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4',5,7-trihydroxy-3,6-dimethoxyflavone

Description

viscosine: a GABA-A receptor agonist with anxiolytic and anticonvulsant activities; isolated from Dodonaea viscosa; structure in first source [MeSH]

Cross-References

ID SourceID
PubMed CID5352032
CHEMBL ID351607
SCHEMBL ID1156264
MeSH IDM0063692

Synonyms (31)

Synonym
trihydroxy-flavone
NSC271638 ,
3,6-dimethoxy-5,7,4'-
22697-65-0
nsc-271638
5,7-dihydroxy-2-(4-hydroxyphenyl)-3,6-dimethoxychromen-4-one
3,6-dimethoxy kaempferol
CHEMBL351607 ,
6-methoxykaempferol 3-methyl ether
LMPK12112867
5,7,4'-trihydroxy-3,6-dimethoxyflavone
bdbm50292535
5,7-dihydroxy-2-(4-hydroxy-phenyl)-3,6-dimethoxy-chromen-4-one
5,7-dihydroxy-2-(4-hydroxyphenyl)-3,6-dimethoxy-4h-chromen-4-one
5,7-dihydroxy-2-(4-hydroxyphenyl)-3,6-dimethoxy-4h-1-benzopyran-4-one
5v53651jor ,
4',5,7-trihydroxy-3,6-dimethoxyflavone
unii-5v53651jor
SCHEMBL1156264
3,6-dimethoxyapigenin
AKOS025287972
DTXSID00177221
4',5,7-trihydroxy-3,6-dimethoxyflavone, >=90% (lc/ms-elsd)
FS-9486
4h-1-benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-3,6-dimethoxy-
6-hydroxykaempferol 3,6-dimethyl ether
6-methoxy-3-o-methylkaempferol
viscosine
galetin 3,6-dimethyl ether
flavone, 4',5,7-trihydroxy-3,6-dimethoxy-
6-hydroxykaempferol 3,6-dimethylether

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Xanthine dehydrogenase/oxidaseBos taurus (cattle)IC500.0400AID1402016; AID338975

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1402017Potency index, ratio of IC50 for allopurinol to IC50 for test compound for inhibition of bovine milk xanthine oxidase using xanthine as substrate preincubated for 15 mins followed by substrate addition measured after 30 mins by UV-VIS spectrophotometric a2018European journal of medicinal chemistry, Jan-01, Volume: 143ISSN: 1768-3254Xanthine oxidase inhibitory activity of natural and hemisynthetic flavonoids from Gardenia oudiepe (Rubiaceae) in vitro and molecular docking studies.
AID162237Cytotoxic dose at which 50% growth of normal cells is inhibited1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
ISSN: 0022-2623
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
ISSN: 0022-2623
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID1198221Cytotoxicity against mouse B16 cells assessed as cell viability after 48 hrs by MTT assay2015European journal of medicinal chemistry, Mar-26, Volume: 93ISSN: 1768-3254Antivascular and anti-parasite activities of natural and hemisynthetic flavonoids from New Caledonian Gardenia species (Rubiaceae).
AID1402016Inhibition of bovine milk xanthine oxidase using xanthine as substrate preincubated for 15 mins followed by substrate addition measured after 30 mins by UV-VIS spectrophotometric analysis2018European journal of medicinal chemistry, Jan-01, Volume: 143ISSN: 1768-3254Xanthine oxidase inhibitory activity of natural and hemisynthetic flavonoids from Gardenia oudiepe (Rubiaceae) in vitro and molecular docking studies.
AID1198220Cytotoxicity against rat L6 cells assessed as viable cells at 1 uM after 72 hrs by MTT assay relative to control2015European journal of medicinal chemistry, Mar-26, Volume: 93ISSN: 1768-3254Antivascular and anti-parasite activities of natural and hemisynthetic flavonoids from New Caledonian Gardenia species (Rubiaceae).
AID1198226Antiplasmodial activity against Plasmodium falciparum FcB1/Columbia infected in human red blood cells assessed as parasite growth inhibition at 10 uM after 48 hrs by [3H]-hypoxanthine incorporation assay relative to control2015European journal of medicinal chemistry, Mar-26, Volume: 93ISSN: 1768-3254Antivascular and anti-parasite activities of natural and hemisynthetic flavonoids from New Caledonian Gardenia species (Rubiaceae).
AID663896Adipogenic activity in mouse 3T3L1 cells assessed as increase in triglyceride level after 8 days relative to control2012Journal of natural products, Apr-27, Volume: 75, Issue:4
ISSN: 1520-6025
Isoprenylated flavonoid and adipogenesis-promoting constituents of Dodonaea viscosa.
AID338975Inhibition of cow milk xanthine oxidaseJournal of natural products, , Volume: 51, Issue:2
ISSN: 0163-3864
Inhibition of cow's milk xanthine oxidase by flavonoids.
AID162238Minimum drug concentration at which 99% of the polio virus is inhibited1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
ISSN: 0022-2623
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID235260Therapeutic Index measured as the ratio of CyD50(polio) / ED99(polio) values1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
ISSN: 0022-2623
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID1198229Antitrypanosomal activity against Trypanosoma brucei gambiense Feo assessed as parasite growth inhibition at 10 uM after 72 hrs by fluorescence assay relative to control2015European journal of medicinal chemistry, Mar-26, Volume: 93ISSN: 1768-3254Antivascular and anti-parasite activities of natural and hemisynthetic flavonoids from New Caledonian Gardenia species (Rubiaceae).
AID338974Inhibition of cow milk xanthine oxidase at 50 ug/mLJournal of natural products, , Volume: 51, Issue:2
ISSN: 0163-3864
Inhibition of cow's milk xanthine oxidase by flavonoids.
AID162249Minimal dose which produces titer reduction at 10 ug/mL (mD RF10e3)1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
ISSN: 0022-2623
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
ISSN: 0022-2623
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.
AID1198225Leishmanicidal activity against promastigote stage of Leishmania amazonensis MHOM/BR/PH8 after 48 hrs by MTT assay2015European journal of medicinal chemistry, Mar-26, Volume: 93ISSN: 1768-3254Antivascular and anti-parasite activities of natural and hemisynthetic flavonoids from New Caledonian Gardenia species (Rubiaceae).
AID1198219Cytotoxicity against rat L6 cells assessed as viable cells at 10 uM after 72 hrs by MTT assay relative to control2015European journal of medicinal chemistry, Mar-26, Volume: 93ISSN: 1768-3254Antivascular and anti-parasite activities of natural and hemisynthetic flavonoids from New Caledonian Gardenia species (Rubiaceae).
AID1198228Antitrypanosomal activity against Trypanosoma brucei gambiense Feo assessed as parasite growth inhibition at 50 uM after 72 hrs by fluorescence assay relative to control2015European journal of medicinal chemistry, Mar-26, Volume: 93ISSN: 1768-3254Antivascular and anti-parasite activities of natural and hemisynthetic flavonoids from New Caledonian Gardenia species (Rubiaceae).
AID1198222Antivascular activity in human EAhy926 cells assessed as concentration require to adopt rounding shape after 2 hrs by microscopic analysis2015European journal of medicinal chemistry, Mar-26, Volume: 93ISSN: 1768-3254Antivascular and anti-parasite activities of natural and hemisynthetic flavonoids from New Caledonian Gardenia species (Rubiaceae).

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (10.00)18.2507
2000's1 (10.00)29.6817
2010's8 (80.00)24.3611
2020's0 (0.00)2.80

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%
Other12 (100.00%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
chloroquineaminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound
anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
201520159.0low000010
guanidinecarboxamidine;
guanidines;
one-carbon compound
1991199133.0low001000
pentamidinearomatic ether;
carboxamidine;
diether
anti-inflammatory agent;
antifungal agent;
calmodulin antagonist;
chemokine receptor 5 antagonist;
EC 2.3.1.48 (histone acetyltransferase) inhibitor;
NMDA receptor antagonist;
S100 calcium-binding protein B inhibitor;
trypanocidal drug;
xenobiotic
201520159.0low000010
colchicinealkaloid;
colchicine
anti-inflammatory agent;
gout suppressant;
mutagen
201520159.0low000010
sakuranetin(2S)-flavan-4-one;
4'-hydroxyflavanones;
dihydroxyflavanone;
flavonoid phytoalexin;
monomethoxyflavanone
antimycobacterial drug;
plant metabolite
2012201212.0low000010
rosiglitazoneaminopyridine;
thiazolidinediones
EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor;
ferroptosis inhibitor;
insulin-sensitizing drug
2012201212.0low000010
5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavoneether;
flavonoids
1991199133.0low001000
3,3',4',5,6,7,8-heptamethoxyflavoneether;
flavonoids
1991199133.0low001000
quercetin7-hydroxyflavonol;
pentahydroxyflavone
antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
1991199133.0low001000
3,7-dimethoxy-5,3',4'-trihydroxyflavonedimethoxyflavone;
trihydroxyflavone
EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor;
metabolite
1991199133.0low001000
quercetin 3-o-methyl ethermonomethoxyflavone;
tetrahydroxyflavone
antimicrobial agent;
metabolite
1991199133.0low001000
3-methylkaempferolmonomethoxyflavone;
trihydroxyflavone
plant metabolite1991201815.0high001030
kaempferol7-hydroxyflavonol;
flavonols;
tetrahydroxyflavone
antibacterial agent;
geroprotector;
human blood serum metabolite;
human urinary metabolite;
human xenobiotic metabolite;
plant metabolite
201520159.0low000010
amphotericin bantibiotic antifungal drug;
macrolide antibiotic;
polyene antibiotic
antiamoebic agent;
antiprotozoal drug;
bacterial metabolite
201520159.0low000010
pachypodoldihydroxyflavone;
trimethoxyflavone
antiemetic;
plant metabolite
1991199133.0low001000
santindihydroxyflavone;
trimethoxyflavone
plant metabolite1991201816.0high001020
Kumatakeninether;
flavonoids
1991201521.0high001010
5,4'-dihydroxy-3,6,7-trimethoxyflavone1991199133.0medium001000
fosbretabulinstilbenoid201520159.0low000010
ermanindihydroxyflavone;
dimethoxyflavone
anti-inflammatory agent;
antimycobacterial drug;
antineoplastic agent;
apoptosis inducer;
plant metabolite
1991199133.0low001000
5-hydroxy-3,3',4',7-tetramethoxyflavone3'-methoxyflavones;
monohydroxyflavone;
tetramethoxyflavone
plant metabolite1991199133.0low001000
allopurinolnucleobase analogue;
organic heterobicyclic compound
antimetabolite;
EC 1.17.3.2 (xanthine oxidase) inhibitor;
gout suppressant;
radical scavenger
201820186.0low000010
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
gamma-aminobutyric acidamino acid zwitterion;
gamma-amino acid;
monocarboxylic acid
human metabolite;
neurotransmitter;
Saccharomyces cerevisiae metabolite;
signalling molecule
201520159.0low000010
chlorinehalide anion;
monoatomic chlorine
cofactor;
Escherichia coli metabolite;
human metabolite
201520159.0low000010
histaminearalkylamino compound;
imidazoles
human metabolite;
mouse metabolite;
neurotransmitter
201520159.0low000010
4-aminopyridineaminopyridine;
aromatic amine
avicide;
orphan drug;
potassium channel blocker
201520159.0low000010
bay-k-8644(trifluoromethyl)benzenes;
C-nitro compound;
dihydropyridine;
methyl ester
201520159.0low000010
verapamilaromatic ether;
nitrile;
polyether;
tertiary amino compound
2014201410.0low000010
glyburidemonochlorobenzenes;
N-sulfonylurea
anti-arrhythmia drug;
EC 2.7.1.33 (pantothenate kinase) inhibitor;
EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor;
hypoglycemic agent
201520159.0low000010
milrinonebipyridines;
nitrile;
pyridone
cardiotonic drug;
EC 3.1.4.17 (3',5'-cyclic-nucleotide phosphodiesterase) inhibitor;
platelet aggregation inhibitor;
vasodilator agent
2014201410.0low000010
potassium chlorideinorganic chloride;
inorganic potassium salt;
potassium salt
fertilizer201520159.0low000010
tetraethylammoniumquaternary ammonium ion201520159.0low000010
carbacholammonium salt;
carbamate ester
cardiotonic drug;
miotic;
muscarinic agonist;
nicotinic acetylcholine receptor agonist;
non-narcotic analgesic
201520159.0low000010
phenylephrinephenols;
phenylethanolamines;
secondary amino compound
alpha-adrenergic agonist;
cardiotonic drug;
mydriatic agent;
nasal decongestant;
protective agent;
sympathomimetic agent;
vasoconstrictor agent
2014201410.0low000010
aminophyllinemixturebronchodilator agent;
cardiotonic drug
2014201410.0low000010
cesium chlorideinorganic caesium salt;
inorganic chloride
phase-transfer catalyst;
vasoconstrictor agent
201520159.0low000010
oxytocinheterodetic cyclic peptide;
peptide hormone
oxytocic;
vasodilator agent
201720177.0low000010
cesiumalkali metal atom201520159.0low000010
sildenafil citratecitrate saltEC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor;
vasodilator agent
2014201410.0low000010
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Muscle Contraction02011201511.0high000020