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362-08-3,MFCD00056413
Catalog No.:AA007AD0

362-08-3 | Estra-1,3,5(10)-trien-17-one,3-hydroxy-2-methoxy-

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1mg
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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA007AD0
Chemical Name:
Estra-1,3,5(10)-trien-17-one,3-hydroxy-2-methoxy-
CAS Number:
362-08-3
Molecular Formula:
C19H24O3
Molecular Weight:
300.3921
MDL Number:
MFCD00056413
SMILES:
COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C
Properties
Computed Properties
 
Complexity:
462  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
1  
XLogP3:
3.1  

Literature

Title: Red Clover Aryl Hydrocarbon Receptor (AhR) and Estrogen Receptor (ER) Agonists Enhance Genotoxic Estrogen Metabolism.

Journal: Chemical research in toxicology 20171120

Title: Structure-activity relationship for the first-in-class clinical steroid sulfatase inhibitor Irosustat (STX64, BN83495).

Journal: ChemMedChem 20111104

Title: A prospective phase II study of 2-methoxyestradiol administered in combination with bevacizumab in patients with metastatic carcinoid tumors.

Journal: Cancer chemotherapy and pharmacology 20110801

Title: Liquid chromatography/mass spectrometry of pre-ionized Girard P derivatives for quantifying estrone and its metabolites in serum from postmenopausal women.

Journal: Rapid communications in mass spectrometry : RCM 20110515

Title: Metabolic alteration of urinary steroids in pre- and post-menopausal women, and men with papillary thyroid carcinoma.

Journal: BMC cancer 20110101

Title: Profiling oestrogens and testosterone in human urine by stable isotope dilution/benchtop gas chromatography-mass spectrometry.

Journal: Steroids 20101212

Title: Estrogens and development of pulmonary hypertension: interaction of estradiol metabolism and pulmonary vascular disease.

Journal: Journal of cardiovascular pharmacology 20101201

Title: Simultaneous determination of eight estrogens and their metabolites in serum using liquid chromatography with electrochemical detection.

Journal: Talanta 20100415

Title: The coordinated p53 and estrogen receptor cis-regulation at an FLT1 promoter SNP is specific to genotoxic stress and estrogenic compound.

Journal: PloS one 20100101

Title: The normal breast microenvironment of premenopausal women differentially influences the behavior of breast cancer cells in vitro and in vivo.

Journal: BMC medicine 20100101

Title: Comparison of estrogens and estrogen metabolites in human breast tissue and urine.

Journal: Reproductive biology and endocrinology : RB&E 20100101

Title: Potent and selective steroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 7, an enzyme that catalyzes the reduction of the key hormones estrone and dihydrotestosterone.

Journal: Journal of medicinal chemistry 20091210

Title: Structure-based design, synthesis and in vitro characterization of potent 17beta-hydroxysteroid dehydrogenase type 1 inhibitors based on 2-substitutions of estrone and D-homo-estrone.

Journal: Bioorganic & medicinal chemistry letters 20091201

Title: Activity of 2 methoxyestradiol (Panzem NCD) in advanced, platinum-resistant ovarian cancer and primary peritoneal carcinomatosis: a Hoosier Oncology Group trial.

Journal: Gynecologic oncology 20091001

Title: The in vivo properties of STX243: a potent angiogenesis inhibitor in breast cancer.

Journal: British journal of cancer 20081104

Title: Synthesis and in vivo antitumor evaluation of 2-methoxyestradiol 3-phosphate, 17-phosphate, and 3,17-diphosphate.

Journal: Journal of medicinal chemistry 20071227

Title: The therapeutic potential of a series of orally bioavailable anti-angiogenic microtubule disruptors as therapy for hormone-independent prostate and breast cancers.

Journal: British journal of cancer 20071217

Title: Evaluation of electrospray ionization and atmospheric pressure chemical ionization for simultaneous detection of estrone and its metabolites using high-performance liquid chromatography/tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20071201

Title: HPLC for stress-free screening of potential prostate cancer marker catechol estrogens in urine using a diamond-electrode electrochemical and a fluorescence detector.

Journal: Journal of separation science 20070901

Title: Effects of a catechol-O-methyltransferase inhibitor on catechol estrogen-induced cellular transformation, chromosome aberrations and apoptosis in Syrian hamster embryo cells.

Journal: International journal of cancer 20070415

Title: Estrogen metabolism modulates bone density in men.

Journal: Calcified tissue international 20070401

Title: Phase I safety, pharmacokinetic and pharmacodynamic studies of 2-methoxyestradiol alone or in combination with docetaxel in patients with locally recurrent or metastatic breast cancer.

Journal: Investigational new drugs 20070201

Title: Urinary phytoestrogen excretion of rats bearing methylnitrosourea-induced mammary carcinoma in response to treatment with 2-methoxyestradiol.

Journal: The Journal of steroid biochemistry and molecular biology 20070201

Title: 2-methoxyestradiol inhibits differentiation and is cytotoxic to osteoclasts.

Journal: Journal of cellular biochemistry 20061001

Title: Plasma protein binding of the investigational anticancer agent 2-methoxyestradiol.

Journal: Anti-cancer drugs 20060901

Title: Analysis of fifteen estrogen metabolites using packed column supercritical fluid chromatography-mass spectrometry.

Journal: Analytical chemistry 20060301

Title: The role of 17beta-hydroxysteroid dehydrogenases in modulating the activity of 2-methoxyestradiol in breast cancer cells.

Journal: Cancer research 20060101

Title: The Association of the COMT V158M Polymorphism with Endometrial/Ovarian Cancer in HNPCC Families Adhering to the Amsterdam Criteria.

Journal: Hereditary cancer in clinical practice 20060101

Title: A phase II multicenter, randomized, double-blind, safety trial assessing the pharmacokinetics, pharmacodynamics, and efficacy of oral 2-methoxyestradiol capsules in hormone-refractory prostate cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050915

Title: A-ring-substituted estrogen-3-O-sulfamates: potent multitargeted anticancer agents.

Journal: Journal of medicinal chemistry 20050811

Title: Selective insensitivity of ZR-75-1 human breast cancer cells to 2-methoxyestradiol: evidence for type II 17beta-hydroxysteroid dehydrogenase as the underlying cause.

Journal: Cancer research 20050701

Title: Effects of dioxin on metabolism of estrogens in waste incinerator workers.

Journal: Archives of environmental & occupational health 20050101

Title: The oxidative metabolism of estrogen modulates response to ERT/HRT in postmenopausal women.

Journal: Bone 20040901

Title: Inhibition of in vitro angiogenesis by 2-methoxy- and 2-ethyl-estrogen sulfamates.

Journal: International journal of cancer 20040420

Title: Pharmacokinetics and efficacy of 2-methoxyoestradiol and 2-methoxyoestradiol-bis-sulphamate in vivo in rodents.

Journal: British journal of cancer 20040223

Title: Recent translational research: antiangiogenic therapy for breast cancer - where do we stand?

Journal: Breast cancer research : BCR 20040101

Title: Comparison of ex vivo inhibitory effect between 2-hydroxyestradiol and its 17-sulfate on rat hepatic microsomal lipid peroxidation.

Journal: Lipids 20030801

Title: The effects of 2-substituted oestrogen sulphamates on the growth of prostate and ovarian cancer cells.

Journal: The Journal of steroid biochemistry and molecular biology 20030201

Title: Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults.

Journal: Steroids 20010101

Title: Involvement of genotoxic effects in the initiation of estrogen-induced cellular transformation: studies using Syrian hamster embryo cells treated with 17beta-estradiol and eight of its metabolites.

Journal: International journal of cancer 20000401

Title: Inhibition of deoxyglucose uptake in MCF-7 breast cancer cells by 2-methoxyestrone and 2-methoxyestrone-3-O-sulfamate.

Journal: Molecular and cellular endocrinology 20000225

Title: Lewis KM, et al. pKa values of estrone, 17 beta-estradiol and 2-methoxyestrone. Steroids. 1979 Nov;34(5):485-99.

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Tags:362-08-3 Molecular Formula|362-08-3 MDL|362-08-3 SMILES|362-08-3 Estra-1,3,5(10)-trien-17-one,3-hydroxy-2-methoxy-