase 10Homo sapiens (human)
cellular senescenceMitogen-activated protein kinase 10Homo sapiens (human)
positive regulation of blood vessel endothelial cell migrationMitogen-activated protein kinase 14Homo sapiens (human)
cellular response to lipopolysaccharideMitogen-activated protein kinase 14Homo sapiens (human)
DNA damage checkpoint signalingMitogen-activated protein kinase 14Homo sapiens (human)
cell morphogenesisMitogen-activated protein kinase 14Homo sapiens (human)
cartilage condensationMitogen-activated protein kinase 14Homo sapiens (human)
angiogenesisMitogen-activated protein kinase 14Homo sapiens (human)
osteoblast differentiationMitogen-activated protein kinase 14Homo sapiens (human)
placenta developmentMitogen-activated protein kinase 14Homo sapiens (human)
response to dietary excessMitogen-activated protein kinase 14Homo sapiens (human)
chondrocyte differentiationMitogen-activated protein kinase 14Homo sapiens (human)
negative regulation of inflammatory response to antigenic stimulusMitogen-activated protein kinase 14Homo sapiens (human)
glucose metabolic processMitogen-activated protein kinase 14Homo sapiens (human)
regulation of transcription by RNA polymerase IIMitogen-activated protein kinase 14Homo sapiens (human)
transcription by RNA polymerase IIMitogen-activated protein kinase 14Homo sapiens (human)
apoptotic processMitogen-activated protein kinase 14Homo sapiens (human)
chemotaxisMitogen-activated protein kinase 14Homo sapiens (human)
signal transductionMitogen-activated protein kinase 14Homo sapiens (human)
cell surface receptor signaling pathwayMitogen-activated protein kinase 14Homo sapiens (human)
cell surface receptor protein serine/threonine kinase signaling pathwayMitogen-activated protein kinase 14Homo sapiens (human)
skeletal muscle tissue developmentMitogen-activated protein kinase 14Homo sapiens (human)
positive regulation of gene expressionMitogen-activated protein kinase 14Homo sapiens (human)
positive regulation of myotube differentiationMitogen-activated protein kinase 14Homo sapiens (human)
peptidyl-serine phosphorylationMitogen-activated protein kinase 14Homo sapiens (human)
fatty acid oxidationMitogen-activated protein kinase 14Homo sapiens (human)
platelet activationMitogen-activated protein kinase 14Homo sapiens (human)
regulation of ossificationMitogen-activated protein kinase 14Homo sapiens (human)
osteoclast differentiationMitogen-activated protein kinase 14Homo sapiens (human)
stress-activated protein kinase signaling cascadeMitogen-activated protein kinase 14Homo sapiens (human)
positive regulation of cyclase activityMitogen-activated protein kinase 14Homo sapiens (human)
lipopolysaccharide-mediated signaling pathwayMitogen-activated protein kinase 14Homo sapiens (human)
response to muramyl dipeptideMitogen-activated protein kinase 14Homo sapiens (human)
positive regulation of interleukin-12 productionMitogen-activated protein kinase 14Homo sapiens (human)
response to insulinMitogen-activated protein kinase 14Homo sapiens (human)
negative regulation of hippo signalingMitogen-activated protein kinase 14Homo sapiens (human)
intracellular signal transductionMitogen-activated protein kinase 14Homo sapiens (human)
cellular response to vascular endothelial growth factor stimulusMitogen-activated protein kinase 14Homo sapiens (human)
response to muscle stretchMitogen-activated protein kinase 14Homo sapiens (human)
p38MAPK cascadeMitogen-activated protein kinase 14Homo sapiens (human)
positive regulation of protein import into nucleusMitogen-activated protein kinase 14Homo sapiens (human)
signal transduction in response to DNA damageMitogen-activated protein kinase 14Homo sapiens (human)
positive regulation of erythrocyte differentiationMitogen-activated protein kinase 14Homo sapiens (human)
positive regulation of myoblast differentiationMitogen-activated protein kinase 14Homo sapiens (human)
positive regulation of transcription by RNA polymerase IIMitogen-activated protein kinase 14Homo sapiens (human)
glucose importMitogen-activated protein kinase 14Homo sapiens (human)
positive regulation of glucose importMitogen-activated protein kinase 14Homo sapiens (human)
vascular endothelial growth factor receptor signaling pathwayMitogen-activated protein kinase 14Homo sapiens (human)
stem cell differentiationMitogen-activated protein kinase 14Homo sapiens (human)
striated muscle cell differentiationMitogen-activated protein kinase 14Homo sapiens (human)
positive regulation of muscle cell differentiationMitogen-activated protein kinase 14Homo sapiens (human)
stress-activated MAPK cascadeMitogen-activated protein kinase 14Homo sapiens (human)
positive regulation of cardiac muscle cell proliferationMitogen-activated protein kinase 14Homo sapiens (human)
bone developmentMitogen-activated protein kinase 14Homo sapiens (human)
3'-UTR-mediated mRNA stabilizationMitogen-activated protein kinase 14Homo sapiens (human)
cellular response to lipoteichoic acidMitogen-activated protein kinase 14Homo sapiens (human)
cellular response to tumor necrosis factorMitogen-activated protein kinase 14Homo sapiens (human)
cellular response to ionizing radiationMitogen-activated protein kinase 14Homo sapiens (human)
cellular response to UV-BMitogen-activated protein kinase 14Homo sapiens (human)
negative regulation of canonical Wnt signaling pathwayMitogen-activated protein kinase 14Homo sapiens (human)
positive regulation of brown fat cell differentiationMitogen-activated protein kinase 14Homo sapiens (human)
cellular senescenceMitogen-activated protein kinase 14Homo sapiens (human)
stress-induced premature senescenceMitogen-activated protein kinase 14Homo sapiens (human)
cellular response to virusMitogen-activated protein kinase 14Homo sapiens (human)
regulation of synaptic membrane adhesionMitogen-activated protein kinase 14Homo sapiens (human)
regulation of cytokine production involved in inflammatory responseMitogen-activated protein kinase 14Homo sapiens (human)
positive regulation of myoblast fusionMitogen-activated protein kinase 14Homo sapiens (human)
positive regulation of reactive oxygen species metabolic processMitogen-activated protein kinase 14Homo sapiens (human)
cell morphogenesisNADPH oxidase 4Homo sapiens (human)
heart processNADPH oxidase 4Homo sapiens (human)
superoxide metabolic processNADPH oxidase 4Homo sapiens (human)
inflammatory responseNADPH oxidase 4Homo sapiens (human)
negative regulation of cell population proliferationNADPH oxidase 4Homo sapiens (human)
gene expressionNADPH oxidase 4Homo sapiens (human)
superoxide anion generationNADPH oxidase 4Homo sapiens (human)
bone resorptionNADPH oxidase 4Homo sapiens (human)
homocysteine metabolic processNADPH oxidase 4Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionNADPH oxidase 4Homo sapiens (human)
cardiac muscle cell differentiationNADPH oxidase 4Homo sapiens (human)
positive regulation of protein tyrosine kinase activityNADPH oxidase 4Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeNADPH oxidase 4Homo sapiens (human)
cellular response to glucose stimulusNADPH oxidase 4Homo sapiens (human)
reactive oxygen species biosynthetic processNADPH oxidase 4Homo sapiens (human)
positive regulation of DNA biosynthetic processNADPH oxidase 4Homo sapiens (human)
defense responseNADPH oxidase 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (32)

Processvia Protein(s)Taxonomy
protease bindingPlasminogenHomo sapiens (human)
endopeptidase activityPlasminogenHomo sapiens (human)
serine-type endopeptidase activityPlasminogenHomo sapiens (human)
signaling receptor bindingPlasminogenHomo sapiens (human)
protein bindingPlasminogenHomo sapiens (human)
serine-type peptidase activityPlasminogenHomo sapiens (human)
enzyme bindingPlasminogenHomo sapiens (human)
kinase bindingPlasminogenHomo sapiens (human)
protein domain specific bindingPlasminogenHomo sapiens (human)
apolipoprotein bindingPlasminogenHomo sapiens (human)
protein-folding chaperone bindingPlasminogenHomo sapiens (human)
protein antigen bindingPlasminogenHomo sapiens (human)
JUN kinase activityMitogen-activated protein kinase 10Homo sapiens (human)
MAP kinase kinase activityMitogen-activated protein kinase 10Homo sapiens (human)
protein bindingMitogen-activated protein kinase 10Homo sapiens (human)
ATP bindingMitogen-activated protein kinase 10Homo sapiens (human)
protein serine kinase activityMitogen-activated protein kinase 10Homo sapiens (human)
protein serine/threonine kinase activityMitogen-activated protein kinase 14Homo sapiens (human)
MAP kinase activityMitogen-activated protein kinase 14Homo sapiens (human)
MAP kinase kinase activityMitogen-activated protein kinase 14Homo sapiens (human)
protein bindingMitogen-activated protein kinase 14Homo sapiens (human)
ATP bindingMitogen-activated protein kinase 14Homo sapiens (human)
enzyme bindingMitogen-activated protein kinase 14Homo sapiens (human)
protein phosphatase bindingMitogen-activated protein kinase 14Homo sapiens (human)
mitogen-activated protein kinase p38 bindingMitogen-activated protein kinase 14Homo sapiens (human)
NFAT protein bindingMitogen-activated protein kinase 14Homo sapiens (human)
protein serine kinase activityMitogen-activated protein kinase 14Homo sapiens (human)
nucleotide bindingNADPH oxidase 4Homo sapiens (human)
protein bindingNADPH oxidase 4Homo sapiens (human)
electron transfer activityNADPH oxidase 4Homo sapiens (human)
NAD(P)H oxidase H2O2-forming activityNADPH oxidase 4Homo sapiens (human)
superoxide-generating NAD(P)H oxidase activityNADPH oxidase 4Homo sapiens (human)
oxygen sensor activityNADPH oxidase 4Homo sapiens (human)
heme bindingNADPH oxidase 4Homo sapiens (human)
flavin adenine dinucleotide bindingNADPH oxidase 4Homo sapiens (human)
modified amino acid bindingNADPH oxidase 4Homo sapiens (human)
superoxide-generating NADPH oxidase activityNADPH oxidase 4Homo sapiens (human)
NADPH oxidase H202-forming activityNADPH oxidase 4Homo sapiens (human)
protein tyrosine kinase bindingNADPH oxidase 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (28)

Processvia Protein(s)Taxonomy
extracellular regionPlasminogenHomo sapiens (human)
extracellular spacePlasminogenHomo sapiens (human)
plasma membranePlasminogenHomo sapiens (human)
external side of plasma membranePlasminogenHomo sapiens (human)
cell surfacePlasminogenHomo sapiens (human)
platelet alpha granule lumenPlasminogenHomo sapiens (human)
collagen-containing extracellular matrixPlasminogenHomo sapiens (human)
extracellular exosomePlasminogenHomo sapiens (human)
blood microparticlePlasminogenHomo sapiens (human)
Schaffer collateral - CA1 synapsePlasminogenHomo sapiens (human)
glutamatergic synapsePlasminogenHomo sapiens (human)
extracellular spacePlasminogenHomo sapiens (human)
nucleoplasmMitogen-activated protein kinase 10Homo sapiens (human)
cytoplasmMitogen-activated protein kinase 10Homo sapiens (human)
mitochondrionMitogen-activated protein kinase 10Homo sapiens (human)
cytosolMitogen-activated protein kinase 10Homo sapiens (human)
plasma membraneMitogen-activated protein kinase 10Homo sapiens (human)
nucleusMitogen-activated protein kinase 10Homo sapiens (human)
cytoplasmMitogen-activated protein kinase 10Homo sapiens (human)
cytosolMitogen-activated protein kinase 14Homo sapiens (human)
spindle poleMitogen-activated protein kinase 14Homo sapiens (human)
extracellular regionMitogen-activated protein kinase 14Homo sapiens (human)
nucleusMitogen-activated protein kinase 14Homo sapiens (human)
nucleoplasmMitogen-activated protein kinase 14Homo sapiens (human)
cytoplasmMitogen-activated protein kinase 14Homo sapiens (human)
mitochondrionMitogen-activated protein kinase 14Homo sapiens (human)
cytosolMitogen-activated protein kinase 14Homo sapiens (human)
nuclear speckMitogen-activated protein kinase 14Homo sapiens (human)
secretory granule lumenMitogen-activated protein kinase 14Homo sapiens (human)
glutamatergic synapseMitogen-activated protein kinase 14Homo sapiens (human)
ficolin-1-rich granule lumenMitogen-activated protein kinase 14Homo sapiens (human)
nucleusMitogen-activated protein kinase 14Homo sapiens (human)
cytoplasmMitogen-activated protein kinase 14Homo sapiens (human)
nucleusNADPH oxidase 4Homo sapiens (human)
nucleolusNADPH oxidase 4Homo sapiens (human)
mitochondrionNADPH oxidase 4Homo sapiens (human)
endoplasmic reticulumNADPH oxidase 4Homo sapiens (human)
endoplasmic reticulum membraneNADPH oxidase 4Homo sapiens (human)
plasma membraneNADPH oxidase 4Homo sapiens (human)
focal adhesionNADPH oxidase 4Homo sapiens (human)
membraneNADPH oxidase 4Homo sapiens (human)
perinuclear region of cytoplasmNADPH oxidase 4Homo sapiens (human)
perinuclear endoplasmic reticulumNADPH oxidase 4Homo sapiens (human)
plasma membraneNADPH oxidase 4Homo sapiens (human)
NADPH oxidase complexNADPH oxidase 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (52)

Assay IDTitleYearJournalArticle
AID1188617Anticancer activity against human Calu1 cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID1188614Anticancer activity against human HOP62 cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID718316Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide generation incubated for 24 hrs2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID1188615Anticancer activity against human H1299 cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID718310Effect on alpha-tubulin protein expression in mouse RAW264.7 cells up to 10 uM pre-treated for 30 mins before LPS challenge for 18 hrs by immunoblot2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID1153997Intracellular melanogenesis-stimulating activity in mouse B16F0 cells at 6.25 uM after 72 hrs by spectrophotometry relative to control2014Bioorganic & medicinal chemistry, Jul-01, Volume: 22, Issue:13
Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK.
AID1154003Cytotoxicity against mouse B16F0 cells assessed as cell viability at 25 uM after 72 hrs by MTT assay2014Bioorganic & medicinal chemistry, Jul-01, Volume: 22, Issue:13
Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK.
AID1154005Cytotoxicity against mouse B16F0 cells assessed as cell viability at 6.25 uM after 72 hrs by MTT assay2014Bioorganic & medicinal chemistry, Jul-01, Volume: 22, Issue:13
Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK.
AID718314Antioxidant activity assessed as nitric oxide free radical scavenging activity by UV-visible spectroscopy2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID162237Cytotoxic dose at which 50% growth of normal cells is inhibited1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID666771Inhibition of thrombin in New Zealand rabbit plasma assessed as fibrinogen level at 100 uM by coagulometry2012European journal of medicinal chemistry, Aug, Volume: 54Metabolism-based synthesis, biologic evaluation and SARs analysis of O-methylated analogs of quercetin as thrombin inhibitors.
AID162238Minimum drug concentration at which 99% of the polio virus is inhibited1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID718311Antiinflammatory activity in mouse RAW264.7 cells assessed as reduction of LPS-induced iNOS protein expression pre-treated for 30 mins before LPS challenge for 18 hrs by immunoblot2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID510243Inhibition of NOX4 expressed in HEK293 FS cells at 10 uM assessed as H2O2 production by H2O2/Tyr/LPO assay2010Journal of medicinal chemistry, Sep-23, Volume: 53, Issue:18
Small-molecule inhibitors of NADPH oxidase 4.
AID718313Cytotoxicity against mouse RAW264.7 cells at 50 uM incubated for 24 hrs in absence of LPS by MTT assay2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID162242Maximal non-toxic dose (MNTD) that shows antiviral activity.1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID1188613Anticancer activity against human NCI-H522 cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID235260Therapeutic Index measured as the ratio of CyD50(polio) / ED99(polio) values1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID378554Inhibition of plasmin2005Journal of natural products, Mar, Volume: 68, Issue:3
Sesquiterpenoids and plasmin-inhibitory flavonoids from Blumea balsamifera.
AID1153995Intracellular melanogenesis-stimulating activity in mouse B16F0 cells at 25 uM after 72 hrs by spectrophotometry relative to control2014Bioorganic & medicinal chemistry, Jul-01, Volume: 22, Issue:13
Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK.
AID1188611Anticancer activity against human NCI-H1944 cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID510245Cytotoxicity against human free style HEK293 cells after 72 hrs2010Journal of medicinal chemistry, Sep-23, Volume: 53, Issue:18
Small-molecule inhibitors of NADPH oxidase 4.
AID718309Antiinflammatory activity in mouse RAW264.7 cells assessed as reduction of LPS-induced IkappaBalpha degradation at 30 uM pre-treated for 30 mins before LPS challenge and measured after 10 mins by immunoblot2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID1154004Cytotoxicity against mouse B16F0 cells assessed as cell viability at 12.5 uM after 72 hrs by MTT assay2014Bioorganic & medicinal chemistry, Jul-01, Volume: 22, Issue:13
Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK.
AID718315Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced TNFalpha production incubated for 24 hrs by ELISA2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID1154000Extracellular melanogenesis-stimulating activity in mouse B16F0 cells at 12.5 uM after 72 hrs by spectrophotometry relative to control2014Bioorganic & medicinal chemistry, Jul-01, Volume: 22, Issue:13
Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK.
AID666769Inhibition of thrombin in New Zealand rabbit plasma assessed as prothrombin time at 100 uM by coagulometry2012European journal of medicinal chemistry, Aug, Volume: 54Metabolism-based synthesis, biologic evaluation and SARs analysis of O-methylated analogs of quercetin as thrombin inhibitors.
AID1188612Anticancer activity against human H266 cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID1188616Anticancer activity against human 292G cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID1188610Anticancer activity against human NCI-H1792 cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID337741Cytotoxicity against mouse P388 cells
AID510246Inhibition of NOX4 expressed in HEK293 FS cells at 10 uM assessed as H2O2 production by H2O2/Tyr/LPO assay substituted with 3 uM H2O22010Journal of medicinal chemistry, Sep-23, Volume: 53, Issue:18
Small-molecule inhibitors of NADPH oxidase 4.
AID1188619Anticancer activity against human LOXIMVI cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID1188607Anticancer activity against human A549 cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID1188609Anticancer activity against human H460 cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID1154001Extracellular melanogenesis-stimulating activity in mouse B16F0 cells at 6.25 uM after 72 hrs by spectrophotometry relative to control2014Bioorganic & medicinal chemistry, Jul-01, Volume: 22, Issue:13
Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK.
AID1188620Anticancer activity against human M14 cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID1188621Anticancer activity against human SKBR cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID666770Inhibition of thrombin in New Zealand rabbit plasma assessed as activated partial thromboplastin time at 100 uM after 3 mins by coagulometry2012European journal of medicinal chemistry, Aug, Volume: 54Metabolism-based synthesis, biologic evaluation and SARs analysis of O-methylated analogs of quercetin as thrombin inhibitors.
AID666768Inhibition of thrombin in New Zealand rabbit plasma assessed as thrombin time at 100 uM after 3 mins by coagulometry2012European journal of medicinal chemistry, Aug, Volume: 54Metabolism-based synthesis, biologic evaluation and SARs analysis of O-methylated analogs of quercetin as thrombin inhibitors.
AID1188608Anticancer activity against human NCI-H157 cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID162249Minimal dose which produces titer reduction at 10 ug/mL (mD RF10e3)1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID1153996Intracellular melanogenesis-stimulating activity in mouse B16F0 cells at 12.5 uM after 72 hrs by spectrophotometry relative to control2014Bioorganic & medicinal chemistry, Jul-01, Volume: 22, Issue:13
Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK.
AID162244The ratio of the poliovirus viral titer of the virus control (reduction factor) to the viral titer in the presence of the maximal non-toxic dose (RF MNTD)1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID1188622Anticancer activity against human HeLa cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID1153999Extracellular melanogenesis-stimulating activity in mouse B16F0 cells at 25 uM after 72 hrs by spectrophotometry relative to control2014Bioorganic & medicinal chemistry, Jul-01, Volume: 22, Issue:13
Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK.
AID718312Cytotoxicity against mouse RAW264.7 cells at 50 uM incubated for 24 hrs in presence of LPS by MTT assay2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID718306Antiinflammatory activity in mouse RAW264.7 cells assessed as reduction of LPS-induced IkappaBalpha resynthesis at 30 uM pre-treated for 30 mins before LPS challenge by immunoblot2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID510244Inhibition of NOX4 expressed in HEK293 FS cells assessed as H2O2 production by H2O2/Tyr/LPO assay2010Journal of medicinal chemistry, Sep-23, Volume: 53, Issue:18
Small-molecule inhibitors of NADPH oxidase 4.
AID1188618Anticancer activity against human M4E cells by HTS assay2014Bioorganic & medicinal chemistry letters, Sep-15, Volume: 24, Issue:18
Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer.
AID718308Antiinflammatory activity in mouse RAW264.7 cells assessed as reduction of LPS-induced IkappaBalpha degradation at 30 uM pre-treated for 30 mins before LPS challenge and measured after 15 mins by immunoblot2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID1799639Kinase Assay from Article 10.1002/cbic.201000487: \\Biological evaluation and structural determinants of p38u00CEu00B1 mitogen-activated-protein kinase and c-Jun-N-terminal kinase 3 inhibition by flavonoids.\\2010Chembiochem : a European journal of chemical biology, Dec-10, Volume: 11, Issue:18
Biological evaluation and structural determinants of p38α mitogen-activated-protein kinase and c-Jun-N-terminal kinase 3 inhibition by flavonoids.
[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's2 (14.29)18.2507
2000's4 (28.57)29.6817
2010's8 (57.14)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: 12.03

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 Index12.03 (24.57)
Research Supply Index2.77 (2.92)
Research Growth Index4.80 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.03)

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%
Other15 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]