Page last updated: 2024-09-27

2-(4-hydroxyphenyl)-5,6,7-trimethoxy-4H-1-benzopyran-4-one

Description

2-(4-hydroxyphenyl)-5,6,7-trimethoxy-4H-1-benzopyran-4-one : A trimethoxyflavone that is flavone substituted by methoxy groups at positions 5, 6 and 7 and a hydroxy group at position 4'. [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]

Cross-References

ID SourceID
PubMed CID243759
CHEMBL ID74490
CHEBI ID79510
SCHEMBL ID735537

Synonyms (21)

Synonym
CHEMBL74490 ,
chebi:79510 ,
nsc53906
6938-18-7
nsc-53906
NCI60_004327
4'-hydroxy-5,6,7-trimethoxyflavone
2-(4-hydroxyphenyl)-5,6,7-trimethoxy-4h-1-benzopyran-4-one
4h-1-benzopyran-4-one, 2-(4-hydroxyphenyl)-5,6,7-trimethoxy-
2-(4-hydroxyphenyl)-5,6,7-trimethoxy-chromen-4-one
bdbm50064136
2-(4-hydroxyphenyl)-5,6,7-trimethoxychromen-4-one
unii-ok09yo2bp5
ok09yo2bp5 ,
nsc 53906
SCHEMBL735537
2-(4-hydroxyphenyl)-5,6,7-trimethoxy-4h-chromen-4-one
DTXSID40219472
PJRWXHDCKWSIRU-UHFFFAOYSA-N
Q27148597
flavone, 4'-hydroxy-5,6,7-trimethoxy-

Drug Classes (2)

ClassDescription
trimethoxyflavoneA methoxyflavone that is flavone substituted by three methoxy groups.
monohydroxyflavoneA hydroxyflavone carrying a single hydroxy substituent.
[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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AcetylcholinesteraseElectrophorus electricus (electric eel)IC50 (µMol)100.00000.00000.94539.9400AID1193209
AcetylcholinesteraseRattus norvegicus (Norway rat)IC50 (µMol)300.00000.00020.52597.2000AID1192720; AID1484814
CholinesteraseEquus caballus (horse)IC50 (µMol)100.00000.00002.22149.4000AID1193211
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID1193211Inhibition of equine serum BChE using acetylthiocholine chloride as substrate after 15 mins by Ellman spectrophotometric method2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
Design, synthesis and evaluation of novel 5,6,7-trimethoxyflavone-6-chlorotacrine hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1484831Metal chelating activity assessed as inhibition of Cu2+ induced amyloid beta (1 to 42) aggregation at 25 uM after 24 hrs by ThT-based fluorometric method relative to control2017European journal of medicinal chemistry, Jul-28, Volume: 135Design, synthesis and evaluation of scutellarein-O-acetamidoalkylbenzylamines as potential multifunctional agents for the treatment of Alzheimer's disease.
AID404008Cytotoxicity against human KB cells
AID1484818Antioxidant activity assessed as trolox equivalents of AAPH radical scavenging activity at 1 to 10 uM preincubated for 15 mins followed by AAPH addition measured every 60 sec for 90 mins by ORAC-FL assay2017European journal of medicinal chemistry, Jul-28, Volume: 135Design, synthesis and evaluation of scutellarein-O-acetamidoalkylbenzylamines as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1192721Inhibition of rat serum BuChE using butyrylthiocholine iodide as substrate after 15 mins by Ellman method2015Bioorganic & medicinal chemistry, Feb-15, Volume: 23, Issue:4
Multifunctional scutellarin-rivastigmine hybrids with cholinergic, antioxidant, biometal chelating and neuroprotective properties for the treatment of Alzheimer's disease.
AID404069In vivo antitumor activity against mouse L1210 cells
AID1484832Metal chelating activity assessed as disaggregation of Cu2+ induced amyloid beta (1 to 42) fibrils at 25 uM treated for 24 hrs post Cu2+ treatment for 24 hrs by ThT-based fluorometric method relative to control2017European journal of medicinal chemistry, Jul-28, Volume: 135Design, synthesis and evaluation of scutellarein-O-acetamidoalkylbenzylamines as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1193209Inhibition of electric eel AChE using acetylthiocholine chloride as substrate after 15 mins by Ellman spectrophotometric method2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
Design, synthesis and evaluation of novel 5,6,7-trimethoxyflavone-6-chlorotacrine hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1484819Inhibition of human erythrocyte AChE using acetylthiocholine iodide as substrate after 15 mins by Ellman's method2017European journal of medicinal chemistry, Jul-28, Volume: 135Design, synthesis and evaluation of scutellarein-O-acetamidoalkylbenzylamines as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1484814Inhibition of rat cortex homogenate AChE using acetylthiocholine iodide as substrate after 15 mins in presence of BuChE inhibitor iso-OMPA by Ellman's method2017European journal of medicinal chemistry, Jul-28, Volume: 135Design, synthesis and evaluation of scutellarein-O-acetamidoalkylbenzylamines as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1192729Neuroprotective effect against H2O2-induced rat PC12 cell injury assessed as cell viability at 10 uM incubated for 2 hrs prior to H2O2 challenge measured after 24 hrs by MTT assay (Rvb = 57.6%)2015Bioorganic & medicinal chemistry, Feb-15, Volume: 23, Issue:4
Multifunctional scutellarin-rivastigmine hybrids with cholinergic, antioxidant, biometal chelating and neuroprotective properties for the treatment of Alzheimer's disease.
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.
AID1484815Inhibition of rat serum BuChE using butyrylthiocholine iodide as substrate after 15 mins by Ellman's method2017European journal of medicinal chemistry, Jul-28, Volume: 135Design, synthesis and evaluation of scutellarein-O-acetamidoalkylbenzylamines as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1192728Antioxidant activity assessed as trolox equivalent of APPH-induced radical scavenging activity by ORAC-FL method2015Bioorganic & medicinal chemistry, Feb-15, Volume: 23, Issue:4
Multifunctional scutellarin-rivastigmine hybrids with cholinergic, antioxidant, biometal chelating and neuroprotective properties for the treatment of Alzheimer's disease.
AID1193214Inhibition of self-induced Abeta(1 to 42) (unknown origin) aggregation at 25 uM after 24 hrs by Thioflavin T-based fluorometric assay2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
Design, synthesis and evaluation of novel 5,6,7-trimethoxyflavone-6-chlorotacrine hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1192720Inhibition of rat cortex AChE using acetylthiocholine iodide as substrate after 15 mins by Ellman method2015Bioorganic & medicinal chemistry, Feb-15, Volume: 23, Issue:4
Multifunctional scutellarin-rivastigmine hybrids with cholinergic, antioxidant, biometal chelating and neuroprotective properties for the treatment of Alzheimer's disease.
AID1484816Inhibition of electric eel AChE using acetylthiocholine iodide as substrate after 15 mins by Ellman's method2017European journal of medicinal chemistry, Jul-28, Volume: 135Design, synthesis and evaluation of scutellarein-O-acetamidoalkylbenzylamines as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1193213Antioxidant activity assessed as Trolox equivalent per microM of compound after 15 mins by oxygen radical absorbance capacity fluorescein assay2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
Design, synthesis and evaluation of novel 5,6,7-trimethoxyflavone-6-chlorotacrine hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID404067In vivo antitumor activity against mouse S180 cells
AID1484828Inhibition of human erythrocyte AChE induced amyloid beta (1 to 40) aggregation at 100 uM after 24 hrs by ThT-based fluorometric method relative to control2017European journal of medicinal chemistry, Jul-28, Volume: 135Design, synthesis and evaluation of scutellarein-O-acetamidoalkylbenzylamines as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1193210Inhibition of human erythrocyte AChE using acetylthiocholine chloride as substrate after 15 mins by Ellman spectrophotometric method2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
Design, synthesis and evaluation of novel 5,6,7-trimethoxyflavone-6-chlorotacrine hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1484826Inhibition of amyloid beta (1 to 42) (unknown origin) self aggregation at 25 uM after 24 hrs by ThT-based fluorometric method relative to control2017European journal of medicinal chemistry, Jul-28, Volume: 135Design, synthesis and evaluation of scutellarein-O-acetamidoalkylbenzylamines as potential multifunctional agents for the treatment of Alzheimer's disease.
AID404070In vivo antitumor activity against mouse CA-755 cells
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (4)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (25.00)18.2507
2000's0 (0.00)29.6817
2010's3 (75.00)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%
Other5 (100.00%)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]