Page last updated: 2024-09-24

4',5,6,7-tetramethoxyflavone

Description

4',5,6,7-tetramethoxyflavone: structure given in first source; from plant Eupatorium odoratum [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

4',5,6,7-tetramethoxyflavone : A tetramethoxyflavone that is the tetra-O-methyl derivative of scutellarein. [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]

FloraRankFlora DefinitionFamilyFamily Definition
EupatoriumgenusA plant genus of the family ASTERACEAE. Ingestion has been associated with MILK SICKNESS. The common name of thoroughwort is also used for other plants including CHROMOLAENA; Hebeclinium, and Koanophyllon.[MeSH]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 CID96118
CHEMBL ID75349
CHEBI ID34357
SCHEMBL ID739115
MeSH IDM0197035

Synonyms (62)

Synonym
chebi:34357 ,
CHEMBL75349
tetra-o-methylscutellarein
4',6,7-tetramethoxyflavone
tetramethyl-o-scutellarin
nsc-53908
1168-42-9
4h-1-benzopyran-4-one,6,7-trimethoxy-2-(4-methoxyphenyl)-
scutellarein tetramethyl ether
NSC53908 ,
flavone,5,6,7-tetramethoxy-
NCIMECH_000290
NCI60_004329
MLS001048998
smr000387012
4h-1-benzopyran-4-one, 5,6,7-trimethoxy-2-(4-methoxyphenyl)-
NCGC00179960-01
5,6,7,4'-tetramethoxyflavone
4', 5,6,7-tetramethoxyflavone
5,6,7-trimethoxy-2-(4-methoxyphenyl)-4h-chromen-4-one
4h-1-benzopyran-4-one, 5,6, 7-trimethoxy-2-(4-methoxyphenyl)-
5,6,7-trimethoxy-2-(4-methoxyphenyl)chromen-4-one
flavone, 4',5,6,7-tetramethoxy-
ACON1_001966
OPREA1_070007
4',5,6,7-tetramethoxyflavone
scutellarein tetramethylether
BRD-K36475601-001-01-8
LMPK12111167
5,6,7-trimethoxy-2-(4-methoxyphenyl)-4h-1-benzopyran-4-one
scutellarein 5,6,7,4'-tetramethyl ether
HMS2271J05
nsc 53908
unii-dwn851iyg6
dwn851iyg6 ,
AKOS015969703
CCG-35304
FT-0633423
tetramethylscutellarein
SCHEMBL739115
T3970
mfcd00017442
bdbm50451668
flavone, 5,6,7,4'-tetramethoxy
5,6,7-trimethoxy-2-(4-methoxyphenyl)-4h-chromen-4-one #
4',5,6,7-tetramethoxy flavone
DTXSID60151522 ,
scutellareintetramethylether
ncgc00179960-02!5,6,7-trimethoxy-2-(4-methoxyphenyl)chromen-4-one
4',5,6,7-tetramethoxy-flavone
flavone, 4',5,6,7-tetramethoxy- (8ci)
pectolinarigenin dimethyl ether
5-methoxysalvigenin
HY-N4314
Q27116014
BCP10002
CS-0032724
tetrametlglscutellarein
MS-25233
STL578194
E80724
dtxcid4074013

Roles (2)

RoleDescription
antimutagenAn agent that reduces or interferes with the mutagenic actions or effects of a substance.
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 (1)

ClassDescription
tetramethoxyflavoneAny methoxyflavone with four methoxy substituents.
[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]

Protein Targets (9)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LuciferasePhotinus pyralis (common eastern firefly)Potency26.85450.007215.758889.3584AID588342
glp-1 receptor, partialHomo sapiens (human)Potency3.98110.01846.806014.1254AID624417
ATAD5 protein, partialHomo sapiens (human)Potency29.08100.004110.890331.5287AID504467
TDP1 proteinHomo sapiens (human)Potency21.14460.000811.382244.6684AID686978; AID686979
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency28.18380.011212.4002100.0000AID1030
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency9.20000.00419.984825.9290AID504444
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency63.09570.050127.073689.1251AID588590
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency10.00000.00798.23321,122.0200AID2551
TAR DNA-binding protein 43Homo sapiens (human)Potency3.16231.778316.208135.4813AID652104
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Processvia Protein(s)Taxonomy
negative regulation of protein phosphorylationTAR DNA-binding protein 43Homo sapiens (human)
mRNA processingTAR DNA-binding protein 43Homo sapiens (human)
RNA splicingTAR DNA-binding protein 43Homo sapiens (human)
negative regulation of gene expressionTAR DNA-binding protein 43Homo sapiens (human)
regulation of protein stabilityTAR DNA-binding protein 43Homo sapiens (human)
positive regulation of insulin secretionTAR DNA-binding protein 43Homo sapiens (human)
response to endoplasmic reticulum stressTAR DNA-binding protein 43Homo sapiens (human)
positive regulation of protein import into nucleusTAR DNA-binding protein 43Homo sapiens (human)
regulation of circadian rhythmTAR DNA-binding protein 43Homo sapiens (human)
regulation of apoptotic processTAR DNA-binding protein 43Homo sapiens (human)
negative regulation by host of viral transcriptionTAR DNA-binding protein 43Homo sapiens (human)
rhythmic processTAR DNA-binding protein 43Homo sapiens (human)
regulation of cell cycleTAR DNA-binding protein 43Homo sapiens (human)
3'-UTR-mediated mRNA destabilizationTAR DNA-binding protein 43Homo sapiens (human)
3'-UTR-mediated mRNA stabilizationTAR DNA-binding protein 43Homo sapiens (human)
nuclear inner membrane organizationTAR DNA-binding protein 43Homo sapiens (human)
amyloid fibril formationTAR DNA-binding protein 43Homo sapiens (human)
regulation of gene expressionTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
double-stranded DNA bindingTAR DNA-binding protein 43Homo sapiens (human)
RNA bindingTAR DNA-binding protein 43Homo sapiens (human)
mRNA 3'-UTR bindingTAR DNA-binding protein 43Homo sapiens (human)
protein bindingTAR DNA-binding protein 43Homo sapiens (human)
lipid bindingTAR DNA-binding protein 43Homo sapiens (human)
identical protein bindingTAR DNA-binding protein 43Homo sapiens (human)
pre-mRNA intronic bindingTAR DNA-binding protein 43Homo sapiens (human)
molecular condensate scaffold activityTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
intracellular non-membrane-bounded organelleTAR DNA-binding protein 43Homo sapiens (human)
nucleusTAR DNA-binding protein 43Homo sapiens (human)
nucleoplasmTAR DNA-binding protein 43Homo sapiens (human)
perichromatin fibrilsTAR DNA-binding protein 43Homo sapiens (human)
mitochondrionTAR DNA-binding protein 43Homo sapiens (human)
cytoplasmic stress granuleTAR DNA-binding protein 43Homo sapiens (human)
nuclear speckTAR DNA-binding protein 43Homo sapiens (human)
interchromatin granuleTAR DNA-binding protein 43Homo sapiens (human)
nucleoplasmTAR DNA-binding protein 43Homo sapiens (human)
chromatinTAR DNA-binding protein 43Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (54)

Assay IDTitleYearJournalArticle
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1651739Antibacterial activity against Enterococcus faecium MB3 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID404070In vivo antitumor activity against mouse CA-755 cells
AID1092127Antifungal activity against Aspergillus niger CICC 2273 assessed as inhibition of mycelial growth by microbroth dilution method2012Journal of agricultural and food chemistry, May-02, Volume: 60, Issue:17
Structure-activity relationship of citrus polymethoxylated flavones and their inhibitory effects on Aspergillus niger.
AID1651742Antibacterial activity against Vancomycin resistant Enterococcus casseliflavus MB159 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID1651733Antibacterial activity against Methicillin-resistant Staphylococcus hominis MB124 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID1651741Antibacterial activity against Enterococcus avium MB119 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID310882Inhibition of HIV1 replication2007Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5
Simple criterion for selection of flavonoid compounds with anti-HIV activity.
AID379054Inhibition of TNFalpha expression in LPS-stimulated human monocytes treated 30 mins before LPS challenge measured after 14 hrs by ELISA1999Journal of natural products, Mar, Volume: 62, Issue:3
Polymethoxylated flavones derived from citrus suppress tumor necrosis factor-alpha expression by human monocytes.
AID1651728Antibacterial activity against Methicillin-resistant Staphylococcus capitis MB71 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID1455930Antimycobacterial activity against Mycobacterium tuberculosis H37Rv2017Journal of natural products, 02-24, Volume: 80, Issue:2
Flavonoids from Erythrina schliebenii.
AID1070435Activation of Nrf2 (unknown origin) expressed in CHO-ARE luc cells at 10 to 30 uM after 18 hrs by luciferase reporter gene assay2014Journal of natural products, Mar-28, Volume: 77, Issue:3
Identification of chromomoric acid C-I as an Nrf2 activator in Chromolaena odorata.
AID360320Antiproliferative activity against human HT1080 cells after 4 days by MTT assay2001Journal of natural products, May, Volume: 64, Issue:5
Five novel highly oxygenated diterpenes of Orthosiphon stamineus from Myanmar.
AID1651730Antibacterial activity against Staphylococcus simulans MB94 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID33151Ability to displace [3H]-CGS- 21680 binding from adenosine A2A receptor.1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
Flavonoid derivatives as adenosine receptor antagonists: a comparison of the hypothetical receptor binding site based on a comparative molecular field analysis model.
AID404067In vivo antitumor activity against mouse S180 cells
AID404069In vivo antitumor activity against mouse L1210 cells
AID1651738Antibacterial activity against Enterococcus faecium MB2 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID33195Ability to displace [125I]-AB-MECA binding from adenosine A3 receptor.1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
Flavonoid derivatives as adenosine receptor antagonists: a comparison of the hypothetical receptor binding site based on a comparative molecular field analysis model.
AID1651724Antibacterial activity against Methicillin-resistant Staphylococcus aureus MB188 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID1651731Antibacterial activity against Staphylococcus lugdunensis MB96 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID1434690Inhibition of sucrose loaded POPC/POPE/POPS/PtdIns(3,4,5)P3 (59:20:20:1) liposome binding to eGFP-fused PDK1 PH domain (unknown origin) expressed in Escherichia coli BL21 at 20 uM after 10 mins by fluorescence spectrophotometry based pull down assay relat2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Inhibitory potential of flavonoids on PtdIns(3,4,5)P3 binding with the phosphoinositide-dependent kinase 1 pleckstrin homology domain.
AID404008Cytotoxicity against human KB cells
AID1651726Antibacterial activity against Methicillin-resistant Staphylococcus epidermidis MB169 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID1651734Antibacterial activity against Vancomycin resistant Enterococcus faecalis MB1 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID1651744Antibacterial activity against Vancomycin resistant Enterococcus gallinarum MB111 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID294156Inhibition of diphenolase activity of mushroom tyrosinase at 0.049 mM2007Bioorganic & medicinal chemistry, Apr-01, Volume: 15, Issue:7
Identification of tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum.
AID1651743Antibacterial activity against Enterococcus durans MB113 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID1651736Antibacterial activity against Vancomycin resistant Enterococcus faecalis MB51 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID1651737Antibacterial activity against Enterococcus faecalis MB76 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID360319Antiproliferative activity against mouse Colon 26-L5 cells after 4 days by MTT assay2001Journal of natural products, May, Volume: 64, Issue:5
Five novel highly oxygenated diterpenes of Orthosiphon stamineus from Myanmar.
AID1651725Antibacterial activity against Methicillin-resistant Staphylococcus epidermidis MB165 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID1651735Antibacterial activity against Vancomycin resistant Enterococcus faecalis MB19 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID94814Inhibitory activity against K562 human chronic myelogenous leukemia cell line using MTT assay after 5 days incubation of the compound2003Bioorganic & medicinal chemistry letters, Nov-03, Volume: 13, Issue:21
The total synthesis of an aurone isolated from Uvaria hamiltonii: aurones and flavones as anticancer agents.
AID1651740Antibacterial activity against Enterococcus faecium MB152 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID1651732Antibacterial activity against Methicillin-resistant Staphylococcus haemolyticus MB115 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID1651729Antibacterial activity against Methicillin-resistant Staphylococcus warneri MB74 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID1651727Antibacterial activity against Staphylococcus saprophyticus MB41 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
AID30342Ability to displace [3H]N6-phenylisopropyladenosine binding from adenosine A1 receptor.1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
Flavonoid derivatives as adenosine receptor antagonists: a comparison of the hypothetical receptor binding site based on a comparative molecular field analysis model.
AID1455931Cytotoxicity against human MDA-MB-231 cells2017Journal of natural products, 02-24, Volume: 80, Issue:2
Flavonoids from Erythrina schliebenii.
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.
AID1651723Antibacterial activity against Methicillin-resistant Staphylococcus aureus MB18 after 24 hrs by microdilution assay2020Journal of natural products, 04-24, Volume: 83, Issue:4
Antibacterial and ATP Synthesis Modulating Compounds from
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (21)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (19.05)18.2507
2000's6 (28.57)29.6817
2010's9 (42.86)24.3611
2020's2 (9.52)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%
Reviews1 (4.55%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (95.45%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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]