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=CC=C2C(OC3=C2C(=O)OC4=C3C=CC(O)=C4)=C1
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
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 |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 Dec |
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| Synthesis of hapten and conjugates of coumestrol and development of immunoassay. | 2003 Dec |
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| Phytoestrogens modulate binding response of estrogen receptors alpha and beta to the estrogen response element. | 2003 Dec 17 |
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| Coumestrol as well as isoflavones in soybean extract prevent bone resorption in ovariectomized rats. | 2003 Sep |
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| Regulation of low-density lipoprotein receptor activity by estrogens and phytoestrogens in a HepG2 cell model. | 2004 |
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| Estrogen and phytoestrogen regulate the mRNA expression of adrenomedullin and adrenomedullin receptor components in the rat uterus. | 2004 Aug 31 |
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| An isotope dilution gas chromatographic-mass spectrometric method for the simultaneous assay of estrogens and phytoestrogens in urine. | 2004 Dec |
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| The effect of the phytoestrogen coumestrol on the NZB/W F1 murine model of systemic lupus. | 2004 Dec |
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| 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 Jul |
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| Antidepressant effects of ERbeta-selective estrogen receptor modulators in the forced swim test. | 2004 Jul |
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| Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor alpha (ERalpha) and ERbeta in human cells. | 2004 Jul |
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| Isoflavonoid accumulation in soybean hairy roots upon treatment with Fusarium solani. | 2004 Jul-Aug |
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| Effects of phytoestrogens and environmental estrogens on osteoblastic differentiation in MC3T3-E1 cells. | 2004 Mar 1 |
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| Targeting oestrogen to kill the cancer but not the patient. | 2004 Mar 8 |
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| Differential effects of isoflavones and lignans on invasiveness of MDA-MB-231 breast cancer cells in vitro. | 2004 May 10 |
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| Impact of the phytoestrogen content of laboratory animal feed on the gene expression profile of the reproductive system in the immature female rat. | 2004 Nov |
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| Xenoestrogen-induced ERK-1 and ERK-2 activation via multiple membrane-initiated signaling pathways. | 2004 Nov |
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| Cumulative dietary energy intake determines the onset of puberty in female rats. | 2004 Nov |
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| Prenatal estrogen exposure differentially affects estrogen receptor-associated proteins in rat testis gonocytes. | 2004 Nov |
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| Survey of estrogenic activity in fish feed by yeast estrogen-screen assay. | 2004 Oct |
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| Effects of the phytoestrogen coumestrol on RANK-ligand-induced differentiation of osteoclasts. | 2004 Oct 15 |
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| Combinatory effects of phytoestrogens and 17beta-estradiol on proliferation and apoptosis in MCF-7 breast cancer cells. | 2005 Apr |
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| Comparative study of oestrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells. | 2005 Apr |
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| Xenoestrogens at picomolar to nanomolar concentrations trigger membrane estrogen receptor-alpha-mediated Ca2+ fluxes and prolactin release in GH3/B6 pituitary tumor cells. | 2005 Apr |
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| Phytoestrogens as inhibitors of fungal 17beta-hydroxysteroid dehydrogenase. | 2005 Aug |
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| Leukotoxin diols from ground corncob bedding disrupt estrous cyclicity in rats and stimulate MCF-7 breast cancer cell proliferation. | 2005 Dec |
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| Suppressive effect of neonatal treatment with a phytoestrogen, coumestrol, on lordosis and estrous cycle in female rats. | 2005 Jan 15 |
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| 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 Jul |
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| Genotoxicity of phytoestrogens. | 2005 Jul 1 |
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| [Effects of phytoestrogens on gap junctional intercellular communication]. | 2005 Mar |
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| New cytotoxic prenylated isoflavonoids from Bituminaria morisiana. | 2005 Mar |
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| Binding of estrogenic compounds to recombinant estrogen receptor-alpha: application to environmental analysis. | 2005 Mar |
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| Modulation of tumor formation and intestinal cell migration by estrogens in the Apc(Min/+) mouse model of colorectal cancer. | 2005 Mar |
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| The effect of two dietary and a synthetic phytoestrogen on transepithelial calcium transport in human intestinal-like Caco-2 cells. | 2005 Mar |
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| An efficient synthesis of coumestrol and coumestans by iodocyclization and Pd-catalyzed intramolecular lactonization. | 2005 Nov 25 |
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| Fetal exposure to phytoestrogens--the difference in phytoestrogen status between mother and fetus. | 2005 Oct |
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| Phytoestrogens induce differential estrogen receptor alpha- or Beta-mediated responses in transfected breast cancer cells. | 2005 Sep |
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| Phytoestrogens as inhibitors of fungal 17beta-hydroxysteroid dehydrogenase. | 2005 Sep |
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| ERbeta-selective estrogen receptor modulators produce antianxiety behavior when administered systemically to ovariectomized rats. | 2005 Sep |
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| Effects of phytoestrogens on testosterone secretion by Leydig cells from Biłgoraj ganders (Anser anser). | 2006 Apr |
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| Maternal genistein alters coat color and protects Avy mouse offspring from obesity by modifying the fetal epigenome. | 2006 Apr |
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| 17Beta-hydroxysteroid dehydrogenase (17beta-HSD) in scleractinian corals and zooxanthellae. | 2006 Apr |
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| Xenoestrogen action in breast cancer: impact on ER-dependent transcription and mitogenesis. | 2006 Apr |
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| Differential response to phytoestrogens in endocrine sensitive and resistant breast cancer cells in vitro. | 2006 Aug 1 |
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| Analysis of the promoter-specific estrogenic potency of the phytoestrogens genistein, daidzein and coumestrol. | 2006 Feb |
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| The chemical and biologic profile of a red clover (Trifolium pratense L.) phase II clinical extract. | 2006 Mar |
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| ERbeta-selective SERMs produce mnemonic-enhancing effects in the inhibitory avoidance and water maze tasks. | 2006 Mar |
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| LDL-antioxidant pterocarpans from roots of Glycine max (L.) Merr. | 2006 Mar 22 |
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| Chemical components with health implications in wild and cultivated Mexican common bean seeds (Phaseolus vulgaris L.). | 2006 Mar 22 |
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| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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.
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NCI_THESAURUS |
C68532
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V7NW98OB34
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5281707
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DTXSID6022399
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3908
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COUMESTROL
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207-525-6
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22842
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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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SUBSTANCE RECORD
