Page last updated: 2024-12-08

2'-hydroxyflavone

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

Description

2'-hydroxyflavone: isolated from Daphnopsis sellowiana; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
Daphnopsisgenus[no description available]ThymelaeaceaeA plant family of the order Myrtales, subclass Rosidae, class Magnoliopsida. They are mainly trees and shrubs. Many members contain mucilage and COUMARINS.[MeSH]

Cross-References

ID SourceID
PubMed CID161860
CHEMBL ID144278
CHEBI ID179319
SCHEMBL ID312255
MeSH IDM0157328

Synonyms (16)

Synonym
CHEBI:179319
35244-11-2
2-(2-hydroxyphenyl)chromen-4-one
2'-hydroxyflavone
CHEMBL144278
2'-hydroxy flavone
LMPK12110080
4h-1-benzopyran-4-one, 2-(2-hydroxyphenyl)-
2-(2-hydroxyphenyl)-4h-chromen-4-one (3d)
bdbm150758
SCHEMBL312255
AKOS022660297
Q63396640
DTXSID00901987
noname_1182
2-hydroxyflavanone,98%

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Hence, our data support that the synthetic 4'-dimethylamino-7,8-dihydroxyflavone and its lead both are orally bioavailable TrkB agonists and possess potent antidepressant effects."( A synthetic 7,8-dihydroxyflavone derivative promotes neurogenesis and exhibits potent antidepressant effect.
Chan, CB; France, S; He, K; Huang, J; Jang, SW; Jia, Y; Liu, X; Luo, HR; Phun, LH; Pradoldej, S; Xiao, G; Ye, K, 2010
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
flavonesA member of the class of flavonoid with a 2-aryl-1-benzopyran-4-one (2-arylchromen-4-one) skeleton and its substituted derivatives.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Androgen receptorHomo sapiens (human)IC50 (µMol)5.50000.00000.875310.0000AID1408545; AID1408552
Amine oxidase [flavin-containing] AHomo sapiens (human)Ki3.25000.00192.379710.0000AID1801003
Amine oxidase [flavin-containing] BHomo sapiens (human)Ki3.25000.00061.777110.0000AID1801003
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (71)

Processvia Protein(s)Taxonomy
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)
biogenic amine metabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
positive regulation of signal transductionAmine oxidase [flavin-containing] AHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
response to xenobiotic stimulusAmine oxidase [flavin-containing] BHomo sapiens (human)
response to toxic substanceAmine oxidase [flavin-containing] BHomo sapiens (human)
response to aluminum ionAmine oxidase [flavin-containing] BHomo sapiens (human)
response to selenium ionAmine oxidase [flavin-containing] BHomo sapiens (human)
negative regulation of serotonin secretionAmine oxidase [flavin-containing] BHomo sapiens (human)
phenylethylamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
substantia nigra developmentAmine oxidase [flavin-containing] BHomo sapiens (human)
response to lipopolysaccharideAmine oxidase [flavin-containing] BHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to ethanolAmine oxidase [flavin-containing] BHomo sapiens (human)
positive regulation of dopamine metabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
hydrogen peroxide biosynthetic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to corticosteroneAmine oxidase [flavin-containing] BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (29)

Processvia Protein(s)Taxonomy
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)
protein bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
electron transfer activityAmine oxidase [flavin-containing] BHomo sapiens (human)
identical protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
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)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] AHomo sapiens (human)
cytosolAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial envelopeAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] BHomo sapiens (human)
dendriteAmine oxidase [flavin-containing] BHomo sapiens (human)
neuronal cell bodyAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1860355Selectivity index, log ratio of Inhibition of CYP450 in human liver microsomes assessed as inhibition of EpETrE formation in presence of arachidonic acid to Inhibition of CYP450 in human liver microsomes assessed as inhibition of 20-HETE formation in pres
AID180900The dose required to produce a 50% gastroprotection level relative to control1995Journal of medicinal chemistry, Dec-08, Volume: 38, Issue:25
Synthesis and biological evaluation of substituted flavones as gastroprotective agents.
AID1408553Antiproliferative activity against human LNCAP cells assessed as reduction in cell growth treated every 2 days for 4 days by hemocytometry2018European journal of medicinal chemistry, Sep-05, Volume: 1575'-Chloro-2,2'-dihydroxychalcone and related flavanoids as treatments for prostate cancer.
AID1408554Antiproliferative activity against human PC3 cells assessed as reduction in cell growth treated every 2 days for 4 days by hemocytometry2018European journal of medicinal chemistry, Sep-05, Volume: 1575'-Chloro-2,2'-dihydroxychalcone and related flavanoids as treatments for prostate cancer.
AID1408552Antagonist activity at AR in human LNCAP cells assessed as reduction in DHT-induced cell growth treated for every 2 days for 4 days by hemocytometry2018European journal of medicinal chemistry, Sep-05, Volume: 1575'-Chloro-2,2'-dihydroxychalcone and related flavanoids as treatments for prostate cancer.
AID605243Agonist activity at TrkB in E17 rat primary cortical neurons assessed as AKT phosphorylation at Ser 473 at 500 nM after 15 mins by ELISA2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
A synthetic 7,8-dihydroxyflavone derivative promotes neurogenesis and exhibits potent antidepressant effect.
AID1860354Inhibition of CYP450 in human liver microsomes assessed as inhibition of EpETrE formation at 10 uM in presence of arachidonic acid and NADPH by multi-enzyme assay based LC-MS/MS analysis relative to control
AID349305Binding affinity to GABAA receptor2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
QSAR modeling of the interaction of flavonoids with GABA(A) receptor.
AID1860353Inhibition of CYP450 in human liver microsomes assessed as inhibition of 20-HETE formation at 10 uM in presence of arachidonic acid and NADPH by multi-enzyme assay based LC-MS/MS analysis relative to control
AID188853Percent protection from gastric damage in rats relative to vehicle control following intraperitoneal administration of 20 mg/Kg1995Journal of medicinal chemistry, Dec-08, Volume: 38, Issue:25
Synthesis and biological evaluation of substituted flavones as gastroprotective agents.
AID1408545Antagonist activity at AR in human LNCAP cells assessed as reduction in DHT-induced transcriptional activation after 24 hrs by luciferase reporter gene assay2018European journal of medicinal chemistry, Sep-05, Volume: 1575'-Chloro-2,2'-dihydroxychalcone and related flavanoids as treatments for prostate cancer.
AID1408555Antiproliferative activity against human DU145 cells assessed as reduction in cell growth treated every 2 days for 4 days by hemocytometry2018European journal of medicinal chemistry, Sep-05, Volume: 1575'-Chloro-2,2'-dihydroxychalcone and related flavanoids as treatments for prostate cancer.
AID1801003Fluorimetric Assay from Article 10.1016/j.bioorg.2014.11.008: \\Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones.\\2015Bioorganic chemistry, Feb, Volume: 58Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (11.11)18.2507
2000's2 (22.22)29.6817
2010's3 (33.33)24.3611
2020's3 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.58

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 Index12.58 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.97 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.58)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (10.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (90.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]