2-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=CC(O)=C(O)C=C34)[C@@H]1CC[C@@H]2O

InChI

InChIKey=DILDHNKDVHLEQB-XSSYPUMDSA-N

InChI=1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/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
Determination of estradiol metabolites in human liver microsome by high performance liquid chromatography-electrochemistry detector.	2001 Apr	11742592
2-Hydroxyestradiol attenuates the development of obesity, the metabolic syndrome, and vascular and renal dysfunction in obese ZSF1 rats.	2001 Dec	11714885
Role of cytochrome P450 in estradiol metabolism in vitro.	2001 Feb	11741520
Catecholamines abrogate antimitogenic effects of 2-hydroxyestradiol on human aortic vascular smooth muscle cells.	2001 Nov	11701460
Estrogen metabolism and the diet-cancer connection: rationale for assessing the ratio of urinary hydroxylated estrogen metabolites.	2002 Apr	11991791
Methoxyestradiols mediate estradiol-induced antimitogenesis in human aortic SMCs.	2002 Apr	11967242
Catecholamines block 2-hydroxyestradiol-induced antimitogenesis in mesangial cells.	2002 Apr	11967239
Catechol estrogen formation in liver microsomes from female ACI and Sprague-Dawley rats: comparison of 2- and 4-hydroxylation revisited.	2002 Aug	12151356
Reduction of post injury neointima formation due to 17beta-estradiol and phytoestrogen treatment is not influenced by the pure synthetic estrogen receptor antagonist ICI 182,780 in vitro.	2002 Aug 6	12162794
Role of methoxyestradiols in the growth inhibitory effects of estradiol on human glomerular mesangial cells.	2002 Feb	11882583
Methoxyestradiols mediate the antimitogenic effects of locally applied estradiol on cardiac fibroblast growth.	2002 Feb	11882582
2-methoxyestradiol induces interferon gene expression and apoptosis in osteosarcoma cells.	2002 Feb	11856647
Highly specific anti-estradiol antibodies: structural characterisation and binding diversity.	2002 Jan 25	11812141
Pro-oxidant and antioxidant potential of catecholestrogens against ferrylmyoglobin-induced oxidative stress.	2002 Jul 11	12117560
Estradiol enhances and estriol inhibits the expression of CYP1A1 induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin in a mouse ovarian cancer cell line.	2002 Jul 15	12093619
Catecholestrogen sulfation: possible role in carcinogenesis.	2002 Mar 29	11906176
Reactions of estradiol-2,3-quinone with deoxyribonucleosides: possible insights in the reactivity of estrogen quinones with DNA.	2002 May	12018999
Stimulatory effect of cigarette smoking on the 15 alpha-hydroxylation of estradiol by human term placenta.	2002 May	12011817
Crystal structure of human sex hormone-binding globulin in complex with 2-methoxyestradiol reveals the molecular basis for high affinity interactions with C-2 derivatives of estradiol.	2002 Nov 22	12228253
The redox protein thioredoxin-1 regulates the constitutive and inducible expression of the estrogen metabolizing cytochromes P450 1B1 and 1A1 in MCF-7 human breast cancer cells.	2002 Oct	12376470
Tissue content of hydroxyestrogens in relation to survival of breast cancer patients.	2002 Oct	12374682
The association of breast mitogens with mammographic densities.	2002 Oct 7	12373602
Investigation of the regio- and stereo-selectivity of deoxyguanosine linkage to deuterated 2-hydroxyestradiol by using liquid chromatography/ESI-ion trap mass spectrometry.	2003 Apr	12686483
Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms.	2003 Aug	12865317
Methoxyestradiols mediate the antimitogenic effects of 17beta-estradiol: direct evidence from catechol-O-methyltransferase-knockout mice.	2003 Dec 16	14662705
Methylation of 2-hydroxyestradiol in isolated organs.	2003 Jul	12771046
[Studies on 2-hydroxyestradiol 17-sulfate derived from fetoplacental unit: the antioxidant as a potential defense substance against preeclampsia].	2003 Jun	12822484
Medical hypothesis: hyperhomocysteinemia is a risk factor for estrogen-induced hormonal cancer.	2003 Mar	12579301
Prevention of mammary carcinogenesis by short-term estrogen and progestin treatments.	2004	14680498
A gas chromatography/mass spectrometry assay to measure estradiol, catecholestradiols, and methoxyestradiols in plasma.	2004 Apr	15183691
Catecholamines block the antimitogenic effect of estradiol on human coronary artery smooth muscle cells.	2004 Aug	15292328
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	15276617
In vitro model of mammary estrogen metabolism: structural and kinetic differences between catechol estrogens 2- and 4-hydroxyestradiol.	2004 Sep	15377160
Estradiol metabolites are potent mitogenic substances for human ovarian cancer cells.	2005	16122183
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	16404153
Lycopene and beta-carotene ameliorate catechol estrogen-mediated DNA damage.	2005 Feb	15822859
Estradiol metabolites attenuate renal and cardiovascular injury induced by chronic nitric oxide synthase inhibition.	2005 Jul	15965351
Effects of dioxin on metabolism of estrogens in waste incinerator workers.	2005 Jul-Aug	17214292
Specific binding of 4-hydroxyestradiol to mouse uterine protein: evidence of a physiological role for 4-hydroxyestradiol.	2005 May	15845916
Regulation of CFTR channels by HCO(3)--sensitive soluble adenylyl cyclase in human airway epithelial cells.	2005 Nov	15958523
Estradiol metabolites attenuate monocrotaline-induced pulmonary hypertension in rats.	2005 Oct	16160593
Tyrosinase-catalyzed oxidation of 17beta-estradiol: structure elucidation of the products formed beyond catechol estrogen quinones.	2005 Sep	16167833
Effect of catecholestrogen administration during adriamycin-induced cardiomyopathy in ovariectomized rat.	2005 Sep	16087475
2-Hydroxyestradiol-17beta-induced oocyte maturation in catfish (Heteropneustes fossilis) involves protein kinase C and its interaction with protein phosphatases.	2006 Aug	16730203
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	16411670
Involvement of mitogen-activated protein kinase in 2-hydroxyestradiol-17beta-induced oocyte maturation in the catfish Heteropneustes fossilis and a note on possible interaction with protein phosphatases.	2006 Jul	16554054
Estrogen metabolites and systolic blood pressure in a population-based sample of postmenopausal women.	2006 Mar	16384842
Effects of gonadotrophin in vivo and 2-hydroxyoestradiol-17beta in vitro on follicular steroid hormone profile associated with oocyte maturation in the catfish Heteropneustes fossilis.	2006 May	16648301
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Estrogens, enzyme variants, and breast cancer: a risk model.	2006 Sep	16985022

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:48:17 GMT 2025` Edited by `admin` on `Mon Mar 31 17:48:17 GMT 2025`
Record UNII	AYU2L67YUU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-HYDROXYESTRADIOL

Common Name

English

NSC-61711

Preferred Name

English

ESTRADIOL METABOLITE (2-HYDROXYESTRADIOL)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2181