Page last updated: 2024-12-07

4'-methoxyflavanone

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

Description

4'-methoxyflavanone is a naturally occurring flavonoid found in various plants, including citrus fruits. It exhibits diverse biological activities, including antioxidant, anti-inflammatory, and anti-cancer properties. Research has focused on its potential therapeutic applications, particularly in treating cardiovascular diseases and neurodegenerative disorders. The compound is often studied for its ability to inhibit the formation of reactive oxygen species and modulate signaling pathways involved in inflammation and cell growth. Its synthesis can be achieved through various methods, including enzymatic and chemical approaches. The pharmacological effects of 4'-methoxyflavanone have been investigated in both in vitro and in vivo models, suggesting its potential as a promising lead compound for drug development.'

4'-methoxyflavanone : The parent member of the class of 4'-methoxyflavanones that is flavanone which is substituted by a methoxy group at the 4'-position. [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 CID102928
CHEMBL ID241909
CHEBI ID63329
SCHEMBL ID127704

Synonyms (45)

Synonym
nsc50187
flavanone, 4'-methoxy-
nsc-50187
4h-1-benzopyran-4-one,3-dihydro-2-(4-methoxyphenyl)-
4'-methoxyflavanone
ACON1_000211
4h-1-benzopyran-4-one, 2,3-dihydro-2-(4-methoxyphenyl)-
2-(4-methoxyphenyl)chroman-4-one
2-(4-methoxyphenyl)-2,3-dihydro-4h-chromen-4-one
MEGXP0_001700
2-(4-methoxy-phenyl)-chroman-4-one
MLS000574900
smr000156254
97005-76-0
OPREA1_635195
OPREA1_176638
CHEMBL241909 ,
BRD-A59654870-001-01-6
bdbm50310195
4''-methoxyflavanone
(+/-)-2-(4-methoxyphenyl)chroman-4-one
3034-08-0
2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
C19895
ST070122
HMS2194L24
unii-xr5e5l2zyw
4'-methoxyflavanone, (s)-
4h-1-benzopyran-4-one, 2,3-dihydro-2-(4-methoxyphenyl)-, (s)-
xr5e5l2zyw ,
(s)-2,3-dihydro-2-(4-methoxyphenyl)-4h-1-benzopyran-4-one
FT-0634615
HMS3328G04
SCHEMBL127704
AKOS024283785
QIUYUYOXCGBABP-UHFFFAOYSA-N
2-(4-methoxyphenyl)-2,3-dihydro-4h-chromen-4-one #
mfcd00017704
CHEBI:63329
2,3-dihydro-2-(4-methoxyphenyl)-4h-1-benzopyran-4-one
DTXSID80914217
2-(4-methoxyphenyl)-2,3-dihydro-4h-1-benzopyran-4-one
D86466
2-(4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one
WS-01001
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
4'-methoxyflavanonesAny methoxyflavanone having a methoxy substituent located at position 4'.
[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 (15)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Ferritin light chainEquus caballus (horse)Potency50.11875.623417.292931.6228AID485281
LuciferasePhotinus pyralis (common eastern firefly)Potency15.10140.007215.758889.3584AID588342
BRCA1Homo sapiens (human)Potency11.22020.89137.722525.1189AID624202
ATAD5 protein, partialHomo sapiens (human)Potency20.59620.004110.890331.5287AID504466; AID504467
TDP1 proteinHomo sapiens (human)Potency26.10110.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency12.58930.180013.557439.8107AID1460
nonstructural protein 1Influenza A virus (A/WSN/1933(H1N1))Potency11.22020.28189.721235.4813AID2326
P53Homo sapiens (human)Potency44.66840.07319.685831.6228AID504706
NPC intracellular cholesterol transporter 1 precursorHomo sapiens (human)Potency5.62340.01262.451825.0177AID485313
chromobox protein homolog 1Homo sapiens (human)Potency79.43280.006026.168889.1251AID540317
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency12.99530.00419.984825.9290AID504444
ras-related protein Rab-9AHomo sapiens (human)Potency2.81840.00022.621531.4954AID485297
serine/threonine-protein kinase PLK1Homo sapiens (human)Potency37.68580.168316.404067.0158AID720504
Rap guanine nucleotide exchange factor 4Homo sapiens (human)Potency79.43283.981146.7448112.2020AID720708
[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)
Amine oxidase [flavin-containing] BHomo sapiens (human)IC50 (µMol)2.20000.00001.89149.5700AID461712
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (23)

Processvia Protein(s)Taxonomy
response to xenobiotic stimulusAmine oxidase [flavin-containing] BHomo sapiens (human)
response to toxic substanceAmine oxidase [flavin-containing] BHomo sapiens (human)
response to aluminum ionAmine oxidase [flavin-containing] BHomo sapiens (human)
response to selenium ionAmine oxidase [flavin-containing] BHomo sapiens (human)
negative regulation of serotonin secretionAmine oxidase [flavin-containing] BHomo sapiens (human)
phenylethylamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
substantia nigra developmentAmine oxidase [flavin-containing] BHomo sapiens (human)
response to lipopolysaccharideAmine oxidase [flavin-containing] BHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to ethanolAmine oxidase [flavin-containing] BHomo sapiens (human)
positive regulation of dopamine metabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
hydrogen peroxide biosynthetic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to corticosteroneAmine oxidase [flavin-containing] BHomo sapiens (human)
adaptive immune responseRap guanine nucleotide exchange factor 4Homo sapiens (human)
G protein-coupled receptor signaling pathwayRap guanine nucleotide exchange factor 4Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayRap guanine nucleotide exchange factor 4Homo sapiens (human)
calcium-ion regulated exocytosisRap guanine nucleotide exchange factor 4Homo sapiens (human)
regulation of exocytosisRap guanine nucleotide exchange factor 4Homo sapiens (human)
insulin secretionRap guanine nucleotide exchange factor 4Homo sapiens (human)
positive regulation of insulin secretionRap guanine nucleotide exchange factor 4Homo sapiens (human)
regulation of synaptic vesicle cycleRap guanine nucleotide exchange factor 4Homo sapiens (human)
Ras protein signal transductionRap guanine nucleotide exchange factor 4Homo sapiens (human)
regulation of insulin secretionRap guanine nucleotide exchange factor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

Processvia Protein(s)Taxonomy
protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
electron transfer activityAmine oxidase [flavin-containing] BHomo sapiens (human)
identical protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
guanyl-nucleotide exchange factor activityRap guanine nucleotide exchange factor 4Homo sapiens (human)
protein bindingRap guanine nucleotide exchange factor 4Homo sapiens (human)
cAMP bindingRap guanine nucleotide exchange factor 4Homo sapiens (human)
protein-macromolecule adaptor activityRap guanine nucleotide exchange factor 4Homo sapiens (human)
small GTPase bindingRap guanine nucleotide exchange factor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial envelopeAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] BHomo sapiens (human)
dendriteAmine oxidase [flavin-containing] BHomo sapiens (human)
neuronal cell bodyAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
cytosolRap guanine nucleotide exchange factor 4Homo sapiens (human)
plasma membraneRap guanine nucleotide exchange factor 4Homo sapiens (human)
membraneRap guanine nucleotide exchange factor 4Homo sapiens (human)
hippocampal mossy fiber to CA3 synapseRap guanine nucleotide exchange factor 4Homo sapiens (human)
plasma membraneRap guanine nucleotide exchange factor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay IDTitleYearJournalArticle
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.
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.
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.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
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.
AID404069In vivo antitumor activity against mouse L1210 cells
AID513959Cytotoxicity against human HT-29 cells2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
Identification of chalcones as in vivo liver monofunctional phase II enzymes inducers.
AID461713Selectivity for human MAOB over human MAOA2010Bioorganic & medicinal chemistry, Feb, Volume: 18, Issue:3
A new series of flavones, thioflavones, and flavanones as selective monoamine oxidase-B inhibitors.
AID295380Cytotoxicity against human TK10 cells in aerobic condition assessed as survival at 100 uM by sulforhodamine assay2007Bioorganic & medicinal chemistry, May-15, Volume: 15, Issue:10
Synthetic chalcones, flavanones, and flavones as antitumoral agents: biological evaluation and structure-activity relationships.
AID295381Cytotoxicity against human MCF7 cells ATCC HTB38 in aerobic condition assessed as survival at 100 uM by sulforhodamine assay2007Bioorganic & medicinal chemistry, May-15, Volume: 15, Issue:10
Synthetic chalcones, flavanones, and flavones as antitumoral agents: biological evaluation and structure-activity relationships.
AID404067In vivo antitumor activity against mouse S180 cells
AID404070In vivo antitumor activity against mouse CA-755 cells
AID513957Cytotoxicity against human MCF7 cells2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
Identification of chalcones as in vivo liver monofunctional phase II enzymes inducers.
AID461712Inhibition of human recombinant MAOB expressed in BTI-TN-5B1-4 cells by para-tyramine oxidation assay2010Bioorganic & medicinal chemistry, Feb, Volume: 18, Issue:3
A new series of flavones, thioflavones, and flavanones as selective monoamine oxidase-B inhibitors.
AID295382Cytotoxicity against human HT29 cells ATCC HTB38 in aerobic condition assessed as survival at 100 uM by sulforhodamine assay2007Bioorganic & medicinal chemistry, May-15, Volume: 15, Issue:10
Synthetic chalcones, flavanones, and flavones as antitumoral agents: biological evaluation and structure-activity relationships.
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.
AID1090146Antifungal activity against against Magnaporthe grisea 2005Journal of agricultural and food chemistry, Mar-09, Volume: 53, Issue:5
Binding model construction of antifungal 2-aryl-4-chromanones using CoMFA, CoMSIA, and QSAR analyses.
AID461710Inhibition of human recombinant MAOA expressed in BTI-TN-5B1-4 cells at 100 uM by para-tyramine oxidation assay2010Bioorganic & medicinal chemistry, Feb, Volume: 18, Issue:3
A new series of flavones, thioflavones, and flavanones as selective monoamine oxidase-B inhibitors.
AID513976Toxicity in Sprague-Dawley rat assessed as glutamic-pyruvate level at 250 mg/kg, po (RVb = 22.8 +/-13.2 U/L)2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
Identification of chalcones as in vivo liver monofunctional phase II enzymes inducers.
AID513978Toxicity in Sprague-Dawley rat assessed as change in body weight at 250 mg/kg, po2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
Identification of chalcones as in vivo liver monofunctional phase II enzymes inducers.
AID513975Toxicity in Sprague-Dawley rat assessed as haemoglobin level at 250 mg/kg, po (RVb = 15.1 +/- 4.1 g/L)2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
Identification of chalcones as in vivo liver monofunctional phase II enzymes inducers.
AID513958Cytotoxicity against human TK10 cells2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
Identification of chalcones as in vivo liver monofunctional phase II enzymes inducers.
AID513974Toxicity in Sprague-Dawley rat assessed as leucocyte level at 250 mg/kg, po (RVb = 200 +/- 1500 /uL)2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
Identification of chalcones as in vivo liver monofunctional phase II enzymes inducers.
AID513977Toxicity in Sprague-Dawley rat assessed as glutamic-oxalate transaminase level at 250 mg/kg, po (RVb = 71.4 +/- 7.8 U/L)2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
Identification of chalcones as in vivo liver monofunctional phase II enzymes inducers.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (40.00)29.6817
2010's5 (50.00)24.3611
2020's1 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.87

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 Index11.87 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.87)

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%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]