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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 2-HYDROXYESTRADIOL

SMILES

C[C@@]12CC[C@@]3([H])[C@@]([H])(CCc4cc(c(cc43)O)O)[C@]2([H])CC[C@]1([H])O

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

Approval Year

PubMed

PubMed

TitleDatePubMed
Comparison of ex vivo inhibitory effect between 2-hydroxyestradiol and its 17-sulfate on rat hepatic microsomal lipid peroxidation.
2003 Aug
Methoxyestradiols mediate the antimitogenic effects of 17beta-estradiol: direct evidence from catechol-O-methyltransferase-knockout mice.
2003 Dec 16
Neuroprotective and neurotoxic effects of estrogens.
2003 Nov 14
Activation of matrix metalloproteinase-2 and -9 by 2- and 4-hydroxyestradiol.
2003 Oct
Prevention of mammary carcinogenesis by short-term estrogen and progestin treatments.
2004
A gas chromatography/mass spectrometry assay to measure estradiol, catecholestradiols, and methoxyestradiols in plasma.
2004 Apr
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
Catecholamines block the antimitogenic effect of estradiol on human coronary artery smooth muscle cells.
2004 Aug
Microsomal estrogen metabolism in channel catfish.
2004 Aug-Dec
2-Hydroxyestradiol induces oxidative DNA damage and apoptosis in human mammary epithelial cells.
2004 Dec
Estradiol metabolites as isoform-specific inhibitors of human glutathione S-transferases.
2004 Dec 30
The functional UGT1A1 promoter polymorphism decreases endometrial cancer risk.
2004 Feb 1
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
2-hydroxyestradiol is a prodrug of 2-methoxyestradiol.
2004 Jun
Concentration-dependent mitogenic and antiproliferative actions of 2-methoxyestradiol in estrogen receptor-positive human breast cancer cells.
2004 Mar
Differential regulation of estrogen receptor subtypes alpha and beta in human aortic smooth muscle cells by oligonucleotides and estradiol.
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
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
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
Cytochromes 1A1/1B1- and catechol-O-methyltransferase-derived metabolites mediate estradiol-induced antimitogenesis in human cardiac fibroblast.
2005 Jan
Estradiol metabolites attenuate renal and cardiovascular injury induced by chronic nitric oxide synthase inhibition.
2005 Jul
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
Detection of DNA strand breaks and oxidized DNA bases at the single-cell level resulting from exposure to estradiol and hydroxylated metabolites.
2005 May
Regulation of CFTR channels by HCO(3)--sensitive soluble adenylyl cyclase in human airway epithelial cells.
2005 Nov
Estradiol metabolites attenuate monocrotaline-induced pulmonary hypertension in rats.
2005 Oct
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
Health effects in fish of long-term exposure to effluents from wastewater treatment works.
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
2-Hydroxyestradiol-17beta-induced oocyte maturation in catfish (Heteropneustes fossilis) involves protein kinase C and its interaction with protein phosphatases.
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
2-Hydroxyestradiol-17beta-induced oocyte maturation: involvement of cAMP-protein kinase A and okadaic acid-sensitive protein phosphatases, and their interplay in oocyte maturation in the catfish Heteropneustes fossilis.
2006 Jul
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
Relative effects of estradiol-17beta (E2), catecholestrogens and clomiphene citrate on in vitro oocyte maturation in the catfish Heteropneustes fossilis (Bloch) and E2 inhibition of 2-hydroxyestradiol-induced maturation.
2006 Jun
Mutagenic activity of 4-hydroxyestradiol, but not 2-hydroxyestradiol, in BB rat2 embryonic cells, and the mutational spectrum of 4-hydroxyestradiol.
2006 Mar
Estrogen metabolites and systolic blood pressure in a population-based sample of postmenopausal women.
2006 Mar
Analysis of fifteen estrogen metabolites using packed column supercritical fluid chromatography-mass spectrometry.
2006 Mar 1
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
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
2-methoxyestradiol inhibits differentiation and is cytotoxic to osteoclasts.
2006 Oct 1
Estrogens, enzyme variants, and breast cancer: a risk model.
2006 Sep
Inhibition of the human liver microsomal and human cytochrome P450 1A2 and 3A4 metabolism of estradiol by deployment-related and other chemicals.
2006 Sep
Variants in estrogen metabolism and biosynthesis genes and urinary estrogen metabolites in women with a family history of breast cancer.
2007 Mar
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:17:07 UTC 2021
Edited
by admin
on Sat Jun 26 14:17:07 UTC 2021
Record UNII
AYU2L67YUU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2-HYDROXYESTRADIOL
Common Name English
ESTRADIOL METABOLITE (2-HYDROXYESTRADIOL)
Common Name English
NSC-61711
Code English
Classification Tree Code System Code
NCI_THESAURUS C2181
Created by admin on Sat Jun 26 14:17:08 UTC 2021 , Edited by admin on Sat Jun 26 14:17:08 UTC 2021
Code System Code Type Description
DRUG BANK
DB07706
Created by admin on Sat Jun 26 14:17:08 UTC 2021 , Edited by admin on Sat Jun 26 14:17:08 UTC 2021
PRIMARY
FDA UNII
AYU2L67YUU
Created by admin on Sat Jun 26 14:17:08 UTC 2021 , Edited by admin on Sat Jun 26 14:17:08 UTC 2021
PRIMARY
MESH
C001390
Created by admin on Sat Jun 26 14:17:08 UTC 2021 , Edited by admin on Sat Jun 26 14:17:08 UTC 2021
PRIMARY
EPA CompTox
362-05-0
Created by admin on Sat Jun 26 14:17:08 UTC 2021 , Edited by admin on Sat Jun 26 14:17:08 UTC 2021
PRIMARY
NCI_THESAURUS
C120474
Created by admin on Sat Jun 26 14:17:08 UTC 2021 , Edited by admin on Sat Jun 26 14:17:08 UTC 2021
PRIMARY
WIKIPEDIA
2-Hydroxyestradiol
Created by admin on Sat Jun 26 14:17:08 UTC 2021 , Edited by admin on Sat Jun 26 14:17:08 UTC 2021
PRIMARY
PUBCHEM
247304
Created by admin on Sat Jun 26 14:17:08 UTC 2021 , Edited by admin on Sat Jun 26 14:17:08 UTC 2021
PRIMARY
CAS
362-05-0
Created by admin on Sat Jun 26 14:17:08 UTC 2021 , Edited by admin on Sat Jun 26 14:17:08 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> METABOLITE