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3131-23-5,MFCD00079358
Catalog No.:AA00C7Y5

3131-23-5 | (8R,9S,13S,14S)-3,4-Dihydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one

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1mg
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5mg
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$333.00   $233.00
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10mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00C7Y5
Chemical Name:
(8R,9S,13S,14S)-3,4-Dihydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one
CAS Number:
3131-23-5
Molecular Formula:
C18H22O3
Molecular Weight:
286.3655
MDL Number:
MFCD00079358
SMILES:
O=C1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2O)O
Properties
Properties
 
Form:
Solid  
MP:
>213ºC (dec.)  
Storage:
-20 ℃;  

Computed Properties
 
Complexity:
448  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
XLogP3:
2.8  

Literature

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Journal: Chemical research in toxicology 20171120

Title: NRF2/long noncoding RNA ROR signaling regulates mammary stem cell expansion and protects against estrogen genotoxicity.

Journal: The Journal of biological chemistry 20141107

Title: Endocrine metabolic disorders in patients with breast cancer, carriers of BRCA1 gene mutations.

Journal: Bulletin of experimental biology and medicine 20120301

Title: Effect of tumour necrosis factor-alpha on estrogen metabolic pathways in breast cancer cells.

Journal: Journal of Cancer 20120101

Title: Importance of CYP1A1 polymorphism and its transcriptional regulation in ovarian and endometrial cancer.

Journal: Ginekologia polska 20111201

Title: Catechol metabolites of endogenous estrogens induce redox cycling and generate reactive oxygen species in breast epithelial cells.

Journal: Carcinogenesis 20110801

Title: Estrogen metabolites in the release of inflammatory mediators from human amnion-derived cells.

Journal: Life sciences 20110314

Title: Gender is a risk factor for lung cancer.

Journal: Medical hypotheses 20110301

Title: Estrogen metabolite ratio: Is the 2-hydroxyestrone to 16α-hydroxyestrone ratio predictive for breast cancer?

Journal: International journal of women's health 20110101

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

Journal: BMC cancer 20110101

Title: Raloxifene and desmethylarzoxifene block estrogen-induced malignant transformation of human breast epithelial cells.

Journal: PloS one 20110101

Title: Redox cycling of catechol estrogens generating apurinic/apyrimidinic sites and 8-oxo-deoxyguanosine via reactive oxygen species differentiates equine and human estrogens.

Journal: Chemical research in toxicology 20100816

Title: Degradation of natural estrogen and identification of the metabolites produced by soil isolates of Rhodococcus sp. and Sphingomonas sp.

Journal: Journal of bioscience and bioengineering 20100601

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

Journal: Talanta 20100415

Title: The 4-hydroxyestrone: Electron emission, formation of secondary metabolites and mechanisms of carcinogenesis.

Journal: Journal of photochemistry and photobiology. B, Biology 20100121

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: 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.

Journal: Breast cancer : basic and clinical research 20100101

Title: Sex steroid metabolism polymorphisms and mammographic density in pre- and early perimenopausal women.

Journal: Breast cancer research : BCR 20090101

Title: Contribution of alpha2-adrenoceptors to the mitogenic effect of catecholestrogen in human breast cancer MCF-7 cells.

Journal: The Journal of steroid biochemistry and molecular biology 20080501

Title: Hydroxylated estrogen metabolites influence the proliferation of cultured human monocytes: possible role in synovial tissue hyperplasia.

Journal: Clinical and experimental rheumatology 20080101

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: Substrate specificity of the human UDP-glucuronosyltransferase UGT2B4 and UGT2B7. Identification of a critical aromatic amino acid residue at position 33.

Journal: The FEBS journal 20070301

Title: In vitro short-term test evaluation of catecholestrogens genotoxicity.

Journal: The Journal of steroid biochemistry and molecular biology 20070101

Title: Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.

Journal: Journal of molecular graphics & modelling 20061101

Title: Potential biomarker for early risk assessment of prostate cancer.

Journal: The Prostate 20061001

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

Journal: Analytical chemistry 20060301

Title: Role of polymorphic human cytochrome P450 enzymes in estrone oxidation.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20060301

Title: Characterization of common UGT1A8, UGT1A9, and UGT2B7 variants with different capacities to inactivate mutagenic 4-hydroxylated metabolites of estradiol and estrone.

Journal: Cancer research 20060101

Title: Development of monoclonal antibodies to 4-hydroxyestrogen-2-N-acetylcysteine conjugates: immunoaffinity and spectroscopic studies.

Journal: Chemical research in toxicology 20051001

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

Journal: Archives of environmental & occupational health 20050101

Title: The effects of steroidal estrogens in ACI rat mammary carcinogenesis: 17beta-estradiol, 2-hydroxyestradiol, 4-hydroxyestradiol, 16alpha-hydroxyestradiol, and 4-hydroxyestrone.

Journal: The Journal of endocrinology 20041001

Title: Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.

Journal: The Journal of biological chemistry 20040702

Title: 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.

Journal: The Journal of steroid biochemistry and molecular biology 20040701

Title: Equine estrogen metabolite 4-hydroxyequilenin induces anchorage-independent growth of human mammary epithelial MCF-10A cells: differential gene expression.

Journal: Mutation research 20040604

Title: Identification of UGT2B9*2 and UGT2B33 isolated from female rhesus monkey liver.

Journal: Archives of biochemistry and biophysics 20040601

Title: Estrogen receptor-independent catechol estrogen binding activity: protein binding studies in wild-type, Estrogen receptor-alpha KO, and aromatase KO mice tissues.

Journal: Biochemistry 20040601

Title: Metabolic inactivation of estrogens in breast tissue by UDP-glucuronosyltransferase enzymes: an overview.

Journal: Breast cancer research : BCR 20040101

Title: Spectral characterization of catechol estrogen quinone (CEQ)-derived DNA adducts and their identification in human breast tissue extract.

Journal: Chemical research in toxicology 20030901

Title: Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms.

Journal: Endocrinology 20030801

Title: Detection of estrogen DNA-adducts in human breast tumor tissue and healthy tissue by combined nano LC-nano ES tandem mass spectrometry.

Journal: Journal of the American Society for Mass Spectrometry 20030501

Title: Endogenous estradiol metabolites stimulate the in vitro proliferation of human osteoblastic cells.

Journal: International journal of clinical pharmacology and therapeutics 20030401

Title: Spectroscopic characterization of the 4-hydroxy catechol estrogen quinones-derived GSH and N-acetylated Cys conjugates.

Journal: Chemical research in toxicology 20030301

Title: Stable isotope dilution high-performance liquid chromatography-electrospray ionization mass spectrometry method for endogenous 2- and 4-hydroxyestrones in human urine.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20021125

Title: Estradiol metabolism and malignant disease.

Journal: Maturitas 20020930

Title: Expression of UGT2B7, a UDP-glucuronosyltransferase implicated in the metabolism of 4-hydroxyestrone and all-trans retinoic acid, in normal human breast parenchyma and in invasive and in situ breast cancers.

Journal: The American journal of pathology 20020401

Title: Catecholestrogen sulfation: possible role in carcinogenesis.

Journal: Biochemical and biophysical research communications 20020329

Title: Equine estrogen metabolite 4-hydroxyequilenin induces DNA damage in the rat mammary tissues: formation of single-strand breaks, apurinic sites, stable adducts, and oxidized bases.

Journal: Chemical research in toxicology 20011201

Title: The ability of four catechol estrogens of 17beta-estradiol and estrone to induce DNA adducts in Syrian hamster embryo fibroblasts.

Journal: Carcinogenesis 20010901

Title: Selective synthesis of 4-methoxyestrogen from 4-hydroxyestrogen.

Journal: Steroids 20010801

Title: In vitro generation of peroxynitrite by 2- and 4-hydroxyestrogens in the presence of nitric oxide.

Journal: Chemical research in toxicology 20010501

Title: Evidence that a metabolite of equine estrogens, 4-hydroxyequilenin, induces cellular transformation in vitro.

Journal: Chemical research in toxicology 20010101

Title: Quantitative determination of 3,3'-diindolylmethane in urine of individuals receiving indole-3-carbinol.

Journal: Nutrition and cancer 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: UGT2B23, a novel uridine diphosphate-glucuronosyltransferase enzyme expressed in steroid target tissues that conjugates androgen and estrogen metabolites.

Journal: Endocrinology 19991201

Title: Characterization of rabbit UDP-glucuronosyltransferase UGT1A7: tertiary amine glucuronidation is catalyzed by UGT1A7 and UGT1A4.

Journal: Archives of biochemistry and biophysics 19970815

Title: Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates.

Journal: Drug metabolism and disposition: the biological fate of chemicals 19940101

Title: cDNA cloning and expression of two new members of the human liver UDP-glucuronosyltransferase 2B subfamily.

Journal: Biochemical and biophysical research communications 19930715

Title: Reinduction of the hypnotic effects of thiopental with NSAIDs by decreasing thiopental plasma protein binding in humans.

Journal: Acta anaesthesiologica Scandinavica 19930401

Title: Complementary deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs.

Journal: The Journal of pharmacology and experimental therapeutics 19930101

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Tags:3131-23-5 Molecular Formula|3131-23-5 MDL|3131-23-5 SMILES|3131-23-5 (8R,9S,13S,14S)-3,4-Dihydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one