Compounds > 4',5-dihydroxy-3',6,7,8-tetramethoxyflavone
Page last updated: 2024-09-26

4',5-dihydroxy-3',6,7,8-tetramethoxyflavone

Cross-References

ID SourceID
PubMed CID181092
CHEMBL ID74272
SCHEMBL ID10997058
MeSH IDM0571910

Synonyms (25)

Synonym
CHEMBL74272 ,
NSC654971 ,
5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-6,7,8-trimethoxy-chromen-4-one
5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7,8-trimethoxy-4h-chromen-4-one
NCI60_019001
nsc-654971
5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7,8-trimethoxychromen-4-one
8-methoxycirsilineol
5,4'-dihidroxy-6,7,8,3'-tetramethoxyflavone
7-methylsudachitin
LMPK12111475
7-o-methylsudachietin
5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7,8-trimethoxy-4h-1-benzopyran-4-one
4',5-dihydroxy-3',6,7,8-tetramethoxy-flavone
16520-78-8
72y87o5h1x ,
bdbm50412268
unii-72y87o5h1x
5,4'-dihydroxy-6,7,8,3'-tetramethoxyflavone
SCHEMBL10997058
DTXSID40937048
Q27266108
XM177967
4h-1-benzopyran-4-one, 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7,8-trimethoxy-
AKOS040735618

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Aldo-keto reductase family 1 member B1Rattus norvegicus (Norway rat)IC50 (µMol)45.70880.00041.877310.0000AID342547
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID635943Ratio of IC50 for PMA-stimulated pro MMP9 production in human SRA 01/04 cells to IC50 for TNFalpha-stimulated pro MMP9 production in human SRA 01/04 cells2011Bioorganic & medicinal chemistry, Dec-01, Volume: 19, Issue:23
B-Ring-modified and/or 5-demethylated nobiletin congeners: inhibitory activity against pro-MMP-9 production.
AID635946Cytotoxicity against human SRA 01/04 cells at 64 uM after 24 hrs by LDH release assay2011Bioorganic & medicinal chemistry, Dec-01, Volume: 19, Issue:23
B-Ring-modified and/or 5-demethylated nobiletin congeners: inhibitory activity against pro-MMP-9 production.
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.
AID635947Inhibition of PMA-stimulated pro MMP9 production in human SRA 01/04 cells after 24 hrs by SDS-PAGE based gelatin zymography assay2011Bioorganic & medicinal chemistry, Dec-01, Volume: 19, Issue:23
B-Ring-modified and/or 5-demethylated nobiletin congeners: inhibitory activity against pro-MMP-9 production.
AID342547Inhibition of rat lens aldose reductase2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
QSAR prediction of inhibition of aldose reductase for flavonoids.
AID724431Growth inhibition of human SRA 01/04 cells at 32 uM after 4 days by Alamar blue assay2013Bioorganic & medicinal chemistry letters, Jan-01, Volume: 23, Issue:1
Polymethoxyflavones as agents that prevent formation of cataract: nobiletin congeners show potent growth inhibitory effects in human lens epithelial cells.
AID1190339Displacement of [3H]DPDPE from delta opioid receptor in CD1 mouse whole brain minus cerebellum membranes by liquid scintillation counting2015Journal of natural products, Jan-23, Volume: 78, Issue:1
Methoxyflavones from Stachys glutinosa with binding affinity to opioid receptors: in silico, in vitro, and in vivo studies.
AID1190338Displacement of [3H]DAMGO from mu opioid receptor in CD1 mouse whole brain minus cerebellum membranes by liquid scintillation counting2015Journal of natural products, Jan-23, Volume: 78, Issue:1
Methoxyflavones from Stachys glutinosa with binding affinity to opioid receptors: in silico, in vitro, and in vivo studies.
AID379312Antioxidant scavenging activity against 2,2'-azobis-amidinopropane-induced peroxyl radicals assessed as total oxyradical scavenging capacity relative to Trolox2000Journal of natural products, Mar, Volume: 63, Issue:3
Evaluation of the total peroxyl radical-scavenging capacity of flavonoids: structure-activity relationships.
AID635945Inhibition of TNFalpha-stimulated pro MMP9 production in human SRA 01/04 cells after 24 hrs by SDS-PAGE based gelatin zymography assay2011Bioorganic & medicinal chemistry, Dec-01, Volume: 19, Issue:23
B-Ring-modified and/or 5-demethylated nobiletin congeners: inhibitory activity against pro-MMP-9 production.
AID379313Antioxidant scavenging activity against 2,2'-azobis-amidinopropane-induced peroxyl radicals assessed as total oxyradical scavenging capacity2000Journal of natural products, Mar, Volume: 63, Issue:3
Evaluation of the total peroxyl radical-scavenging capacity of flavonoids: structure-activity relationships.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (16.67)18.2507
2000's2 (33.33)29.6817
2010's3 (50.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceDescriptionRelationhip StrengthStudiesTrialsClassesRoles
colchicine[no description available]medium10alkaloid;
colchicine		anti-inflammatory agent;
gout suppressant;
mutagen
podophyllotoxin[no description available]medium10furonaphthodioxole;
lignan;
organic heterotetracyclic compound		antimitotic;
antineoplastic agent;
keratolytic drug;
microtubule-destabilising agent;
plant metabolite;
tubulin modulator
tangeretin[no description available]medium40pentamethoxyflavoneantineoplastic agent;
plant metabolite
nobiletin[no description available]medium30methoxyflavoneantineoplastic agent;
plant metabolite
4',5,6,7-tetramethoxyflavone[no description available]medium10tetramethoxyflavoneantimutagen;
plant metabolite
quercetin 5,7,3',4'-tetramethyl ether[no description available]medium10flavonols;
tetramethoxyflavone		plant metabolite
5,4'-dihydroxy-3,6,7,8,3'-pentamethoxyflavone[no description available]medium10
5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone[no description available]medium10ether;
flavonoids
3,3',4',5,6,7,8-heptamethoxyflavone[no description available]medium10ether;
flavonoids
sideritoflavone[no description available]medium30ether;
flavonoids
nevadensin[no description available]medium20dihydroxyflavone;
trimethoxyflavone		plant metabolite
2-(4-hydroxyphenyl)-5,6,7-trimethoxy-4H-1-benzopyran-4-one[no description available]medium10monohydroxyflavone;
trimethoxyflavone
4',6-dihydroxy-5,7-dimethoxyflavone[no description available]medium10dihydroxyflavone;
dimethoxyflavone
gardenin a[no description available]medium10
3',4',5'-trimethoxyflavone[no description available]medium10ether;
flavonoids
5-demethylnobiletin[no description available]medium30ether;
flavonoids
5-Hydroxy-7-methoxy-6-methylflavone[no description available]medium10ether;
flavonoids
5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone[no description available]medium10
eupatilin[no description available]medium20dihydroxyflavone;
trimethoxyflavone		anti-inflammatory agent;
anti-ulcer drug;
antineoplastic agent;
EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor;
metabolite
quercetin[no description available]medium207-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
ayanin[no description available]medium10dihydroxyflavone;
trimethoxyflavone		plant metabolite
chrysosplenetin b[no description available]medium10dihydroxyflavone;
tetramethoxyflavone		antiviral agent;
plant metabolite
fisetin[no description available]medium103'-hydroxyflavonoid;
7-hydroxyflavonol;
tetrahydroxyflavone		anti-inflammatory agent;
antioxidant;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
geroprotector;
metabolite;
plant metabolite
hispidulin[no description available]medium10monomethoxyflavone;
trihydroxyflavone		anti-inflammatory agent;
anticonvulsant;
antineoplastic agent;
antioxidant;
apoptosis inducer;
plant metabolite
myricetin[no description available]medium107-hydroxyflavonol;
hexahydroxyflavone		antineoplastic agent;
antioxidant;
cyclooxygenase 1 inhibitor;
food component;
geroprotector;
hypoglycemic agent;
plant metabolite
rhamnetin[no description available]medium10monomethoxyflavone;
tetrahydroxyflavone		anti-inflammatory agent;
antioxidant;
metabolite
centaureidin[no description available]medium10trihydroxyflavone;
trimethoxyflavone		antineoplastic agent;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
plant metabolite
eupatin[no description available]medium10flavonols;
trihydroxyflavone;
trimethoxyflavone
ombuine[no description available]medium10dimethoxyflavone;
flavonols;
trihydroxyflavone		anti-inflammatory agent;
plant metabolite
5,7-dihydroxy-4',6-dimethoxyflavone[no description available]medium10dihydroxyflavone;
dimethoxyflavone		plant metabolite
ermanin[no description available]medium10dihydroxyflavone;
dimethoxyflavone		anti-inflammatory agent;
antimycobacterial drug;
antineoplastic agent;
apoptosis inducer;
plant metabolite
5-hydroxy-3,3',4',7-tetramethoxyflavone[no description available]medium103'-methoxyflavones;
monohydroxyflavone;
tetramethoxyflavone		plant metabolite
5,7,3'-trihydroxy-3,4'-dimethoxyflavone[no description available]medium10dimethoxyflavone;
trihydroxyflavone		antineoplastic agent;
metabolite
ternatin (flavonoid)[no description available]medium10ether;
flavonoids
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid[no description available]medium10chromanol;
monocarboxylic acid;
phenols		antioxidant;
ferroptosis inhibitor;
neuroprotective agent;
radical scavenger;
Wnt signalling inhibitor
rutin[no description available]medium10disaccharide derivative;
quercetin O-glucoside;
rutinoside;
tetrahydroxyflavone		antioxidant;
metabolite
artemetin[no description available]medium10ether;
flavonoids
calycopterin[no description available]medium10ether;
flavonoids
pedalitin[no description available]medium10monomethoxyflavone;
tetrahydroxyflavone		EC 1.17.3.2 (xanthine oxidase) inhibitor;
metabolite
xanthomicrol[no description available]medium40dihydroxyflavone;
trimethoxyflavone		antineoplastic agent;
plant metabolite
cirsiliol[no description available]medium10dimethoxyflavone;
trihydroxyflavone		plant metabolite
cirsilineol[no description available]medium10dihydroxyflavone;
trimethoxyflavone		antineoplastic agent;
plant metabolite
4',6-dihydroxyflavone[no description available]medium10dihydroxyflavone
cirsimaritin[no description available]medium10dihydroxyflavone;
dimethoxyflavone
demethoxysudachitin[no description available]medium10ether;
flavonoids
dexmedetomidine[no description available]medium10trihydroxyflavone;
trimethoxyflavone		antineoplastic agent;
metabolite
axillarin[no description available]medium10dimethoxyflavone;
tetrahydroxyflavone		plant metabolite
6-hydroxyluteolin[no description available]medium10pentahydroxyflavone
3',4'-didemethylnobiletin[no description available]medium30
sudachitin[no description available]medium10ether;
flavonoids
4'-hydroxy-5,6,7,8,3'-pentamethoxyflavone[no description available]medium30ether;
flavonoids
3'-demethylnobiletin[no description available]medium10ether;
flavonoids
gardenin b[no description available]medium10monohydroxyflavone;
tetramethoxyflavone		plant metabolite
morphine chloride[no description available]medium10hydrochloride
ConditionIndicatedRelationship StrengthStudiesTrials
Cataract0low10
Cataract, Membranous0low10
Lens Opacities0low10
Pseudoaphakia0low10

Research Highlights

Safety/Toxicity (1)

ArticleYear
Structure-activity requirements for flavone cytotoxicity and binding to tubulin.
Journal of medicinal chemistry, Jun-18, Volume: 41, Issue: 13		1998
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]