Page last updated: 2024-11-11

5-hydroxy-3,3',4',7-tetramethoxyflavone

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

Description

5-hydroxy-3,7,3',4'-tetramethoxyflavone: from the rhizome of Kaempferia parviflora; inhibits monocyte adhesion and cellular reactive oxygen species production in human umbilical vein endothelial cells [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

5-hydroxy-3,3',4',7-tetramethoxyflavone : A monohydroxyflavone that is 5-hydroxyflavone which is substituted by methoxy groups at positions 3,3',4' and 7. [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 CID5352005
CHEMBL ID77966
CHEBI ID144861
SCHEMBL ID1421755

Synonyms (74)

Synonym
CHEMBL77966 ,
nsc-618937
nsc618937
NCI60_003907
NCI60_005562
NCI60_003909
NCI60_003908
retusine (ariocarpus)
4h-1-benzopyran-4-one,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-
quercetin 3,3',4'-tetramethyl ether
1245-15-4
flavone,3',4',7-tetramethoxy-
nsc-61837
nsc408169
MEGXP0_001881
ACON1_000513
4h-1-benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-
retusin
NSC61837 ,
retusin (ariocarpus)
2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4-benzopyrone
ky73
2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-chromen-4-one
NCGC00169008-01
retusine (van)
BRD-K49158532-001-01-9
2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxychromen-4-one
LMPK12112770
quercetin 3,7,3',4'-tetramethyl ether
5-hydroxy-3,7,3',4'-tetramethoxyflavone
retusin(ariocarpus)
5-hydroxy-3,3',4',7-tetramethoxyflavone
quercetin 3,3',4',7-tetramethyl ether
3,3',4',7-tetramethylquercetin
3,3',4',7-o-tetramethylquercetin
2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4h-1-benzopyran-4-one
3,7,3',4'-tetramethylquercetin
2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4h-chromen-4-one
CHEBI:144861
bdbm50338974
2-(3,4-dimethoxy-phenyl)-5-hydroxy-3,7-dimethoxy-chromen-4-one
quercitin-3,7,3'',4''-tetramethyl ether
5-hydroxy-3,7,3,4-tetramethoxyflavone
unii-m8591903sd
quercetin-3,7,3',4'-tetramethyl ether
einecs 214-991-4
nsc 61837
flavone, 5-hydroxy-3,3',4',7-tetramethoxy-
retusin (van)
quercetin 3,7,3',4'-tetramethylether
quercetin tetramethylether
m8591903sd ,
FT-0633509
CCG-214740
hydroxy-3,3',4',7-tetramethoxyflavone, 5-
3,3',4',7-tetra-o-methylquercetin
quercetin 3,3',4',7-o-tetramethyl ether
mfcd00017420
quercetin-3,7,3',4'-tetramethylether
SCHEMBL1421755
3,7,3',4'-tetra-o-methylquercetin
quercetin, 3,7,3',4'-tetramethyl
2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4h-chromen-4-one #
DTXSID60924839
quercetin 3,3',4',7-tetramethylether
quercetin-3,3',4',7-tetramethylether
Q7317388
BRD-K49158532-001-02-7
CS-0100247
HY-N6829
MS-25624
quercetin-3,3',4',7-etramethylether
E87140
AKOS040760672

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Male rats were orally or intravenously administered a 250 mg/kg concentration of a KP extract, and blood samples were obtained at selected times to determine pharmacokinetic parameters of PMF, TMF, and DMF."( Pharmacokinetics, bioavailability, tissue distribution, excretion, and metabolite identification of methoxyflavones in Kaempferia parviflora extract in rats.
Jay, M; Mekjaruskul, C; Sripanidkulchai, B, 2012
)
0.38

Bioavailability

ExcerptReferenceRelevance
" The methoxyflavones showed low oral bioavailability of 1 to 4%."( Pharmacokinetics, bioavailability, tissue distribution, excretion, and metabolite identification of methoxyflavones in Kaempferia parviflora extract in rats.
Jay, M; Mekjaruskul, C; Sripanidkulchai, B, 2012
)
0.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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 (3)

ClassDescription
tetramethoxyflavoneAny methoxyflavone with four methoxy substituents.
3'-methoxyflavonesAny methoxyflavone with a methoxy substituent at position 3'.
monohydroxyflavoneA hydroxyflavone carrying a single hydroxy substituent.
[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
polymethylated quercetin glucoside biosynthesis I - quercetin series (Chrysosplenium)231
superpathway of polymethylated quercetin/quercetagetin glucoside biosynthesis (Chrysosplenium)246

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
ATP-dependent translocase ABCB1Homo sapiens (human)IC50 (µMol)16.00000.00022.318510.0000AID578762
Multidrug resistance-associated protein 1 Homo sapiens (human)IC50 (µMol)50.00000.00153.71109.6600AID578766
Broad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)IC50 (µMol)0.60000.00401.966610.0000AID578759; AID578760; AID768689; AID768691
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (39)

Processvia Protein(s)Taxonomy
G2/M transition of mitotic cell cycleATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic metabolic processATP-dependent translocase ABCB1Homo sapiens (human)
response to xenobiotic stimulusATP-dependent translocase ABCB1Homo sapiens (human)
phospholipid translocationATP-dependent translocase ABCB1Homo sapiens (human)
terpenoid transportATP-dependent translocase ABCB1Homo sapiens (human)
regulation of response to osmotic stressATP-dependent translocase ABCB1Homo sapiens (human)
transmembrane transportATP-dependent translocase ABCB1Homo sapiens (human)
transepithelial transportATP-dependent translocase ABCB1Homo sapiens (human)
stem cell proliferationATP-dependent translocase ABCB1Homo sapiens (human)
ceramide translocationATP-dependent translocase ABCB1Homo sapiens (human)
export across plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
transport across blood-brain barrierATP-dependent translocase ABCB1Homo sapiens (human)
positive regulation of anion channel activityATP-dependent translocase ABCB1Homo sapiens (human)
carboxylic acid transmembrane transportATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic detoxification by transmembrane export across the plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic transport across blood-brain barrierATP-dependent translocase ABCB1Homo sapiens (human)
regulation of chloride transportATP-dependent translocase ABCB1Homo sapiens (human)
leukotriene metabolic processMultidrug resistance-associated protein 1 Homo sapiens (human)
xenobiotic metabolic processMultidrug resistance-associated protein 1 Homo sapiens (human)
response to xenobiotic stimulusMultidrug resistance-associated protein 1 Homo sapiens (human)
cobalamin transportMultidrug resistance-associated protein 1 Homo sapiens (human)
sphingolipid biosynthetic processMultidrug resistance-associated protein 1 Homo sapiens (human)
cellular response to oxidative stressMultidrug resistance-associated protein 1 Homo sapiens (human)
heme catabolic processMultidrug resistance-associated protein 1 Homo sapiens (human)
xenobiotic transportMultidrug resistance-associated protein 1 Homo sapiens (human)
phospholipid translocationMultidrug resistance-associated protein 1 Homo sapiens (human)
positive regulation of inflammatory responseMultidrug resistance-associated protein 1 Homo sapiens (human)
transmembrane transportMultidrug resistance-associated protein 1 Homo sapiens (human)
cell chemotaxisMultidrug resistance-associated protein 1 Homo sapiens (human)
transepithelial transportMultidrug resistance-associated protein 1 Homo sapiens (human)
cyclic nucleotide transportMultidrug resistance-associated protein 1 Homo sapiens (human)
leukotriene transportMultidrug resistance-associated protein 1 Homo sapiens (human)
monoatomic anion transmembrane transportMultidrug resistance-associated protein 1 Homo sapiens (human)
sphingolipid translocationMultidrug resistance-associated protein 1 Homo sapiens (human)
export across plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
transport across blood-brain barrierMultidrug resistance-associated protein 1 Homo sapiens (human)
cellular response to amyloid-betaMultidrug resistance-associated protein 1 Homo sapiens (human)
carboxylic acid transmembrane transportMultidrug resistance-associated protein 1 Homo sapiens (human)
xenobiotic transport across blood-brain barrierMultidrug resistance-associated protein 1 Homo sapiens (human)
glutathione transmembrane transportMultidrug resistance-associated protein 1 Homo sapiens (human)
lipid transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
organic anion transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
urate transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
biotin transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
sphingolipid biosynthetic processBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
riboflavin transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
urate metabolic processBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
transmembrane transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
transepithelial transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
renal urate salt excretionBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
export across plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
transport across blood-brain barrierBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
cellular detoxificationBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
xenobiotic transport across blood-brain barrierBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (27)

Processvia Protein(s)Taxonomy
protein bindingATP-dependent translocase ABCB1Homo sapiens (human)
ATP bindingATP-dependent translocase ABCB1Homo sapiens (human)
ABC-type xenobiotic transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
efflux transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
ATP hydrolysis activityATP-dependent translocase ABCB1Homo sapiens (human)
transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
ubiquitin protein ligase bindingATP-dependent translocase ABCB1Homo sapiens (human)
ATPase-coupled transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
carboxylic acid transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
phosphatidylcholine floppase activityATP-dependent translocase ABCB1Homo sapiens (human)
phosphatidylethanolamine flippase activityATP-dependent translocase ABCB1Homo sapiens (human)
ceramide floppase activityATP-dependent translocase ABCB1Homo sapiens (human)
floppase activityATP-dependent translocase ABCB1Homo sapiens (human)
ATP bindingMultidrug resistance-associated protein 1 Homo sapiens (human)
ABC-type vitamin B12 transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ABC-type glutathione S-conjugate transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
efflux transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ATP hydrolysis activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ATPase-coupled lipid transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
glutathione transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ATPase-coupled transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
xenobiotic transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ATPase-coupled inorganic anion transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
sphingolipid transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
carboxylic acid transmembrane transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ABC-type transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
ABC-type xenobiotic transporter activityMultidrug resistance-associated protein 1 Homo sapiens (human)
protein bindingBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ATP bindingBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
organic anion transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ABC-type xenobiotic transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
urate transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
biotin transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
efflux transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ATP hydrolysis activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
riboflavin transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ATPase-coupled transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
identical protein bindingBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
protein homodimerization activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
xenobiotic transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
sphingolipid transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
cytoplasmATP-dependent translocase ABCB1Homo sapiens (human)
plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
cell surfaceATP-dependent translocase ABCB1Homo sapiens (human)
membraneATP-dependent translocase ABCB1Homo sapiens (human)
apical plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
extracellular exosomeATP-dependent translocase ABCB1Homo sapiens (human)
external side of apical plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
basal plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
basolateral plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
apical plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
lateral plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
extracellular exosomeMultidrug resistance-associated protein 1 Homo sapiens (human)
basolateral plasma membraneMultidrug resistance-associated protein 1 Homo sapiens (human)
nucleoplasmBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
apical plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
brush border membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
mitochondrial membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
membrane raftBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
external side of apical plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (98)

Assay IDTitleYearJournalArticle
AID265762Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum K12006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.
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.
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.
AID1226455Selectivity index, ratio of IC50 for HEK293 cells to IC50 for human A375 cells2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID265765Inhibition of FabG at 100 uM2006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.
AID666855Cytotoxicity against mouse L929 cells after 5 days by MTS assay2012European journal of medicinal chemistry, Aug, Volume: 54Synthesis of methylated quercetin derivatives and their reversal activities on P-gp- and BCRP-mediated multidrug resistance tumour cells.
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.
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.
AID596672Induction of adipogenesis in mouse 3T3L1 cells assessed as increase in triglyceride level at 10 uM on day 8 relative to control2011Bioorganic & medicinal chemistry, May-01, Volume: 19, Issue:9
Structural requirements of flavonoids for the adipogenesis of 3T3-L1 cells.
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.
AID1226448Cytotoxicity against cisplatin-resistant human A431 cells assessed as cell growth inhibition after 72 hrs by MTT assay2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID578766Inhibition of MRP1 expressed in human 2008 cells assessed as calcein AM accumulation by cell based assay2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).
AID768677Cytotoxicity against MDCK cells expressing BCRP at <100 uM after 72 hrs by MTT assay2013European journal of medicinal chemistry, Sep, Volume: 67Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2.
AID666857Reversal of BCRP-mediated drug resistant in human HEK293/R2 cells assessed as potentiation of topotecan-induced cytotoxicity at 1 uM after 5 days by MTS assay2012European journal of medicinal chemistry, Aug, Volume: 54Synthesis of methylated quercetin derivatives and their reversal activities on P-gp- and BCRP-mediated multidrug resistance tumour cells.
AID1879367Stabilization of [poly(dA).2poly(dT) triplex DNA (unknown origin) assessed as deltaS level temperature at 10 uM by DSC assay (Rvb = 0.0167 mol.K)2022Bioorganic & medicinal chemistry letters, 04-01, Volume: 615-Substituted 3, 3', 4', 7-tetramethoxyflavonoids - A novel class of potent DNA triplex specific binding ligands.
AID1879366Stabilization of [poly(dA).2poly(dT) triplex DNA (unknown origin) assessed as deltaH level temperature at 10 uM by DSC assay (Rvb = 5.19 KJ/mol)2022Bioorganic & medicinal chemistry letters, 04-01, Volume: 615-Substituted 3, 3', 4', 7-tetramethoxyflavonoids - A novel class of potent DNA triplex specific binding ligands.
AID1879373Binding affinity to triplex DNA2 containing 15 nucleotide-long triplex-forming region (unknown origin) at 100 uM at 15 degC by ITC2022Bioorganic & medicinal chemistry letters, 04-01, Volume: 615-Substituted 3, 3', 4', 7-tetramethoxyflavonoids - A novel class of potent DNA triplex specific binding ligands.
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.
AID319548Antiinflammatory activity in human neutrophils assessed as inhibition of fMet-Leu-Phe/Cytochalasin B-induced elastase release2008Journal of natural products, Jan, Volume: 71, Issue:1
Benzoic acid derivatives, acetophenones, and anti-inflammatory constituents from Melicope semecarpifolia.
AID1879372Binding affinity to triplex DNA1 containing 15 nucleotide-long triplex-forming region (unknown origin) at 100 uM by ITC2022Bioorganic & medicinal chemistry letters, 04-01, Volume: 615-Substituted 3, 3', 4', 7-tetramethoxyflavonoids - A novel class of potent DNA triplex specific binding ligands.
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.
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.
AID596673Induction of adipogenesis in mouse 3T3L1 cells assessed as increase in triglyceride level at 30 uM on day 8 relative to control2011Bioorganic & medicinal chemistry, May-01, Volume: 19, Issue:9
Structural requirements of flavonoids for the adipogenesis of 3T3-L1 cells.
AID1677632Cytotoxicity against rat PC12D cells assessed as reduction in cell viability at 30 uM by MTT assay2020Bioorganic & medicinal chemistry letters, 12-01, Volume: 30, Issue:23
Effect of methoxyflavones contained in Kaempferia parviflora on CRE-mediated transcription in PC12D cells.
AID1879364Stabilization of [poly(dA).poly(dT)] triplex DNA (unknown origin) assessed as change in melting temperature at 10 uM by UV based assay2022Bioorganic & medicinal chemistry letters, 04-01, Volume: 615-Substituted 3, 3', 4', 7-tetramethoxyflavonoids - A novel class of potent DNA triplex specific binding ligands.
AID404067In vivo antitumor activity against mouse S180 cells
AID596670Induction of adipogenesis in mouse 3T3L1 cells assessed as increase in triglyceride level at 1 uM on day 8 relative to control2011Bioorganic & medicinal chemistry, May-01, Volume: 19, Issue:9
Structural requirements of flavonoids for the adipogenesis of 3T3-L1 cells.
AID1226449Cytotoxicity against human 2008 cells assessed as cell growth inhibition after 72 hrs by MTT assay2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID1226444Cytotoxicity against human BxPC3 cells assessed as cell growth inhibition after 72 hrs by MTT assay2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID1226443Cytotoxicity against human HCT15 cells assessed as cell growth inhibition after 72 hrs by MTT assay2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID265761Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum NF542006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.
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.
AID1677633Activation of CRE-mediated transcription in rat PC12D cells transfected with pCRE-firefly luciferase and pRL-null-renilla luciferase assessed as increase in CRE-driven firefly luciferase activity at 30 uM by dual luciferase reporter gene assay2020Bioorganic & medicinal chemistry letters, 12-01, Volume: 30, Issue:23
Effect of methoxyflavones contained in Kaempferia parviflora on CRE-mediated transcription in PC12D cells.
AID578762Inhibition of MDR1 expressed in MDCK cells using rhodamine 123 staining by flow cytometry2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).
AID492140Antioxidant activity assessed as formazan formation induced absorbance changes at 25 ppm at 570 nm at 37 degC for 6 hrs by MTT assay2010Journal of natural products, Jul-23, Volume: 73, Issue:7
An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds.
AID1226445Cytotoxicity against human MCF7 cells assessed as cell growth inhibition after 72 hrs by MTT assay2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID578765Inhibition of P-gp expressed in A2780adr cells at 10 uM by calcein AM accumulation assay relative to verapamil2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).
AID768680Cytotoxicity against MDCK cells at 100 uM after 72 hrs by MTT assay2013European journal of medicinal chemistry, Sep, Volume: 67Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2.
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.
AID1226447Cytotoxicity against human A431 cells assessed as cell growth inhibition after 72 hrs by MTT assay2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID666853Cytotoxicity against human LCC-6 cells after 5 days by MTS assay2012European journal of medicinal chemistry, Aug, Volume: 54Synthesis of methylated quercetin derivatives and their reversal activities on P-gp- and BCRP-mediated multidrug resistance tumour cells.
AID1226440Antioxidant activity assessed as DPPH radical scavenging activity at 1 mM after 1 hr2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID1226461Selectivity index, ratio of IC50 for HEK293 cells to IC50 for cisplatin-resistant human A431 cells2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID578843Cytotoxicity against human A2780 cells assessed as intracellular ATP level at 10 uM after 72 hrs by luminometry2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).
AID1226458Selectivity index, ratio of IC50 for HEK293 cells to IC50 for human MCF7 cells2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID1183093Cytotoxicity against human HL60 cells after 72 hrs by MTT assay2014European journal of medicinal chemistry, Sep-12, Volume: 84Synthesis and effects on cell viability of flavonols and 3-methyl ether derivatives on human leukemia cells.
AID666859Reversal of MRP1-mediated drug resistant in human 2008/MRP1 cells assessed as potentiation of doxorubicin-induced cytotoxicity at 1 uM after 5 days by MTS assay2012European journal of medicinal chemistry, Aug, Volume: 54Synthesis of methylated quercetin derivatives and their reversal activities on P-gp- and BCRP-mediated multidrug resistance tumour cells.
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.
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.
AID1226463Selectivity index, ratio of IC50 for HEK293 cells to IC50 for human C13 cells2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
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.
AID666858Reversal of BCRP-mediated drug resistant in human MCF7-MX100 cells assessed as potentiation of topotecan-induced cytotoxicity at 1 uM after 5 days by MTS assay2012European journal of medicinal chemistry, Aug, Volume: 54Synthesis of methylated quercetin derivatives and their reversal activities on P-gp- and BCRP-mediated multidrug resistance tumour cells.
AID1879371Binding affinity to triplex DNA1 containing 15 nucleotide-long triplex-forming region (unknown origin) assessed as change in melting temperature at 10 uM by UV based assay2022Bioorganic & medicinal chemistry letters, 04-01, Volume: 615-Substituted 3, 3', 4', 7-tetramethoxyflavonoids - A novel class of potent DNA triplex specific binding ligands.
AID265763Inhibition of FabZ at 100 uM2006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.
AID578760Inhibition of BCRP expressed in MCF-7 MX cells using Hoechst 33342 staining2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).
AID1879365Stabilization of [poly(dA).2poly(dT) triplex DNA (unknown origin) assessed as melting temperature at 10 uM by DSC assay (Rvb = 36.8 degC)2022Bioorganic & medicinal chemistry letters, 04-01, Volume: 615-Substituted 3, 3', 4', 7-tetramethoxyflavonoids - A novel class of potent DNA triplex specific binding ligands.
AID319546Antiinflammatory activity in human neutrophils assessed as inhibition of fMet-Leu-Phe/Cytochalasin B-induced superoxide anion generation2008Journal of natural products, Jan, Volume: 71, Issue:1
Benzoic acid derivatives, acetophenones, and anti-inflammatory constituents from Melicope semecarpifolia.
AID1226460Selectivity index, ratio of IC50 for HEK293 cells to IC50 for human A431 cells2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID144650In vitro cytotoxic potency against NCI-60 human tumor cell line1998Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13
Structure-activity requirements for flavone cytotoxicity and binding to tubulin.
AID768676Inhibition of human BCRP expressed in MDCK2 cells assessed as potentiation of SN-38-induced cytotoxicity at 5 to 10 uM after 72 hrs by MTT assay2013European journal of medicinal chemistry, Sep, Volume: 67Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2.
AID1879363Binding affinity to duplex DNA (unknown origin) assessed as effect on melting temperature at 10 uM by UV based assay2022Bioorganic & medicinal chemistry letters, 04-01, Volume: 615-Substituted 3, 3', 4', 7-tetramethoxyflavonoids - A novel class of potent DNA triplex specific binding ligands.
AID404008Cytotoxicity against human KB cells
AID337762Cytotoxicity against human KB cells after 72 hrs
AID1705065Inhibition of biotinylated 5-(4-((Z)-3-Carboxy-3-hydroxyacryloyl)-4-(4-chlorobenzyl)piperidine-1-carbonyl)-2-((13,35-dioxo-39-((3aR,4R,6aS)-2-oxohexahydro-1H-thieno[3,4-d]imidazole-4-yl)-3,6,9,16,19,22,25,28,31-nonaoxa-12,34-diazanonatriacontyl)oxy)benzoi2020European journal of medicinal chemistry, Dec-15, Volume: 208Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors.
AID578759Inhibition of BCRP expressed in MDCK cells using Hoechst 33342 staining2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).
AID666856Reversal of p-glycoprotein-mediated drug resistant in human LCC-6/MDR cells assessed as potentiation of paclitaxel-induced cytotoxicity at 1 uM after 5 days by MTS assay2012European journal of medicinal chemistry, Aug, Volume: 54Synthesis of methylated quercetin derivatives and their reversal activities on P-gp- and BCRP-mediated multidrug resistance tumour cells.
AID1100871Antifeedant activity against Spodoptera litura in compound treated cork borer from fresh sweet potato leaves by Choice Leaf-Disk Bioassay2000Journal of agricultural and food chemistry, May, Volume: 48, Issue:5
Insect antifeedant flavonoids from Gnaphalium affine D. Don.
AID578761Inhibition of P-gp expressed in A2780adr cells by calcein AM accumulation assay2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).
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.
AID1226442Cytotoxicity against human A375 cells assessed as cell growth inhibition after 72 hrs by MTT assay2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
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.
AID1226452Resistance factor, ratio of IC50 for cisplatin-resistant human A431 cells to IC50 for human A431 cells2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID1677634Effect on transcription in rat PC12D cells transfected with pCRE-firefly luciferase and pRL-null-renilla luciferase assessed as renilla luciferase activity at 30 uM by dual luciferase reporter gene assay2020Bioorganic & medicinal chemistry letters, 12-01, Volume: 30, Issue:23
Effect of methoxyflavones contained in Kaempferia parviflora on CRE-mediated transcription in PC12D cells.
AID596671Induction of adipogenesis in mouse 3T3L1 cells assessed as increase in triglyceride level at 3 uM on day 8 relative to control2011Bioorganic & medicinal chemistry, May-01, Volume: 19, Issue:9
Structural requirements of flavonoids for the adipogenesis of 3T3-L1 cells.
AID768679Cytotoxicity against MDCK cells expressing BCRP at 100 uM after 72 hrs by MTT assay2013European journal of medicinal chemistry, Sep, Volume: 67Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2.
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.
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.
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.
AID1223530Drug excretion in Wistar rat urine at 750 mg/kg, po after 12 hrs by HPLC-UV analysis2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Pharmacokinetics, bioavailability, tissue distribution, excretion, and metabolite identification of methoxyflavones in Kaempferia parviflora extract in rats.
AID1226457Selectivity index, ratio of IC50 for HEK293 cells to IC50 for human BxPC3 cells2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID1226450Cytotoxicity against human C13 cells assessed as cell growth inhibition after 72 hrs by MTT assay2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID768691Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of Hoechst 33342 preincubated for 30 mins before Hoechst 33342 addition measured after 120 mins by fluorescence assay2013European journal of medicinal chemistry, Sep, Volume: 67Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2.
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.
AID1879370Stabilization of [poly(dA).2poly(dT) triplex DNA (unknown origin) assessed as effect on CD spectrum up to 25 uM by CD spectroscopy2022Bioorganic & medicinal chemistry letters, 04-01, Volume: 615-Substituted 3, 3', 4', 7-tetramethoxyflavonoids - A novel class of potent DNA triplex specific binding ligands.
AID768689Inhibition of human BCRP expressed in MDCK2 cells assessed as accumulation of pheophorbide-A preincubated for 30 mins before pheophorbide-A addition measured after 120 mins by flow cytometry2013European journal of medicinal chemistry, Sep, Volume: 67Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2.
AID1226462Selectivity index, ratio of IC50 for HEK293 cells to IC50 for human 2008 cells2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
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.
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.
AID666854Cytotoxicity against multidrug resistant human LCC-6 cells after 5 days by MTS assay2012European journal of medicinal chemistry, Aug, Volume: 54Synthesis of methylated quercetin derivatives and their reversal activities on P-gp- and BCRP-mediated multidrug resistance tumour cells.
AID1226454Cytotoxicity against HEK293 cells assessed as cell growth inhibition after 72 hrs by MTT assay2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID1226456Selectivity index, ratio of IC50 for HEK293 cells to IC50 for human HCT15 cells2015Journal of medicinal chemistry, May-28, Volume: 58, Issue:10
Selenium-containing chrysin and quercetin derivatives: attractive scaffolds for cancer therapy.
AID1223531Drug excretion in Wistar rat feces at 750 mg/kg, po after 12 hrs by HPLC-UV analysis2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Pharmacokinetics, bioavailability, tissue distribution, excretion, and metabolite identification of methoxyflavones in Kaempferia parviflora extract in rats.
AID404069In vivo antitumor activity against mouse L1210 cells
AID578844Cytotoxicity against human MCF7 cells assessed as intracellular ATP level at 10 uM after 72 hrs by luminometry2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).
AID265764Inhibition of FabI at 100 uM2006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.
AID768678Cytotoxicity against MDCK cells at <100 uM after 72 hrs by MTT assay2013European journal of medicinal chemistry, Sep, Volume: 67Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2.
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.
AID404070In vivo antitumor activity against mouse CA-755 cells
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (19)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (10.53)18.2507
2000's3 (15.79)29.6817
2010's11 (57.89)24.3611
2020's3 (15.79)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.00

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 Index12.00 (24.57)
Research Supply Index3.09 (2.92)
Research Growth Index5.09 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.00)

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%
Other21 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]