Page last updated: 2024-11-10

prunetin

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

Description

prunetin: reduces herpes virus-1 plaque formation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

prunetin : A hydroxyisoflavone that is genistein in which the hydroxy group at position 7 is replaced by a methoxy group. [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 CID5281804
CHEMBL ID491174
CHEBI ID8600
SCHEMBL ID73420
MeSH IDM0221668

Synonyms (62)

Synonym
BIDD:ER0153
SPECTRUM5_000486
BRD-K57546357-001-01-6
4',5-dihydroxy-7-methoxygenistein
CHEBI:8600 ,
4',5-dihydroxy-7-methoxyisoflavone
7-o-methyl-genistein
5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4h-chromen-4-one
5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4-benzopyrone
padmakastein
prunusetin
5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4h-1-benzopyran-4-one
KBIO1_001533
DIVK1C_006589
isoflavone, 4',5-dihydroxy-7-methoxy- (7ci,8ci)
brn 0292155
4h-1-benzopyran-4-one, 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-
einecs 209-018-5
SPECTRUM_001027
SPECTRUM4_001723
BSPBIO_003044
NCGC00178331-01
SMP1_000150
prunetin
552-59-0
KBIO2_006643
KBIOGR_002106
KBIOSS_001507
KBIO3_002264
KBIO2_004075
KBIO2_001507
SPECTRUM3_001402
SPECPLUS_000493
5,4'-dihydroxy-7-methoxyisoflavone
OPREA1_083784
prunetin, >=98.0% (tlc)
CHEMBL491174
LMPK12050353
5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one
5-18-04-00595 (beilstein handbook reference)
isoflavone, 4',5-dihydroxy-7-methoxy-
1tg4h5h11j ,
ccris 8951
unii-1tg4h5h11j
AKOS016010281
bdbm50359990
gtpl6919
prunetin [mi]
SCHEMBL73420
AC-35016
KQMVAGISDHMXJJ-UHFFFAOYSA-N
7-o-methyl genistein
DTXSID3022530
mfcd00016951
AS-71541
5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4h-1-benzopyran-4-one, 9ci
FT-0708556
HY-N2597
BCP09998
Q7253051
CS-0022974
A870240

Research Excerpts

Overview

Prunetin (PRU) is an O-methylated flavonoid that is present in various natural plants. Prunetin is an isomer of biochanin A, and even though it is not very common, its structural relationship to the latter makes it interesting, regarding its biological activity.

ExcerptReferenceRelevance
"Prunetin (PRU) is an O-methylated flavonoid that is present in various natural plants and a primary significant compound found in isoflavone. "( Involvement of NF-κB/PI3K/AKT signaling pathway in the protective effect of prunetin against a diethylnitrosamine induced hepatocellular carcinogenesis in rats.
Chen, H; Li, G; Qi, L; Tian, G, 2022
)
2.39
"Prunetin is an isomer of biochanin A, and even though it is not very common, its structural relationship to the latter makes it interesting, regarding its biological activity."( Comment on the published data concerning the identification of biochanin A and prunetin by LC/ESI-MS.
Beszterda, M; Frański, R; Kasperkowiak, M, 2020
)
1.51
"Prunetin (PRU) is an O-methylated flavonoid that belongs to the group of isoflavone executing beneficial activities."( Compound Prunetin Induces Cell Death in Gastric Cancer Cell with Potent Anti-Proliferative Properties: In Vitro Assay, Molecular Docking, Dynamics, and ADMET Studies.
Bhosale, PB; Ha, SE; Kim, GS; Kim, HH; Kim, SM; Senthil, K; Vetrivel, P, 2020
)
1.7
"Prunetin is an O-methylated isoflavone, which has been found to possess anti-inflammatory activity."( Prunetin inhibits lipopolysaccharide-induced inflammatory cytokine production and MUC5AC expression by inactivating the TLR4/MyD88 pathway in human nasal epithelial cells.
Hu, H; Li, H, 2018
)
2.64
"Prunetin is an O-methylated isoflavone, which is a type of flavonoid. "( Molecular mechanisms underlying the anti-obesity potential of prunetin, an O-methylated isoflavone.
Ahn, TG; An, HJ; Choi, HY; Kim, MD; Kook, YB; Lee, HM; Lee, SD; Park, KS; Yang, G, 2013
)
2.07
"Prunetin is an O-methylated isoflavone, which is found in Prunus yedoensis. "( Anti-inflammatory effect of prunetin via the suppression of NF-κB pathway.
Choi, HY; Ham, I; Yang, G, 2013
)
2.13

Bioavailability

ExcerptReferenceRelevance
" While metabolism and bioavailability of the main IF from both sources have already been investigated, studies are still lacking on the biokinetic behaviour of IF, which are present in red clover in minor amounts."( Absorption of red clover isoflavones in human subjects: results from a pilot study.
Kulling, SE; Maul, R, 2010
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitorAn EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone.
anti-inflammatory agentAny compound that has anti-inflammatory effects.
EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitorAn EC 1.2.1.* (oxidoreductase acting on donor aldehyde/oxo group with NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of aldehyde dehydrogenase (NAD(+)), EC 1.2.1.3.
[role 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]

Drug Classes (2)

ClassDescription
hydroxyisoflavoneMember of the class of isoflavones bearing at least one hydroxy group.
7-methoxyisoflavonesAny methoxyisoflavone that has a methoxy group at the 7-position of the isoflavone moiety.
[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]

Pathways (2)

PathwayProteinsCompounds
isoflavonoid biosynthesis II124
superpathway of isoflavonoids (via naringenin)028
isoflavonoid biosynthesis II128
superpathway of isoflavonoids (via naringenin)034

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Aldehyde dehydrogenase, mitochondrialHomo sapiens (human)Ki0.45000.45000.45000.4500AID341734
Nitric oxide synthase, inducibleMus musculus (house mouse)IC50 (µMol)10.50000.00103.39119.6000AID633943
[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)
Glucocorticoid receptorHomo sapiens (human)EC150 (µMol)3.20000.00053.62157.1000AID429117
Androgen receptorHomo sapiens (human)EC150 (µMol)3.20000.00053.58477.1000AID429115
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (87)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IIGlucocorticoid receptorHomo sapiens (human)
regulation of gluconeogenesisGlucocorticoid receptorHomo sapiens (human)
chromatin organizationGlucocorticoid receptorHomo sapiens (human)
regulation of DNA-templated transcriptionGlucocorticoid receptorHomo sapiens (human)
apoptotic processGlucocorticoid receptorHomo sapiens (human)
chromosome segregationGlucocorticoid receptorHomo sapiens (human)
signal transductionGlucocorticoid receptorHomo sapiens (human)
glucocorticoid metabolic processGlucocorticoid receptorHomo sapiens (human)
gene expressionGlucocorticoid receptorHomo sapiens (human)
microglia differentiationGlucocorticoid receptorHomo sapiens (human)
adrenal gland developmentGlucocorticoid receptorHomo sapiens (human)
regulation of glucocorticoid biosynthetic processGlucocorticoid receptorHomo sapiens (human)
synaptic transmission, glutamatergicGlucocorticoid receptorHomo sapiens (human)
maternal behaviorGlucocorticoid receptorHomo sapiens (human)
intracellular glucocorticoid receptor signaling pathwayGlucocorticoid receptorHomo sapiens (human)
glucocorticoid mediated signaling pathwayGlucocorticoid receptorHomo sapiens (human)
positive regulation of neuron apoptotic processGlucocorticoid receptorHomo sapiens (human)
negative regulation of DNA-templated transcriptionGlucocorticoid receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIGlucocorticoid receptorHomo sapiens (human)
astrocyte differentiationGlucocorticoid receptorHomo sapiens (human)
cell divisionGlucocorticoid receptorHomo sapiens (human)
mammary gland duct morphogenesisGlucocorticoid receptorHomo sapiens (human)
motor behaviorGlucocorticoid receptorHomo sapiens (human)
cellular response to steroid hormone stimulusGlucocorticoid receptorHomo sapiens (human)
cellular response to glucocorticoid stimulusGlucocorticoid receptorHomo sapiens (human)
cellular response to dexamethasone stimulusGlucocorticoid receptorHomo sapiens (human)
cellular response to transforming growth factor beta stimulusGlucocorticoid receptorHomo sapiens (human)
neuroinflammatory responseGlucocorticoid receptorHomo sapiens (human)
positive regulation of miRNA transcriptionGlucocorticoid receptorHomo sapiens (human)
intracellular steroid hormone receptor signaling pathwayGlucocorticoid receptorHomo sapiens (human)
regulation of transcription by RNA polymerase IIGlucocorticoid receptorHomo sapiens (human)
carbohydrate metabolic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
alcohol metabolic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
ethanol catabolic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
aldehyde catabolic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
regulation of dopamine biosynthetic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
regulation of serotonin biosynthetic processAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIAndrogen receptorHomo sapiens (human)
MAPK cascadeAndrogen receptorHomo sapiens (human)
in utero embryonic developmentAndrogen receptorHomo sapiens (human)
regulation of systemic arterial blood pressureAndrogen receptorHomo sapiens (human)
epithelial cell morphogenesisAndrogen receptorHomo sapiens (human)
transcription by RNA polymerase IIAndrogen receptorHomo sapiens (human)
signal transductionAndrogen receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayAndrogen receptorHomo sapiens (human)
cell-cell signalingAndrogen receptorHomo sapiens (human)
spermatogenesisAndrogen receptorHomo sapiens (human)
single fertilizationAndrogen receptorHomo sapiens (human)
positive regulation of cell population proliferationAndrogen receptorHomo sapiens (human)
negative regulation of cell population proliferationAndrogen receptorHomo sapiens (human)
positive regulation of gene expressionAndrogen receptorHomo sapiens (human)
male somatic sex determinationAndrogen receptorHomo sapiens (human)
intracellular estrogen receptor signaling pathwayAndrogen receptorHomo sapiens (human)
androgen receptor signaling pathwayAndrogen receptorHomo sapiens (human)
intracellular receptor signaling pathwayAndrogen receptorHomo sapiens (human)
positive regulation of intracellular estrogen receptor signaling pathwayAndrogen receptorHomo sapiens (human)
Leydig cell differentiationAndrogen receptorHomo sapiens (human)
multicellular organism growthAndrogen receptorHomo sapiens (human)
positive regulation of phosphorylationAndrogen receptorHomo sapiens (human)
positive regulation of MAPK cascadeAndrogen receptorHomo sapiens (human)
positive regulation of insulin-like growth factor receptor signaling pathwayAndrogen receptorHomo sapiens (human)
positive regulation of cell differentiationAndrogen receptorHomo sapiens (human)
negative regulation of integrin biosynthetic processAndrogen receptorHomo sapiens (human)
positive regulation of integrin biosynthetic processAndrogen receptorHomo sapiens (human)
positive regulation of DNA-templated transcriptionAndrogen receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIAndrogen receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIIAndrogen receptorHomo sapiens (human)
insulin-like growth factor receptor signaling pathwayAndrogen receptorHomo sapiens (human)
regulation of developmental growthAndrogen receptorHomo sapiens (human)
animal organ formationAndrogen receptorHomo sapiens (human)
male genitalia morphogenesisAndrogen receptorHomo sapiens (human)
epithelial cell proliferationAndrogen receptorHomo sapiens (human)
negative regulation of epithelial cell proliferationAndrogen receptorHomo sapiens (human)
positive regulation of NF-kappaB transcription factor activityAndrogen receptorHomo sapiens (human)
activation of prostate induction by androgen receptor signaling pathwayAndrogen receptorHomo sapiens (human)
morphogenesis of an epithelial foldAndrogen receptorHomo sapiens (human)
lateral sprouting involved in mammary gland duct morphogenesisAndrogen receptorHomo sapiens (human)
prostate gland growthAndrogen receptorHomo sapiens (human)
prostate gland epithelium morphogenesisAndrogen receptorHomo sapiens (human)
epithelial cell differentiation involved in prostate gland developmentAndrogen receptorHomo sapiens (human)
tertiary branching involved in mammary gland duct morphogenesisAndrogen receptorHomo sapiens (human)
mammary gland alveolus developmentAndrogen receptorHomo sapiens (human)
positive regulation of epithelial cell proliferation involved in prostate gland developmentAndrogen receptorHomo sapiens (human)
cellular response to steroid hormone stimulusAndrogen receptorHomo sapiens (human)
cellular response to estrogen stimulusAndrogen receptorHomo sapiens (human)
cellular response to testosterone stimulusAndrogen receptorHomo sapiens (human)
seminiferous tubule developmentAndrogen receptorHomo sapiens (human)
non-membrane-bounded organelle assemblyAndrogen receptorHomo sapiens (human)
positive regulation of miRNA transcriptionAndrogen receptorHomo sapiens (human)
regulation of protein localization to plasma membraneAndrogen receptorHomo sapiens (human)
negative regulation of extrinsic apoptotic signaling pathwayAndrogen receptorHomo sapiens (human)
male gonad developmentAndrogen receptorHomo sapiens (human)
intracellular steroid hormone receptor signaling pathwayAndrogen receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (42)

Processvia Protein(s)Taxonomy
RNA polymerase II transcription regulatory region sequence-specific DNA bindingGlucocorticoid receptorHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificGlucocorticoid receptorHomo sapiens (human)
core promoter sequence-specific DNA bindingGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specificGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription factor activityGlucocorticoid receptorHomo sapiens (human)
RNA bindingGlucocorticoid receptorHomo sapiens (human)
nuclear receptor activityGlucocorticoid receptorHomo sapiens (human)
nuclear glucocorticoid receptor activityGlucocorticoid receptorHomo sapiens (human)
steroid bindingGlucocorticoid receptorHomo sapiens (human)
protein bindingGlucocorticoid receptorHomo sapiens (human)
zinc ion bindingGlucocorticoid receptorHomo sapiens (human)
TBP-class protein bindingGlucocorticoid receptorHomo sapiens (human)
protein kinase bindingGlucocorticoid receptorHomo sapiens (human)
identical protein bindingGlucocorticoid receptorHomo sapiens (human)
Hsp90 protein bindingGlucocorticoid receptorHomo sapiens (human)
steroid hormone bindingGlucocorticoid receptorHomo sapiens (human)
sequence-specific double-stranded DNA bindingGlucocorticoid receptorHomo sapiens (human)
estrogen response element bindingGlucocorticoid receptorHomo sapiens (human)
aldehyde dehydrogenase (NAD+) activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
aldehyde dehydrogenase [NAD(P)+] activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
phenylacetaldehyde dehydrogenase activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
electron transfer activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
nitroglycerin reductase activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
glyceraldehyde-3-phosphate dehydrogenase (NAD+) (non-phosphorylating) activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
NAD bindingAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
carboxylesterase activityAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
transcription cis-regulatory region bindingAndrogen receptorHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingAndrogen receptorHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificAndrogen receptorHomo sapiens (human)
RNA polymerase II general transcription initiation factor bindingAndrogen receptorHomo sapiens (human)
transcription coactivator bindingAndrogen receptorHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificAndrogen receptorHomo sapiens (human)
chromatin bindingAndrogen receptorHomo sapiens (human)
DNA-binding transcription factor activityAndrogen receptorHomo sapiens (human)
nuclear receptor activityAndrogen receptorHomo sapiens (human)
G protein-coupled receptor activityAndrogen receptorHomo sapiens (human)
signaling receptor bindingAndrogen receptorHomo sapiens (human)
steroid bindingAndrogen receptorHomo sapiens (human)
androgen bindingAndrogen receptorHomo sapiens (human)
protein bindingAndrogen receptorHomo sapiens (human)
beta-catenin bindingAndrogen receptorHomo sapiens (human)
zinc ion bindingAndrogen receptorHomo sapiens (human)
enzyme bindingAndrogen receptorHomo sapiens (human)
ATPase bindingAndrogen receptorHomo sapiens (human)
molecular adaptor activityAndrogen receptorHomo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingAndrogen receptorHomo sapiens (human)
POU domain bindingAndrogen receptorHomo sapiens (human)
molecular condensate scaffold activityAndrogen receptorHomo sapiens (human)
estrogen response element bindingAndrogen receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (15)

Processvia Protein(s)Taxonomy
nucleusGlucocorticoid receptorHomo sapiens (human)
nucleusGlucocorticoid receptorHomo sapiens (human)
nucleoplasmGlucocorticoid receptorHomo sapiens (human)
cytoplasmGlucocorticoid receptorHomo sapiens (human)
mitochondrial matrixGlucocorticoid receptorHomo sapiens (human)
centrosomeGlucocorticoid receptorHomo sapiens (human)
spindleGlucocorticoid receptorHomo sapiens (human)
cytosolGlucocorticoid receptorHomo sapiens (human)
membraneGlucocorticoid receptorHomo sapiens (human)
nuclear speckGlucocorticoid receptorHomo sapiens (human)
synapseGlucocorticoid receptorHomo sapiens (human)
chromatinGlucocorticoid receptorHomo sapiens (human)
protein-containing complexGlucocorticoid receptorHomo sapiens (human)
mitochondrionAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
mitochondrial matrixAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
extracellular exosomeAldehyde dehydrogenase, mitochondrialHomo sapiens (human)
plasma membraneAndrogen receptorHomo sapiens (human)
nucleusAndrogen receptorHomo sapiens (human)
nucleoplasmAndrogen receptorHomo sapiens (human)
cytoplasmAndrogen receptorHomo sapiens (human)
cytosolAndrogen receptorHomo sapiens (human)
nuclear speckAndrogen receptorHomo sapiens (human)
chromatinAndrogen receptorHomo sapiens (human)
protein-containing complexAndrogen receptorHomo sapiens (human)
nucleusAndrogen receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (40)

Assay IDTitleYearJournalArticle
AID1719073Induction of glucose uptake in mouse C2C12 cells at 1 ug/ml2021Bioorganic & medicinal chemistry letters, 03-01, Volume: 35Flavonoids from Sophora alopecuroides L. improve palmitate-induced insulin resistance by inhibiting PTP1B activity in vitro.
AID332640Enhancement of human DNA topoisomerase 2-mediated Escherichia coli pUC8 DNA cleavage assessed as production of linear DNA at 100 ug/ml after 30 mins by agarose gel electrophoresis relative to control1995Journal of natural products, Feb, Volume: 58, Issue:2
Flavonoids as DNA topoisomerase antagonists and poisons: structure-activity relationships.
AID587244Antimicrobial activity against Pseudomonas aeruginosa DSM 1128 at 1 ug/ul after 24 hrs by disk diffusion method2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Antimicrobial isopropenyl-dihydrofuranoisoflavones from Crotalaria lachnophora.
AID429115Agonist activity at androgen receptor in human MDA-kb2 cells assessed as stimulation of luciferase activity by luciferase reporter gene assay2009Bioorganic & medicinal chemistry letters, Aug-15, Volume: 19, Issue:16
Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assay.
AID378967Cytotoxicity against african green monkey Vero cells2006Journal of natural products, Jan, Volume: 69, Issue:1
Isoflavonoids and other compounds from Psorothamnus arborescens with antiprotozoal activities.
AID587247Antifungal activity against Candida albicans DSM 1386 after 24 hrs by disk diffusion method2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Antimicrobial isopropenyl-dihydrofuranoisoflavones from Crotalaria lachnophora.
AID633943Inhibition of iNOS-mediated NO production in LPS-stimulated mouse RAW264.7 cells after 24 hrs by Griess reagent method2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Secondary metabolites from the roots of Neolitsea daibuensis and their anti-inflammatory activity.
AID332648Enhancement of human DNA topoisomerase 2-mediated Escherichia coli pUC8 DNA cleavage assessed as production of linear DNA at 100 ug/ml after 30 mins by agarose gel electrophoresis relative to total DNA1995Journal of natural products, Feb, Volume: 58, Issue:2
Flavonoids as DNA topoisomerase antagonists and poisons: structure-activity relationships.
AID429117Agonist activity at glucocorticoid receptor in human MDA-kb2 cells assessed as stimulation of luciferase activity by luciferase reporter gene assay2009Bioorganic & medicinal chemistry letters, Aug-15, Volume: 19, Issue:16
Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assay.
AID587245Antimicrobial activity against Escherichia coli DSM 682 after 24 hrs by disk diffusion method2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Antimicrobial isopropenyl-dihydrofuranoisoflavones from Crotalaria lachnophora.
AID1719075Inhibition of PTP1B in mouse PA-induced insulin-resistance C2C12 cells assessed as increase in glucose consumption at 1 ug/ml in presence of insulin after 16 hrs2021Bioorganic & medicinal chemistry letters, 03-01, Volume: 35Flavonoids from Sophora alopecuroides L. improve palmitate-induced insulin resistance by inhibiting PTP1B activity in vitro.
AID341734Inhibition of human recombinant ALDH22008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Structure of daidzin, a naturally occurring anti-alcohol-addiction agent, in complex with human mitochondrial aldehyde dehydrogenase.
AID332647Enhancement of human DNA topoisomerase 2-mediated Escherichia coli pUC8 DNA cleavage after 30 mins by agarose gel electrophoresis1995Journal of natural products, Feb, Volume: 58, Issue:2
Flavonoids as DNA topoisomerase antagonists and poisons: structure-activity relationships.
AID429127Antagonist activity at androgen receptor in human MDA-kb2 cells assessed as inhibition of DHT-induced luciferase activity at 100 uM by luciferase reporter gene assay2009Bioorganic & medicinal chemistry letters, Aug-15, Volume: 19, Issue:16
Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assay.
AID525745Inhibition of TNF-alpha-induced Nuclear factor-kappa-B dependent transcriptional activity in human HCT116 cells assessed normalized inhibitory ratio of at 10 uM for 12 hrs by NF-kappaB cis-acting luciferase reporter gene assay relative to untreated contro2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Isoflavone derivatives inhibit NF-κB-dependent transcriptional activity.
AID1719074Induction of glucose uptake in mouse C2C12 cells at 1 ug/ml in presence of insulin2021Bioorganic & medicinal chemistry letters, 03-01, Volume: 35Flavonoids from Sophora alopecuroides L. improve palmitate-induced insulin resistance by inhibiting PTP1B activity in vitro.
AID1719072Cytotoxicity against mouse C2C12 cells assessed as reduction in cell viability by MTT assay2021Bioorganic & medicinal chemistry letters, 03-01, Volume: 35Flavonoids from Sophora alopecuroides L. improve palmitate-induced insulin resistance by inhibiting PTP1B activity in vitro.
AID1065094Induction of osteogenic activity in human MSC assessed as cell differentiation after 14 days by alizarin red staining-based spectrometry relative to vehicle-treated control2014ACS medicinal chemistry letters, Feb-13, Volume: 5, Issue:2
Design, synthesis, and osteogenic activity of daidzein analogs on human mesenchymal stem cells.
AID633944Inhibition of iNOS-mediated NO production in LPS-stimulated mouse RAW264.7 cells after 24 hrs by Griess reagent method relative to control2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Secondary metabolites from the roots of Neolitsea daibuensis and their anti-inflammatory activity.
AID622584Inhibition of NF-kappaB activation expressed in HCT116 cells assessed as inhibition of TNF-alpha-induced transcriptional activation at 10 uM after 12 hrs by luciferase reporter gene assay relative to control2011Bioorganic & medicinal chemistry letters, Oct-15, Volume: 21, Issue:20
Relationship between the structures of flavonoids and their NF-κB-dependent transcriptional activities.
AID1386834Antagonist activity at PR-b (unknown origin) expressed in Ishikawa cells assessed as inhibition of progesterone-induced PRE activity at 50 uM after 24 hrs by luciferase reporter gene based luminescence assay2018Journal of natural products, 09-28, Volume: 81, Issue:9
Irilone from Red Clover ( Trifolium pratense) Potentiates Progesterone Signaling.
AID587242Antimicrobial activity against Staphylococcus aureus DSM 799 at 1 ug/ul after 24 hrs by disk diffusion method2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Antimicrobial isopropenyl-dihydrofuranoisoflavones from Crotalaria lachnophora.
AID1386837Antagonist activity at PR-b (unknown origin) expressed in Ishikawa cells assessed as inhibition of basal PRE activity at 25 to 50 uM after 24 hrs in absence of progesterone by luciferase reporter gene based luminescence assay2018Journal of natural products, 09-28, Volume: 81, Issue:9
Irilone from Red Clover ( Trifolium pratense) Potentiates Progesterone Signaling.
AID332645Inhibition of calf thymus DNA topoisomerase 1 catalytic domain-mediated supercoiled Escherichia coli pUC8 DNA relaxation up to 100 uM after 30 mins by agarose gel electrophoresis1995Journal of natural products, Feb, Volume: 58, Issue:2
Flavonoids as DNA topoisomerase antagonists and poisons: structure-activity relationships.
AID378966Antitrypanosomal activity against Trypanosoma brucei brucei MITat 1.2 variant 221 after 72 hrs2006Journal of natural products, Jan, Volume: 69, Issue:1
Isoflavonoids and other compounds from Psorothamnus arborescens with antiprotozoal activities.
AID358171Inhibition of EGFR in human A431 cells1992Journal of natural products, Nov, Volume: 55, Issue:11
Protein-tyrosine kinase inhibition: mechanism-based discovery of antitumor agents.
AID332642Binding affinity to Escherichia coli pUC8 DNA assessed as production of linear DNA at 100 ug/ml after 30 mins by agarose gel electrophoresis1995Journal of natural products, Feb, Volume: 58, Issue:2
Flavonoids as DNA topoisomerase antagonists and poisons: structure-activity relationships.
AID658416Inhibition of human HCT116 clonogenicity after 7 days by crystal violet staining by densitometric analysis2012Bioorganic & medicinal chemistry letters, Apr-15, Volume: 22, Issue:8
Isoflavones inhibit the clonogenicity of human colon cancer cells.
AID332646Inhibition of human DNA topoisomerase 2 catalytic domain-mediated knotted bacteriophage P4Virl dell0 DNA unknotting up to 100 uM by agarose gel electrophoresis1995Journal of natural products, Feb, Volume: 58, Issue:2
Flavonoids as DNA topoisomerase antagonists and poisons: structure-activity relationships.
AID378965Antileishmanial activity against Leishmania donovani MHOM/SD/62/IS-CL2D axenic amastigotes after 3 days2006Journal of natural products, Jan, Volume: 69, Issue:1
Isoflavonoids and other compounds from Psorothamnus arborescens with antiprotozoal activities.
AID1386836Antagonist activity at PR-b (unknown origin) expressed in Ishikawa cells assessed as inhibition of progesterone-induced PRE activity at >= 25 uM after 24 hrs by luciferase reporter gene based luminescence assay2018Journal of natural products, 09-28, Volume: 81, Issue:9
Irilone from Red Clover ( Trifolium pratense) Potentiates Progesterone Signaling.
AID587246Antifungal activity against Aspergillus niger DSM 1988 after 48 hrs by disk diffusion method2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Antimicrobial isopropenyl-dihydrofuranoisoflavones from Crotalaria lachnophora.
AID633946Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viability after 3 hrs by alamar blue assay2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Secondary metabolites from the roots of Neolitsea daibuensis and their anti-inflammatory activity.
AID639826Inhibition of human recombinant aldose reductase using D-glyceraldehyde as substrate at 15 uM preincubated for 10 mins before substrate addition measured for every 10 secs for 50 mins by spectrophotometry2012Bioorganic & medicinal chemistry, Feb-01, Volume: 20, Issue:3
Construction of an Indonesian herbal constituents database and its use in Random Forest modelling in a search for inhibitors of aldose reductase.
AID429118Antagonist activity at glucocorticoid receptor in human MDA-kb2 cells assessed as inhibition of Dex-induced luciferase activity by luciferase reporter gene assay2009Bioorganic & medicinal chemistry letters, Aug-15, Volume: 19, Issue:16
Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assay.
AID1065107Induction of osteogenic activity in human MSC assessed as cell differentiation at 1 uM after 14 days by alizarin red staining-based spectrometry relative to vehicle-treated control2014ACS medicinal chemistry letters, Feb-13, Volume: 5, Issue:2
Design, synthesis, and osteogenic activity of daidzein analogs on human mesenchymal stem cells.
AID587243Antimicrobial activity against Klebsiella pneumoniae DSM 681 at 1 ug/ul after 24 hrs by disk diffusion method2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Antimicrobial isopropenyl-dihydrofuranoisoflavones from Crotalaria lachnophora.
AID1386844Induction of PR-b degradation in human Ishikawa cells up to 50 uM after 24 hrs by Western blot analysis2018Journal of natural products, 09-28, Volume: 81, Issue:9
Irilone from Red Clover ( Trifolium pratense) Potentiates Progesterone Signaling.
AID1345991Human aldehyde dehydrogenase 2 family member (1.-.-.- Oxidoreductases)2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Structure of daidzin, a naturally occurring anti-alcohol-addiction agent, in complex with human mitochondrial aldehyde dehydrogenase.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (42)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (2.38)18.7374
1990's4 (9.52)18.2507
2000's10 (23.81)29.6817
2010's19 (45.24)24.3611
2020's8 (19.05)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.50

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index29.50 (24.57)
Research Supply Index3.78 (2.92)
Research Growth Index5.25 (4.65)
Search Engine Demand Index35.06 (26.88)
Search Engine Supply Index2.13 (0.95)

This Compound (29.50)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other42 (97.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]