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
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
| 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 |
|---|---|---|
| Variants in estrogen metabolism and biosynthesis genes and urinary estrogen metabolites in women with a family history of breast cancer. | 2007-03 |
|
| Effects of dioxin on metabolism of estrogens in waste incinerator workers. | 2007-01-12 |
|
| Regioselective 2-hydroxylation of 17beta-estradiol by rat cytochrome P4501B1. | 2006-11-01 |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
|
| 2-methoxyestradiol inhibits differentiation and is cytotoxic to osteoclasts. | 2006-10-01 |
|
| Estrogens, enzyme variants, and breast cancer: a risk model. | 2006-09 |
|
| Inhibition of the human liver microsomal and human cytochrome P450 1A2 and 3A4 metabolism of estradiol by deployment-related and other chemicals. | 2006-09 |
|
| 2-Hydroxyestradiol-17beta-induced oocyte maturation in catfish (Heteropneustes fossilis) involves protein kinase C and its interaction with protein phosphatases. | 2006-08 |
|
| 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. | 2006-07 |
|
| 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. | 2006-07 |
|
| 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. | 2006-06 |
|
| 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. | 2006-05 |
|
| Comparison of possible carcinogenic estradiol metabolites: effects on proliferation, apoptosis and metastasis of human breast cancer cells. | 2006-04-20 |
|
| Estradiol and its metabolites 4-hydroxyestradiol and 2-hydroxyestradiol induce mutations in human breast epithelial cells. | 2006-04-15 |
|
| Health effects in fish of long-term exposure to effluents from wastewater treatment works. | 2006-04 |
|
| Analysis of fifteen estrogen metabolites using packed column supercritical fluid chromatography-mass spectrometry. | 2006-03-01 |
|
| Mutagenic activity of 4-hydroxyestradiol, but not 2-hydroxyestradiol, in BB rat2 embryonic cells, and the mutational spectrum of 4-hydroxyestradiol. | 2006-03 |
|
| Estrogen metabolites and systolic blood pressure in a population-based sample of postmenopausal women. | 2006-03 |
|
| 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 |
|
| 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 |
|
| Regulation of CFTR channels by HCO(3)--sensitive soluble adenylyl cyclase in human airway epithelial cells. | 2005-11 |
|
| Estradiol metabolites attenuate monocrotaline-induced pulmonary hypertension in rats. | 2005-10 |
|
| Tyrosinase-catalyzed oxidation of 17beta-estradiol: structure elucidation of the products formed beyond catechol estrogen quinones. | 2005-09 |
|
| Effect of catecholestrogen administration during adriamycin-induced cardiomyopathy in ovariectomized rat. | 2005-09 |
|
| Estradiol metabolites attenuate renal and cardiovascular injury induced by chronic nitric oxide synthase inhibition. | 2005-07 |
|
| Specific binding of 4-hydroxyestradiol to mouse uterine protein: evidence of a physiological role for 4-hydroxyestradiol. | 2005-05 |
|
| Detection of DNA strand breaks and oxidized DNA bases at the single-cell level resulting from exposure to estradiol and hydroxylated metabolites. | 2005-05 |
|
| Lycopene and beta-carotene ameliorate catechol estrogen-mediated DNA damage. | 2005-02 |
|
| Cytochromes 1A1/1B1- and catechol-O-methyltransferase-derived metabolites mediate estradiol-induced antimitogenesis in human cardiac fibroblast. | 2005-01 |
|
| 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 |
|
| Estradiol metabolites as isoform-specific inhibitors of human glutathione S-transferases. | 2004-12-30 |
|
| 2-Hydroxyestradiol induces oxidative DNA damage and apoptosis in human mammary epithelial cells. | 2004-12 |
|
| The effects of steroidal estrogens in ACI rat mammary carcinogenesis: 17beta-estradiol, 2-hydroxyestradiol, 4-hydroxyestradiol, 16alpha-hydroxyestradiol, and 4-hydroxyestrone. | 2004-10 |
|
| Resveratrol inhibits TCDD-induced expression of CYP1A1 and CYP1B1 and catechol estrogen-mediated oxidative DNA damage in cultured human mammary epithelial cells. | 2004-10 |
|
| In vitro model of mammary estrogen metabolism: structural and kinetic differences between catechol estrogens 2- and 4-hydroxyestradiol. | 2004-09 |
|
| Catecholamines block the antimitogenic effect of estradiol on human coronary artery smooth muscle cells. | 2004-08 |
|
| 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 |
|
| Microsomal estrogen metabolism in channel catfish. | 2004-06-05 |
|
| 2-hydroxyestradiol is a prodrug of 2-methoxyestradiol. | 2004-06 |
|
| Differential regulation of estrogen receptor subtypes alpha and beta in human aortic smooth muscle cells by oligonucleotides and estradiol. | 2004-05 |
|
| 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. | 2004-04-01 |
|
| A gas chromatography/mass spectrometry assay to measure estradiol, catecholestradiols, and methoxyestradiols in plasma. | 2004-04 |
|
| Concentration-dependent mitogenic and antiproliferative actions of 2-methoxyestradiol in estrogen receptor-positive human breast cancer cells. | 2004-03 |
|
| The functional UGT1A1 promoter polymorphism decreases endometrial cancer risk. | 2004-02-01 |
|
| Prevention of mammary carcinogenesis by short-term estrogen and progestin treatments. | 2004 |
|
| Methoxyestradiols mediate the antimitogenic effects of 17beta-estradiol: direct evidence from catechol-O-methyltransferase-knockout mice. | 2003-12-16 |
|
| Neuroprotective and neurotoxic effects of estrogens. | 2003-11-14 |
|
| Activation of matrix metalloproteinase-2 and -9 by 2- and 4-hydroxyestradiol. | 2003-10 |
|
| Comparison of ex vivo inhibitory effect between 2-hydroxyestradiol and its 17-sulfate on rat hepatic microsomal lipid peroxidation. | 2003-08 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:48:17 GMT 2025
by
admin
on
Mon Mar 31 17:48:17 GMT 2025
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| Record UNII |
AYU2L67YUU
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| Record Status |
Validated (UNII)
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| Record Version |
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-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
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Common Name | English | ||
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Preferred Name | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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NCI_THESAURUS |
C2181
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admin on Mon Mar 31 17:48:17 GMT 2025 , Edited by admin on Mon Mar 31 17:48:17 GMT 2025
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| Code System | Code | Type | Description | ||
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DB07706
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61711
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AYU2L67YUU
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C001390
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DTXSID3022372
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C120474
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2-Hydroxyestradiol
Created by
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247304
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362-05-0
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> METABOLITE |
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