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 |
|---|---|---|
| A case-control study of dietary phytoestrogens and testicular cancer risk. | 2002 |
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| Human 17beta-hydroxysteroid dehydrogenase type 5 is inhibited by dietary flavonoids. | 2002 |
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| Stimulation of alkaline phosphatase activity in Ishikawa cells induced by various phytoestrogens and synthetic estrogens. | 2002 Dec |
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| Increases in mouse uterine heat shock protein levels are a sensitive and specific response to uterotrophic agents. | 2002 Dec |
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| Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin. | 2002 Feb |
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| Effects of the environmental estrogens bisphenol A, o,p'-DDT, p-tert-octylphenol and coumestrol on apoptosis induction, cell proliferation and the expression of estrogen sensitive molecular parameters in the human breast cancer cell line MCF-7. | 2002 Jan |
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| Neurobehavioral actions of coumestrol and related isoflavonoids in rodents. | 2002 Jan-Feb |
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| Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids. | 2002 Jul |
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| Pharmacological profile of 6,12-dihydro-3-methoxy-1-benzopyrano[3,4-b] [1,4]benzothiazin-6-one, a novel human estrogen receptor agonist. | 2002 Mar |
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| Estrogenic isoflavones in rodent diets. | 2002 Mar 10 |
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| Detection of phytoestrogens in samples of second trimester human amniotic fluid. | 2002 Mar 28 |
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| Daidzein, coumestrol and zearalenone affect lipogenesis and lipolysis in rat adipocytes. | 2002 May |
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| Assessing estrogenic activity of phytochemicals using transcriptional activation and immature mouse uterotrophic responses. | 2002 Sep 25 |
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| Effect of in utero-administered coumestrol, equol, and organic selenium on biomarkers for phase 2 enzyme capacity and redox status. | 2003 |
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| Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. | 2003 |
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| Activation of estrogen receptor alpha and ERbeta by 4-methylbenzylidene-camphor in human and rat cells: comparison with phyto- and xenoestrogens. | 2003 Apr 30 |
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| 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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| The effects of the phytoestrogen, coumestrol, on gonadotropin-releasing hormone (GnRH) mRNA expression in GT1-7 GnRH neurones. | 2003 Feb |
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| Urinary and serum concentrations of seven phytoestrogens in a human reference population subset. | 2003 Jul |
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| Phytoestrogens: recent developments. | 2003 Jul |
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| Phyto-oestrogen levels in foods: the design and construction of the VENUS database. | 2003 Jun |
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| Cell-transforming activity and mutagenicity of 5 phytoestrogens in cultured mammalian cells. | 2003 Jun 20 |
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| Prenatal exposure to estrogenic compounds alters the expression pattern of platelet-derived growth factor receptors alpha and beta in neonatal rat testis: identification of gonocytes as targets of estrogen exposure. | 2003 Mar |
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| Distinct molecular conformations of the estrogen receptor alpha complex exploited by environmental estrogens. | 2003 Nov 1 |
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| Determination of rat oral bioavailability of soy-derived phytoestrogens using an automated on-column extraction procedure and electrospray tandem mass spectrometry. | 2003 Oct 25 |
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| Coumestrol as well as isoflavones in soybean extract prevent bone resorption in ovariectomized rats. | 2003 Sep |
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| The OECD program to validate the rat uterotrophic bioassay. Phase 2: dietary phytoestrogen analyses. | 2003 Sep |
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| Partial purification and characterisation of a 2,4,5-trichlorophenol detoxifying O-glucosyltransferase from wheat. | 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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| The effect of the phytoestrogen coumestrol on the NZB/W F1 murine model of systemic lupus. | 2004 Dec |
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| Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake. | 2004 Jan 9 |
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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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| 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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| 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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| Phytoestrogens as inhibitors of fungal 17beta-hydroxysteroid dehydrogenase. | 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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| The chemical and biologic profile of a red clover (Trifolium pratense L.) phase II clinical extract. | 2006 Mar |
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| LDL-antioxidant pterocarpans from roots of Glycine max (L.) Merr. | 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
