Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H22O3 |
| Molecular Weight | 286.3655 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=C(O)C(O)=CC=C34)[C@@H]1CCC2=O
InChI
InChIKey=XQZVQQZZOVBNLU-QDTBLXIISA-N
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
| Molecular Formula | C18H22O3 |
| Molecular Weight | 286.3655 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11054642
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11054642
4-Hydroxyestrone (4-OHE1) is a carcinogenic metabolite originating from 17beta-estradiol (17β-E2) hormone. 4-OHE1 was a partial estrogen agonist on cancellous bone turnover, similar to 17β-E2, is able to emit electrons from its excited singlet state. The quantum yield is nearly the same like this of 17β-E2 and decreases with increasing substrate concentration, but enhances with temperature. The 4-OHE1 transient derived from the electron ejection process is leading to the formation of a secondary metabolite by reaction with the present C2H4OH radical. This fact indicates, that depending on the life habits of a person, a variety of metabolites can be formed, also such initiating cancer.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| NRF2/long noncoding RNA ROR signaling regulates mammary stem cell expansion and protects against estrogen genotoxicity. | 2014-11-07 |
|
| 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. | 2010-12-16 |
|
| Redox cycling of catechol estrogens generating apurinic/apyrimidinic sites and 8-oxo-deoxyguanosine via reactive oxygen species differentiates equine and human estrogens. | 2010-08-16 |
|
| Comparison of estrogens and estrogen metabolites in human breast tissue and urine. | 2010-08-02 |
|
| Degradation of natural estrogen and identification of the metabolites produced by soil isolates of Rhodococcus sp. and Sphingomonas sp. | 2010-06 |
|
| The normal breast microenvironment of premenopausal women differentially influences the behavior of breast cancer cells in vitro and in vivo. | 2010-05-21 |
|
| Simultaneous determination of eight estrogens and their metabolites in serum using liquid chromatography with electrochemical detection. | 2010-04-15 |
|
| The 4-hydroxyestrone: Electron emission, formation of secondary metabolites and mechanisms of carcinogenesis. | 2010-01-21 |
|
| Sex steroid metabolism polymorphisms and mammographic density in pre- and early perimenopausal women. | 2009 |
|
| Hydroxylated estrogen metabolites influence the proliferation of cultured human monocytes: possible role in synovial tissue hyperplasia. | 2008-11-27 |
|
| Contribution of alpha2-adrenoceptors to the mitogenic effect of catecholestrogen in human breast cancer MCF-7 cells. | 2008-05 |
|
| 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. | 2007-12-01 |
|
| HPLC for stress-free screening of potential prostate cancer marker catechol estrogens in urine using a diamond-electrode electrochemical and a fluorescence detector. | 2007-09 |
|
| Effects of a catechol-O-methyltransferase inhibitor on catechol estrogen-induced cellular transformation, chromosome aberrations and apoptosis in Syrian hamster embryo cells. | 2007-04-15 |
|
| Substrate specificity of the human UDP-glucuronosyltransferase UGT2B4 and UGT2B7. Identification of a critical aromatic amino acid residue at position 33. | 2007-03 |
|
| Effects of dioxin on metabolism of estrogens in waste incinerator workers. | 2007-01-12 |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
|
| Potential biomarker for early risk assessment of prostate cancer. | 2006-10-01 |
|
| In vitro short-term test evaluation of catecholestrogens genotoxicity. | 2006-06-12 |
|
| Analysis of fifteen estrogen metabolites using packed column supercritical fluid chromatography-mass spectrometry. | 2006-03-01 |
|
| Role of polymorphic human cytochrome P450 enzymes in estrone oxidation. | 2006-03 |
|
| Characterization of common UGT1A8, UGT1A9, and UGT2B7 variants with different capacities to inactivate mutagenic 4-hydroxylated metabolites of estradiol and estrone. | 2006-01-01 |
|
| Development of monoclonal antibodies to 4-hydroxyestrogen-2-N-acetylcysteine conjugates: immunoaffinity and spectroscopic studies. | 2005-10 |
|
| The effects of steroidal estrogens in ACI rat mammary carcinogenesis: 17beta-estradiol, 2-hydroxyestradiol, 4-hydroxyestradiol, 16alpha-hydroxyestradiol, and 4-hydroxyestrone. | 2004-10 |
|
| Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation. | 2004-07-02 |
|
| 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. | 2004-07 |
|
| Equine estrogen metabolite 4-hydroxyequilenin induces anchorage-independent growth of human mammary epithelial MCF-10A cells: differential gene expression. | 2004-06-04 |
|
| Estrogen receptor-independent catechol estrogen binding activity: protein binding studies in wild-type, Estrogen receptor-alpha KO, and aromatase KO mice tissues. | 2004-06-01 |
|
| Identification of UGT2B9*2 and UGT2B33 isolated from female rhesus monkey liver. | 2004-06-01 |
|
| Metabolic inactivation of estrogens in breast tissue by UDP-glucuronosyltransferase enzymes: an overview. | 2004 |
|
| Spectral characterization of catechol estrogen quinone (CEQ)-derived DNA adducts and their identification in human breast tissue extract. | 2003-09 |
|
| Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. | 2003-08 |
|
| Detection of estrogen DNA-adducts in human breast tumor tissue and healthy tissue by combined nano LC-nano ES tandem mass spectrometry. | 2003-05 |
|
| Endogenous estradiol metabolites stimulate the in vitro proliferation of human osteoblastic cells. | 2003-04 |
|
| Spectroscopic characterization of the 4-hydroxy catechol estrogen quinones-derived GSH and N-acetylated Cys conjugates. | 2003-03 |
|
| Estradiol metabolism and malignant disease. | 2002-09-30 |
|
| 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. | 2002-04 |
|
| Catecholestrogen sulfation: possible role in carcinogenesis. | 2002-03-29 |
|
| 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. | 2001-12 |
|
| The ability of four catechol estrogens of 17beta-estradiol and estrone to induce DNA adducts in Syrian hamster embryo fibroblasts. | 2001-09 |
|
| Selective synthesis of 4-methoxyestrogen from 4-hydroxyestrogen. | 2001-08 |
|
| In vitro generation of peroxynitrite by 2- and 4-hydroxyestrogens in the presence of nitric oxide. | 2001-05 |
|
| Evidence that a metabolite of equine estrogens, 4-hydroxyequilenin, induces cellular transformation in vitro. | 2001-01 |
|
| Quantitative determination of 3,3'-diindolylmethane in urine of individuals receiving indole-3-carbinol. | 2001 |
|
| 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. | 2000-04-01 |
|
| Characterization of rabbit UDP-glucuronosyltransferase UGT1A7: tertiary amine glucuronidation is catalyzed by UGT1A7 and UGT1A4. | 1997-08-15 |
|
| Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates. | 1994-09-01 |
|
| cDNA cloning and expression of two new members of the human liver UDP-glucuronosyltransferase 2B subfamily. | 1993-07-15 |
|
| Reinduction of the hypnotic effects of thiopental with NSAIDs by decreasing thiopental plasma protein binding in humans. | 1993-04 |
|
| Complementary deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs. | 1993-01 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:35:33 GMT 2025
by
admin
on
Mon Mar 31 17:35:33 GMT 2025
|
| Record UNII |
3MN57C55S2
|
| Record Status |
Validated (UNII)
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| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
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Preferred Name | English | ||
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Common Name | English | ||
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Systematic Name | English |
| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C2181
Created by
admin on Mon Mar 31 17:35:33 GMT 2025 , Edited by admin on Mon Mar 31 17:35:33 GMT 2025
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| Code System | Code | Type | Description | ||
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4-Hydroxyestrone
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C114469
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3MN57C55S2
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9971251
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C026418
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3131-23-5
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DTXSID00904312
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87602
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