Compounds > 2,4,2',4'-Tetrahydroxychalcone
Page last updated: 2024-08-02 14:25:51

2,4,2',4'-Tetrahydroxychalcone

Description

2,4,2',4'-Tetrahydroxychalcone : no description available [CHeBI]

Cross-References

ID SourceID
PubMed CID10107266
CHEMBL ID394855
SCHEMBL ID675094
CHEBI ID196260

Synonyms (11)

Synonym
(e)-1,3-bis(2,4-dihydroxyphenyl)prop-2-en-1-one
2,4,2',4'-tetrahydroxychalcone
LMPK12120128
2,2',4,4'-tetrahydroxychalcone
CHEMBL394855 ,
bdbm50203985
2,2'',4,4''-tetrahydroxychalcone
2,4,2'',4''-tetrahydroxychalcone
CHEBI:196260
SCHEMBL675094
PD148015

Drug Classes (1)

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

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Polyphenol oxidase 2Agaricus bisporusIC505.0000AID293950; AID730305
TyrosinaseMus musculus (house mouse)IC505.0000AID1611932
TyrosinaseHomo sapiens (human)IC500.0700AID1611934
Beta-secretase 1Homo sapiens (human)IC500.6200AID1803028

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1611934Inhibition of tyrosinase (unknown origin)2018Journal of medicinal chemistry, 09-13, Volume: 61, Issue:17
ISSN: 1520-4804		Inhibitors of Melanogenesis: An Updated Review.
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
ISSN: 1520-6025		Chalcones as Modulators of Neutrophil Oxidative Burst under Physiological and High Glucose Conditions.
AID730306Competitive inhibition of mushroom tyrosinase assessed as reduction in L-DOPA oxidation by Lineweaver-Burk plot2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
ISSN: 1464-3391		Design and synthesis of 3,5-diaryl-4,5-dihydro-1H-pyrazoles as new tyrosinase inhibitors.
AID357965Inhibition of aromatase from human placental microsomes2001Journal of natural products, Oct, Volume: 64, Issue:10
ISSN: 0163-3864		Aromatase inhibitors from Broussonetia papyrifera.
AID1607883Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide production after 24 hrs by Griess reagent based assay2019European journal of medicinal chemistry, Oct-01, Volume: 179ISSN: 1768-3254Human disorders associated with inflammation and the evolving role of natural products to overcome.
AID293950Inhibition of mushroom tyrosinase2007Bioorganic & medicinal chemistry, Mar-15, Volume: 15, Issue:6
ISSN: 0968-0896		Synthesis and evaluation of 2',4',6'-trihydroxychalcones as a new class of tyrosinase inhibitors.
AID1480924Inhibition of alpha-glucosidase (unknown origin) using PNP glycoside as substrate pretreated for 30 mins followed by substrate addition after 60 secs by spectrophotometric method2017European journal of medicinal chemistry, Apr-21, Volume: 130ISSN: 1768-3254Analogues of xanthones--Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates.
AID1611932Inhibition of tyrosinase in mouse B16 cells assessed as reduction in melanin synthesis after 1 hr2018Journal of medicinal chemistry, 09-13, Volume: 61, Issue:17
ISSN: 1520-4804		Inhibitors of Melanogenesis: An Updated Review.
AID1698232Effect on cell viability in human neutrophils assessed as decrease in cell viability at 12.5 uM after 1 hr by Propidium staining based flow cytometric analysis2020Journal of natural products, 10-23, Volume: 83, Issue:10
ISSN: 1520-6025		Chalcones as Modulators of Neutrophil Oxidative Burst under Physiological and High Glucose Conditions.
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
ISSN: 1520-6025		Chalcones as Modulators of Neutrophil Oxidative Burst under Physiological and High Glucose Conditions.
AID1713993Inhibition of monophenolase activity of mushroom tyrosinase using L-Tyrosine substrate incubated for 10 mins followed by substrate addition and measured for 15 mins2016Bioorganic & medicinal chemistry, 11-15, Volume: 24, Issue:22
ISSN: 1464-3391
AID730305Inhibition of mushroom tyrosinase assessed as reduction in diphenolase activity using L-DOPA substrate pre-incubated for 20 mins at 30 degC2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
ISSN: 1464-3391		Design and synthesis of 3,5-diaryl-4,5-dihydro-1H-pyrazoles as new tyrosinase inhibitors.
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
ISSN: 1475-6374		Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1).

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (22.22)29.6817
2010's6 (66.67)24.3611
2020's1 (11.11)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (22.22%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (77.78%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one
0
chalcones00low000000
1-phenyl-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one
0
chalcones00low000000
2'-hydroxychalcone
0
chalcones;
phenols		anti-inflammatory agent00low000000
isoliquiritigenin
0
chalconesantineoplastic agent;
biological pigment;
EC 1.14.18.1 (tyrosinase) inhibitor;
GABA modulator;
geroprotector;
metabolite;
NMDA receptor antagonist		00low000000
xanthohumol
0
aromatic ether;
chalcones;
polyphenol		anti-HIV-1 agent;
antineoplastic agent;
antiviral agent;
apoptosis inducer;
EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor;
metabolite		00low000000
cardamonin
0
chalcones00low000000
4'-methoxychalcone
0
chalcones00low000000
2',4',6'-Trihydroxydihydrochalcone
0
chalcones00low000000
naringenin chalcone
0
chalcones;
polyphenol		anti-allergic agent;
anti-inflammatory agent;
metabolite		00low000000
butein
0
chalcones;
polyphenol		antineoplastic agent;
antioxidant;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
geroprotector;
hypoglycemic agent;
plant metabolite;
radiosensitizing agent;
tyrosine kinase inhibitor		00low000000
isobavachalcone
0
chalcones;
polyphenol		antibacterial agent;
metabolite;
platelet aggregation inhibitor		00low000000
isobutrin
0
beta-D-glucoside;
chalcones;
monosaccharide derivative;
phenols		anti-inflammatory agent;
hepatoprotective agent;
plant metabolite		00low000000
okanin
0
benzenetriol;
chalcones		plant metabolite00low000000
sofalcone
0
aromatic ether;
chalcones;
monocarboxylic acid		anti-ulcer drug;
antibacterial agent;
gastrointestinal drug;
plant metabolite		00low000000
4-hydroxychalcone
0
chalcones;
phenols		antihypertensive agent;
plant metabolite		00low000000
4'-hydroxychalcone
0
chalcones;
phenols		anti-inflammatory agent;
antineoplastic agent		00low000000
2',6'-dihydroxy-4'-methoxychalcone
0
chalcones00low000000
isosalipurposide
0
beta-D-glucoside;
chalcones;
monosaccharide derivative;
resorcinols		antioxidant;
plant metabolite		00low000000
licochalcone a
0
chalcones00low000000
licochalcone b
0
chalcones00low000000
sappanchalcone
0
catechols;
chalcones;
monomethoxybenzene		anti-allergic agent;
anti-inflammatory agent;
antioxidant;
metabolite		00low000000
3-deoxysappanchalcone
0
chalcones;
monomethoxybenzene;
phenols		metabolite00low000000
calythropsin
0
chalcones00low000000
flavokawain a
0
chalcones00low000000
flavokawain b
0
chalcones;
dimethoxybenzene;
phenols		anti-inflammatory agent;
antileishmanial agent;
antineoplastic agent;
apoptosis inducer;
metabolite		00low000000
Isoliquiritigenin 4,4'-dimethyl ether
0
chalcones00low000000
4-chlorochalcone
0
chalcones;
monochlorobenzenes		00low000000
2',3,4-trihydroxychalcone
0
catechols;
chalcones		00low000000
Crotaoprostrin
0
chalcones00low000000
2',5'-dihydroxychalcone
0
chalcones00low000000
4-hydroxycordoin
0
aromatic ether;
chalcones;
polyphenol		anti-inflammatory agent;
antibacterial agent;
plant metabolite		00low000000
derricidin
0
chalcones00low000000
isocordoin
0
chalcones00low000000
helichrysetin
0
chalcones00low000000
Lonchocarpin
0
chalcones00low000000
flavokawain C
0
chalcones00low000000
3-o-methylbutein
0
chalcones00low000000
4-hydroxyderricin
0
chalcones00low000000
perflubron
0
2-acyl-4-prenylphloroglucinol;
chalcones		plant metabolite00low000000
bavachalcone
0
chalcones00low000000
2',4',6'-trihydroxychalcone
0
chalconesantifungal agent;
plant metabolite		00low000000
Uvangoletin
0
chalcones00low000000
morachalcone a
0
chalcones00low000000
myrigalone b
0
chalcones00low000000
xanthohumol c
0
chalcones00low000000
2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone
0
chalcones;
monomethoxybenzene;
resorcinols		EC 3.2.1.18 (exo-alpha-sialidase) inhibitor;
plant metabolite		00low000000
4-Methoxylonchocarpin
0
chalcones00low000000
Kanzonol B
0
chalcones00low000000
Xanthoangelol D
0
chalcones00low000000
3-hydroxyphloretin
0
chalcones00low000000
linderol a
0
chalcones00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
hydroquinone
1
benzenediol;
hydroquinones		antioxidant;
carcinogenic agent;
cofactor;
Escherichia coli metabolite;
human xenobiotic metabolite;
mouse metabolite;
skin lightening agent		201820186.0low000010
5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl 3,4,5-trihydroxybenzoate
1
catechin201920195.0medium000010
aminoglutethimide
1
dicarboximide;
piperidones;
substituted aniline		adrenergic agent;
anticonvulsant;
antineoplastic agent;
EC 1.14.14.14 (aromatase) inhibitor		2001200123.0low000100
aspirin
1
benzoic acids;
phenyl acetates;
salicylates		anticoagulant;
antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
EC 1.1.1.188 (prostaglandin-F synthase) inhibitor;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
plant activator;
platelet aggregation inhibitor;
prostaglandin antagonist;
teratogenic agent		201920195.0low000010
celecoxib
1
organofluorine compound;
pyrazoles;
sulfonamide;
toluenes		cyclooxygenase 2 inhibitor;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug		201920195.0low000010
beta-thujaplicin
1
cyclic ketone;
enol;
monoterpenoid		antibacterial agent;
antifungal agent;
antineoplastic agent;
antiplasmodial drug;
plant metabolite		201820186.0low000010
kojic acid
3
4-pyranones;
enol;
primary alcohol		Aspergillus metabolite;
EC 1.10.3.1 (catechol oxidase) inhibitor;
EC 1.10.3.2 (laccase) inhibitor;
EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor;
EC 1.14.18.1 (tyrosinase) inhibitor;
EC 1.4.3.3 (D-amino-acid oxidase) inhibitor;
NF-kappaB inhibitor;
skin lightening agent		2007201811.3low000120
pd 169316
1
imidazoles201820186.0low000010
sb 202190
1
imidazoles;
organofluorine compound;
phenols;
pyridines		apoptosis inducer;
EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor		201820186.0low000010
gamma-thujaplicin
1
cyclic ketone201820186.0low000010
1-deoxynojirimycin
1
2-(hydroxymethyl)piperidine-3,4,5-triol;
piperidine alkaloid		anti-HIV agent;
anti-obesity agent;
bacterial metabolite;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
hepatoprotective agent;
hypoglycemic agent;
plant metabolite		201720177.0low000010
betulinic acid
1
hydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-HIV agent;
anti-inflammatory agent;
antimalarial;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
plant metabolite		201920195.0low000010
1-hydroxy-2(1h)-pyridinone
1
201820186.0low000010
zaluzanin C
1
gamma-lactone;
guaiane sesquiterpenoid;
organic heterotricyclic compound;
secondary alcohol;
sesquiterpene lactone		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
metabolite		201920195.0medium000010
alpha-thujaplicin
1
201820186.0medium000010
syringaresinol
1
aromatic ether;
furofuran;
lignan;
polyether;
polyphenol		plant metabolite201920195.0low000010
loliolide
1
benzofuransmetabolite2001200123.0low000100
aromadedrin
1
4'-hydroxyflavanones;
dihydroflavonols;
secondary alpha-hydroxy ketone;
tetrahydroxyflavanone		metabolite2001200123.0low000100
salicylideneaniline
1
201820186.0low000010
sb 203580
1
imidazoles;
monofluorobenzenes;
pyridines;
sulfoxide		EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor;
geroprotector;
Hsp90 inhibitor;
neuroprotective agent		201820186.0low000010
moracin m
2
benzofurans2001201814.5medium000110
4-n-butylresorcinol
1
resorcinols201820186.0low000010
marmesin
1
marmesin2001200123.0low000100
naringenin
1
(2S)-flavan-4-one;
naringenin		expectorant;
plant metabolite		2001200123.0low000100
arbutin
1
beta-D-glucoside;
monosaccharide derivative		Escherichia coli metabolite;
plant metabolite		201820186.0low000010
resveratrol
3
resveratrolantioxidant;
phytoalexin;
plant metabolite;
quorum sensing inhibitor;
radical scavenger		2001201911.3low000120
trans-4-coumaric acid
1
4-coumaric acidfood component;
mouse metabolite;
plant metabolite		201820186.0low000010
chalcone
1
chalconeEC 3.2.1.1 (alpha-amylase) inhibitor202020204.0low000010
2,2'-dihydroxychalcone
2
201120208.5medium000020
isoliquiritigenin
3
chalconesantineoplastic agent;
biological pigment;
EC 1.14.18.1 (tyrosinase) inhibitor;
GABA modulator;
geroprotector;
metabolite;
NMDA receptor antagonist		201120198.3low000030
curcumin
1
aromatic ether;
beta-diketone;
diarylheptanoid;
enone;
polyphenol		anti-inflammatory agent;
antifungal agent;
antineoplastic agent;
biological pigment;
contraceptive drug;
dye;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor;
EC 1.8.1.9 (thioredoxin reductase) inhibitor;
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor;
EC 3.5.1.98 (histone deacetylase) inhibitor;
flavouring agent;
food colouring;
geroprotector;
hepatoprotective agent;
immunomodulator;
iron chelator;
ligand;
lipoxygenase inhibitor;
metabolite;
neuroprotective agent;
nutraceutical;
radical scavenger		201920195.0low000010
quercetin 3-o-methyl ether
1
monomethoxyflavone;
tetrahydroxyflavone		antimicrobial agent;
metabolite		201920195.0low000010
naringenin chalcone
1
chalcones;
polyphenol		anti-allergic agent;
anti-inflammatory agent;
metabolite		201720177.0low000010
butein
1
chalcones;
polyphenol		antineoplastic agent;
antioxidant;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
geroprotector;
hypoglycemic agent;
plant metabolite;
radiosensitizing agent;
tyrosine kinase inhibitor		2011201113.0low000010
hispidol
1
hydroxyauroneplant metabolite201820186.0low000010
isobavachalcone
2
chalcones;
polyphenol		antibacterial agent;
metabolite;
platelet aggregation inhibitor		2001201914.0low000110
norathyriol
1
polyphenol;
xanthones		antineoplastic agent;
EC 2.7.11.13 (protein kinase C) inhibitor;
plant metabolite		201920195.0low000010
myricitrin
1
alpha-L-rhamnoside;
glycosyloxyflavone;
monosaccharide derivative;
pentahydroxyflavone		anti-allergic agent;
EC 1.14.13.39 (nitric oxide synthase) inhibitor;
EC 2.7.11.13 (protein kinase C) inhibitor;
plant metabolite		201920195.0low000010
trans-2,3',4,5'-tetrahydroxystilbene
1
stilbenoid201820186.0low000010
acteoside
1
catechols;
cinnamate ester;
disaccharide derivative;
glycoside;
polyphenol		anti-inflammatory agent;
antibacterial agent;
antileishmanial agent;
neuroprotective agent;
plant metabolite		201920195.0low000010
4-hydroxychalcone
1
chalcones;
phenols		antihypertensive agent;
plant metabolite		202020204.0low000010
broussonin a
1
2001200123.0medium000100
broussonin b
1
2001200123.0high000100
Isolicoflavonol
1
flavones2001200123.0medium000100
methyl-p-coumarate
1
4-coumaric acid methyl ester201820186.0low000010
muromonab-cd3
1
extended flavonoid;
pyranochromane;
trihydroxyflavone		anti-inflammatory agent;
plant metabolite		201920195.0low000010
2'-hydroxy-4-methoxychalcone
1
202020204.0low000010
ergosterol-5,8-peroxide
1
3beta-sterol;
ergostanoid;
organic peroxide;
phytosterols		antimycobacterial drug;
antineoplastic agent;
metabolite;
trypanocidal drug		201920195.0low000010
guttiferone e
1
201920195.0low000010
flavokawain a
1
chalcones202020204.0low000010
lichexanthone
1
aromatic ether;
phenols;
xanthones		plant metabolite201920195.0medium000010
2',4'-dihydroxychalcone
1
2007200717.0low000100
4-chlorochalcone
1
chalcones;
monochlorobenzenes		202020204.0medium000010
1,3,5,6-tetrahydroxyxanthone
1
201920195.0medium000010
Norartocarpetin
2
flavones201320198.0high000020
24-ethyl-4-cholesten-3-one
1
C29-steroid;
steroid		metabolite201920195.0low000010
2',3,4-trihydroxychalcone
1
catechols;
chalcones		2007200717.0medium000100
Crotaoprostrin
1
chalcones202020204.0medium000010
lyoniside
1
beta-D-glucoside;
monosaccharide derivative;
steroid saponin		plant metabolite201920195.0low000010
2,4,2'-trihydroxychalcone
1
2011201113.0low000010
broussochalcone a
1
2001200123.0low000100
mulberroside a
1
glycoside;
stilbenoid		201820186.0low000010
13-oxo-9,11-octadecadienoic acid
1
13-oxo-9,11-octadecadienoic acidmetabolite;
mouse metabolite		201920195.0high000010
bavachalcone
1
chalcones2001200123.0low000100
2',4',6'-trihydroxychalcone
1
chalconesantifungal agent;
plant metabolite		2007200717.0medium000100
cajanine
1
stilbenoid201920195.0low000010
morachalcone a
2
chalcones2001201814.5high000110
ginsenoside rb1
1
ginsenoside;
glycoside;
tetracyclic triterpenoid		anti-inflammatory drug;
anti-obesity agent;
apoptosis inhibitor;
neuroprotective agent;
plant metabolite;
radical scavenger		201820186.0low000010
chikusetsu saponin iva
1
triterpenoid saponinmetabolite201920195.0low000010
bavachin
1
2001200123.0low000100
subamolide a
1
201820186.0high000010
Norartocarpanone
2
flavanones201320198.0high000020
(E)-1,7-Bis(4-hydroxyphenyl)hept-4-en-3-one
1
diarylheptanoid201920195.0medium000010
mulberrofuran g
1
2001200123.0medium000100
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Arthritis, Rheumatoid0
1
201920195.0medium000010
Benign Neoplasms0
1
201920195.0medium000010
Cardiovascular Diseases0
1
201920195.0medium000010
Dermatoses0
1
201920195.0medium000010
Inflammation0
1
201920195.0medium000010
Innate Inflammatory Response0
1
201920195.0medium000010
Neoplasms0
1
201920195.0medium000010
Pregnancy0
1
2001200123.0medium000100
Rheumatoid Arthritis0
1
201920195.0medium000010
Skin Diseases0
1
201920195.0medium000010