Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H8O5 |
| Molecular Weight | 268.221 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC2=C(C=C1)C3=C(O2)C4=C(OC3=O)C=C(O)C=C4
InChI
InChIKey=ZZIALNLLNHEQPJ-UHFFFAOYSA-N
InChI=1S/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H
| Molecular Formula | C15H8O5 |
| Molecular Weight | 268.221 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Coumestrol is one of the major phytoestrogens, which is abundant in soybeans, legumes, and spinach. It competitively binds the estrogen receptors ERα and ERβ. Besides coumestrol is an endogenous antagonist of the human pregnane X receptor. It is known, that antagonizing the action of the human nuclear xenobiotic receptor pregnane X receptor (PXR) may have important clinical implications in preventing drug-drug interactions and improving therapeutic efficacy. Coumestrol epigenetically suppresses cancer cell proliferation, due to its inhibition of natural haspin kinase. Coumestrol exhibits broad anti-cancer effects against skin melanoma, lung cancer, breast cancer and some others cancer cell growth. Besides, was also shown the beneficial effects of coumestrol in various biological processes including, neuroprotective effects on the nervous system, and the function of the female reproductive system. However, the experiments for male rodents have strongly suggested a deleterious effect of oral, low concentration phytoestrogen content in adult male diets.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P03372 Gene ID: 2099.0 Gene Symbol: ESR1 Target Organism: Homo sapiens (Human) |
0.14 nM [Ki] | ||
Target ID: Q92731|||O75584 Gene ID: 2100.0 Gene Symbol: ESR2 Target Organism: Homo sapiens (Human) |
0.07 nM [Ki] | ||
Target ID: O75469|||Q9UJ26 Gene ID: 8856.0 Gene Symbol: NR1I2 Target Organism: Homo sapiens (Human) |
|||
Target ID: Q8TF76 Gene ID: 83903.0 Gene Symbol: GSG2 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
|
| Differential response to phytoestrogens in endocrine sensitive and resistant breast cancer cells in vitro. | 2006-08-01 |
|
| Effects of phytoestrogens on testosterone secretion by Leydig cells from Biłgoraj ganders (Anser anser). | 2006-04 |
|
| Maternal genistein alters coat color and protects Avy mouse offspring from obesity by modifying the fetal epigenome. | 2006-04 |
|
| 17Beta-hydroxysteroid dehydrogenase (17beta-HSD) in scleractinian corals and zooxanthellae. | 2006-04 |
|
| Xenoestrogen action in breast cancer: impact on ER-dependent transcription and mitogenesis. | 2006-04 |
|
| LDL-antioxidant pterocarpans from roots of Glycine max (L.) Merr. | 2006-03-22 |
|
| Chemical components with health implications in wild and cultivated Mexican common bean seeds (Phaseolus vulgaris L.). | 2006-03-22 |
|
| The chemical and biologic profile of a red clover (Trifolium pratense L.) phase II clinical extract. | 2006-03 |
|
| ERbeta-selective SERMs produce mnemonic-enhancing effects in the inhibitory avoidance and water maze tasks. | 2006-03 |
|
| Analysis of the promoter-specific estrogenic potency of the phytoestrogens genistein, daidzein and coumestrol. | 2006-02 |
|
| Leukotoxin diols from ground corncob bedding disrupt estrous cyclicity in rats and stimulate MCF-7 breast cancer cell proliferation. | 2005-12 |
|
| An efficient synthesis of coumestrol and coumestans by iodocyclization and Pd-catalyzed intramolecular lactonization. | 2005-11-25 |
|
| Fetal exposure to phytoestrogens--the difference in phytoestrogen status between mother and fetus. | 2005-10 |
|
| Phytoestrogens induce differential estrogen receptor alpha- or Beta-mediated responses in transfected breast cancer cells. | 2005-09 |
|
| Phytoestrogens as inhibitors of fungal 17beta-hydroxysteroid dehydrogenase. | 2005-09 |
|
| ERbeta-selective estrogen receptor modulators produce antianxiety behavior when administered systemically to ovariectomized rats. | 2005-09 |
|
| Phytoestrogens as inhibitors of fungal 17beta-hydroxysteroid dehydrogenase. | 2005-08 |
|
| Genotoxicity of phytoestrogens. | 2005-07-01 |
|
| Inhibition of 3alpha-hydroxysteroid dehydrogenase (3alpha-HSD) activity of human lung microsomes by genistein, daidzein, coumestrol and C(18)-, C(19)- and C(21)-hydroxysteroids and ketosteroids. | 2005-07 |
|
| Combinatory effects of phytoestrogens and 17beta-estradiol on proliferation and apoptosis in MCF-7 breast cancer cells. | 2005-04 |
|
| Comparative study of oestrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells. | 2005-04 |
|
| Xenoestrogens at picomolar to nanomolar concentrations trigger membrane estrogen receptor-alpha-mediated Ca2+ fluxes and prolactin release in GH3/B6 pituitary tumor cells. | 2005-04 |
|
| [Effects of phytoestrogens on gap junctional intercellular communication]. | 2005-03 |
|
| New cytotoxic prenylated isoflavonoids from Bituminaria morisiana. | 2005-03 |
|
| Binding of estrogenic compounds to recombinant estrogen receptor-alpha: application to environmental analysis. | 2005-03 |
|
| Modulation of tumor formation and intestinal cell migration by estrogens in the Apc(Min/+) mouse model of colorectal cancer. | 2005-03 |
|
| The effect of two dietary and a synthetic phytoestrogen on transepithelial calcium transport in human intestinal-like Caco-2 cells. | 2005-03 |
|
| Suppressive effect of neonatal treatment with a phytoestrogen, coumestrol, on lordosis and estrous cycle in female rats. | 2005-01-15 |
|
| An isotope dilution gas chromatographic-mass spectrometric method for the simultaneous assay of estrogens and phytoestrogens in urine. | 2004-12 |
|
| The effect of the phytoestrogen coumestrol on the NZB/W F1 murine model of systemic lupus. | 2004-12 |
|
| Impact of the phytoestrogen content of laboratory animal feed on the gene expression profile of the reproductive system in the immature female rat. | 2004-11 |
|
| Xenoestrogen-induced ERK-1 and ERK-2 activation via multiple membrane-initiated signaling pathways. | 2004-11 |
|
| Cumulative dietary energy intake determines the onset of puberty in female rats. | 2004-11 |
|
| Prenatal estrogen exposure differentially affects estrogen receptor-associated proteins in rat testis gonocytes. | 2004-11 |
|
| Effects of the phytoestrogen coumestrol on RANK-ligand-induced differentiation of osteoclasts. | 2004-10-15 |
|
| Survey of estrogenic activity in fish feed by yeast estrogen-screen assay. | 2004-10 |
|
| Estrogen and phytoestrogen regulate the mRNA expression of adrenomedullin and adrenomedullin receptor components in the rat uterus. | 2004-08-31 |
|
| Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types. | 2004-07 |
|
| Antidepressant effects of ERbeta-selective estrogen receptor modulators in the forced swim test. | 2004-07 |
|
| Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor alpha (ERalpha) and ERbeta in human cells. | 2004-07 |
|
| Differential effects of isoflavones and lignans on invasiveness of MDA-MB-231 breast cancer cells in vitro. | 2004-05-10 |
|
| Targeting oestrogen to kill the cancer but not the patient. | 2004-03-08 |
|
| Effects of phytoestrogens and environmental estrogens on osteoblastic differentiation in MC3T3-E1 cells. | 2004-03-01 |
|
| Regulation of low-density lipoprotein receptor activity by estrogens and phytoestrogens in a HepG2 cell model. | 2004 |
|
| Phytoestrogens modulate binding response of estrogen receptors alpha and beta to the estrogen response element. | 2003-12-17 |
|
| Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. | 2003-12 |
|
| Synthesis of hapten and conjugates of coumestrol and development of immunoassay. | 2003-12 |
|
| Isoflavonoid accumulation in soybean hairy roots upon treatment with Fusarium solani. | 2003-11-05 |
|
| Coumestrol as well as isoflavones in soybean extract prevent bone resorption in ovariectomized rats. | 2003-09 |
Sample Use Guides
in mice: 10, 20 or 40 μg/Kg body weight for two weeks
Route of Administration:
Oral
Coumestrol, is an antagonist of the nuclear receptor PXR (NR1I2). Coumestrol at concentrations above 1.0 microm competed in scintillation proximity assays with a labeled PXR agonist for binding to the ligand-binding cavity. Mammalian two-hybrid assays and transient transcription data using ligand-binding-cavity mutant forms of PXR show that coumestrol also antagonizes coregulator recruitment. This effect is likely by binding to a surface outside the ligand-binding pocket.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:44:04 GMT 2025
by
admin
on
Mon Mar 31 18:44:04 GMT 2025
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| Record UNII |
V7NW98OB34
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| Record Status |
Validated (UNII)
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| Record Version |
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Download
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NCI_THESAURUS |
C68532
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V7NW98OB34
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5281707
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3908
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COUMESTROL
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m3822
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479-13-0
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C93321
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D003375
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