Page last updated: 2024-11-08

5,7-dimethoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

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

Cross-References

ID SourceID
PubMed CID378567
CHEMBL ID107131
CHEBI ID110206
SCHEMBL ID2879027

Synonyms (65)

Synonym
5,7-dimethoxy-2-phenyl-chroman-4-one
5,7-dimethoxy-2-phenyl-2,3-dihydro-4h-chromen-4-one
1036-72-2
BRD-A90249268-001-03-2
SPECTRUM5_000466
DIVK1C_006969
NCI60_021335
BSPBIO_002034
NSC661206 ,
5,7-dimethoxyflavanon
nsc-661206
SPECTRUM_000324
SPECTRUM4_001873
ACON1_001227
MEGXP0_000558
5,7-dimethoxyflavanone
36052-66-1
NCGC00142553-01
KBIOGR_002369
KBIO2_005940
KBIO1_001913
KBIOSS_000804
KBIO2_003372
KBIO2_000804
KBIO3_001534
SPBIO_001573
SPECTRUM3_000587
SPECTRUM2_001357
SPECPLUS_000873
NCGC00142553-02
NCGC00142553-03
LMPK12140217
pinocembrin 5,7-dimethyl ether
CHEBI:110206
5,7-dimethoxy-2-phenyl-2,3-dihydrochromen-4-one
dimethylpinocembrin
CHEMBL107131 ,
bdbm50338969
5,7-dimethoxy-2-phenylchroman-4-one
flavanone, 5,7-dimethoxy-
nsc 661206
CCG-38839
FT-0619849
SCHEMBL2879027
alpinetin methyl ether
4h-1-benzopyran-4-one, 2,3-dihydro-5,7-dimethoxy-2-phenyl-
IAFBOKYTDSDNHV-UHFFFAOYSA-N
5,7-dimethoxy-2-phenyl-2,3-dihydro-4h-chromen-4-one #
5,7-dimethoxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-4-one
Q27189587
mfcd00143414
sr-05000002541
SR-05000002541-1
1277188-85-8
(2r)-2,3-dihydro-5,7-dimethoxy-2-phenyl-4h-1-benzopyran-4-one
BRD-A90249268-001-04-0
FT-0775382
5,7-dimethoxylflavanone
5,7-dimethoxy-2-phenyl-2,3-dihydro-4h-1-benzopyran-4-one
DTXSID20908493
B0005-053969
CS-0637334
HY-N10879
4h-1-benzopyran-4-one, 2,3-dihydro-5,7-dimethoxy-2-phenyl-, (2s)-
FS-7880
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
flavonoidsAny organic molecular entity whose stucture is based on derivatives of a phenyl-substituted 1-phenylpropane possessing a C15 or C16 skeleton, or such a structure which is condensed with a C6-C3 lignan precursors. The term is a 'superclass' comprising all members of the classes of flavonoid, isoflavonoid, neoflavonoid, chalcones, dihydrochalcones, aurones, pterocarpan, coumestans, rotenoid, flavonolignan, homoflavonoid and flavonoid oligomers. Originally restricted to natural products, the term is also applied to synthetic compounds related to them.
etherAn organooxygen compound with formula ROR, where R is not hydrogen.
[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 (27)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID893
Chain B, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID893
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency31.62280.177814.390939.8107AID2147
Chain A, CruzipainTrypanosoma cruziPotency39.81070.002014.677939.8107AID1476
TDP1 proteinHomo sapiens (human)Potency33.49830.000811.382244.6684AID686978
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency28.18380.011212.4002100.0000AID1030
regulator of G-protein signaling 4Homo sapiens (human)Potency5.32330.531815.435837.6858AID504845
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency39.81070.001815.663839.8107AID894
mitogen-activated protein kinase 1Homo sapiens (human)Potency31.62280.039816.784239.8107AID995
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency12.58930.031610.279239.8107AID884; AID885
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Broad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)IC50 (µMol)24.50000.00401.966610.0000AID578759; AID578760
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (14)

Processvia Protein(s)Taxonomy
lipid transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
organic anion transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
urate transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
biotin transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
sphingolipid biosynthetic processBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
riboflavin transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
urate metabolic processBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
transmembrane transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
transepithelial transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
renal urate salt excretionBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
export across plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
transport across blood-brain barrierBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
cellular detoxificationBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
xenobiotic transport across blood-brain barrierBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
protein bindingBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ATP bindingBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
organic anion transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ABC-type xenobiotic transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
urate transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
biotin transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
efflux transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ATP hydrolysis activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
riboflavin transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ATPase-coupled transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
identical protein bindingBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
protein homodimerization activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
xenobiotic transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
sphingolipid transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
nucleoplasmBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
apical plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
brush border membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
mitochondrial membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
membrane raftBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
external side of apical plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID480467Cytotoxicity against human NCI-H187 cells after 5 days by Resazurin Microplate Assay2010Bioorganic & medicinal chemistry letters, May-01, Volume: 20, Issue:9
Cytotoxicity against KB and NCI-H187 cell lines of modified flavonoids from Kaempferia parviflora.
AID622584Inhibition of NF-kappaB activation expressed in HCT116 cells assessed as inhibition of TNF-alpha-induced transcriptional activation at 10 uM after 12 hrs by luciferase reporter gene assay relative to control2011Bioorganic & medicinal chemistry letters, Oct-15, Volume: 21, Issue:20
Relationship between the structures of flavonoids and their NF-κB-dependent transcriptional activities.
AID578765Inhibition of P-gp expressed in A2780adr cells at 10 uM by calcein AM accumulation assay relative to verapamil2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).
AID578844Cytotoxicity against human MCF7 cells assessed as intracellular ATP level at 10 uM after 72 hrs by luminometry2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).
AID102612The compound was tested for antiproliferative activity against MCF-7 human breast cancer cells2001Bioorganic & medicinal chemistry letters, Dec-17, Volume: 11, Issue:24
Flavonoids: structural requirements for antiproliferative activity on breast cancer cells.
AID480465Cytotoxicity against human KB cells after 3 days by Resazurin Microplate Assay2010Bioorganic & medicinal chemistry letters, May-01, Volume: 20, Issue:9
Cytotoxicity against KB and NCI-H187 cell lines of modified flavonoids from Kaempferia parviflora.
AID578759Inhibition of BCRP expressed in MDCK cells using Hoechst 33342 staining2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).
AID578760Inhibition of BCRP expressed in MCF-7 MX cells using Hoechst 33342 staining2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).
AID353303Increase in EGR1 mRNA expression in human HEK293 cells at 20 ug/mL after 6 to 12 hrs by dual-glo luciferase assay relative to control2009Bioorganic & medicinal chemistry letters, Apr-15, Volume: 19, Issue:8
Relationships between the structures of flavanone derivatives and their effects in enhancing early growth response-1 gene expression.
AID578843Cytotoxicity against human A2780 cells assessed as intracellular ATP level at 10 uM after 72 hrs by luminometry2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).
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.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (28.57)29.6817
2010's5 (71.43)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.51

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 Index12.51 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.51)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]