Page last updated: 2024-11-12

4-Methoxylonchocarpin

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 CID10472189
CHEMBL ID369768
CHEBI ID180251
SCHEMBL ID13534952

Synonyms (13)

Synonym
51589-67-4
CHEBI:180251
(e)-1-(5-hydroxy-2,2-dimethylchromen-6-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
4-methoxylonchocarpin
LMPK12120079
(e)-1-(5-hydroxy-2,2-dimethyl-chromen-6-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
CHEMBL369768 ,
2-propen-1-one, 1-(5-hydroxy-2,2-dimethyl-2h-1-benzopyran-6-yl)-3-(4-methoxyphenyl)-, (2e)-
4-hydroxylonchocarpin methyl ether
SCHEMBL13534952
bdbm50505207
HY-N11768
CS-0834514

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Pharmacokinetic studies indicated that low oral bioavailability due to poor ADME properties."( Synthesis and insight into the structure-activity relationships of chalcones as antimalarial agents.
Gupta, S; Kancharla, P; Khaliq, T; Korthikunta, V; Kumar, V; Mohammad, IS; Puri, SK; Raju, KS; Sijwali, PS; Soni, A; Srivastava, K; Srivastava, RK; Tadigoppula, N, 2013
)
0.39

Dosage Studied

ExcerptRelevanceReference
" Furthermore, 5b could significantly suppress the progression of carrageenan-induced hind paw edema compared to indomethacin at a dosage of 10 mg/kg/day, and dose-dependently ameliorated the development of adjuvant-induced arthritis (AIA) validated by arthritic scores and H&E staining of joints."( Rational design, synthesis, and pharmacological properties of pyranochalcone derivatives as potent anti-inflammatory agents.
Cao, D; Chen, J; Chen, L; Deng, C; Li, X; Liang, X; Ma, L; Peng, A; Peng, F; Qiu, J; Ran, Y; Wang, G; Wei, Y; Xiang, M; Xie, C; Yang, Z; Ye, H, 2012
)
0.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
chalconesA ketone that is 1,3-diphenylpropenone (benzylideneacetophenone), ArCH=CH(=O)Ar, and its derivatives formed by substitution.
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
CholinesteraseHomo sapiens (human)IC50 (µMol)101.91000.00001.559910.0000AID1524946
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)74.71000.00000.933210.0000AID1524945
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (25)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processCholinesteraseHomo sapiens (human)
learningCholinesteraseHomo sapiens (human)
negative regulation of cell population proliferationCholinesteraseHomo sapiens (human)
neuroblast differentiationCholinesteraseHomo sapiens (human)
peptide hormone processingCholinesteraseHomo sapiens (human)
response to alkaloidCholinesteraseHomo sapiens (human)
cocaine metabolic processCholinesteraseHomo sapiens (human)
negative regulation of synaptic transmissionCholinesteraseHomo sapiens (human)
response to glucocorticoidCholinesteraseHomo sapiens (human)
response to folic acidCholinesteraseHomo sapiens (human)
choline metabolic processCholinesteraseHomo sapiens (human)
acetylcholine catabolic processCholinesteraseHomo sapiens (human)
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
amyloid-beta bindingCholinesteraseHomo sapiens (human)
catalytic activityCholinesteraseHomo sapiens (human)
acetylcholinesterase activityCholinesteraseHomo sapiens (human)
cholinesterase activityCholinesteraseHomo sapiens (human)
protein bindingCholinesteraseHomo sapiens (human)
hydrolase activity, acting on ester bondsCholinesteraseHomo sapiens (human)
enzyme bindingCholinesteraseHomo sapiens (human)
choline bindingCholinesteraseHomo sapiens (human)
identical protein bindingCholinesteraseHomo sapiens (human)
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
extracellular regionCholinesteraseHomo sapiens (human)
nuclear envelope lumenCholinesteraseHomo sapiens (human)
endoplasmic reticulum lumenCholinesteraseHomo sapiens (human)
blood microparticleCholinesteraseHomo sapiens (human)
plasma membraneCholinesteraseHomo sapiens (human)
extracellular spaceCholinesteraseHomo sapiens (human)
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID730542Antimalarial activity against schizont stage of chloroquine-sensitive Plasmodium falciparum 3D7 after more than 40 hrs by Giemsa staining-based light microscopic analysis2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
Synthesis and insight into the structure-activity relationships of chalcones as antimalarial agents.
AID1697935Antiproliferative activity against human K562 cells assessed as reduction in cell viability at 25 uM after 72 hrs by MTS assay relative to control2020Journal of natural products, 10-23, Volume: 83, Issue:10
Natural and Semisynthetic Chalcones as Dual FLT3 and Microtubule Polymerization Inhibitors.
AID666600Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production incubated for 2 hrs prior to LPS-challenge measured after 22 hrs by Griess method relative to untreated control2012European journal of medicinal chemistry, Aug, Volume: 54Rational design, synthesis, and pharmacological properties of pyranochalcone derivatives as potent anti-inflammatory agents.
AID252018In-vitro antileishmanial activity was tested against extracellular promastigotes of Leishmania donovani at dose of 50 ug/mL2004Bioorganic & medicinal chemistry letters, Aug-02, Volume: 14, Issue:15
A convenient and biogenetic type synthesis of few naturally occurring chromeno dihydrochalcones and their in vitro antileishmanial activity.
AID1524945Inhibition of AChE (unknown origin) using acetylthiocholine iodide as substrate by spectrophotometry based Ellman's method2019Bioorganic & medicinal chemistry letters, 05-15, Volume: 29, Issue:10
Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa.
AID1697933Antiproliferative activity against human MV4-11 cells assessed as reduction in cell viability at 25 uM after 72 hrs by MTS assay relative to control2020Journal of natural products, 10-23, Volume: 83, Issue:10
Natural and Semisynthetic Chalcones as Dual FLT3 and Microtubule Polymerization Inhibitors.
AID1697934Antiproliferative activity against human MV4-11 cells assessed as reduction in cell viability at 50 uM after 72 hrs by MTS assay relative to control2020Journal of natural products, 10-23, Volume: 83, Issue:10
Natural and Semisynthetic Chalcones as Dual FLT3 and Microtubule Polymerization Inhibitors.
AID1524946Inhibition of BChE (unknown origin) using butyrylthiocholine iodide as substrate by spectrophotometry based Ellman's method2019Bioorganic & medicinal chemistry letters, 05-15, Volume: 29, Issue:10
Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa.
AID1524944Inhibition of BChE (unknown origin) at 20 ug/mL using butyrylthiocholine iodide as substrate by spectrophotometry based Ellman's method2019Bioorganic & medicinal chemistry letters, 05-15, Volume: 29, Issue:10
Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa.
AID1697936Antiproliferative activity against human K562 cells assessed as reduction in cell viability at 50 uM after 72 hrs by MTS assay relative to control2020Journal of natural products, 10-23, Volume: 83, Issue:10
Natural and Semisynthetic Chalcones as Dual FLT3 and Microtubule Polymerization Inhibitors.
AID1524947Selectivity index, ratio of IC50 for inhibition of AChE (unknown origin) to IC50 for inhibition of BChE (unknown origin)2019Bioorganic & medicinal chemistry letters, 05-15, Volume: 29, Issue:10
Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa.
AID251991In-vitro antileishmanial activity was tested against intracellular amastigotes of Leishmania donovani at dose 50 ug/mL2004Bioorganic & medicinal chemistry letters, Aug-02, Volume: 14, Issue:15
A convenient and biogenetic type synthesis of few naturally occurring chromeno dihydrochalcones and their in vitro antileishmanial activity.
AID1524943Inhibition of AChE (unknown origin) at 20 ug/mL using acetylthiocholine iodide as substrate by spectrophotometry based Ellman's method2019Bioorganic & medicinal chemistry letters, 05-15, Volume: 29, Issue:10
Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa.
AID730539Antimalarial activity against schizont stage of chloroquine-sensitive Plasmodium falciparum 3D7 assessed as reduction in parasitemia at 50 ug/ml after more than 40 hrs by Giemsa staining-based light microscopy2013Journal of medicinal chemistry, Jan-10, Volume: 56, Issue:1
Synthesis and insight into the structure-activity relationships of chalcones as antimalarial agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's3 (60.00)24.3611
2020's1 (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: 13.28

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 Index13.28 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index5.08 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.28)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]