Compounds > irigenin
Page last updated: 2024-11-11

irigenin

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

Description

irigenin: a phytoestrogen derived from Belamcanda chinensis with an antiproliferative effect on prostate cancer cells in vitro [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

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. [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]

FloraRankFlora DefinitionFamilyFamily Definition
Belamcanda chinensisspecies[no description available]IridaceaeA plant family of the Asparagales order. Comprised of perennial herbs with BULBS, corms, or RHIZOMES and grass-like leaves with bisexual flowers that have 2 whorls of petaloid tepals which are usually showy.[MeSH]

Cross-References

ID SourceID
PubMed CID5464170
CHEMBL ID487013
CHEBI ID81409
SCHEMBL ID554864
MeSH IDM0497499

Synonyms (32)

Synonym
irigenin
548-76-5
C17957
CHEMBL487013
chebi:81409 ,
5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxychromen-4-one
5,7,3'-trimethoxy-6,4',5'-trimethoxyisoflavone
LMPK12050417
einecs 208-958-3
5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4-benzopyrone
6o4nx37350 ,
unii-6o4nx37350
S9121
CCG-214382
SCHEMBL554864
irigenin [mi]
3',5,7-trihydroxy-4',5',6-trimethoxyisoflavone
5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4h-1-benzopyran-4-one
5,7,3'-trihydroxy-6,4',5'-trimethoxyisoflavone
AC-35036
DTXSID90203285
SR-05000002617-1
sr-05000002617
AKOS030632868
mfcd00597047
BS-17232
Q2481557
5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4h-chromen-4-one
CS-0022931
HY-N2587
FT-0775730
A923655

Research Excerpts

Effects

ExcerptReferenceRelevance
"Irigenin (IR) has antioxidative properties."( Irigenin alleviates angiotensin II-induced oxidative stress and apoptosis in HUVEC cells by activating Nrf2 pathway.
Guan, J; Jiang, X; Lu, J; Shi, J; Wang, W; Xue, T; Zhang, Q, 2021)		2.79

Pharmacokinetics

ExcerptReferenceRelevance
" This method was successfully applied to a pharmacokinetic study of the three isoflavones after oral administration of Rhizoma Belamcandae extract to rats."( Simultaneous determination of tectorigenin, irigenin and irisflorentin in rat plasma and urine by UHPLC-MS/MS: application to pharmacokinetics.
Gu, Y; Wang, R; Wang, XJ; Yang, WJ; Zhang, WD, 2011)		0.63
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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.
4'-methoxyisoflavonesAny methoxyisoflavone which has a methoxy group at the 4-position of the phenyl 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]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID377458Estrogenic activity in human T47D cells assessed as drug level causing stimulation of cell proliferation equivalent to 100 pM estradiol by alamar blue assay2005Journal of natural products, Mar, Volume: 68, Issue:3
Phenolic constituents of the rhizomes of the Thai medicinal plant Belamcanda chinensis with proliferative activity for two breast cancer cell lines.
AID377456Estrogenic activity in human MCF7 cells assessed as drug level causing stimulation of cell proliferation equivalent to 100 pM estradiol by alamar blue assay2005Journal of natural products, Mar, Volume: 68, Issue:3
Phenolic constituents of the rhizomes of the Thai medicinal plant Belamcanda chinensis with proliferative activity for two breast cancer cell lines.
AID377455Estrogenic activity in human MCF7 cells assessed as drug level causing stimulation of cell proliferation equivalent to 10 pM estradiol by alamar blue assay2005Journal of natural products, Mar, Volume: 68, Issue:3
Phenolic constituents of the rhizomes of the Thai medicinal plant Belamcanda chinensis with proliferative activity for two breast cancer cell lines.
AID377457Estrogenic activity in human T47D cells assessed as drug level causing stimulation of cell proliferation equivalent to 10 pM estradiol by alamar blue assay2005Journal of natural products, Mar, Volume: 68, Issue:3
Phenolic constituents of the rhizomes of the Thai medicinal plant Belamcanda chinensis with proliferative activity for two breast cancer cell lines.
AID338974Inhibition of cow milk xanthine oxidase at 50 ug/mL
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (28.57)29.6817
2010's5 (35.71)24.3611
2020's5 (35.71)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.56

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 Index23.56 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.81 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.56)

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%
Other17 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
methane
Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).		2.2110alkane;
gas molecular entity;
mononuclear parent hydride;
one-carbon compound		bacterial metabolite;
fossil fuel;
greenhouse gas
boric acid
[no description available]		2.0210boric acidsastringent
2,2',4,4'-tetrahydroxybenzophenone
[no description available]		2.2110
androsin
androsin: phenol glycoside which prevents allergen & platelet-activating factor induced bronchial obstruction in guinea pigs in vivo prior to inhalation challenge		2.0210
irisflorentin
irisflorentin: bioactive substance isolated from Rhizoma Belamcandae; structure in first source		7.44204'-methoxyisoflavones
angiotensin ii
Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).		7.3110amino acid zwitterion;
angiotensin II		human metabolite
resveratrol
trans-resveratrol : A resveratrol in which the double bond has E configuration.		2.0210resveratrolantioxidant;
phytoalexin;
plant metabolite;
quorum sensing inhibitor;
radical scavenger
dinoprostone
prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.		2.0310prostaglandins Ehuman metabolite;
mouse metabolite;
oxytocic
genistein
[no description available]		2.02107-hydroxyisoflavonesantineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
geroprotector;
human urinary metabolite;
phytoestrogen;
plant metabolite;
tyrosine kinase inhibitor
iridin
iridin : A glycosyloxyisoflavone that is irigenin substituted by a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage.		7.49204'-methoxyisoflavones;
7-hydroxyisoflavones 7-O-beta-D-glucoside;
hydroxyisoflavone;
monosaccharide derivative		plant metabolite
irilone
irilone: structure in first source. irilone : A hydroxyisoflavone that is 6,7-methylenedioxyisoflavone substituted by hydroxy groups at positions 5 and 4'.		2.2110hydroxyisoflavone;
organic heterotricyclic compound;
oxacycle		antineoplastic agent;
immunomodulator;
metabolite
tectoridin
tectoridin: glycosylated tectorigenin. tectoridin : A glycosyloxyisoflavone that is tectorigenin substituted by a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage.		7.48207-hydroxyisoflavones 7-O-beta-D-glucoside;
hydroxyisoflavone;
methoxyisoflavone;
monosaccharide derivative		plant metabolite
tectorigenin
tectorigenin: tectoridin is glycosylated form. tectorigenin : A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 5, 7 and 4' respectively.		2.97407-hydroxyisoflavones;
methoxyisoflavone		anti-inflammatory agent;
plant metabolite
phytoestrogens
Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.		2.0210
ConditionIndicatedRelationship StrengthStudiesTrials
Breast Cancer
[description not available]		02.0210
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.0210
Cardiac Toxicity
[description not available]		02.2510
Innate Inflammatory Response
[description not available]		02.2510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		07.2510
Cardiotoxicity
Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.		07.2510
Cancer of Stomach
[description not available]		02.1710
Stomach Neoplasms
Tumors or cancer of the STOMACH.		02.1710
Cancer of Lung
[description not available]		02.1310
Metastase
[description not available]		02.1310
Lung Neoplasms
Tumors or cancer of the LUNG.		02.1310
Neoplasm Metastasis
The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.		02.1310
Cancer of Prostate
[description not available]		02.0210
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.0210