Page last updated: 2024-11-08

2,2'-dihydroxychalcone

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

Description

2,2'-dihydroxychalcone: an antineoplastic agent; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID638277
CHEMBL ID150755
MeSH IDM0550264

Synonyms (34)

Synonym
nsc636811
nsc-636811
(e)-1,3-bis(2-hydroxyphenyl)prop-2-en-1-one ,
1,3-bis(2-hydroxyphenyl)-2-propen-1-one
2-propen-1-one, 1,3-bis(2-hydroxyphenyl)-
2,2'-dihydroxychalcone
acrylophenone, 2'-hydroxy-3-(o-hydroxyphenyl)-
15131-80-3
nsc-73256
nsc73256
(2e)-1,3-bis(2-hydroxyphenyl)prop-2-en-1-one
inchi=1/c15h12o3/c16-13-7-3-1-5-11(13)9-10-15(18)12-6-2-4-8-14(12)17/h1-10,16-17h/b10-9
2-propen-1-one, 1,3-bis(2-hydroxyphenyl)-, (2e)-
AR-683/41961171
LMPK12120186
d-501
CHEMBL150755 ,
AKOS001017081
chalcone, 2,2'-dihydroxy-
nsc 73256
AB00709632-01
34000-30-1
bdbm50015607
KSHCTKZLHCSARH-MDZDMXLPSA-N
nsc 636811
2,2'-dihydroxychalchone
mfcd00017715
2,2'-dihydroxychalcone, aldrichcpr
Z56791055
CS-0210670
STL192073
2,2-dihydroxychalcone
DTXSID101257980
(2e)-1,3-bis(2-hydroxyphenyl)-2-propen-1-one

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
"A total of 30 chalcone analogues was synthesized via a base catalyzed Claisen Schmidt condensation and screened for their in vitro antibacterial activity against Methicillin-sensitive Staphylococcus aureus (MSSA) and Methicillin-resistant Staphylococcus aureus (MRSA) alone or in combination with non beta-lactam antibiotics namely ciprofloxacin, chloramphenicol, erythromycin, vancomycin, doxycycline and gentamicin."( Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics.
Do, TH; Huynh, TN; Ngo, TD; Thai, KM; Tran, CD; Tran, NC; Tran, TD, 2012
)
0.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
CholinesteraseHomo sapiens (human)IC50 (µMol)13.00000.00001.559910.0000AID1142531
Beta-glucuronidaseHomo sapiens (human)IC50 (µMol)1.60000.02003.08337.4000AID1656436
Beta-secretase 1Homo sapiens (human)IC50 (µMol)60.00000.00061.619410.0000AID1803028
Xanthine dehydrogenase/oxidaseBos taurus (cattle)IC50 (µMol)87.40000.00303.10159.8000AID1461517
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Substance-P receptorCavia porcellus (domestic guinea pig)CD4.70000.90004.50009.8000AID144377
Quinone oxidoreductaseMus musculus (house mouse)CD4.70000.20002.74219.8000AID144377
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (35)

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)
carbohydrate metabolic processBeta-glucuronidaseHomo sapiens (human)
glycosaminoglycan catabolic processBeta-glucuronidaseHomo sapiens (human)
heparan sulfate proteoglycan catabolic processBeta-glucuronidaseHomo sapiens (human)
chondroitin sulfate catabolic processBeta-glucuronidaseHomo sapiens (human)
hyaluronan catabolic processBeta-glucuronidaseHomo sapiens (human)
glucuronoside catabolic processBeta-glucuronidaseHomo sapiens (human)
proteolysisBeta-secretase 1Homo sapiens (human)
membrane protein ectodomain proteolysisBeta-secretase 1Homo sapiens (human)
response to lead ionBeta-secretase 1Homo sapiens (human)
protein processingBeta-secretase 1Homo sapiens (human)
amyloid-beta formationBeta-secretase 1Homo sapiens (human)
amyloid precursor protein catabolic processBeta-secretase 1Homo sapiens (human)
positive regulation of neuron apoptotic processBeta-secretase 1Homo sapiens (human)
amyloid-beta metabolic processBeta-secretase 1Homo sapiens (human)
detection of mechanical stimulus involved in sensory perception of painBeta-secretase 1Homo sapiens (human)
prepulse inhibitionBeta-secretase 1Homo sapiens (human)
cellular response to copper ionBeta-secretase 1Homo sapiens (human)
cellular response to manganese ionBeta-secretase 1Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionBeta-secretase 1Homo sapiens (human)
signaling receptor ligand precursor processingBeta-secretase 1Homo sapiens (human)
cellular response to amyloid-betaBeta-secretase 1Homo sapiens (human)
amyloid fibril formationBeta-secretase 1Homo sapiens (human)
xanthine catabolic processXanthine dehydrogenase/oxidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (27)

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)
beta-glucuronidase activityBeta-glucuronidaseHomo sapiens (human)
signaling receptor bindingBeta-glucuronidaseHomo sapiens (human)
protein domain specific bindingBeta-glucuronidaseHomo sapiens (human)
carbohydrate bindingBeta-glucuronidaseHomo sapiens (human)
amyloid-beta bindingBeta-secretase 1Homo sapiens (human)
endopeptidase activityBeta-secretase 1Homo sapiens (human)
aspartic-type endopeptidase activityBeta-secretase 1Homo sapiens (human)
protein bindingBeta-secretase 1Homo sapiens (human)
peptidase activityBeta-secretase 1Homo sapiens (human)
beta-aspartyl-peptidase activityBeta-secretase 1Homo sapiens (human)
enzyme bindingBeta-secretase 1Homo sapiens (human)
protein serine/threonine kinase bindingBeta-secretase 1Homo sapiens (human)
xanthine dehydrogenase activityXanthine dehydrogenase/oxidaseBos taurus (cattle)
xanthine oxidase activityXanthine dehydrogenase/oxidaseBos taurus (cattle)
iron ion bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
molybdenum ion bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
protein homodimerization activityXanthine dehydrogenase/oxidaseBos taurus (cattle)
molybdopterin cofactor bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
flavin adenine dinucleotide bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
2 iron, 2 sulfur cluster bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
FAD bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (31)

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 regionBeta-glucuronidaseHomo sapiens (human)
extracellular spaceBeta-glucuronidaseHomo sapiens (human)
membraneBeta-glucuronidaseHomo sapiens (human)
azurophil granule lumenBeta-glucuronidaseHomo sapiens (human)
lysosomal lumenBeta-glucuronidaseHomo sapiens (human)
intracellular membrane-bounded organelleBeta-glucuronidaseHomo sapiens (human)
extracellular exosomeBeta-glucuronidaseHomo sapiens (human)
ficolin-1-rich granule lumenBeta-glucuronidaseHomo sapiens (human)
extracellular spaceBeta-glucuronidaseHomo sapiens (human)
lysosomeBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
early endosomeBeta-secretase 1Homo sapiens (human)
late endosomeBeta-secretase 1Homo sapiens (human)
multivesicular bodyBeta-secretase 1Homo sapiens (human)
endoplasmic reticulum lumenBeta-secretase 1Homo sapiens (human)
Golgi apparatusBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
synaptic vesicleBeta-secretase 1Homo sapiens (human)
cell surfaceBeta-secretase 1Homo sapiens (human)
endosome membraneBeta-secretase 1Homo sapiens (human)
membraneBeta-secretase 1Homo sapiens (human)
axonBeta-secretase 1Homo sapiens (human)
dendriteBeta-secretase 1Homo sapiens (human)
neuronal cell bodyBeta-secretase 1Homo sapiens (human)
membrane raftBeta-secretase 1Homo sapiens (human)
recycling endosomeBeta-secretase 1Homo sapiens (human)
Golgi-associated vesicle lumenBeta-secretase 1Homo sapiens (human)
hippocampal mossy fiber to CA3 synapseBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
extracellular spaceXanthine dehydrogenase/oxidaseBos taurus (cattle)
peroxisomeXanthine dehydrogenase/oxidaseBos taurus (cattle)
xanthine dehydrogenase complexXanthine dehydrogenase/oxidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (29)

Assay IDTitleYearJournalArticle
AID670958Antibacterial activity against methicillin-sensitive Staphylococcus aureus ATCC 25923 after 24 hrs by microdilution method2012Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14
Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics.
AID1698237Inhibition of PMA-induce ROS/RNS generation in human neutrophils measured up to 30 mins in presence of 5.5 mM glucose by luminol-amplified chemiluminescence method2020Journal of natural products, 10-23, Volume: 83, Issue:10
Chalcones as Modulators of Neutrophil Oxidative Burst under Physiological and High Glucose Conditions.
AID670964Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 43300 after 24 hrs by microdilution method in presence of non-beta lactam antibiotic ciprofloxacin2012Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14
Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics.
AID1515153Antiproliferative activity against human PC3 cells after 72 hrs by CyQuant dye-based assay2019Bioorganic & medicinal chemistry, 01-01, Volume: 27, Issue:1
Design, synthesis and QSAR study of 2'-hydroxy-4'-alkoxy chalcone derivatives that exert cytotoxic activity by the mitochondrial apoptotic pathway.
AID144377Ability to induce NAD(P)H quinone reductase activity in cultured Hepa 1c1c7 murine hepatoma cells.1998Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26
Chemoprotective properties of phenylpropenoids, bis(benzylidene)cycloalkanones, and related Michael reaction acceptors: correlation of potencies as phase 2 enzyme inducers and radical scavengers.
AID1461521Antioxidant activity assessed as DPPH free radical scavenging activity incubated for 30 mins at 2000 uM2017Bioorganic & medicinal chemistry letters, 08-01, Volume: 27, Issue:15
Synthesis and evaluation of hydroxychalcones as multifunctional non-purine xanthine oxidase inhibitors for the treatment of hyperuricemia.
AID670962Antibacterial activity against methicillin-sensitive Staphylococcus aureus ATCC 25923 after 24 hrs by microdilution method in presence of non-beta lactam antibiotic gentamycin2012Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14
Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics.
AID310866Inhibition of fMLP/CB-stimulated release of lysozyme in rat neutrophils2007European journal of medicinal chemistry, Feb, Volume: 42, Issue:2
A review of anti-infective and anti-inflammatory chalcones.
AID1698242Inhibition of PMA-induce ROS/RNS generation in human neutrophils measured up to 30 mins in presence of 30 mM glucose by luminol-amplified chemiluminescence method2020Journal of natural products, 10-23, Volume: 83, Issue:10
Chalcones as Modulators of Neutrophil Oxidative Burst under Physiological and High Glucose Conditions.
AID517463Induction of Hsf1 DNA binding affinity in human HT-29 cells at 8 uM after 2 hrs2010Bioorganic & medicinal chemistry letters, Oct-15, Volume: 20, Issue:20
Radiosensitization of cancer cells by hydroxychalcones.
AID517462Cytotoxicity against human HT-29 cells assessed as plating efficiency at 10 uM2010Bioorganic & medicinal chemistry letters, Oct-15, Volume: 20, Issue:20
Radiosensitization of cancer cells by hydroxychalcones.
AID517465Phototoxicity against human HT-29 cells at 10 uM irradiated with 4 Gy/min2010Bioorganic & medicinal chemistry letters, Oct-15, Volume: 20, Issue:20
Radiosensitization of cancer cells by hydroxychalcones.
AID670960Antibacterial activity against methicillin-sensitive Staphylococcus aureus ATCC 25923 after 24 hrs by microdilution method in presence of non-beta lactam antibiotic Doxycycline2012Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14
Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics.
AID1592021Inhibition of recombinant human N-terminal His-tagged PDI expressed in Escherichia coli BL21 (DE3) pLysS assessed as reduction in enzyme-mediated bovine insulin aggregation2019Journal of medicinal chemistry, 04-11, Volume: 62, Issue:7
Design, Synthesis, and Biological Evaluation of Novel Allosteric Protein Disulfide Isomerase Inhibitors.
AID1461517Inhibition of bovine milk xanthine oxidase pre-incubated for 30 mins followed by xanthine addition and measured every 30 secs for 5 mins by spectrophotometry2017Bioorganic & medicinal chemistry letters, 08-01, Volume: 27, Issue:15
Synthesis and evaluation of hydroxychalcones as multifunctional non-purine xanthine oxidase inhibitors for the treatment of hyperuricemia.
AID1698235Effect on cell viability in human neutrophils assessed as decrease in cell viability at 25 uM after 1 hr by Propidium staining based flow cytometric analysis2020Journal of natural products, 10-23, Volume: 83, Issue:10
Chalcones as Modulators of Neutrophil Oxidative Burst under Physiological and High Glucose Conditions.
AID1142530Inhibition of yeast alpha-glucosidase type 3 using p-nitrophenyl-alpha-D-glucopyranoside as substrate preincubated with substrate for 5 mins prior to enzyme challenge for 30 mins by absorbance analysis2014European journal of medicinal chemistry, Jun-10, Volume: 80Dual inhibition of the α-glucosidase and butyrylcholinesterase studied by molecular field topology analysis.
AID1656436Inhibition of beta-glucuronidase (unknown origin)2020European journal of medicinal chemistry, Feb-01, Volume: 187Therapeutic significance of β-glucuronidase activity and its inhibitors: A review.
AID670965Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 43300 after 24 hrs by microdilution method in presence of non-beta lactam antibiotic gentamycin2012Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14
Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics.
AID310865Inhibition of fMLP/CB-stimulated release of beta-glucuronidase in rat neutrophils2007European journal of medicinal chemistry, Feb, Volume: 42, Issue:2
A review of anti-infective and anti-inflammatory chalcones.
AID670963Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 43300 after 24 hrs by microdilution method in presence of non-beta lactam antibiotic Doxycycline2012Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14
Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics.
AID670944Antibacterial activity against methicillin-sensitive Staphylococcus aureus ATCC 25923 at 102.4 mg/ml after 24 hrs by disc diffusion method2012Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14
Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics.
AID1142531Inhibition of BChE (unknown origin) using BCh iodide as substrate preincubated for 15 mins prior to substrate addition measured after 10 mins by Ellman's method2014European journal of medicinal chemistry, Jun-10, Volume: 80Dual inhibition of the α-glucosidase and butyrylcholinesterase studied by molecular field topology analysis.
AID517461Induction in heat-induced cell killing in human HT-29 cells2010Bioorganic & medicinal chemistry letters, Oct-15, Volume: 20, Issue:20
Radiosensitization of cancer cells by hydroxychalcones.
AID670961Antibacterial activity against methicillin-sensitive Staphylococcus aureus ATCC 25923 after 24 hrs by microdilution method in presence of non-beta lactam antibiotic ciprofloxacin2012Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14
Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics.
AID670951Antibacterial activity against methicillin-sensitive Staphylococcus aureus ATCC 43300 at 102.4 mg/ml after 24 hrs by disc diffusion method2012Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14
Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics.
AID1461520Antioxidant activity assessed as ABTS free radical scavenging activity by measuring trolox equivalents after 6 mins2017Bioorganic & medicinal chemistry letters, 08-01, Volume: 27, Issue:15
Synthesis and evaluation of hydroxychalcones as multifunctional non-purine xanthine oxidase inhibitors for the treatment of hyperuricemia.
AID670959Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 43300 after 24 hrs by microdilution method2012Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14
Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics.
AID1803028Biochemical Assay from Article 10.3109/14756366.2010.543420: \\Design, synthesis and SAR study of hydroxychalcone inhibitors of human u00DF-secretase (BACE1).\\2011Journal of enzyme inhibition and medicinal chemistry, Oct, Volume: 26, Issue:5
Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (8.33)18.2507
2000's1 (8.33)29.6817
2010's8 (66.67)24.3611
2020's2 (16.67)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 Index2.56 (2.92)
Research Growth Index5.08 (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%
Reviews2 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]