Home Other Building Blocks (8R,9S,13S,14S,16R)-3,16-Dihydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one

(8R,9S,13S,14S,16R)-3,16-Dihydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one

CAS No.:
566-76-7
Catalog Number:
AG00EBMG
Molecular Formula:
C18H22O3
Molecular Weight:
286.3655
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$194
- +
5mg
≥98%
1 week
United States
$539
- +
10mg
≥98%
1 week
United States
$814
- +
Product Description
Catalog Number:
AG00EBMG
Chemical Name:
(8R,9S,13S,14S,16R)-3,16-Dihydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one
CAS Number:
566-76-7
Molecular Formula:
C18H22O3
Molecular Weight:
286.3655
MDL Number:
MFCD00870436
IUPAC Name:
(8R,9S,13S,14S,16R)-3,16-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
InChI:
InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1
InChI Key:
WPOCIZJTELRQMF-QFXBJFAPSA-N
SMILES:
Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1C[C@H](C2=O)O)C
UNII:
JY611949JU
Properties
Complexity:
448  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0
Exact Mass:
286.157g/mol
Formal Charge:
0
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
286.371g/mol
Monoisotopic Mass:
286.157g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
57.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.6  
Literature
Title Journal
The relation of urinary estrogen metabolites with mammographic densities in premenopausal women. Cancer epidemiology 20121001
Association between physical activity and urinary estrogens and estrogen metabolites in premenopausal women. The Journal of clinical endocrinology and metabolism 20121001
Urinary estrogen metabolites in two soy trials with premenopausal women. European journal of clinical nutrition 20120901
Activity of the estrogen-metabolizing enzyme cytochrome P450 1B1 influences the development of pulmonary arterial hypertension. Circulation 20120828
Estrogen metabolism and autoimmunity. Autoimmunity reviews 20120501
Urinary estrogen metabolites during a randomized soy trial. Nutrition and cancer 20120201
Analysis of multiplex endogenous estrogen metabolites in human urine using ultra-fast liquid chromatography-tandem mass spectrometry: a case study for breast cancer. Analytica chimica acta 20120120
Anti-proliferative effects of Chinese herb Cornus officinalis in a cell culture model for estrogen receptor-positive clinical breast cancer. Molecular medicine reports 20120101
Postmenopausal circulating levels of 2- and 16α-hydroxyestrone and risk of endometrial cancer. British journal of cancer 20111025
The effect of tamoxifen and raloxifene on estrogen metabolism and endometrial cancer risk. The Journal of steroid biochemistry and molecular biology 20110901
Liquid chromatography/mass spectrometry of pre-ionized Girard P derivatives for quantifying estrone and its metabolites in serum from postmenopausal women. Rapid communications in mass spectrometry : RCM 20110515
3,3'-diindolylmethane modulates estrogen metabolism in patients with thyroid proliferative disease: a pilot study. Thyroid : official journal of the American Thyroid Association 20110301
Dietary fiber and serum 16α-hydroxyestrone, an estrogen metabolite associated with lower systolic blood pressure. Nutrition (Burbank, Los Angeles County, Calif.) 20110101
Estrogen metabolite ratio: Is the 2-hydroxyestrone to 16α-hydroxyestrone ratio predictive for breast cancer? International journal of women's health 20110101
Coffee consumption and risk of cancers: a meta-analysis of cohort studies. BMC cancer 20110101
A preliminary study of the effectiveness of chinese therapeutic food on regulating female reproductive hormones. Integrative medicine insights 20110101
The role of female hormones on lung function in chronic lung diseases. BMC women's health 20110101
Serum concentrations of selected endogenous estrogen and estrogen metabolites in pre- and post-menopausal Chinese women with osteoarthritis. Journal of endocrinological investigation 20101001
A new approach to measuring estrogen exposure and metabolism in epidemiologic studies. The Journal of steroid biochemistry and molecular biology 20100801
Comparison of liquid chromatography-tandem mass spectrometry, RIA, and ELISA methods for measurement of urinary estrogens. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20100101
Effect of flaxseed consumption on urinary levels of estrogen metabolites in postmenopausal women. Nutrition and cancer 20100101
Effects of a breast-health herbal formula supplement on estrogen metabolism in pre- and post-menopausal women not taking hormonal contraceptives or supplements: a randomized controlled trial. Breast cancer : basic and clinical research 20100101
Serum estrogen metabolites and systolic blood pressure among middle-aged and older women and men. American journal of hypertension 20091101
Estrone/17beta-estradiol conversion to, and tumor necrosis factor inhibition by, estrogen metabolites in synovial cells of patients with rheumatoid arthritis and patients with osteoarthritis. Arthritis and rheumatism 20091001
Urinary estrogen metabolites in women at high risk for breast cancer. Carcinogenesis 20090901
Circulating estrogen metabolites and risk for breast cancer in premenopausal women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20090801
Ethnicity, body size, and estrogen levels in postmenopausal Hispanic and non-Hispanic white women. Journal of women's health (2002) 20090401
An improved method for the simultaneous analysis of phenolic and steroidal estrogens in water and sediment. Talanta 20090215
Estrogen hydroxylation--the good and the bad. Annals of the New York Academy of Sciences 20090201
16alpha-hydroxyestrone inhibits estrogen sulfotransferase activity in human liver cancer cells. Annals of the New York Academy of Sciences 20090201
Lycium barbarum inhibits growth of estrogen receptor positive human breast cancer cells by favorably altering estradiol metabolism. Nutrition and cancer 20090101
Urinary estrogen metabolites and prostate cancer: a case-control study and meta-analysis. Journal of experimental & clinical cancer research : CR 20090101
Daidzein-metabolizing phenotypes in relation to serum hormones and sex hormone binding globulin, and urinary estrogen metabolites in premenopausal women in the United States. Cancer causes & control : CCC 20081201
Coffee intake and CYP1A2*1F genotype predict breast volume in young women: implications for breast cancer. British journal of cancer 20081104
Fat/fiber intakes and sex hormones in healthy premenopausal women in USA. The Journal of steroid biochemistry and molecular biology 20081101
Levels of sex steroid and cardiovascular disease measures in premenopausal and hormone-treated women at midlife: implications for the 'timing hypothesis'. Archives of internal medicine 20081027
Past oral contraceptive use and current dietary soy isoflavones influence estrogen metabolism in postmenopausal monkeys (Macaca fascicularis). Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20081001
Circulating 2-hydroxy- and 16alpha-hydroxy estrone levels and risk of breast cancer among postmenopausal women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20080801
Oestrogen metabolites in relation to isoprostanes as a measure of oxidative stress. Clinical endocrinology 20080501
Involvement of peroxiredoxin IV in the 16alpha-hydroxyestrone-induced proliferation of human MCF-7 breast cancer cells. Cell biology international 20080401
Phytoestrogens and breast cancer prevention: possible mechanisms of action. Environmental health perspectives 20080401
Exercise effect on oxidative stress is independent of change in estrogen metabolism. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20080101
Development and statistical validation of a quantitative method for the determination of steroid hormones in environmental water by column liquid chromatography/tandem mass spectrometry. Journal of AOAC International 20080101
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 of chromatography. B, Analytical technologies in the biomedical and life sciences 20071201
A pilot and feasibility study on the effects of naturopathic botanical and dietary interventions on sex steroid hormone metabolism in premenopausal women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20070801
The effects of soygerm extracts on blood lipoproteins, antioxidative capacity and urinary estrogen metabolites in postmenopausal women on hormone therapy. International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics 20070701
Breast cancer: are oestrogen metabolites carcinogenic? Maturitas 20070520
Soy isoflavonoid effects on endogenous estrogen metabolism in postmenopausal female monkeys. Carcinogenesis 20070401
Effects of aerobic exercise training on estrogen metabolism in premenopausal women: a randomized controlled trial. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20070401
Variants in estrogen metabolism and biosynthesis genes and urinary estrogen metabolites in women with a family history of breast cancer. Breast cancer research and treatment 20070301
Urinary phytoestrogen excretion of rats bearing methylnitrosourea-induced mammary carcinoma in response to treatment with 2-methoxyestradiol. The Journal of steroid biochemistry and molecular biology 20070201
Changes in 2-hydroxyestrone and 16alpha-hydroxyestrone metabolism with flaxseed consumption: modification by COMT and CYP1B1 genotype. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20070201
Enhanced NF kappa B and AP-1 transcriptional activity associated with antiestrogen resistant breast cancer. BMC cancer 20070101
In vitro short-term test evaluation of catecholestrogens genotoxicity. The Journal of steroid biochemistry and molecular biology 20070101
Soy isoflavone intake and estrogen excretion patterns in young women: effect of probiotic administration. In vivo (Athens, Greece) 20070101
Moderate coffee and alcohol consumption improves the estrogen metabolite profile in adjuvant treated breast cancer patients: a pilot study comparing pre- and post-operative levels. Molecular genetics and metabolism 20061201
Estrogens and autoimmune diseases. Annals of the New York Academy of Sciences 20061101
CYP1A1 and CYP1B1 polymorphisms and their association with estradiol and estrogen metabolites in women who are premenopausal and perimenopausal. The American journal of medicine 20060901
Optimisation of derivatisation for the analysis of estrogenic compounds in water by solid-phase extraction gas chromatography-mass spectrometry. Analytica chimica acta 20060901
Estradiol and its metabolites and their association with knee osteoarthritis. Arthritis and rheumatism 20060801
Selected diet and lifestyle factors are associated with estrogen metabolites in a multiracial/ethnic population of women. The Journal of nutrition 20060601
A hormonal association between estrogen metabolism and proliferative thyroid disease. Otolaryngology--head and neck surgery : official journal of American Academy of Otolaryngology-Head and Neck Surgery 20060601
Comparison of possible carcinogenic estradiol metabolites: effects on proliferation, apoptosis and metastasis of human breast cancer cells. Maturitas 20060420
Obesity, hormone therapy, estrogen metabolism and risk of postmenopausal breast cancer. International journal of cancer 20060301
Effects of docosahexaenoic acid supplementation on blood lipids, estrogen metabolism, and in vivo oxidative stress in postmenopausal vegetarian women. European journal of clinical nutrition 20060301
Estrogen metabolites and systolic blood pressure in a population-based sample of postmenopausal women. The Journal of clinical endocrinology and metabolism 20060301
Analysis of fifteen estrogen metabolites using packed column supercritical fluid chromatography-mass spectrometry. Analytical chemistry 20060301
Role of polymorphic human cytochrome P450 enzymes in estrone oxidation. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20060301
Comparison of plasma and urinary levels of 2-hydroxyestrogen and 16 alpha-hydroxyestrogen metabolites. Molecular genetics and metabolism 20060201
Estrogen metabolism and breast cancer. Epidemiology (Cambridge, Mass.) 20060101
A randomized phase II trial of indole-3-carbinol in the treatment of vulvar intraepithelial neoplasia. International journal of gynecological cancer : official journal of the International Gynecological Cancer Society 20060101
Mitogenic estrogen metabolites alter the expression of 17beta-estradiol-regulated proteins including heat shock proteins in human MCF-7 breast cancer cells. Molecules and cells 20051231
Urinary hydroxyestrogens and breast cancer risk among postmenopausal women: a prospective study. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20050901
Estrogenic effect of yam ingestion in healthy postmenopausal women. Journal of the American College of Nutrition 20050801
The relationship between physical activity and 2-hydroxyestrone, 16alpha-hydroxyestrone, and the 2/16 ratio in premenopausal women (United States). Cancer causes & control : CCC 20050501
Partition of endocrine-disrupting chemicals between colloids and dissolved phase as determined by cross-flow ultrafiltration. Environmental science & technology 20050415
Degradation of estradiol and ethinyl estradiol by activated sludge and by a defined mixed culture. Applied microbiology and biotechnology 20050401
Differential effects of 16alpha-hydroxyestrone and 2-methoxyestradiol on cyclin D1 involving the transcription factor ATF-2 in MCF-7 breast cancer cells. Journal of molecular endocrinology 20050201
Estradiol metabolites are potent mitogenic substances for human ovarian cancer cells. European journal of gynaecological oncology 20050101
A common CYP1B1 polymorphism is associated with 2-OHE1/16-OHE1 urinary estrone ratio. Clinical chemistry and laboratory medicine 20050101
Urinary estrogen metabolites, prostate specific antigen, and body mass index among African-American men in South Carolina. Cancer detection and prevention 20050101
The oxidative metabolism of estrogen modulates response to ERT/HRT in postmenopausal women. Bone 20040901
Effects of estrogens and metabolites on endometrial carcinogenesis in young adult mice initiated with N-ethyl-N'-nitro-N-nitrosoguanidine. Cancer letters 20040728
Microwave-assisted extraction followed by gas chromatography-mass spectrometry for the determination of endocrine disrupting chemicals in river sediments. Journal of chromatography. A 20040604
Physical activity, body size, and estrogen metabolism in women. Cancer causes & control : CCC 20040601
High levels of oxidative DNA damage in lymphocyte DNA of premenopausal breast cancer patients from Egypt. International journal of environmental health research 20040401
Endogenous estradiol metabolism during treatment with oral contraceptives. International journal of clinical pharmacology and therapeutics 20040301
Synovial fluid estrogens in rheumatoid arthritis. Autoimmunity reviews 20040301
Association of CYP17, CYP19, CYP1B1, and COMT polymorphisms with serum and urinary sex hormone concentrations in postmenopausal women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20040101
Sex hormones influence on the immune system: basic and clinical aspects in autoimmunity. Lupus 20040101
Pilot study: effect of 3,3'-diindolylmethane supplements on urinary hormone metabolites in postmenopausal women with a history of early-stage breast cancer. Nutrition and cancer 20040101
Increased estrogen formation and estrogen to androgen ratio in the synovial fluid of patients with rheumatoid arthritis. The Journal of rheumatology 20031201
Estrogen metabolites and the risk of breast cancer in older women. Epidemiology (Cambridge, Mass.) 20031101
[Estrogen-dependent neoplasia - what is the significance of estradiol metabolites]. Zentralblatt fur Gynakologie 20031101
Human cytochrome P450 3A7 has a distinct high catalytic activity for the 16alpha-hydroxylation of estrone but not 17beta-estradiol. Cancer research 20031001
Activation of matrix metalloproteinase-2 and -9 by 2- and 4-hydroxyestradiol. The Journal of steroid biochemistry and molecular biology 20031001
Urinary equol excretion in relation to 2-hydroxyestrone and 16alpha-hydroxyestrone concentrations: an observational study of young to middle-aged women. The Journal of steroid biochemistry and molecular biology 20030701
Influence of postmenopausal hormone replacement therapy on an estrogen metabolite biomarker of risk for breast cancer. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20030601
Predictors of the plasma ratio of 2-hydroxyestrone to 16alpha-hydroxyestrone among pre-menopausal, nulliparous women from four ethnic groups. Carcinogenesis 20030501
Endogenous estradiol metabolites stimulate the in vitro proliferation of human osteoblastic cells. International journal of clinical pharmacology and therapeutics 20030401
A preliminary study of the effect of fluoxetine treatment on the 2:16-alpha-hydroxyestrone ratio in young women. Therapeutic drug monitoring 20030201
Estrogens in female thyroid cancer: alteration of urinary profiles in pre- and post-operative cases. Cancer letters 20030110
Urinary estrogen metabolites and breast cancer: differential pattern of risk found with pre- versus post-treatment collection. Steroids 20030101
Urinary estrogen metabolites and prostate cancer: a case-control study in the United States. Cancer causes & control : CCC 20021201
Tissue content of hydroxyestrogens in relation to survival of breast cancer patients. Clinical cancer research : an official journal of the American Association for Cancer Research 20021001
Estrogen metabolism and the diet-cancer connection: rationale for assessing the ratio of urinary hydroxylated estrogen metabolites. Alternative medicine review : a journal of clinical therapeutic 20020401
Urinary 2-hydroxyestrone/16alpha-hydroxyestrone ratio and family history of breast cancer in premenopausal women. Breast cancer research and treatment 20020301
Regulation of cell cycle and cyclins by 16alpha-hydroxyestrone in MCF-7 breast cancer cells. Journal of molecular endocrinology 20011201
The effects of postmenopausal hormone replacement therapy and oral contraceptives on the endogenous estradiol metabolism. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20011201
Relationship between estradiol 16 alpha-hydroxylation and human papillomavirus infection in cervical cell transformation. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20011001
Preferential growth stimulation of mammary glands over uterine endometrium in female rats by a naturally occurring estradiol-17beta-fatty acid ester. Cancer research 20010801
Tissue-selective effects of continuous release of 2-hydroxyestrone and 16alpha-hydroxyestrone on bone, uterus and mammary gland in ovariectomized growing rats. The Journal of endocrinology 20010701
Urinary estrogen metabolites and mammographic parenchymal patterns in postmenopausal women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20010601
Re: CYP17 promoter polymorphism and breast cancer in Australian women under age forty years. Journal of the National Cancer Institute 20010404
Determination of estradiol metabolites in human liver microsome by high performance liquid chromatography-electrochemistry detector. Acta pharmacologica Sinica 20010401
Epidemiological study of urinary 6beta-hydroxycortisol to cortisol ratios and breast cancer risk. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20010301
Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults. Steroids 20010101
Oestrogen and progesterone increase the levels of apoptosis induced by the human papillomavirus type 16 E2 and E7 proteins. The Journal of general virology 20010101
Indole-3-carbinol in women with SLE: effect on estrogen metabolism and disease activity. Lupus 20010101
Increased urinary excretion of 2-hydroxyestrone but not 16alpha-hydroxyestrone in premenopausal women during a soya diet containing isoflavones. Cancer research 20000301
Rapid inhibition of rat brain mitochondrial proton F0F1-ATPase activity by estrogens: comparison with Na+, K+ -ATPase of porcine cortex. European journal of pharmacology 19990226
Estrogenic and antiestrogenic activities of 16alpha- and 2-hydroxy metabolites of 17beta-estradiol in MCF-7 and T47D human breast cancer cells. The Journal of steroid biochemistry and molecular biology 19981201
Anti-oestrogen antibodies in users of oral contraceptives and in patients with systemic lupus erythematosus. Clinical and experimental immunology 19870101
Properties