4-HYDROXYESTRADIOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H24O3
Molecular Weight	288.3814
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=C(O)C(O)=CC=C34)[C@@H]1CC[C@@H]2O

InChI

InChIKey=QOZFCKXEVSGWGS-ZHIYBZGJSA-N

InChI=1S/C18H24O3/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/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C18H24O3
Molecular Weight	288.3814
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Hydroxyestrogens inhibit angiogenesis in swine ovarian follicles.	2008-10	18662972
Catecholestrogens induce oxidative stress and malignant transformation in human endometrial glandular cells: protective effect of catechol-O-methyltransferase.	2008-09-15	18566989
CYP1B1 variants are associated with prostate cancer in non-Hispanic and Hispanic Caucasians.	2008-09	18544568
17-Beta estradiol and hydroxyestradiols interact via the NF-kappa B pathway to elevate cyclooxygenase 2 expression and prostaglandin E2 secretion in human bronchial epithelial cells.	2008-08	18480072
Prevention of estrogen-DNA adduct formation in MCF-10F cells by resveratrol.	2008-07-15	18423413
Leu432Val polymorphism in CYP1B1 as a susceptible factor towards predisposition to primary open-angle glaucoma.	2008-05-08	18483560
Preferential induction of cytochrome P450 1A1 over cytochrome P450 1B1 in human breast epithelial cells following exposure to quercetin.	2008-05	18456490
Phytoestrogens and breast cancer prevention: possible mechanisms of action.	2008-04	18414622
Reduction of estrogen-induced transformation of mouse mammary epithelial cells by N-acetylcysteine.	2008-03	18226522
Soy isoflavones decrease the catechol-O-methyltransferase-mediated inactivation of 4-hydroxyestradiol in cultured MCF-7 cells.	2008-02	18192686
Association of the CYP1B1*3 allele with survival in patients with prostate cancer receiving docetaxel.	2008-01	18187806
Phytoestrogens modulate the expression of 17alpha-estradiol metabolizing enzymes in cultured MCF-7 cells.	2008	18497090
Inhibition of depurinating estrogen-DNA adduct formation by natural compounds.	2007-12	18039013
Etheno-DNA adduct formation in rats gavaged with linoleic acid, oleic acid and coconut oil is organ- and gender specific.	2007-11-01	17521682
Catechol-estrogen modified DNA: a better antigen for cancer autoantibody.	2007-09-01	17632072
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	17668912
Porcine follicular fluids: comparison of solid-phase extraction and matrix solid-phase dispersion for the GC-MS determination of hormones during follicular growth.	2007-07-27	17459644
Cytochrome P450 isoforms catalyze formation of catechol estrogen quinones that react with DNA.	2007-07	17570247
Formation of depurinating N3Adenine and N7Guanine adducts by MCF-10F cells cultured in the presence of 4-hydroxyestradiol.	2007-04-15	17230531
Effects of dioxin on metabolism of estrogens in waste incinerator workers.	2007-01-12	17214292
Regioselective 2-hydroxylation of 17beta-estradiol by rat cytochrome P4501B1.	2006-11-01	16893557
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Potential biomarker for early risk assessment of prostate cancer.	2006-10-01	16894534
Estrogens, enzyme variants, and breast cancer: a risk model.	2006-09	16985022
Catechol estrogen quinones as initiators of breast and other human cancers: implications for biomarkers of susceptibility and cancer prevention.	2006-08	16675129
Comparison of possible carcinogenic estradiol metabolites: effects on proliferation, apoptosis and metastasis of human breast cancer cells.	2006-04-20	16213115
Estradiol and its metabolites 4-hydroxyestradiol and 2-hydroxyestradiol induce mutations in human breast epithelial cells.	2006-04-15	16287077
Health effects in fish of long-term exposure to effluents from wastewater treatment works.	2006-04	16818251
Is there a causal association between genotoxicity and the imposex effect?	2006-04	16818242
Mutagenic activity of 4-hydroxyestradiol, but not 2-hydroxyestradiol, in BB rat2 embryonic cells, and the mutational spectrum of 4-hydroxyestradiol.	2006-03	16544955
Characterization of common UGT1A8, UGT1A9, and UGT2B7 variants with different capacities to inactivate mutagenic 4-hydroxylated metabolites of estradiol and estrone.	2006-01-01	16397224
The greater reactivity of estradiol-3,4-quinone vs estradiol-2,3-quinone with DNA in the formation of depurinating adducts: implications for tumor-initiating activity.	2006-01	16411670
Mitogenic estrogen metabolites alter the expression of 17beta-estradiol-regulated proteins including heat shock proteins in human MCF-7 breast cancer cells.	2005-12-31	16404153
4-Hydroxyestradiol induces oxidative stress and apoptosis in human mammary epithelial cells: possible protection by NF-kappaB and ERK/MAPK.	2005-10-01	15901486
Development of monoclonal antibodies to 4-hydroxyestrogen-2-N-acetylcysteine conjugates: immunoaffinity and spectroscopic studies.	2005-10	16533015
Cytochrome P450-mediated metabolism of estrogens and its regulation in human.	2005-09-28	16112414
Tyrosinase-catalyzed oxidation of 17beta-estradiol: structure elucidation of the products formed beyond catechol estrogen quinones.	2005-09	16167833
Effect of catecholestrogen administration during adriamycin-induced cardiomyopathy in ovariectomized rat.	2005-09	16087475
Estrogenic and genotoxic potential of equol and two hydroxylated metabolites of Daidzein in cultured human Ishikawa cells.	2005-07-28	15993745
Specific binding of 4-hydroxyestradiol to mouse uterine protein: evidence of a physiological role for 4-hydroxyestradiol.	2005-05	15845916
Detection of DNA strand breaks and oxidized DNA bases at the single-cell level resulting from exposure to estradiol and hydroxylated metabolites.	2005-05	15662657
Nitric oxide enhances catechol estrogen-induced oxidative stress in LNCaP cells.	2005-04	16028364
Invasiveness of breast cancer cells MDA-MB-231 through extracellular matrix is increased by the estradiol metabolite 4-hydroxyestradiol.	2005-02-20	15499624
Lycopene and beta-carotene ameliorate catechol estrogen-mediated DNA damage.	2005-02	15822859
Genetic polymorphisms in human SULT1A1 and UGT1A1 genes associate with breast tumor characteristics: a case-series study.	2005	16280036
Estradiol metabolites are potent mitogenic substances for human ovarian cancer cells.	2005	16122183
The effects of steroidal estrogens in ACI rat mammary carcinogenesis: 17beta-estradiol, 2-hydroxyestradiol, 4-hydroxyestradiol, 16alpha-hydroxyestradiol, and 4-hydroxyestrone.	2004-10	15525577
In vitro model of mammary estrogen metabolism: structural and kinetic differences between catechol estrogens 2- and 4-hydroxyestradiol.	2004-09	15377160
Lack of association of CYP1 B1*3 polymorphism and ovarian cancer in a Caucasian population.	2004-07-17	15255550
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	15276617

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:53:51 GMT 2025` Edited by `admin` on `Mon Mar 31 17:53:51 GMT 2025`
Record UNII	C3ZO03450E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1,3,5(10)-ESTRATRIENE-3,4,17.BETA.-TRIOL

Preferred Name

English

4-HYDROXYESTRADIOL

Common Name

English

ESTRADIOL METABOLITE (4-HYDROXYESTRADIOL)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C347