Page last updated: 2024-11-11

5,4'-dihydroxy-3,6,7-trimethoxyflavone

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

Description

5,4'-dihydroxy-3,6,7-trimethoxyflavone: from Microliabum polymnioides; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
Microliabumgenus[no description available]AsteraceaeA large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]

Cross-References

ID SourceID
PubMed CID5320462
CHEMBL ID165509
SCHEMBL ID2217068
MeSH IDM000611565

Synonyms (27)

Synonym
569-80-2
5-hydroxy-2-(4-hydroxyphenyl)-3,6,7-trimethoxy-4h-1-benzopyran-4-one
4h-1-benzopyran-4-one, 5-hydroxy-2-(4-hydroxyphenyl)-3,6,7-trimethoxy-
penduletin
CHEMBL165509 ,
5,4'-dihydroxy-3,6,7-trimethoxyflavone
LMPK12112874
5-hydroxy-2-(4-hydroxyphenyl)-3,6,7-trimethoxychromen-4-one
5,4''-dihydroxy-3,6,7-trimethoxyflavanone
5-hydroxy-2-(4-hydroxy-phenyl)-3,6,7-trimethoxy-chromen-4-one
bdbm50338973
SCHEMBL2217068
YSXFFLGRZJWNFM-UHFFFAOYSA-N
5-hydroxy-2-(4-hydroxyphenyl)-3,6,7-trimethoxy-4h-chromen-4-one #
2-(4-hydroxyphenyl)-3,6,7-trimethoxy-5-hydroxy-4h-1-benzopyran-4-one (penduletin)
DTXSID00205437
AKOS032948446
5,4'-dihydroxy-3,6,7-trimethoxyflavone; 6-hydroxykaempferol 3,6,7-trimethyl ether
nsc659549
nsc-659549
XP161712
FS-10029
CS-0023216
HY-N3096
flavone, 4',5-dihydroxy-3,6,7-trimethoxy-
FD7R8D6VZB
4',5-dihydroxy-3,6,7-trimethoxyflavone
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
ATP-dependent translocase ABCB1Homo sapiens (human)IC50 (µMol)14.00000.00022.318510.0000AID578762
Broad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)IC50 (µMol)1.60000.00401.966610.0000AID578759; AID578760
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (26)

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)
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 (21)

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)
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 (11)

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)
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 (22)

Assay IDTitleYearJournalArticle
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.
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).
AID399299Inhibition of aldose reductase at 0.1 uM
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).
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).
AID399170Trypanocidal activity against Trypanosoma cruzi Y strain trypomastigotes infected in Swiss albino mouse blood assessed as reduction of parasitemia at 500 ug/mL after 24 hrs relative to control1997Journal of natural products, Aug, Volume: 60, Issue:8
Trypanocidal flavonoids from Trixis vauthieri.
AID422404Antitubercular activity against Mycobacterium tuberculosis H37Rv after 2 weeks2009Journal of natural products, Feb-27, Volume: 72, Issue:2
seco-Abietane diterpenoids, a phenylethanoid derivative, and antitubercular constituents from Callicarpa pilosissima.
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.
AID399298Inhibition of aldose reductase at 0.01 uM
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.
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).
AID199696Minimum drug concentration at which 99% of the rhino virus is inhibited.1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID235261Therapeutic Index measured as the ratio of CyD50 (rhino) / ED99 (rhino) values.1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus 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.
AID199695Cytotoxic dose at which 50% growth of normal cells is inhibited against rhino virus infection.1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
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).
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.
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).
AID399301Inhibition of aldose reductase at 10 uM
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.
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).
AID399300Inhibition of aldose reductase at 1 uM
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (25.00)18.2507
2000's1 (12.50)29.6817
2010's4 (50.00)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.77

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 Index12.77 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index5.08 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.77)

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]