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479-13-0 | 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one
CAS No: 479-13-0 Catalog No: AG003IR8 MDL No:MFCD00016885
Product Description
Catalog Number:
AG003IR8
Chemical Name:
3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one
CAS Number:
479-13-0
Molecular Formula:
C15H8O5
Molecular Weight:
268.2210
MDL Number:
MFCD00016885
IUPAC Name:
3,9-dihydroxy-[1]benzofuro[3,2-c]chromen-6-one
InChI:
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
InChI Key:
ZZIALNLLNHEQPJ-UHFFFAOYSA-N
SMILES:
Oc1ccc2c(c1)oc(=O)c1c2oc2c1ccc(c2)O
EC Number:
207-525-6
UNII:
V7NW98OB34
NSC Number:
22842
Properties
Complexity:
411
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
268.037g/mol
Formal Charge:
0
Heavy Atom Count:
20
Hydrogen Bond Acceptor Count:
5
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
268.224g/mol
Monoisotopic Mass:
268.037g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
79.9A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.8
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| Structure-based virtual screening for plant-based ERbeta-selective ligands as potential preventative therapy against age-related neurodegenerative diseases. | Journal of medicinal chemistry 20050519 |
| Simultaneous quantitation of free and conjugated phytoestrogens in Leguminosae by liquid chromatography-tandem mass spectrometry. | Talanta 20050515 |
| Xenoestrogens at picomolar to nanomolar concentrations trigger membrane estrogen receptor-alpha-mediated Ca2+ fluxes and prolactin release in GH3/B6 pituitary tumor cells. | Environmental health perspectives 20050401 |
| Comparative study of oestrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells. | The Journal of steroid biochemistry and molecular biology 20050401 |
| Combinatory effects of phytoestrogens and 17beta-estradiol on proliferation and apoptosis in MCF-7 breast cancer cells. | The Journal of steroid biochemistry and molecular biology 20050401 |
| The effect of two dietary and a synthetic phytoestrogen on transepithelial calcium transport in human intestinal-like Caco-2 cells. | European journal of nutrition 20050301 |
| Modulation of tumor formation and intestinal cell migration by estrogens in the Apc(Min/+) mouse model of colorectal cancer. | Carcinogenesis 20050301 |
| Binding of estrogenic compounds to recombinant estrogen receptor-alpha: application to environmental analysis. | Environmental health perspectives 20050301 |
| New cytotoxic prenylated isoflavonoids from Bituminaria morisiana. | Planta medica 20050301 |
| [Effects of phytoestrogens on gap junctional intercellular communication]. | Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine] 20050301 |
| Suppressive effect of neonatal treatment with a phytoestrogen, coumestrol, on lordosis and estrous cycle in female rats. | Brain research bulletin 20050115 |
| The effect of the phytoestrogen coumestrol on the NZB/W F1 murine model of systemic lupus. | Journal of autoimmunity 20041201 |
| An isotope dilution gas chromatographic-mass spectrometric method for the simultaneous assay of estrogens and phytoestrogens in urine. | The Journal of steroid biochemistry and molecular biology 20041201 |
| Prenatal estrogen exposure differentially affects estrogen receptor-associated proteins in rat testis gonocytes. | Biology of reproduction 20041101 |
| Cumulative dietary energy intake determines the onset of puberty in female rats. | Environmental health perspectives 20041101 |
| Xenoestrogen-induced ERK-1 and ERK-2 activation via multiple membrane-initiated signaling pathways. | Environmental health perspectives 20041101 |
| Impact of the phytoestrogen content of laboratory animal feed on the gene expression profile of the reproductive system in the immature female rat. | Environmental health perspectives 20041101 |
| Effects of the phytoestrogen coumestrol on RANK-ligand-induced differentiation of osteoclasts. | Toxicology 20041015 |
| Survey of estrogenic activity in fish feed by yeast estrogen-screen assay. | Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 20041001 |
| Estrogen and phytoestrogen regulate the mRNA expression of adrenomedullin and adrenomedullin receptor components in the rat uterus. | Molecular and cellular endocrinology 20040831 |
| Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor alpha (ERalpha) and ERbeta in human cells. | Toxicological sciences : an official journal of the Society of Toxicology 20040701 |
| Antidepressant effects of ERbeta-selective estrogen receptor modulators in the forced swim test. | Pharmacology, biochemistry, and behavior 20040701 |
| 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. | The Journal of steroid biochemistry and molecular biology 20040701 |
| Differential effects of isoflavones and lignans on invasiveness of MDA-MB-231 breast cancer cells in vitro. | Cancer letters 20040510 |
| Estrogen receptor ligands. Part 1: The discovery of flavanoids with subtype selectivity. | Bioorganic & medicinal chemistry letters 20040322 |
| Targeting oestrogen to kill the cancer but not the patient. | British journal of cancer 20040308 |
| Effects of phytoestrogens and environmental estrogens on osteoblastic differentiation in MC3T3-E1 cells. | Toxicology 20040301 |
| Coumestrol, bisphenol-A, DDT, and TCDD modulation of interleukin-2 expression in activated CD+4 Jurkat T cells. | International journal of environmental research and public health 20040301 |
| Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake. | The Journal of biological chemistry 20040109 |
| Isoflavonoid accumulation in soybean hairy roots upon treatment with Fusarium solani. | Plant physiology and biochemistry : PPB 20040101 |
| Regulation of low-density lipoprotein receptor activity by estrogens and phytoestrogens in a HepG2 cell model. | Annals of nutrition & metabolism 20040101 |
| Phytoestrogens modulate binding response of estrogen receptors alpha and beta to the estrogen response element. | Journal of agricultural and food chemistry 20031217 |
| Synthesis of hapten and conjugates of coumestrol and development of immunoassay. | Steroids 20031201 |
| Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. | Biological & pharmaceutical bulletin 20031201 |
| Distinct molecular conformations of the estrogen receptor alpha complex exploited by environmental estrogens. | Cancer research 20031101 |
| Determination of rat oral bioavailability of soy-derived phytoestrogens using an automated on-column extraction procedure and electrospray tandem mass spectrometry. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20031025 |
| Partial purification and characterisation of a 2,4,5-trichlorophenol detoxifying O-glucosyltransferase from wheat. | Phytochemistry 20030901 |
| The OECD program to validate the rat uterotrophic bioassay. Phase 2: dietary phytoestrogen analyses. | Environmental health perspectives 20030901 |
| Coumestrol as well as isoflavones in soybean extract prevent bone resorption in ovariectomized rats. | Endocrine regulations 20030901 |
| Phytoestrogens: recent developments. | Planta medica 20030701 |
| Urinary and serum concentrations of seven phytoestrogens in a human reference population subset. | Journal of exposure analysis and environmental epidemiology 20030701 |
| Cell-transforming activity and mutagenicity of 5 phytoestrogens in cultured mammalian cells. | International journal of cancer 20030620 |
| Phyto-oestrogen levels in foods: the design and construction of the VENUS database. | The British journal of nutrition 20030601 |
| Activation of estrogen receptor alpha and ERbeta by 4-methylbenzylidene-camphor in human and rat cells: comparison with phyto- and xenoestrogens. | Toxicology letters 20030430 |
| 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. | Biology of reproduction 20030301 |
| The effects of the phytoestrogen, coumestrol, on gonadotropin-releasing hormone (GnRH) mRNA expression in GT1-7 GnRH neurones. | Journal of neuroendocrinology 20030201 |
| Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. | Rapid communications in mass spectrometry : RCM 20030101 |
| Effect of in utero-administered coumestrol, equol, and organic selenium on biomarkers for phase 2 enzyme capacity and redox status. | Nutrition and cancer 20030101 |
| Increases in mouse uterine heat shock protein levels are a sensitive and specific response to uterotrophic agents. | Environmental health perspectives 20021201 |
| Stimulation of alkaline phosphatase activity in Ishikawa cells induced by various phytoestrogens and synthetic estrogens. | The Journal of steroid biochemistry and molecular biology 20021201 |
| Ability of structurally diverse natural products and synthetic chemicals to induce gene expression mediated by estrogen receptors from various species. | The Journal of steroid biochemistry and molecular biology 20021001 |
| Assessing estrogenic activity of phytochemicals using transcriptional activation and immature mouse uterotrophic responses. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020925 |
| Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids. | Bioscience, biotechnology, and biochemistry 20020701 |
| Comparison of the oestrogenic effects of infant milk formulae, oestradiol and the phytoestrogen coumestrol delivered continuously in the drinking water to ovariectomised mice. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20020501 |
| Daidzein, coumestrol and zearalenone affect lipogenesis and lipolysis in rat adipocytes. | Phytomedicine : international journal of phytotherapy and phytopharmacology 20020501 |
| Synthesis and cytotoxic activity of new 2,4-diaryl-4H,5H-pyrano[3,2-c]benzopyran-5-ones on MCF-7 cells. | Die Pharmazie 20020401 |
| Detection of phytoestrogens in samples of second trimester human amniotic fluid. | Toxicology letters 20020328 |
| Estrogenic isoflavones in rodent diets. | Toxicology letters 20020310 |
| Pharmacological profile of 6,12-dihydro-3-methoxy-1-benzopyrano[3,4-b] [1,4]benzothiazin-6-one, a novel human estrogen receptor agonist. | Biological & pharmaceutical bulletin 20020301 |
| Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin. | Reproduction (Cambridge, England) 20020201 |
| O-Glucosyltransferase activities toward phenolic natural products and xenobiotics in wheat and herbicide-resistant and herbicide-susceptible black-grass (Alopecurus myosuroides). | Phytochemistry 20020101 |
| Interaction of phytoestrogens with estrogen receptors alpha and beta (II). | Biological & pharmaceutical bulletin 20020101 |
| Neurobehavioral actions of coumestrol and related isoflavonoids in rodents. | Neurotoxicology and teratology 20020101 |
| 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. | The Journal of steroid biochemistry and molecular biology 20020101 |
| Human 17beta-hydroxysteroid dehydrogenase type 5 is inhibited by dietary flavonoids. | Advances in experimental medicine and biology 20020101 |
| The influence of coumestrol, zearalenone, and genistein administration on insulin receptors and insulin secretion in ovariectomized rats. | Journal of receptor and signal transduction research 20020101 |
| A case-control study of dietary phytoestrogens and testicular cancer risk. | Nutrition and cancer 20020101 |
| Reciprocal mutagenesis between human alpha(L349, M528) and rainbow trout (M317, I496) estrogen receptor residues demonstrates their importance in ligand binding and gene expression at different temperatures. | Molecular and cellular endocrinology 20011025 |
| Regulation of phenobarbital-mediated induction of CYP102 (cytochrome P450(BM-3)) in Bacillus megaterium by phytochemicals from soy and green tea. | Journal of agricultural and food chemistry 20011001 |
| High resolution screening of plant natural product extracts for estrogen receptor alpha and beta binding activity using an online HPLC-MS biochemical detection system. | Journal of biomolecular screening 20011001 |
| Comparison of an array of in vitro assays for the assessment of the estrogenic potential of natural and synthetic estrogens, phytoestrogens and xenoestrogens. | Toxicology 20010914 |
| Potential estrogenic and antiestrogenic activity of the cyclic siloxane octamethylcyclotetrasiloxane (D4) and the linear siloxane hexamethyldisiloxane (HMDS) in immature rats using the uterotrophic assay. | Toxicological sciences : an official journal of the Society of Toxicology 20010901 |
| Effects of the phytoestrogen coumestrol on locomotor and fear-related behaviors in female mice. | Hormones and behavior 20010801 |
| Molecular identification of potential selective estrogen receptor modulator (SERM) like properties of phytoestrogens in the human breast cancer cell line MCF-7. | Planta medica 20010801 |
| Common phytochemicals are ecdysteroid agonists and antagonists: a possible evolutionary link between vertebrate and invertebrate steroid hormones. | The Journal of steroid biochemistry and molecular biology 20010601 |
| Phytochemical glyceollins, isolated from soy, mediate antihormonal effects through estrogen receptor alpha and beta. | The Journal of clinical endocrinology and metabolism 20010401 |
| Coumestrol antagonizes neuroendocrine actions of estrogen via the estrogen receptor alpha. | Experimental biology and medicine (Maywood, N.J.) 20010401 |
| Phytoestrogens and gonadotropin-releasing hormone pulse generator activity and pituitary luteinizing hormone release in the rat. | Endocrinology 20010301 |
| Evaluation of the genotoxicity of the phytoestrogen, coumestrol, in AHH-1 TK(+/-) human lymphoblastoid cells. | Mutation research 20010301 |
| Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5. | Molecular and cellular endocrinology 20010122 |
| Effects of binary mixtures of six xenobiotics on hormone concentrations and morphometric endpoints of northern bobwhite quail (Colinus virginianus). | Chemosphere 20010101 |
| Pilot study of a specific dietary supplement in tumor-bearing mice and in stage IIIB and IV non-small cell lung cancer patients. | Nutrition and cancer 20010101 |
| Differential estrogen receptor binding of estrogenic substances: a species comparison. | The Journal of steroid biochemistry and molecular biology 20001115 |
| Inhibitory effect of natural and environmental estrogens on thymic hormone production in thymus epithelial cell culture. | International journal of immunopharmacology 19991201 |
| Estrogen receptor activation via activation function 2 predicts agonism of xenoestrogens in normal and neoplastic cells of the uterine myometrium. | Cancer research 19990701 |
| Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. | Endocrinology 19981001 |
| Identification of estrogen receptor beta2, a functional variant of estrogen receptor beta expressed in normal rat tissues. | Endocrinology 19980301 |
| Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. | Endocrinology 19970301 |
| The phytoestrogen coumestrol is a naturally occurring antagonist of the human pregnane X receptor. | Molecular endocrinology (Baltimore, Md.) |
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