Home Other Building Blocks (17β)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol

(17β)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol

CAS No.:
362-07-2
Catalog Number:
AG0037YB
Molecular Formula:
C19H26O3
Molecular Weight:
302.4079
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
98%(HPLC)
In Stock USA
United States
$53
- +
10mg
98%(HPLC)
In Stock USA
United States
$83
- +
25mg
98%(HPLC)
In Stock USA
United States
$169
- +
50mg
98%(HPLC)
In Stock USA
United States
$286
- +
Product Description
Catalog Number:
AG0037YB
Chemical Name:
(17β)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol
CAS Number:
362-07-2
Molecular Formula:
C19H26O3
Molecular Weight:
302.4079
MDL Number:
MFCD00010489
IUPAC Name:
(8R,9S,13S,14S,17S)-2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
InChI:
InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1
InChI Key:
CQOQDQWUFQDJMK-SSTWWWIQSA-N
SMILES:
COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
UNII:
6I2QW73SR5
Properties
Complexity:
425  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0
Exact Mass:
302.188g/mol
Formal Charge:
0
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
302.414g/mol
Monoisotopic Mass:
302.188g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
49.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4  
Literature
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Comparison of estrogens and estrogen metabolites in human breast tissue and urine. Reproductive biology and endocrinology : RB&E 20100101
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Identifying molecular effects of diet through systems biology: influence of herring diet on sterol metabolism and protein turnover in mice. PloS one 20100101
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Mass spectrometric measurement of differential reactivity of cysteine to localize protein-ligand binding sites. Application to tubulin-binding drugs. Analytical biochemistry 20040915
In vitro model of mammary estrogen metabolism: structural and kinetic differences between catechol estrogens 2- and 4-hydroxyestradiol. Chemical research in toxicology 20040901
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Improved survival of mice bearing liver metastases of colon cancer cells treated with a combination of radioimmunotherapy and antiangiogenic therapy. European journal of nuclear medicine and molecular imaging 20040701
New drugs for treatment of multiple myeloma. The Lancet. Oncology 20040701
2-Alkylsulfanyl estrogen derivatives: synthesis of a novel class of multi-targeted anti-tumour agents. Bioorganic & medicinal chemistry letters 20040621
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Differential regulation of estrogen receptor subtypes alpha and beta in human aortic smooth muscle cells by oligonucleotides and estradiol. The Journal of clinical endocrinology and metabolism 20040501
Mitochondrial superoxide dismutase: a promising target for new anticancer therapies. Current medicinal chemistry 20040501
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A gas chromatography/mass spectrometry assay to measure estradiol, catecholestradiols, and methoxyestradiols in plasma. Steroids 20040401
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Estrogens and anti-estrogens: key mediators of prostate carcinogenesis and new therapeutic candidates. Journal of cellular biochemistry 20040215
A comparative study on the effects of 2,3,7,8,-tetrachlorodibenzo-p-dioxin polychlorinated biphenyl126 and estrogen in human bronchial epithelial cells. Toxicology and applied pharmacology 20040215
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A simple quantitative method for evaluation of angiogenesis activity. Assay and drug development technologies 20040201
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Effects of several dioxin-like compounds on estrogen metabolism in the malignant MCF-7 and nontumorigenic MCF-10A human mammary epithelial cell lines. Toxicology and applied pharmacology 20030801
The effects of 2-methoxy oestrogens and their sulphamoylated derivatives in conjunction with TNF-alpha on endothelial and fibroblast cell growth, morphology and apoptosis. The Journal of steroid biochemistry and molecular biology 20030801
Comparison of ex vivo inhibitory effect between 2-hydroxyestradiol and its 17-sulfate on rat hepatic microsomal lipid peroxidation. Lipids 20030801
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Synthesis and evaluation of a novel nonsteroidal-specific endothelial cell proliferation inhibitor. Journal of medicinal chemistry 20030410
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Medical hypothesis: hyperhomocysteinemia is a risk factor for estrogen-induced hormonal cancer. International journal of oncology 20030301
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Effect of tamoxifen and 2-methoxyestradiol alone and in combination on human breast cancer cell proliferation. The Journal of steroid biochemistry and molecular biology 20030201
Growth inhibition of multi-drug-resistant breast cancer cells by 2-methoxyoestradiol-bis-sulphamate and 2-ethyloestradiol-bis-sulphamate. The Journal of steroid biochemistry and molecular biology 20030201
The effects of 2-substituted oestrogen sulphamates on the growth of prostate and ovarian cancer cells. The Journal of steroid biochemistry and molecular biology 20030201
Inhibition of MCF-7 breast cancer cell proliferation and in vivo steroid sulphatase activity by 2-methoxyoestradiol-bis-sulphamate. The Journal of steroid biochemistry and molecular biology 20030201
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The effect of endogenous estradiol metabolites on the proliferation of human breast cancer cells. Life sciences 20030110
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Novel therapies for multiple myeloma. British journal of haematology 20030101
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INGN 201: Ad-p53, Ad5CMV-p53, Adenoviral p53, INGN 101, p53 gene therapy--Introgen, RPR/INGN 201. BioDrugs : clinical immunotherapeutics, biopharmaceuticals and gene therapy 20030101
Opposite regulation of XIAP and Smac/DIABLO in the rat endometrium in response to 17beta-estradiol at estrus. Reproductive biology and endocrinology : RB&E 20030101
2-Methoxyestradiol induces p53-associated apoptosis of colorectal cancer cells. Cancer letters 20021210
A new, practical synthesis of 2-methoxyestradiols. Steroids 20021201
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Promising preclinical activity of 2-methoxyestradiol in multiple myeloma. Clinical cancer research : an official journal of the American Association for Cancer Research 20021201
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Regulation of the activation of nuclear factor kappaB by mitochondrial respiratory function: evidence for the reactive oxygen species-dependent and -independent pathways. Antioxidants & redox signaling 20021201
Crystal structure of human sex hormone-binding globulin in complex with 2-methoxyestradiol reveals the molecular basis for high affinity interactions with C-2 derivatives of estradiol. The Journal of biological chemistry 20021122
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Evidence for genomic and nongenomic actions of estrogen in growth plate regulation in female and male rats at the onset of sexual maturation. The Journal of endocrinology 20021101
The effect of exchanging various substituents at the 2-position of 2-methoxyestradiol on cytotoxicity in human cancer cell cultures and inhibition of tubulin polymerization. Journal of medicinal chemistry 20021010
Estradiol metabolism and malignant disease. Maturitas 20020930
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2-Methoxyestradiol overcomes drug resistance in multiple myeloma cells. Blood 20020915
Novel therapies for multiple myeloma. Blood reviews 20020901
Evidence that 2-methoxyestradiol suppresses proliferation and accelerates apoptosis in normal rat growth plate chondrocytes. Journal of cancer research and clinical oncology 20020901
2-Methoxyestradiol inhibits proliferation and induces apoptosis independently of estrogen receptors alpha and beta. Cancer research 20020701
Tumour microvessel density as predictor of chemotherapy response in breast cancer patients. British journal of cancer 20020617
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Introduction of a novel proliferation assay for pharmacological studies allowing the combination of BrdU detection and phenotyping. Journal of immunological methods 20020601
2-Methoxyestradiol and analogs as novel antiproliferative agents: analysis of three-dimensional quantitative structure-activity relationships for DNA synthesis inhibition and estrogen receptor binding. Molecular pharmacology 20020501
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells. The Journal of biological chemistry 20020419
A radical approach to cancer. Medical science monitor : international medical journal of experimental and clinical research 20020401
Catecholamines block 2-hydroxyestradiol-induced antimitogenesis in mesangial cells. Hypertension (Dallas, Tex. : 1979) 20020401
Methoxyestradiols mediate estradiol-induced antimitogenesis in human aortic SMCs. Hypertension (Dallas, Tex. : 1979) 20020401
Cytotoxicity of estradiol, equilin, equilenin, and their derivatives on Chinese hamster V79 cells. Drug and chemical toxicology 20020201
2-methoxyestradiol induces interferon gene expression and apoptosis in osteosarcoma cells. Bone 20020201
Role of methoxyestradiols in the growth inhibitory effects of estradiol on human glomerular mesangial cells. Hypertension (Dallas, Tex. : 1979) 20020201
Safety and pharmacokinetics of intravitreal 2-methoxyestradiol implants in normal rabbit and pharmacodynamics in a rat model of choroidal neovascularization. Experimental eye research 20020201
Dual effect of 2-methoxyestradiol on cell cycle events in human osteosarcoma 143B cells. Acta biochimica Polonica 20020101
Reduction of post injury neointima formation due to 17beta-estradiol and phytoestrogen treatment is not influenced by the pure synthetic estrogen receptor antagonist ICI 182,780 in vitro. BMC cardiovascular disorders 20020101
Mitochondrial defects in cancer. Molecular cancer 20020101
Identification of small molecule binding sites within proteins using phage display technology. Combinatorial chemistry & high throughput screening 20011101
Catecholamines abrogate antimitogenic effects of 2-hydroxyestradiol on human aortic vascular smooth muscle cells. Arteriosclerosis, thrombosis, and vascular biology 20011101
Estradiol, in the CNS, targets several physiologically relevant membrane-associated proteins. Brain research. Brain research reviews 20011101
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Anti-angiogenic therapy and radioimmunotherapy in colon cancer xenografts. European journal of nuclear medicine 20010901
2-methoxyestradiol does not inhibit superoxide dismutase. Archives of biochemistry and biophysics 20010815
2-Methoxyestradiol induces G2/M arrest and apoptosis in prostate cancer. Biochemical and biophysical research communications 20010803
2-Methoxyestradiol, an endogenous estradiol metabolite, differentially inhibits granulosa and endothelial cell mitosis: a potential follicular antiangiogenic regulator. Biology of reproduction 20010801
2-Methoxyestradiol-induced caspase-3 activation and apoptosis occurs through G(2)/M arrest dependent and independent pathways in gastric carcinoma cells. Cancer 20010801
Inhibition of large-conductance calcium-activated potassium channel by 2-methoxyestradiol in cultured vascular endothelial (HUV-EC-C) cells. The Journal of membrane biology 20010801
Structure-effect relationship in the induction of mitotic phase-specific abnormality of centrosome integrity and multipolar spindles by steroidal estrogens and their derivatives in cultured mammalian cells. The Journal of steroid biochemistry and molecular biology 20010801
2-Methoxymethylestradiol: a new 2-methoxy estrogen analog that exhibits antiproliferative activity and alters tubulin dynamics. The Journal of steroid biochemistry and molecular biology 20010801
The physiological estrogen metabolite 2-methoxyestradiol reduces tumor growth and induces apoptosis in human solid tumors. Journal of cancer research and clinical oncology 20010701
2-methoxyestradiol blocks cell-cycle progression at G(2)/M phase and inhibits growth of human prostate cancer cells. Molecular carcinogenesis 20010701
Aromatase regulation and breast cancer. Clinical endocrinology 20010501
The antiangiogenic property of docetaxel is synergistic with a recombinant humanized monoclonal antibody against vascular endothelial growth factor or 2-methoxyestradiol but antagonized by endothelial growth factors. Cancer research 20010415
Estradiol metabolites inhibit endothelin synthesis by an estrogen receptor-independent mechanism. Hypertension (Dallas, Tex. : 1979) 20010201
Effects of estradiol and its metabolites on glomerular endothelial nitric oxide synthesis and mesangial cell growth. Hypertension (Dallas, Tex. : 1979) 20010201
Increased 2-methoxyestradiol production in human coronary versus aortic vascular cells. Hypertension (Dallas, Tex. : 1979) 20010201
Opposite effects of microtubule-stabilizing and microtubule-destabilizing drugs on biogenesis of mitochondria in mammalian cells. Journal of cell science 20010101
Angiogenesis in the pathogenesis of inflammatory joint and lung diseases. Arthritis research 20010101
Therapeutic angiogenesis inhibitors in the treatment of cancer. Advances in internal medicine 20010101
An ex vivo angiogenesis assay utilizing commercial porcine carotid artery: modification of the rat aortic ring assay. Angiogenesis 20010101
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Comparison of 2-methoxyestradiol-induced, docetaxel-induced, and paclitaxel-induced apoptosis in hepatoma cells and its correlation with reactive oxygen species. Cancer 20000901
Inhibition of deoxyglucose uptake in MCF-7 breast cancer cells by 2-methoxyestrone and 2-methoxyestrone-3-O-sulfamate. Molecular and cellular endocrinology 20000225
12-O-tetradecanoylphorbol-13-acetate upregulates the Ah receptor and differentially alters CYP1B1 and CYP1A1 expression in MCF-7 breast cancer cells. Journal of cellular biochemistry 19980901
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