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
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C(O)=C(O)C=C4
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
| 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 |
|---|---|---|
| Increased estrogen formation and estrogen to androgen ratio in the synovial fluid of patients with rheumatoid arthritis. | 2003 Dec |
|
| Sequential action of phase I and II enzymes cytochrome p450 1B1 and glutathione S-transferase P1 in mammary estrogen metabolism. | 2003 Dec 1 |
|
| Effect of frying-meat emission particulate on 17beta-estradiol 2- and 4-hydroxylation in human lung adenocarcinoma CL5 cells. | 2003 Jun 27 |
|
| Spectroscopic characterization of the 4-hydroxy catechol estrogen quinones-derived GSH and N-acetylated Cys conjugates. | 2003 Mar |
|
| Activation of matrix metalloproteinase-2 and -9 by 2- and 4-hydroxyestradiol. | 2003 Oct |
|
| Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003 Oct |
|
| Prevention of mammary carcinogenesis by short-term estrogen and progestin treatments. | 2004 |
|
| 4-Hydroxy estradiol but not 2-hydroxy estradiol induces expression of hypoxia-inducible factor 1alpha and vascular endothelial growth factor A through phosphatidylinositol 3-kinase/Akt/FRAP pathway in OVCAR-3 and A2780-CP70 human ovarian carcinoma cells. | 2004 Apr 1 |
|
| Metabolism and DNA binding studies of 4-hydroxyestradiol and estradiol-3,4-quinone in vitro and in female ACI rat mammary gland in vivo. | 2004 Feb |
|
| Strong inhibitory effects of common tea catechins and bioflavonoids on the O-methylation of catechol estrogens catalyzed by human liver cytosolic catechol-O-methyltransferase. | 2004 May |
|
| The effects of steroidal estrogens in ACI rat mammary carcinogenesis: 17beta-estradiol, 2-hydroxyestradiol, 4-hydroxyestradiol, 16alpha-hydroxyestradiol, and 4-hydroxyestrone. | 2004 Oct |
|
| Resveratrol inhibits TCDD-induced expression of CYP1A1 and CYP1B1 and catechol estrogen-mediated oxidative DNA damage in cultured human mammary epithelial cells. | 2004 Oct |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Catecholestrogens induce oxidative stress and malignant transformation in human endometrial glandular cells: protective effect of catechol-O-methyltransferase. | 2008 Sep 15 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:19:05 GMT 2023
by
admin
on
Fri Dec 15 15:19:05 GMT 2023
|
| Record UNII |
C3ZO03450E
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C347
Created by
admin on Fri Dec 15 15:19:05 GMT 2023 , Edited by admin on Fri Dec 15 15:19:05 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
C3ZO03450E
Created by
admin on Fri Dec 15 15:19:05 GMT 2023 , Edited by admin on Fri Dec 15 15:19:05 GMT 2023
|
PRIMARY | |||
|
62845
Created by
admin on Fri Dec 15 15:19:05 GMT 2023 , Edited by admin on Fri Dec 15 15:19:05 GMT 2023
|
PRIMARY | |||
|
5282360
Created by
admin on Fri Dec 15 15:19:05 GMT 2023 , Edited by admin on Fri Dec 15 15:19:05 GMT 2023
|
PRIMARY | |||
|
4-Hydroxyestradiol
Created by
admin on Fri Dec 15 15:19:05 GMT 2023 , Edited by admin on Fri Dec 15 15:19:05 GMT 2023
|
PRIMARY | |||
|
5976-61-4
Created by
admin on Fri Dec 15 15:19:05 GMT 2023 , Edited by admin on Fri Dec 15 15:19:05 GMT 2023
|
PRIMARY | |||
|
DTXSID3022374
Created by
admin on Fri Dec 15 15:19:05 GMT 2023 , Edited by admin on Fri Dec 15 15:19:05 GMT 2023
|
PRIMARY | |||
|
C120473
Created by
admin on Fri Dec 15 15:19:05 GMT 2023 , Edited by admin on Fri Dec 15 15:19:05 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> METABOLITE |
|
