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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24O3
Molecular Weight 288.382
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-HYDROXYESTRADIOL

SMILES

C[C@@]12CC[C@]3([H])c4ccc(c(c4CC[C@@]3([H])[C@]2([H])CC[C@]1([H])O)O)O

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 288.382
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Lack of association of CYP1 B1*3 polymorphism and ovarian cancer in a Caucasian population.
2004 Apr-Jun
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 Jul
The effects of steroidal estrogens in ACI rat mammary carcinogenesis: 17beta-estradiol, 2-hydroxyestradiol, 4-hydroxyestradiol, 16alpha-hydroxyestradiol, and 4-hydroxyestrone.
2004 Oct
Phytochemicals inhibit catechol-O-methyltransferase activity in cytosolic fractions from healthy human mammary tissues: implications for catechol estrogen-induced DNA damage.
2004 Oct
In vitro model of mammary estrogen metabolism: structural and kinetic differences between catechol estrogens 2- and 4-hydroxyestradiol.
2004 Sep
Genetic polymorphisms in human SULT1A1 and UGT1A1 genes associate with breast tumor characteristics: a case-series study.
2005
Estradiol metabolites are potent mitogenic substances for human ovarian cancer cells.
2005
Nitric oxide enhances catechol estrogen-induced oxidative stress in LNCaP cells.
2005 Apr
Mitogenic estrogen metabolites alter the expression of 17beta-estradiol-regulated proteins including heat shock proteins in human MCF-7 breast cancer cells.
2005 Dec 31
Lycopene and beta-carotene ameliorate catechol estrogen-mediated DNA damage.
2005 Feb
Invasiveness of breast cancer cells MDA-MB-231 through extracellular matrix is increased by the estradiol metabolite 4-hydroxyestradiol.
2005 Feb 20
Estrogenic and genotoxic potential of equol and two hydroxylated metabolites of Daidzein in cultured human Ishikawa cells.
2005 Jul 28
Effects of dioxin on metabolism of estrogens in waste incinerator workers.
2005 Jul-Aug
Specific binding of 4-hydroxyestradiol to mouse uterine protein: evidence of a physiological role for 4-hydroxyestradiol.
2005 May
Development of monoclonal antibodies to 4-hydroxyestrogen-2-N-acetylcysteine conjugates: immunoaffinity and spectroscopic studies.
2005 Oct
4-Hydroxyestradiol induces oxidative stress and apoptosis in human mammary epithelial cells: possible protection by NF-kappaB and ERK/MAPK.
2005 Oct 1
Tyrosinase-catalyzed oxidation of 17beta-estradiol: structure elucidation of the products formed beyond catechol estrogen quinones.
2005 Sep
Effect of catecholestrogen administration during adriamycin-induced cardiomyopathy in ovariectomized rat.
2005 Sep
Cytochrome P450-mediated metabolism of estrogens and its regulation in human.
2005 Sep 28
Health effects in fish of long-term exposure to effluents from wastewater treatment works.
2006 Apr
Is there a causal association between genotoxicity and the imposex effect?
2006 Apr
Estradiol and its metabolites 4-hydroxyestradiol and 2-hydroxyestradiol induce mutations in human breast epithelial cells.
2006 Apr 15
Comparison of possible carcinogenic estradiol metabolites: effects on proliferation, apoptosis and metastasis of human breast cancer cells.
2006 Apr 20
Catechol estrogen quinones as initiators of breast and other human cancers: implications for biomarkers of susceptibility and cancer prevention.
2006 Aug
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 Jan
Characterization of common UGT1A8, UGT1A9, and UGT2B7 variants with different capacities to inactivate mutagenic 4-hydroxylated metabolites of estradiol and estrone.
2006 Jan 1
Mutagenic activity of 4-hydroxyestradiol, but not 2-hydroxyestradiol, in BB rat2 embryonic cells, and the mutational spectrum of 4-hydroxyestradiol.
2006 Mar
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Regioselective 2-hydroxylation of 17beta-estradiol by rat cytochrome P4501B1.
2006 Nov 1
Potential biomarker for early risk assessment of prostate cancer.
2006 Oct 1
Estrogens, enzyme variants, and breast cancer: a risk model.
2006 Sep
Formation of depurinating N3Adenine and N7Guanine adducts by MCF-10F cells cultured in the presence of 4-hydroxyestradiol.
2007 Apr 15
Inhibition of depurinating estrogen-DNA adduct formation by natural compounds.
2007 Dec
Cytochrome P450 isoforms catalyze formation of catechol estrogen quinones that react with DNA.
2007 Jul
Porcine follicular fluids: comparison of solid-phase extraction and matrix solid-phase dispersion for the GC-MS determination of hormones during follicular growth.
2007 Jul 27
Etheno-DNA adduct formation in rats gavaged with linoleic acid, oleic acid and coconut oil is organ- and gender specific.
2007 Nov 1
HPLC for stress-free screening of potential prostate cancer marker catechol estrogens in urine using a diamond-electrode electrochemical and a fluorescence detector.
2007 Sep
Catechol-estrogen modified DNA: a better antigen for cancer autoantibody.
2007 Sep 1
Phytoestrogens modulate the expression of 17alpha-estradiol metabolizing enzymes in cultured MCF-7 cells.
2008
Phytoestrogens and breast cancer prevention: possible mechanisms of action.
2008 Apr
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 Aug
Soy isoflavones decrease the catechol-O-methyltransferase-mediated inactivation of 4-hydroxyestradiol in cultured MCF-7 cells.
2008 Feb
Association of the CYP1B1*3 allele with survival in patients with prostate cancer receiving docetaxel.
2008 Jan
Prevention of estrogen-DNA adduct formation in MCF-10F cells by resveratrol.
2008 Jul 15
Reduction of estrogen-induced transformation of mouse mammary epithelial cells by N-acetylcysteine.
2008 Mar
Preferential induction of cytochrome P450 1A1 over cytochrome P450 1B1 in human breast epithelial cells following exposure to quercetin.
2008 May
Leu432Val polymorphism in CYP1B1 as a susceptible factor towards predisposition to primary open-angle glaucoma.
2008 May 8
Hydroxyestrogens inhibit angiogenesis in swine ovarian follicles.
2008 Oct
CYP1B1 variants are associated with prostate cancer in non-Hispanic and Hispanic Caucasians.
2008 Sep
Catecholestrogens induce oxidative stress and malignant transformation in human endometrial glandular cells: protective effect of catechol-O-methyltransferase.
2008 Sep 15
Patents

Patents

Substance Class Chemical
Created
by admin
on Sat Jun 26 04:49:42 UTC 2021
Edited
by admin
on Sat Jun 26 04:49:42 UTC 2021
Record UNII
C3ZO03450E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-HYDROXYESTRADIOL
Common Name English
1,3,5(10)-ESTRATRIENE-3,4,17.BETA.-TRIOL
Systematic Name English
ESTRADIOL METABOLITE (4-HYDROXYESTRADIOL)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C347
Created by admin on Sat Jun 26 04:49:42 UTC 2021 , Edited by admin on Sat Jun 26 04:49:42 UTC 2021
Code System Code Type Description
FDA UNII
C3ZO03450E
Created by admin on Sat Jun 26 04:49:42 UTC 2021 , Edited by admin on Sat Jun 26 04:49:42 UTC 2021
PRIMARY
PUBCHEM
5282360
Created by admin on Sat Jun 26 04:49:42 UTC 2021 , Edited by admin on Sat Jun 26 04:49:42 UTC 2021
PRIMARY
CAS
5976-61-4
Created by admin on Sat Jun 26 04:49:42 UTC 2021 , Edited by admin on Sat Jun 26 04:49:42 UTC 2021
PRIMARY
EPA CompTox
5976-61-4
Created by admin on Sat Jun 26 04:49:42 UTC 2021 , Edited by admin on Sat Jun 26 04:49:42 UTC 2021
PRIMARY
NCI_THESAURUS
C120473
Created by admin on Sat Jun 26 04:49:42 UTC 2021 , Edited by admin on Sat Jun 26 04:49:42 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> METABOLITE