Compounds > 2-chloro-4',6'-dimethoxy-2'-hydroxychalcone
Page last updated: 2024-11-11

2-chloro-4',6'-dimethoxy-2'-hydroxychalcone

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Description

2-chloro-4',6'-dimethoxy-2'-hydroxychalcone: induces glutathione biosynthesis; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5978982
CHEMBL ID252869
SCHEMBL ID5424478
MeSH IDM0572959

Synonyms (8)

Synonym
3-(2-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)-2-propen-1-one
AQ-358/42003074
CHEMBL252869 ,
(e)-3-(2-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one
bdbm50360497
2-chloro-4',6'-dimethoxy-2'-hydroxychalcone
SCHEMBL5424478
2-chloro-4',6'-dimethoxy-2'-hydroxychalcone, aldrichcpr
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Broad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)IC50 (µMol)4.04500.00401.966610.0000AID638477; AID638478
[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
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 (25)

Assay IDTitleYearJournalArticle
AID1244038Antimicrobial activity against Trichophyton rubrum clinical isolates2015European journal of medicinal chemistry, Aug-28, Volume: 101Chalcone scaffolds as anti-infective agents: structural and molecular target perspectives.
AID659238Increase in intracellular GSH level in human MCF7 cells expressing antioxidant response element at 10 uM after 24 hrs by HPLC analysis2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID659245Induction of Nrf2 transcriptional activity in human MCF7 cells antioxidant response element at 5 uM after 18 hrs by luciferase reporter gene assay relative to tert-butylhydroquinone2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID638477Inhibition of BCRP in human MCF7/MX cells assessed as Hoechst 33342 accumulation preincubated for 30 mins by Fluorometry2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein.
AID638478Inhibition of human BCRP expressed in MDCK2 cells assessed as Hoechst 33342 accumulation preincubated for 30 mins by fluorimetry2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein.
AID659244Induction of Nrf2 transcriptional activity in human MCF7 cells antioxidant response element at 5 uM after 18 hrs by luciferase reporter gene assay relative to sulforaphane2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID659239Increase in GCL holoenzyme formation in human MCF7 cells expressing antioxidant response element at 20 uM after 6 hrs by native-PAGE immunoblotting technique2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID659241Increase in GCLM level in human MCF7 cells expressing antioxidant response element at 20 uM after 6 hrs by SDS-PAGE immunoblotting technique2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID659247Induction of Nrf2 transcriptional activity in human MCF7 cells antioxidant response element at 5 uM after 18 hrs by luciferase reporter gene assay in presence of catalytic antioxidant MnTDE-1,3-IP5+2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID659237Increase in intracellular GSH level in human MCF7 cells expressing antioxidant response element at 10 uM after 24 hrs by HPLC analysis in presence of GCL inhibitor buthionine sulfoximine2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID659243Induction of Nrf2 transcriptional activity in human MCF7 cells antioxidant response element at 5 uM after 18 hrs by luciferase reporter gene assay relative to 2,5-DHC2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID310847Antifungal activity against Trichophyton rubrum2007European journal of medicinal chemistry, Feb, Volume: 42, Issue:2
A review of anti-infective and anti-inflammatory chalcones.
AID659248Cytotoxicity against human MCF7 cells expressing antioxidant response element assessed as LDH release after 48 hrs2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID659251Increase in intracellular GSH level in human MCF7 cells expressing antioxidant response element at 10 uM after 24 hrs in presence of p38 MAPK inhibitor SB2035802012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID659240Increase in GCLC level in human MCF7 cells expressing antioxidant response element at 20 uM after 6 hrs by SDS-PAGE immunoblotting technique2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID659242Increase in intracellular GSH level in human MCF7 cells expressing antioxidant response element at 10 uM after 24 hrs in presence of JNK inhibitor SP6001252012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID1244037Antimicrobial activity against Trichophyton rubrum2015European journal of medicinal chemistry, Aug-28, Volume: 101Chalcone scaffolds as anti-infective agents: structural and molecular target perspectives.
AID659246Induction of Nrf2 transcriptional activity in human MCF7 cells antioxidant response element at 5 uM after 18 hrs by luciferase reporter gene assay in presence of p38 MAPK inhibitor SB2035802012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID638551Inhibition of MRP1 overexpressed in human 2008 MRP1 cells assessed as calcein AM accumulation at 10 uM by fluorimetry2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein.
AID638550Inhibition of MDR1 in human A2780adr cells assessed as calcein AM accumulation at 10 uM by fluorimetry2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
Investigation of chalcones and benzochalcones as inhibitors of breast cancer resistance protein.
AID659252Increase in intracellular GSH level in human MCF7 cells expressing antioxidant response element at 10 uM after 24 hrs in presence of catalytic antioxidant MnTDE-1,3IP5+2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID329735Cell cycle arrest in human K562 cells assessed as accumulation at G2/M phase at 10 uM after 24 hrs by flow cytometry2008Journal of medicinal chemistry, Apr-10, Volume: 51, Issue:7
Antimitotic and antiproliferative activities of chalcones: forward structure-activity relationship.
AID659236Increase in intracellular GSH level in human MCF7 cells expressing antioxidant response element at 10 uM after 24 hrs by HPLC analysis relative to control2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID659249Induction of Nrf2 transcriptional activity in human MCF7 cells antioxidant response element at 5 uM after 18 hrs by luciferase reporter gene assay in presence of JNK inhibitor SP6001252012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
AID659235Increase in intracellular GSH level in human MCF7 cells expressing antioxidant response element at 10 uM after 6 hrs by HPLC analysis relative to control2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
A synthetic chalcone as a potent inducer of glutathione biosynthesis.
[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's2 (40.00)29.6817
2010's3 (60.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.84

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 Index12.84 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.63 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.84)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (40.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other3 (60.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
phloretin
[no description available]		3.1310dihydrochalconesantineoplastic agent;
plant metabolite
sulforaphane
sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.		2.0710isothiocyanate;
sulfoxide		antineoplastic agent;
antioxidant;
EC 3.5.1.98 (histone deacetylase) inhibitor;
plant metabolite
vincristine
[no description available]		2.0410acetate ester;
formamides;
methyl ester;
organic heteropentacyclic compound;
organic heterotetracyclic compound;
tertiary alcohol;
tertiary amino compound;
vinca alkaloid		antineoplastic agent;
drug;
microtubule-destabilising agent;
plant metabolite;
tubulin modulator
2-tert-butylhydroquinone
2-tert-butylhydroquinone: an anticarcinogenic and chemopreventive agent. 2-tert-butylhydroquinone : A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.		2.0710hydroquinonesfood antioxidant
asebogenin
asebogenin: from Piper longicaudatum; structure in first source. asebogenin : A member of the class of dihydrochalcones that is the 4'-methyl ether derivative of phloretin.		3.1310dihydrochalconesplant metabolite
chalcone
trans-chalcone : The trans-isomer of chalcone.		4.3730chalconeEC 3.2.1.1 (alpha-amylase) inhibitor
2'-hydroxychalcone
2'-hydroxychalcone : A member of the class of chalcones that is trans-chalcone substituted by a hydroxy group at position 2'.		3.5520chalcones;
phenols		anti-inflammatory agent
2,2'-dihydroxychalcone
2,2'-dihydroxychalcone: an antineoplastic agent; structure in first source		3.1310
isoliquiritigenin
[no description available]		3.1310chalconesantineoplastic agent;
biological pigment;
EC 1.14.18.1 (tyrosinase) inhibitor;
GABA modulator;
geroprotector;
metabolite;
NMDA receptor antagonist
xanthohumol
xanthohumol: from hop plant, Humulus lupulus. xanthohumol : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells.		3.1310aromatic ether;
chalcones;
polyphenol		anti-HIV-1 agent;
antineoplastic agent;
antiviral agent;
apoptosis inducer;
EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor;
metabolite
cardamonin
cardamonin: found in Zingiberaceae; structure in first source		3.1310chalcones
butein
[no description available]		3.1310chalcones;
polyphenol		antineoplastic agent;
antioxidant;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
geroprotector;
hypoglycemic agent;
plant metabolite;
radiosensitizing agent;
tyrosine kinase inhibitor
isobavachalcone
isobavachalcone: RN given for (E)-isomer; structure in first source. isobavachalcone : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4' and a prenyl group at position 3'.		3.1310chalcones;
polyphenol		antibacterial agent;
metabolite;
platelet aggregation inhibitor
4-hydroxychalcone
4-hydroxychalcone: structure in first source. 4-hydroxychalcone : A member of the class of chalcones that is trans-chalcone substituted by a hydroxy group at position 4.		3.2110chalcones;
phenols		antihypertensive agent;
plant metabolite
2',6'-dihydroxy-4'-methoxychalcone
2',6'-dihydroxy-4'-methoxychalcone: isolated from Piper aduncum; structure in first source		4.0820chalcones
licochalcone a
licochalcone A: has both anti-inflammatory and antineoplastic activities; structure given in first source; isolated from root of Glycyrrhiza inflata; RN given refers to (E)-isomer		4.0820chalcones
2'-hydroxy-4-methoxychalcone
[no description available]		2.0710
2',6'-dimethoxychalcone
[no description available]		2.4620aromatic compound
flavokawain a
flavokawain A: from kava extract, induces apoptosis in bladder cancer cells; structure in first source		2.0710chalcones
flavokawain b
flavokawain B: from Piper methysticum Forst (Kava Kava) roots; structure in first source. flavokawain B : A member of the class of chalcones that consists of trans-chalcone substituted by hydroxy group at positions 2' and methoxy groups at positions 4' and 6'. Isolated from Piper methysticum and Piper rusbyi, it exhibits antileishmanial, anti-inflammatory and antineoplastic activities.		2.4620chalcones;
dimethoxybenzene;
phenols		anti-inflammatory agent;
antileishmanial agent;
antineoplastic agent;
apoptosis inducer;
metabolite
Isoliquiritigenin 4,4'-dimethyl ether
[no description available]		2.0710chalcones
2',4'-dihydroxychalcone
2',4'-dihydroxychalcone: RN given refers to (E)-isomer; RN for cpd without isomeric designation not available 6/89; structure given in first source		3.5520
4-chlorochalcone
4-chlorochalcone : A member of the class of chalcones that is trans-chalcone substituted by a chloro group at position 4.		3.1310chalcones;
monochlorobenzenes
2',5'-dihydroxychalcone
2',5'-dihydroxychalcone: structure given in first source		2.0710chalcones
4-hydroxylonchocarpin
4-hydroxylonchocarpin: structure in first source		3.1310
metochalcone
metochalcone: structure		2.0710
3-o-methylbutein
3-O-methylbutein: RN given refers to (E)-isomer; structure given in first source		3.1310chalcones
ro 09-0410
Ro 09-0410: structure given in first source		3.2110
2',4',6'-trihydroxychalcone
pinocembrin chalcone: isolated from Helichrysum trilineatum; structure in first source. pinocembrin chalcone : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2', 4' and 6' respectively.		3.1310chalconesantifungal agent;
plant metabolite
ko 143
[no description available]		2.0710beta-carbolines;
tert-butyl ester
2',3,4,4'-tetrahydroxy-5-prenylchalcone
[no description available]		3.1310
ConditionIndicatedRelationship StrengthStudiesTrials
Adverse Drug Event
[description not available]		02.0410
Drug-Related Side Effects and Adverse Reactions
Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.		02.0410
Breast Cancer
[description not available]		02.0710
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.0710