Page last updated: 2024-12-08

5,6,7-trimethoxyflavone

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

Description

baicalein 5,6,7-trimethyl ether: stimulates fatty acid beta-oxidation; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

5,6,7-trimethoxyflavone : A trimethoxyflavone that is the 5,6,7-trimethyl ether derivative of baicalein. It has been isolated from the plant Callicarpa japonica and has been shown to exhibit antiviral activity. [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
CallicarpagenusA plant genus of the family Lamiaceae. Members contain clerodane DITERPENES and callicarpone.[MeSH]LamiaceaeThe mint plant family. They are characteristically aromatic, and many of them are cultivated for their oils. Most have square stems, opposite leaves, and two-lipped, open-mouthed, tubular corollas (united petals), with five-lobed, bell-like calyxes (united sepals).[MeSH]
Callicarpa japonicaspecies[no description available]LamiaceaeThe mint plant family. They are characteristically aromatic, and many of them are cultivated for their oils. Most have square stems, opposite leaves, and two-lipped, open-mouthed, tubular corollas (united petals), with five-lobed, bell-like calyxes (united sepals).[MeSH]

Cross-References

ID SourceID
PubMed CID442583
CHEMBL ID182992
CHEBI ID2980
SCHEMBL ID971297
MeSH IDM0279351

Synonyms (32)

Synonym
CHEBI:2980 ,
5,6,7-trimethoxy-2-phenyl-4h-chromen-4-one
ACON1_001643
NCGC00180294-01
973-67-1
baicalein 5,6,7-trimethyl ether
5,6,7-trimethoxy-2-phenyl-chromen-4-one
5,6,7-trimethoxyflavone
baicalein-5,6,7-trimethylether
BRD-K64806788-001-01-4
5,6,7-trimethoxy-2-phenylchromen-4-one
baicalein trimethyl ether
CHEMBL182992
LMPK12111100
A845707
ST056254
S9328
FT-0619807
SCHEMBL971297
5,6,7-trimethylbaicalein
HJNJAUYFFFOFBW-UHFFFAOYSA-N
DTXSID30331879
5,6,7-trimethoxyflavone, aldrichcpr
mfcd00017457
AKOS027381289
AS-59613
HY-110398
Q27105905
CCG-267599
CS-0040433
F82210
4h-1-benzopyran-4-one,5,6,7-trimethoxy-2-phenyl-
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
anti-HSV-1 agentAn anti-HSV agent agent that destroys or inhibits the replication of herpes simplex virus-1.
[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
trimethoxyflavoneA methoxyflavone that is flavone substituted by three methoxy groups.
[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]

Bioassays (27)

Assay IDTitleYearJournalArticle
AID1860353Inhibition of CYP450 in human liver microsomes assessed as inhibition of 20-HETE formation at 10 uM in presence of arachidonic acid and NADPH by multi-enzyme assay based LC-MS/MS analysis relative to control
AID357254Antifungal activity against Candida albicans ATCC 900282002Journal of natural products, Dec, Volume: 65, Issue:12
Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.
AID237331cLogD was determined2004Journal of medicinal chemistry, Oct-21, Volume: 47, Issue:22
Increased anti-P-glycoprotein activity of baicalein by alkylation on the A ring.
AID338974Inhibition of cow milk xanthine oxidase at 50 ug/mL
AID247607Inhibitory activity against KB cell line after 72 h of drug exposure2004Journal of medicinal chemistry, Oct-21, Volume: 47, Issue:22
Increased anti-P-glycoprotein activity of baicalein by alkylation on the A ring.
AID1860355Selectivity index, log ratio of Inhibition of CYP450 in human liver microsomes assessed as inhibition of EpETrE formation in presence of arachidonic acid to Inhibition of CYP450 in human liver microsomes assessed as inhibition of 20-HETE formation in pres
AID647697Antiinflammatory activity against mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production at 25 uM preincubated for 1 hr before LPS challenge measured after 24 hrs by Griess method2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
4'-bromo-5,6,7-trimethoxyflavone represses lipopolysaccharide-induced iNOS and COX-2 expressions by suppressing the NF-κB signaling pathway in RAW 264.7 macrophages.
AID647698Antiinflammatory activity against mouse RAW264.7 cells assessed as inhibition of LPS-induced PGE2 production at 25 uM by EIA2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
4'-bromo-5,6,7-trimethoxyflavone represses lipopolysaccharide-induced iNOS and COX-2 expressions by suppressing the NF-κB signaling pathway in RAW 264.7 macrophages.
AID245888Maximum intracellular vinblastine accumulation of the KB/MDR cells caused by the compound in 1 h2004Journal of medicinal chemistry, Oct-21, Volume: 47, Issue:22
Increased anti-P-glycoprotein activity of baicalein by alkylation on the A ring.
AID1628067Growth inhibition of human MCF7 cells at 10 uM by MTT assay relative to control2016Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17
Synthesis of novel flavone derivatives possessing substituted benzamides and their biological evaluation against human cancer cells.
AID357253Inhibition of Saccharomyces cerevisiae fatty acid synthase2002Journal of natural products, Dec, Volume: 65, Issue:12
Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.
AID1628066Growth inhibition of human HepG2 cells at 10 uM by MTT assay relative to control2016Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17
Synthesis of novel flavone derivatives possessing substituted benzamides and their biological evaluation against human cancer cells.
AID245264Minimum inhibitory concentration against gram positive Bacillus sphaericus (MTCC 11) using broth dilution method2005Bioorganic & medicinal chemistry letters, Sep-01, Volume: 15, Issue:17
Synthesis and in vitro study of novel 7-O-acyl derivatives of Oroxylin A as antibacterial agents.
AID1628068Growth inhibition of human HepG2 cells by MTT assay2016Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17
Synthesis of novel flavone derivatives possessing substituted benzamides and their biological evaluation against human cancer cells.
AID1628069Growth inhibition of human MCF7 cells by MTT assay2016Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17
Synthesis of novel flavone derivatives possessing substituted benzamides and their biological evaluation against human cancer cells.
AID245270Minimum inhibitory concentration against gram negative Klebsiella aerogenes (MTCC 39) using broth dilution method2005Bioorganic & medicinal chemistry letters, Sep-01, Volume: 15, Issue:17
Synthesis and in vitro study of novel 7-O-acyl derivatives of Oroxylin A as antibacterial agents.
AID647701Cytotoxicity against mouse LPS-stimulated RAW264.7 cells assessed as effect on cell viability up to 50 uM after 24 hrs2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
4'-bromo-5,6,7-trimethoxyflavone represses lipopolysaccharide-induced iNOS and COX-2 expressions by suppressing the NF-κB signaling pathway in RAW 264.7 macrophages.
AID245252Minimum inhibitory concentration against gram positive Bacillus subtilis (MTCC 441) using broth dilution method2005Bioorganic & medicinal chemistry letters, Sep-01, Volume: 15, Issue:17
Synthesis and in vitro study of novel 7-O-acyl derivatives of Oroxylin A as antibacterial agents.
AID1860354Inhibition of CYP450 in human liver microsomes assessed as inhibition of EpETrE formation at 10 uM in presence of arachidonic acid and NADPH by multi-enzyme assay based LC-MS/MS analysis relative to control
AID1668637Inhibition of human liver FBP1 at 200 uM incubated for 5 mins by fluorescence method relative to control2020Journal of natural products, 05-22, Volume: 83, Issue:5
Structural Specificity of Flavonoids in the Inhibition of Human Fructose 1,6-Bisphosphatase.
AID647702Cytotoxicity against mouse RAW264.7 cells assessed as effect on cell viability up to 50 uM after 24 hrs2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
4'-bromo-5,6,7-trimethoxyflavone represses lipopolysaccharide-induced iNOS and COX-2 expressions by suppressing the NF-κB signaling pathway in RAW 264.7 macrophages.
AID357255Antifungal activity against Cryptococcus neoformans ATCC 901132002Journal of natural products, Dec, Volume: 65, Issue:12
Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.
AID647696Cytotoxicity against mouse RAW264.7 cells2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
4'-bromo-5,6,7-trimethoxyflavone represses lipopolysaccharide-induced iNOS and COX-2 expressions by suppressing the NF-κB signaling pathway in RAW 264.7 macrophages.
AID247665Inhibitory activity against KB/MDR cell line after 72 hr of drug exposure2004Journal of medicinal chemistry, Oct-21, Volume: 47, Issue:22
Increased anti-P-glycoprotein activity of baicalein by alkylation on the A ring.
AID245345Minimum inhibitory concentration against gram negative Chromobacterium violaceum (MTCC 2656) using broth dilution method2005Bioorganic & medicinal chemistry letters, Sep-01, Volume: 15, Issue:17
Synthesis and in vitro study of novel 7-O-acyl derivatives of Oroxylin A as antibacterial agents.
AID246154Concentration that causes 50% of maximum vinblastine accumulation in KB/MDR cells in 1 h2004Journal of medicinal chemistry, Oct-21, Volume: 47, Issue:22
Increased anti-P-glycoprotein activity of baicalein by alkylation on the A ring.
AID245279Minimum inhibitory concentration against gram positive Staphylococcus aureus (MTCC 96) using broth dilution method2005Bioorganic & medicinal chemistry letters, Sep-01, Volume: 15, Issue:17
Synthesis and in vitro study of novel 7-O-acyl derivatives of Oroxylin A as antibacterial agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (6.67)18.2507
2000's6 (40.00)29.6817
2010's5 (33.33)24.3611
2020's3 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.32

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 Index12.32 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index5.15 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.32)

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%
Other16 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]