Page last updated: 2024-11-09

6-hydroxyflavanone

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

Description

6-hydroxyflavanone : A monohydroxyflavanone that is flavanone substituted by a hydroxy group at position 6. [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 CID2734580
CHEMBL ID195033
CHEBI ID34471
SCHEMBL ID126598

Synonyms (38)

Synonym
4250-77-5
6-hydroxyflavanone
OPREA1_761592
6-hydroxyflavanone, 99%
IDI1_011957
MAYBRIDGE3_000570
6-hydroxy-2-phenyl-2,3-dihydro-4h-chromen-4-one
CHEBI:34471 ,
HMS1432J20
6-hydroxy-flavanone
CHEMBL195033 ,
bdbm50296861
inchi=1/c15h12o3/c16-11-6-7-14-12(8-11)13(17)9-15(18-14)10-4-2-1-3-5-10/h1-8,15-16h,9h2
6-hydroxy-2-phenylchroman-4-one
xyhwpqueoobiow-uhfffaoysa-
H1027
6-hydroxy-2-phenyl-2,3-dihydrochromen-4-one
6-hydroxy-2-phenyl-3,4-dihydro-2h-1-benzopyran-4-one
BMSE000985
4h-1-benzopyran-4-one, 2,3-dihydro-6-hydroxy-2-phenyl-
unii-1f174812mp
(+/-)-6-hydroxyflavanone
flavanone, 6-hydroxy-
1f174812mp ,
FT-0621166
AKOS015856201
SCHEMBL126598
mfcd00017485
DTXSID1022429
CCG-233325
6-hydroxy-2-phenyl-chroman-4-one
AS-60586
F0001-1180
Q27116092
nsc804064
nsc-804064
A872871
PD182938
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
fungal xenobiotic metaboliteAny fungal metabolite produced by metabolism of a xenobiotic compound in fungi.
[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 (1)

ClassDescription
monohydroxyflavanoneAny hydroxyflavanone carrying a single hydroxy substituent.
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Androgen receptorHomo sapiens (human)IC50 (µMol)3.30000.00000.875310.0000AID429119
Androgen receptorRattus norvegicus (Norway rat)IC50 (µMol)18.62090.00101.979414.1600AID255211
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (56)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (23)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID353303Increase in EGR1 mRNA expression in human HEK293 cells at 20 ug/mL after 6 to 12 hrs by dual-glo luciferase assay relative to control2009Bioorganic & medicinal chemistry letters, Apr-15, Volume: 19, Issue:8
Relationships between the structures of flavanone derivatives and their effects in enhancing early growth response-1 gene expression.
AID406996Inhibition of human recombinant 17beta-HSD2 expressed in HEK293 cell lysate assessed as conversion of radiolabeled estrone to estradiol at 40 uM2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries.
AID423363Antimicrobial activity against vancomycin-resistant Enterococcus faecalis after 20 hrs by broth microdilution method2009Journal of natural products, Apr, Volume: 72, Issue:4
Screening of flavonoids as candidate antibiotics against Enterococcus faecalis.
AID429129Agonist activity at glucocorticoid receptor in human MDA-kb2 cells assessed as stimulation of 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.
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.
AID406994Inhibition of human recombinant 17beta-HSD1 expressed in HEK293 cell lysate assessed as conversion of radiolabeled estrone to estradiol at 20 uM2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries.
AID423365Binding affinity to Enterococcus faecalis KAS3 by fluorescence quenching analysis2009Journal of natural products, Apr, Volume: 72, Issue:4
Screening of flavonoids as candidate antibiotics against Enterococcus faecalis.
AID406997Inhibition of human recombinant 17beta-HSD2 expressed in HEK293 cell lysate assessed as conversion of radiolabeled estrone to estradiol2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries.
AID423362Antimicrobial activity against Enterococcus faecalis after 20 hrs by broth microdilution method2009Journal of natural products, Apr, Volume: 72, Issue:4
Screening of flavonoids as candidate antibiotics against Enterococcus faecalis.
AID429128Agonist activity at androgen receptor in human MDA-kb2 cells assessed as stimulation of 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.
AID456319ABTS radical scavenging activity assessed as vitamin C equivalent antioxidant capacity2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids.
AID1364658Inhibition of human 17beta-HSD2 expressed in HEK293 cell lysates assessed as residual enzyme activity at 40 uM incubated for 10 mins using [2,4,6,7-3H]-estradiol and NAD+ by scintillation counting method2017Journal of natural products, 04-28, Volume: 80, Issue:4
Potential Antiosteoporotic Natural Product Lead Compounds That Inhibit 17β-Hydroxysteroid Dehydrogenase Type 2.
AID255211Inhibitory concentration against recombinant rat androgen receptor expressed in Escherichia coli using [3H]methyltrienolone (R 1881)2005Journal of medicinal chemistry, Sep-08, Volume: 48, Issue:18
Impact of induced fit on ligand binding to the androgen receptor: a multidimensional QSAR study to predict endocrine-disrupting effects of environmental chemicals.
AID456317Antioxidant activity assessed as trolox equivalent by TEAC assay2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids.
AID353304Increase in EGR1 mRNA expression in human HeLa cells after 1 hr by Western blotting2009Bioorganic & medicinal chemistry letters, Apr-15, Volume: 19, Issue:8
Relationships between the structures of flavanone derivatives and their effects in enhancing early growth response-1 gene expression.
AID406995Inhibition of human recombinant 17beta-HSD1 expressed in HEK293 cell lysate assessed as conversion of radiolabeled estrone to estradiol2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries.
AID429119Antagonist activity at androgen receptor in human MDA-kb2 cells assessed as inhibition of DHT-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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (71.43)29.6817
2010's2 (28.57)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: 12.19

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 Index12.19 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.27 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.19)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]