Compounds > irilone
Page last updated: 2024-12-10

irilone

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

Description

irilone: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

irilone : A hydroxyisoflavone that is 6,7-methylenedioxyisoflavone substituted by hydroxy groups at positions 5 and 4'. [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 CID5281779
CHEMBL ID3527329
CHEBI ID5970
SCHEMBL ID12073700
MeSH IDM0523213

Synonyms (23)

Synonym
irilone
41653-81-0
bdbm50088502
chebi:5970 ,
chembl3527329 ,
LMPK12050383
5,4'-dihydroxy-6,7-methylenedioxyisoflavone
9-hydroxy-7-(4-hydroxyphenyl)-[1,3]dioxolo[4,5-g]chromen-8-one
irolone
9-hydroxy-7-(4-hydroxyphenyl)-8h-[1,3]dioxolo[4,5-g]chromen-8-one
9-hydroxy-7-(4-hydroxyphenyl)-8h-1,3-dioxolo[4,5-g]-1-benzopyran-8-one
SCHEMBL12073700
irilone (isoflavone)
DTXSID60415191
9-hydroxy-7-(4-hydroxyphenyl)-8h-1,3-dioxolo[4,5-g][1]benzopyran-8-one, 9ci
Q6069737
3-(4-hydroxyphenyl)-5-hydroxy-6,7-(methylenebisoxy)-4h-1-benzopyran-4-one
fb3ftt7lyk ,
7-(4-hydroxyphenyl)-9-oxidanyl-(1,3)dioxolo(4,5-g)chromen-8-one
9-hydroxy-7-(4-hydroxyphenyl)-8h-1,3-dioxolo[4,5-g][1]benzopyran-8-one
8h-1,3-dioxolo[4,5-g][1]benzopyran-8-one, 9-hydroxy-7-(4-hydroxyphenyl)-
AKOS040763532
FS-8118

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"Intestinal bacteria may influence bioavailability and physiological activity of dietary isoflavones."( The red clover isoflavone irilone is largely resistant to degradation by the human gut microbiota.
Blaut, M; Braune, A; Kulling, SE; Maul, R; Schebb, NH, 2010)		0.66
" 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 (3)

RoleDescription
immunomodulatorBiologically active substance whose activity affects or plays a role in the functioning of the immune system.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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 (3)

ClassDescription
hydroxyisoflavoneMember of the class of isoflavones bearing at least one hydroxy group.
oxacycleAny organic heterocyclic compound containing at least one ring oxygen atom.
organic heterotricyclic compoundAn organic tricyclic compound in which at least one of the rings of the tricyclic skeleton contains one or more heteroatoms.
[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 (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
UDP-glucuronosyltransferase 1A1 Homo sapiens (human)Ki11.30008.50008.50008.5000AID1216375; AID1216389
[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)
UDP-glucuronosyltransferase 1A9Homo sapiens (human)Km5.00005.00006.830010.0000AID1216370
UDP-glucuronosyltransferase 1A1 Homo sapiens (human)Km28.75004.49006.51339.0000AID1216383; AID1216406
UDP-glucuronosyltransferase 1A7Homo sapiens (human)Km9.40005.00007.20009.4000AID1216405
UDP-glucuronosyltransferase 1A10Homo sapiens (human)Km10.30002.74004.21005.6800AID1216385
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (24)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processUDP-glucuronosyltransferase 1A9Homo sapiens (human)
retinoic acid metabolic processUDP-glucuronosyltransferase 1A9Homo sapiens (human)
flavone metabolic processUDP-glucuronosyltransferase 1A9Homo sapiens (human)
cellular glucuronidationUDP-glucuronosyltransferase 1A9Homo sapiens (human)
flavonoid glucuronidationUDP-glucuronosyltransferase 1A9Homo sapiens (human)
xenobiotic glucuronidationUDP-glucuronosyltransferase 1A9Homo sapiens (human)
liver developmentUDP-glucuronosyltransferase 1A9Homo sapiens (human)
liver developmentUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
bilirubin conjugationUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
xenobiotic metabolic processUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
acute-phase responseUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
response to nutrientUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
steroid metabolic processUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
estrogen metabolic processUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
animal organ regenerationUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
response to lipopolysaccharideUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
retinoic acid metabolic processUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
response to starvationUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
negative regulation of steroid metabolic processUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
flavone metabolic processUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
cellular glucuronidationUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
flavonoid glucuronidationUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
xenobiotic glucuronidationUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
biphenyl catabolic processUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
cellular response to ethanolUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
cellular response to glucocorticoid stimulusUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
cellular response to estradiol stimulusUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
xenobiotic metabolic processUDP-glucuronosyltransferase 1A7Homo sapiens (human)
estrogen metabolic processUDP-glucuronosyltransferase 1A7Homo sapiens (human)
coumarin metabolic processUDP-glucuronosyltransferase 1A7Homo sapiens (human)
retinoic acid metabolic processUDP-glucuronosyltransferase 1A7Homo sapiens (human)
flavone metabolic processUDP-glucuronosyltransferase 1A7Homo sapiens (human)
cellular glucuronidationUDP-glucuronosyltransferase 1A7Homo sapiens (human)
flavonoid glucuronidationUDP-glucuronosyltransferase 1A7Homo sapiens (human)
xenobiotic glucuronidationUDP-glucuronosyltransferase 1A7Homo sapiens (human)
liver developmentUDP-glucuronosyltransferase 1A7Homo sapiens (human)
lipid metabolic processUDP-glucuronosyltransferase 1A10Homo sapiens (human)
xenobiotic metabolic processUDP-glucuronosyltransferase 1A10Homo sapiens (human)
flavone metabolic processUDP-glucuronosyltransferase 1A10Homo sapiens (human)
cellular glucuronidationUDP-glucuronosyltransferase 1A10Homo sapiens (human)
liver developmentUDP-glucuronosyltransferase 1A10Homo sapiens (human)
fatty acid metabolic processUDP-glucuronosyltransferase 1A8Homo sapiens (human)
steroid metabolic processUDP-glucuronosyltransferase 1A8Homo sapiens (human)
coumarin metabolic processUDP-glucuronosyltransferase 1A8Homo sapiens (human)
retinoic acid metabolic processUDP-glucuronosyltransferase 1A8Homo sapiens (human)
negative regulation of fatty acid metabolic processUDP-glucuronosyltransferase 1A8Homo sapiens (human)
negative regulation of steroid metabolic processUDP-glucuronosyltransferase 1A8Homo sapiens (human)
flavone metabolic processUDP-glucuronosyltransferase 1A8Homo sapiens (human)
flavonoid glucuronidationUDP-glucuronosyltransferase 1A8Homo sapiens (human)
xenobiotic glucuronidationUDP-glucuronosyltransferase 1A8Homo sapiens (human)
liver developmentUDP-glucuronosyltransferase 1A8Homo sapiens (human)
cellular glucuronidationUDP-glucuronosyltransferase 1A8Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
retinoic acid bindingUDP-glucuronosyltransferase 1A9Homo sapiens (human)
glucuronosyltransferase activityUDP-glucuronosyltransferase 1A9Homo sapiens (human)
enzyme bindingUDP-glucuronosyltransferase 1A9Homo sapiens (human)
protein homodimerization activityUDP-glucuronosyltransferase 1A9Homo sapiens (human)
protein heterodimerization activityUDP-glucuronosyltransferase 1A9Homo sapiens (human)
retinoic acid bindingUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
enzyme inhibitor activityUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
steroid bindingUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
glucuronosyltransferase activityUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
enzyme bindingUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
protein homodimerization activityUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
protein heterodimerization activityUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
retinoic acid bindingUDP-glucuronosyltransferase 1A7Homo sapiens (human)
enzyme inhibitor activityUDP-glucuronosyltransferase 1A7Homo sapiens (human)
protein kinase C bindingUDP-glucuronosyltransferase 1A7Homo sapiens (human)
glucuronosyltransferase activityUDP-glucuronosyltransferase 1A7Homo sapiens (human)
enzyme bindingUDP-glucuronosyltransferase 1A7Homo sapiens (human)
protein homodimerization activityUDP-glucuronosyltransferase 1A7Homo sapiens (human)
protein heterodimerization activityUDP-glucuronosyltransferase 1A7Homo sapiens (human)
retinoic acid bindingUDP-glucuronosyltransferase 1A10Homo sapiens (human)
protein kinase C bindingUDP-glucuronosyltransferase 1A10Homo sapiens (human)
glucuronosyltransferase activityUDP-glucuronosyltransferase 1A10Homo sapiens (human)
enzyme bindingUDP-glucuronosyltransferase 1A10Homo sapiens (human)
protein homodimerization activityUDP-glucuronosyltransferase 1A10Homo sapiens (human)
protein heterodimerization activityUDP-glucuronosyltransferase 1A10Homo sapiens (human)
retinoic acid bindingUDP-glucuronosyltransferase 1A8Homo sapiens (human)
enzyme inhibitor activityUDP-glucuronosyltransferase 1A8Homo sapiens (human)
steroid bindingUDP-glucuronosyltransferase 1A8Homo sapiens (human)
fatty acid bindingUDP-glucuronosyltransferase 1A8Homo sapiens (human)
glucuronosyltransferase activityUDP-glucuronosyltransferase 1A8Homo sapiens (human)
enzyme bindingUDP-glucuronosyltransferase 1A8Homo sapiens (human)
protein homodimerization activityUDP-glucuronosyltransferase 1A8Homo sapiens (human)
protein heterodimerization activityUDP-glucuronosyltransferase 1A8Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
endoplasmic reticulumUDP-glucuronosyltransferase 1A9Homo sapiens (human)
endoplasmic reticulum membraneUDP-glucuronosyltransferase 1A9Homo sapiens (human)
endoplasmic reticulumUDP-glucuronosyltransferase 1A9Homo sapiens (human)
endoplasmic reticulumUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
endoplasmic reticulum membraneUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
plasma membraneUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
perinuclear region of cytoplasmUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
endoplasmic reticulum chaperone complexUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
cytochrome complexUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
endoplasmic reticulumUDP-glucuronosyltransferase 1A1 Homo sapiens (human)
endoplasmic reticulumUDP-glucuronosyltransferase 1A7Homo sapiens (human)
endoplasmic reticulum membraneUDP-glucuronosyltransferase 1A7Homo sapiens (human)
endoplasmic reticulumUDP-glucuronosyltransferase 1A7Homo sapiens (human)
endoplasmic reticulumUDP-glucuronosyltransferase 1A10Homo sapiens (human)
endoplasmic reticulum membraneUDP-glucuronosyltransferase 1A10Homo sapiens (human)
endoplasmic reticulumUDP-glucuronosyltransferase 1A10Homo sapiens (human)
endoplasmic reticulumUDP-glucuronosyltransferase 1A8Homo sapiens (human)
endoplasmic reticulum membraneUDP-glucuronosyltransferase 1A8Homo sapiens (human)
endoplasmic reticulumUDP-glucuronosyltransferase 1A8Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (89)

Assay IDTitleYearJournalArticle
AID1782514Induction of estrogen receptor in human T47D cells assessed as increase in PR-A protein expression at 10 uM incubated for 24 hrs in presence of progesterone by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782513Induction of estrogen receptor in human T47D cells assessed as increase in PR-A protein expression at 10 uM incubated for 24 hrs by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216381Drug metabolism in Sprague-Dawley rat liver microsomes assessed as substrate inhibition of IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216371Activity of human recombinant UGT1A10 assessed as IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782508Repression of dexamethasone-induced HRE/Luc activity in human OVCAR-5 cells at 10 uM incubated for 24 hrs by luciferase reporter gene assay2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216384Activity of human recombinant UGT1A8 assessed as IRI-O-4'-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216386Drug metabolism in human liver microsomes assessed as IRI-O-4'-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216380Drug metabolism in human liver microsomes assessed as substrate inhibition of IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216383Activity of human recombinant UGT1A1 assessed as IRI-O-4'-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782501Increase in PR-B protein expression in human Ishikawa PR-B cells at 10 uM incubated for 24 hrs in presence of 100 nM progesterone by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216360Activity of human recombinant UGT1A9 assessed as intrinsic clearance incubated for 5 mins prior to UDPGA addition measured after 90 mins2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1386835Agonist activity at PR-b (unknown origin) expressed in Ishikawa cells assessed as increase in PRE activity at 50 uM after 24 hrs by luciferase reporter gene based luminescence assay (Rvb = 25.7 No_unit)2018Journal of natural products, 09-28, Volume: 81, Issue:9
Irilone from Red Clover ( Trifolium pratense) Potentiates Progesterone Signaling.
AID1216399Drug metabolism assessed as human recombinant UGT1A9-mediated irilone-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by HPLC-DAD analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216362Activity of human recombinant UGT1A8 assessed as intrinsic clearance incubated for 5 mins prior to UDPGA addition measured after 90 mins2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216407Activity of human recombinant UGT1A10 assessed as intrinsic clearance incubated for 5 mins prior to UDPGA addition measured after 90 mins2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216373Drug metabolism in Sprague-Dawley rat liver microsomes assessed as IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782489Induction of epithelial cells proliferation in uterus of ovariectomized CD-1 mouse at 4 mg/kg, ip administered once a day for 7 days and measured on day 7 at 6 hrs post-last dosage by PCNA staining based immunohistochemistry (Rvb = 33.3%)2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782477Effect on R5020-induced PR-B phosphorylation at Ser294 residue in human T47D cells at 10 uM incubated for 60 mins by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216366Intrinsic clearance in human liver microsomes incubated for 5 mins prior to UDPGA addition measured after 90 mins2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216379Substrate inhibition of human recombinant UGT1A10 assessed as IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216376Substrate inhibition of human recombinant UGT1A7 assessed as IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782484Effect on R5020-induced PR-A phosphorylation at Ser294 residue in human T47D cells at 10 uM incubated for 60 mins by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782490Induction of epithelial cells proliferation in uterus of ovariectomized CD-1 mouse at 4 mg/kg, ip administered once a day for 7 days in presence of progesterone and measured on day 7 at 6 hrs post-last dosage by PCNA staining based immunohistochemistry (R2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216408Drug metabolism assessed as human recombinant UGT1A1-mediated irilone-O-4'-monoglucuronide formation at 25 uM incubated for 5 mins prior to UDPGA addition measured after 90 mins by HPLC-DAD analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782494Induction of HRE/Luc activity in human Ishikawa null cells at 10 uM incubated for 24 hrs in presence of progesterone by luciferase reporter gene assay2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782493Induction of glucocorticoid receptor in human Ishikawa PR-B cells transfected with scrambled siRNA assessed as potentiation of progesterone signalling by measuring increase in HRE/Luc activity at 10 uM incubated for 24 hrs in presence of progesterone by l2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216370Activity of human recombinant UGT1A9 assessed as IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782478Induction of estrogen receptor in human T47D cells assessed as potentiation of progesterone transcriptional activity by measuring increase in HRE-Luc activity at 10 uM measured after 24 hrs in presence of 5 nM progesterone by HRE-dependent dual luciferase2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216393Drug metabolism assessed as human recombinant UGT1A7-mediated irilone-O-5-monoglucuronide formation at 25 uM incubated for 5 mins prior to UDPGA addition measured after 90 mins by HPLC-DAD analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782498Effect on PR-A phosphorylation at Ser294 residue in human T47D cells at 10 uM incubated for 60 mins by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216385Activity of human recombinant UGT1A10 assessed as IRI-O-4'-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782488Induction of HRE/Luc activity in human Ishikawa null cells at 10 uM incubated for 24 hrs by luciferase reporter gene assay2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1386843Agonist activity at PR-b (unknown origin) expressed in Ishikawa cells assessed as increase in PRE activity at 1 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.
AID1782500Effect on PR-B protein expression in human Ishikawa PR-B cells at 10 uM incubated for 24 hrs by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
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.
AID1216389Substrate inhibition of human recombinant UGT1A1 assessed as IRI-O-4'-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1386841Agonist activity at PR-b (unknown origin) expressed in Ishikawa cells assessed as increase in progesterone-induced PRE activity at 25 uM after 24 hrs by luciferase reporter gene based luminescence assay relative to control2018Journal of natural products, 09-28, Volume: 81, Issue:9
Irilone from Red Clover ( Trifolium pratense) Potentiates Progesterone Signaling.
AID1782480Induction of estrogen receptor in human T47D cells assessed as increase in HRE-luc activity at 10 uM measured after 24 hrs by HRE-dependent dual luciferase reporter gene assay relative to control2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782496Increase in GR protein expression in human Ishikawa PR-B cells at 10 uM incubated for 24 hrs by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216361Activity of human recombinant UGT1A1 assessed as intrinsic clearance incubated for 5 mins prior to UDPGA addition measured after 90 mins2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782499Effect on PR-B phosphorylation at Ser294 residue in human T47D cells at 10 uM incubated for 60 mins by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782491In vivo potentiation of progesterone signalling in ovariectomized CD-1 mouse assessed as increase in FKBP5 expression in reproductive tract at 4 mg/kg, ip administered once a day for 7 days in presence of progesterone and measured on day 7 at 6 hrs post-l2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782510Effect on PR-A protein expression in human Ishikawa PR-B cells at 10 uM incubated for 24 hrs by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216378Substrate inhibition of human recombinant UGT1A9 assessed as IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216355Substrate inhibition of human recombinant UGT1A8 assessed as IRI-O-4'-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216374Drug metabolism in pig liver microsomes assessed as IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782507Agonist activity at GR in human OVCAR-5 cells assessed as induction of HRE/Luc activity at 1 to 10 uM incubated for 24 hrs by luciferase reporter gene assay2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782497Increase in GR protein expression in human OVCAR-5 cells at 10 uM incubated for 24 hrs by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216365Intrinsic clearance in Sprague-Dawley rat liver microsomes incubated for 5 mins prior to UDPGA addition measured after 90 mins2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216406Activity of human recombinant UGT1A1 assessed as IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782503Induction of estrogen receptor in human T47D cells assessed as increase in PR-B protein expression at 10 uM incubated for 24 hrs by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782505Induction of estrogen receptor in human T47D cells assessed as increase in PR-B protein expression at 10 uM incubated for 24 hrs in presence of SERM, 4-OH-TAM and progesterone by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782482Induction of estrogen receptor in human T47D cells assessed as increase in PR-A protein expression at 10 uM incubated for 24 hrs in presence of SERM, 4-OH-TAM by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1386846Antiproliferative activity against human PEO1 cells at 1 to 50 uM after 5 days by SRB assay2018Journal of natural products, 09-28, Volume: 81, Issue:9
Irilone from Red Clover ( Trifolium pratense) Potentiates Progesterone Signaling.
AID1216372Drug metabolism in human liver microsomes assessed as IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216356Substrate inhibition of human recombinant UGT1A10 assessed as IRI-O-4'-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216397Drug metabolism assessed as human recombinant UGT1A8-mediated irilone-O-4'-monoglucuronide formation at 25 uM incubated for 5 mins prior to UDPGA addition measured after 90 mins by HPLC-DAD analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782485Induction of estrogen receptor in human T47D cells assessed as increase in ERE/Luc activity at 10 uM measured after 24 hrs by luciferase reporter gene assay relative to control2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782506Induction of estrogen receptor in human T47D cells assessed as increase in PR-A protein expression at 10 uM incubated for 24 hrs in presence of SERM, 4-OH-TAM and progesterone by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782481Induction of glucocorticoid receptor in human Ishikawa PR-B cells assessed as increase in HRE-luc activity at 10 uM measured after 24 hrs by HRE-dependent dual luciferase reporter gene assay relative to control2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782495Potentiation of progesterone receptor signalling in human Ishikawa null cells transfected with wild type PR assessed as induction of HRE/uc activity at 10 uM incubated for 24 hrs by luciferase reporter gene assay relative to control2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216369Activity of human recombinant UGT1A8 assessed as IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216396Drug metabolism assessed as human recombinant UGT1A8-mediated irilone-O-5-monoglucuronide formation at 25 uM incubated for 5 mins prior to UDPGA addition measured after 90 mins by HPLC-DAD analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1386842Agonist activity at PR-b (unknown origin) expressed in Ishikawa cells assessed as increase in progesterone-induced PRE activity at 50 uM after 24 hrs by luciferase reporter gene based luminescence assay relative to control2018Journal of natural products, 09-28, Volume: 81, Issue:9
Irilone from Red Clover ( Trifolium pratense) Potentiates Progesterone Signaling.
AID1782512Decrease in PR-A protein expression in human Ishikawa PR-B cells at 10 uM incubated for 24 hrs in presence of 100 nM progesterone by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782504Induction of estrogen receptor in human T47D cells assessed as increase in PR-B protein expression at 10 uM incubated for 24 hrs in presence of progesterone by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216375Substrate inhibition of human recombinant UGT1A1 assessed as IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216394Drug metabolism assessed as human recombinant UGT1A7-mediated irilone-O-4'-monoglucuronide formation at 25 uM incubated for 5 mins prior to UDPGA addition measured after 90 mins by HPLC-DAD analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216358Drug metabolism in Sprague-Dawley rat liver microsomes assessed as substrate inhibition of IRI-O-4'-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216401Drug metabolism assessed as human recombinant UGT1A10-mediated irilone-O-4'-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by HPLC-DAD analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216359Drug metabolism in pig liver microsomes assessed as substrate inhibition of IRI-O-4'-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782492Induction of HRE/Luc activity in human Ishikawa PR-B cells transfected with GR siRNA at 10 uM incubated for 24 hrs in presence of progesterone by luciferase reporter gene assay relative to control2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216382Drug metabolism in pig liver microsomes assessed as substrate inhibition of IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216390Drug metabolism assessed as human recombinant UGT1A1-mediated irilone-O-5-monoglucuronide formation at 25 uM incubated for 5 mins prior to UDPGA addition measured after 90 mins by HPLC-DAD analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216405Activity of human recombinant UGT1A7 assessed as IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216391Drug metabolism assessed as human recombinant UGT2B15-mediated glucuronidation incubated for 5 mins prior to UDPGA addition measured after 90 mins by HPLC-DAD analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782483Induction of estrogen receptor in human T47D cells assessed as increase in PR-B protein expression at 10 uM incubated for 24 hrs in presence of SERM, 4-OH-TAM by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216377Substrate inhibition of human recombinant UGT1A8 assessed as IRI-O-5-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216388Drug metabolism in pig liver microsomes assessed as IRI-O-4'-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782511Increase in PR-A protein expression in human Ishikawa PR-B cells at 10 uM incubated for 24 hrs in presence of 100 nM progesterone by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216363Activity of human recombinant UGT1A7 assessed as intrinsic clearance incubated for 5 mins prior to UDPGA addition measured after 90 mins2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1216357Drug metabolism in human liver microsomes assessed as substrate inhibition of IRI-O-4'-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782509Repression of dexamethasone-induced HRE/Luc activity in human OVCAR-5 cells at 1 to 5 uM incubated for 24 hrs by luciferase reporter gene assay2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782479Induction of glucocorticoid receptor in human Ishikawa PR-B cells assessed as potentiation of progesterone transcriptional activity by measuring increase in HRE-Luc activity at 10 uM measured after 24 hrs in presence of 5 to 100 nM progesterone by HRE-dep2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1782487Potentiation of progesterone signalling in human Ishikawa null cells transfected with wild type PR assessed as induction of HRE/uc activity at 10 uM incubated for 24 hrs in presence of progesterone by luciferase reporter gene assay relative to control2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1216387Drug metabolism in Sprague-Dawley rat liver microsomes assessed as IRI-O-4'-monoglucuronide formation incubated for 5 mins prior to UDPGA addition measured after 90 mins by Eadie-Hoftsee plot analysis2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
AID1782502Decrease in PR-B protein expression in human Ishikawa PR-B cells at 10 uM incubated for 24 hrs in presence of 100 nM progesterone by western blot analysis2021Journal of natural products, 12-24, Volume: 84, Issue:12
Irilone, a Red Clover Isoflavone, Combined with Progesterone Enhances PR Signaling through the Estrogen and Glucocorticoid Receptors.
AID1386847Antiproliferative activity against human PEO1 cells at 25 to 50 uM after 5 days by SRB assay2018Journal of natural products, 09-28, Volume: 81, Issue:9
Irilone from Red Clover ( Trifolium pratense) Potentiates Progesterone Signaling.
AID1216364Intrinsic clearance in pig liver microsomes incubated for 5 mins prior to UDPGA addition measured after 90 mins2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
Glucuronidation of the red clover isoflavone irilone by liver microsomes from different species and human UDP-glucuronosyltransferases.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (13.33)29.6817
2010's12 (80.00)24.3611
2020's1 (6.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.48

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 Index22.48 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index4.72 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.48)

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%
Other16 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
methanol
Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.		2.2110alkyl alcohol;
one-carbon compound;
primary alcohol;
volatile organic compound		amphiprotic solvent;
Escherichia coli metabolite;
fuel;
human metabolite;
mouse metabolite;
Mycoplasma genitalium metabolite
2-methylpentane
Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.		2.2110alkane
2,2',4,4'-tetrahydroxybenzophenone
[no description available]		2.2110
mifepristone
Mifepristone: A progestational and glucocorticoid hormone antagonist. Its inhibition of progesterone induces bleeding during the luteal phase and in early pregnancy by releasing endogenous prostaglandins from the endometrium or decidua. As a glucocorticoid receptor antagonist, the drug has been used to treat hypercortisolism in patients with nonpituitary CUSHING SYNDROME.		2.17103-oxo-Delta(4) steroid;
acetylenic compound;
tertiary amino compound		abortifacient;
contraceptive drug;
hormone antagonist;
synthetic oral contraceptive
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		2.520D-glucopyranoseepitope;
mouse metabolite
glycosides
[no description available]		2.5420
biochanin a
[no description available]		2.81304'-methoxyisoflavones;
7-hydroxyisoflavones		antineoplastic agent;
EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor;
phytoestrogen;
plant metabolite;
tyrosine kinase inhibitor
formononetin
[no description available]		3.03404'-methoxyisoflavones;
7-hydroxyisoflavones		phytoestrogen;
plant metabolite
7,3'-dihydroxy-4'-methoxyisoflavone
7,3'-dihydroxy-4'-methoxyisoflavone: isolated from Astragali radix; structure in first source. calycosin : A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at the 3' position and a methoxy group at the 4' position.		2.05104'-methoxyisoflavones;
7-hydroxyisoflavones		antioxidant;
metabolite
genistein
[no description available]		3.18507-hydroxyisoflavonesantineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
geroprotector;
human urinary metabolite;
phytoestrogen;
plant metabolite;
tyrosine kinase inhibitor
tricin
tricin: from Spartina cynosuroides and other plants; structure		2.05103'-methoxyflavones;
dimethoxyflavone;
trihydroxyflavone		EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
metabolite
daidzein
[no description available]		2.06107-hydroxyisoflavonesantineoplastic agent;
EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
phytoestrogen;
plant metabolite
irisolidone
irisolidone: isolated from the flowers and rhizomes of Pueraria thunbergiana; structure in first source		2.05104'-methoxyisoflavones
prunetin
prunetin: reduces herpes virus-1 plaque formation. prunetin : A hydroxyisoflavone that is genistein in which the hydroxy group at position 7 is replaced by a methoxy group.		2.81307-methoxyisoflavones;
hydroxyisoflavone		anti-inflammatory agent;
EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor;
EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor;
metabolite
psi-baptigenin
pseudobaptigenin : A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone and in which the phenyl group at position 3 is replaced by a 1,3-benzodioxol-5-yl group.		2.51207-hydroxyisoflavones;
benzodioxoles		antiprotozoal drug;
plant metabolite
calycosin-7-o-beta-d-glucopyranoside
calycosin-7-O-beta-D-glucoside: from Radix Astragali. calycosin-7-O-beta-D-glucoside : A glycosyloxyisoflavone that is calycosin substituted by a beta-D-glucopyranosyl residue at position at 7 via a glycosidic linkage.		2.17104'-methoxyisoflavones;
7-hydroxyisoflavones 7-O-beta-D-glucoside;
hydroxyisoflavone;
monosaccharide derivative
irigenin
irigenin: a phytoestrogen derived from Belamcanda chinensis with an antiproliferative effect on prostate cancer cells in vitro. irigenin : A hydroxyisoflavone that is isoflavone substituted by hydroxy groups at positions 5, 7 and 3' and methoxy groups at positions 6, 4' and 5' respectively.		2.21104'-methoxyisoflavones;
hydroxyisoflavone		plant metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Menopause
The last menstrual period. Permanent cessation of menses (MENSTRUATION) is usually defined after 6 to 12 months of AMENORRHEA in a woman over 45 years of age. In the United States, menopause generally occurs in women between 48 and 55 years of age.		02.0610
Chromosome-Defective Micronuclei
[description not available]		02.1110