Home Other Building Blocks 4-HYDROXYESTRONE

4-HYDROXYESTRONE

CAS No.:
3131-23-5
Catalog Number:
AG00C80X
Molecular Formula:
C18H22O3
Molecular Weight:
286.3655
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Product Description
Catalog Number:
AG00C80X
Chemical Name:
4-HYDROXYESTRONE
CAS Number:
3131-23-5
Molecular Formula:
C18H22O3
Molecular Weight:
286.3655
MDL Number:
MFCD00079358
IUPAC Name:
(8R,9S,13S,14S)-3,4-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
InChI:
InChI=1S/C18H22O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,19,21H,2-3,5,7-9H2,1H3/t11-,12-,14+,18+/m1/s1
InChI Key:
XQZVQQZZOVBNLU-QDTBLXIISA-N
SMILES:
O=C1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2O)O
UNII:
3MN57C55S2
Properties
Complexity:
448  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
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:
2.8  
Literature
Title Journal
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Gender is a risk factor for lung cancer. Medical hypotheses 20110301
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The 4-hydroxyestrone: Electron emission, formation of secondary metabolites and mechanisms of carcinogenesis. Journal of photochemistry and photobiology. B, Biology 20100121
The normal breast microenvironment of premenopausal women differentially influences the behavior of breast cancer cells in vitro and in vivo. BMC medicine 20100101
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HPLC for stress-free screening of potential prostate cancer marker catechol estrogens in urine using a diamond-electrode electrochemical and a fluorescence detector. Journal of separation science 20070901
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Potential biomarker for early risk assessment of prostate cancer. The Prostate 20061001
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Characterization of common UGT1A8, UGT1A9, and UGT2B7 variants with different capacities to inactivate mutagenic 4-hydroxylated metabolites of estradiol and estrone. Cancer research 20060101
Development of monoclonal antibodies to 4-hydroxyestrogen-2-N-acetylcysteine conjugates: immunoaffinity and spectroscopic studies. Chemical research in toxicology 20051001
Effects of dioxin on metabolism of estrogens in waste incinerator workers. Archives of environmental & occupational health 20050101
The effects of steroidal estrogens in ACI rat mammary carcinogenesis: 17beta-estradiol, 2-hydroxyestradiol, 4-hydroxyestradiol, 16alpha-hydroxyestradiol, and 4-hydroxyestrone. The Journal of endocrinology 20041001
Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation. The Journal of biological chemistry 20040702
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
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Identification of UGT2B9*2 and UGT2B33 isolated from female rhesus monkey liver. Archives of biochemistry and biophysics 20040601
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Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology 20030801
Detection of estrogen DNA-adducts in human breast tumor tissue and healthy tissue by combined nano LC-nano ES tandem mass spectrometry. Journal of the American Society for Mass Spectrometry 20030501
Endogenous estradiol metabolites stimulate the in vitro proliferation of human osteoblastic cells. International journal of clinical pharmacology and therapeutics 20030401
Spectroscopic characterization of the 4-hydroxy catechol estrogen quinones-derived GSH and N-acetylated Cys conjugates. Chemical research in toxicology 20030301
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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. The American journal of pathology 20020401
Catecholestrogen sulfation: possible role in carcinogenesis. Biochemical and biophysical research communications 20020329
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. Chemical research in toxicology 20011201
The ability of four catechol estrogens of 17beta-estradiol and estrone to induce DNA adducts in Syrian hamster embryo fibroblasts. Carcinogenesis 20010901
Selective synthesis of 4-methoxyestrogen from 4-hydroxyestrogen. Steroids 20010801
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Evidence that a metabolite of equine estrogens, 4-hydroxyequilenin, induces cellular transformation in vitro. Chemical research in toxicology 20010101
Quantitative determination of 3,3'-diindolylmethane in urine of individuals receiving indole-3-carbinol. Nutrition and cancer 20010101
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