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517-09-9,MFCD00003619
Catalog No.:AA00D8NO

517-09-9 | EQUILENIN

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1mg
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25mg
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00D8NO
Chemical Name:
EQUILENIN
CAS Number:
517-09-9
Molecular Formula:
C18H18O2
Molecular Weight:
266.3343
MDL Number:
MFCD00003619
SMILES:
Oc1ccc2c(c1)ccc1c2CC[C@]2([C@H]1CCC2=O)C
Properties
Computed Properties
 
Complexity:
418  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
XLogP3:
3.5  

Literature

Title: Gene expression analyses of vitellogenin, choriogenin and estrogen receptor subtypes in the livers of male medaka (Oryzias latipes) exposed to equine estrogens.

Journal: Journal of applied toxicology : JAT 20161101

Title: Endocrine-disrupting potentials of equine estrogens equilin, equilenin, and their metabolites, in the medaka Oryzias latipes: in silico and DNA microarray studies.

Journal: Journal of applied toxicology : JAT 20150901

Title: The naphthol selective estrogen receptor modulator (SERM), LY2066948, is oxidized to an o-quinone analogous to the naphthol equine estrogen, equilenin.

Journal: Chemico-biological interactions 20120305

Title: Specificity of human aldo-keto reductases, NAD(P)H:quinone oxidoreductase, and carbonyl reductases to redox-cycle polycyclic aromatic hydrocarbon diones and 4-hydroxyequilenin-o-quinone.

Journal: Chemical research in toxicology 20111219

Title: Redox cycling of catechol estrogens generating apurinic/apyrimidinic sites and 8-oxo-deoxyguanosine via reactive oxygen species differentiates equine and human estrogens.

Journal: Chemical research in toxicology 20100816

Title: Unexpected hormonal activity of a catechol equine estrogen metabolite reveals reversible glutathione conjugation.

Journal: Chemical research in toxicology 20100816

Title: In this issue. Estrogen double whammy.

Journal: Chemical research in toxicology 20100816

Title: Solvation response along the reaction coordinate in the active site of ketosteroid isomerase.

Journal: Journal of the American Chemical Society 20100512

Title: Potent and selective steroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 7, an enzyme that catalyzes the reduction of the key hormones estrone and dihydrotestosterone.

Journal: Journal of medicinal chemistry 20091210

Title: Binding balls: fast detection of binding sites using a property of spherical Fourier transform.

Journal: Journal of computational biology : a journal of computational molecular cell biology 20091101

Title: Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: I. Optimization of separation protocol.

Journal: Journal of chromatography. A 20091030

Title: NMR and computational studies of stereoisomeric equine estrogen-derived DNA cytidine adducts in oligonucleotide duplexes: opposite orientations of diastereomeric forms.

Journal: Biochemistry 20090804

Title: Development of a liquid chromatography electrospray ionization tandem mass spectrometry method for analysis of stable 4-hydroxyequilenin-DNA adducts in human breast cancer cells.

Journal: Chemical research in toxicology 20090601

Title: In the mix: equine estrogens used in HRT.

Journal: Environmental science & technology 20090515

Title: Estrogen Receptor {alpha} Enhances the Rate of Oxidative DNA Damage by Targeting an Equine Estrogen Catechol Metabolite to the Nucleus.

Journal: The Journal of biological chemistry 20090327

Title: Determination of absolute configurations of 4-hydroxyequilenin-cytosine and -adenine adducts by optical rotatory dispersion, electronic circular dichroism, density functional theory calculations, and mass spectrometry.

Journal: Chemical research in toxicology 20080901

Title: Conformational properties of equilenin-DNA adducts: stereoisomer and base effects.

Journal: Chemical research in toxicology 20080501

Title: Oxidative DNA damage in XPC-knockout and its wild mice treated with equine estrogen.

Journal: Chemical research in toxicology 20080501

Title: Analysis of steroidal estrogens as pyridine-3-sulfonyl derivatives by liquid chromatography electrospray tandem mass spectrometry.

Journal: Analytical biochemistry 20080401

Title: Estrogenic activity of the equine estrogen metabolite, 4-methoxyequilenin.

Journal: Advances in experimental medicine and biology 20080101

Title: Activation of estrogen receptor-mediated gene transcription by the equine estrogen metabolite, 4-methoxyequilenin, in human breast cancer cells.

Journal: Endocrinology 20071001

Title: Mechanism of translesion synthesis past an equine estrogen-DNA adduct by Y-family DNA polymerases.

Journal: Journal of molecular biology 20070831

Title: 4-hydroxyequilenin-adenine lesions in DNA duplexes: stereochemistry, damage site, and structure.

Journal: Biochemistry 20070109

Title: Response of human mammary epithelial cells to DNA damage induced by 4-hydroxyequilenin: Lack of p53-mediated G1 arrest.

Journal: Chemico-biological interactions 20060710

Title: Synthesis and in vitro antibacterial activity of novel heterocyclic derivatives of 18-nor-equilenin.

Journal: European journal of medicinal chemistry 20060701

Title: Induction of cytochrome P450-1A by the equine estrogen equilenin, a new endogenous aryl hydrocarbon receptor ligand.

Journal: The Journal of steroid biochemistry and molecular biology 20060101

Title: Characterization of two new variants of human catechol O-methyltransferase in vitro.

Journal: Cancer letters 20051208

Title: Equilenin-derived DNA adducts to cytosine in DNA duplexes: structures and thermodynamics.

Journal: Biochemistry 20051108

Title: Base selectivity and effects of sequence and DNA secondary structure on the formation of covalent adducts derived from the equine estrogen metabolite 4-hydroxyequilenin.

Journal: Chemical research in toxicology 20051101

Title: Functional and structural comparisons of cysteine residues in the Val108 wild type and Met108 variant of human soluble catechol O-methyltransferase.

Journal: Chemico-biological interactions 20050415

Title: Small exterior hydrophobic cluster contributes to conformational stability and steroid binding in ketosteroid isomerase from Pseudomonas putida biotype B.

Journal: The FEBS journal 20050401

Title: Altered apoptotic response in MCF 10A cells treated with the equine estrogen metabolite, 4-hydroxyequilenin.

Journal: Toxicology letters 20041230

Title: Translesion synthesis past equine estrogen-derived 2'-deoxycytidine DNA adducts by human DNA polymerases eta and kappa.

Journal: Biochemistry 20040907

Title: [Development of novel type of transition metal-catalyzed cascade reactions utilizing small ring systems and the applications].

Journal: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20040701

Title: Equine estrogen metabolite 4-hydroxyequilenin induces anchorage-independent growth of human mammary epithelial MCF-10A cells: differential gene expression.

Journal: Mutation research 20040604

Title: Equine catechol estrogen 4-hydroxyequilenin is a more potent inhibitor of the variant form of catechol-O-methyltransferase.

Journal: Chemical research in toxicology 20040401

Title: Complete 1H and 13C NMR spectral assignment of 17-hydroxy epimeric sterols with planar A or A and B rings.

Journal: Magnetic resonance in chemistry : MRC 20040301

Title: The conserved cis-Pro39 residue plays a crucial role in the proper positioning of the catalytic base Asp38 in ketosteroid isomerase from Comamonas testosteroni.

Journal: The Biochemical journal 20031015

Title: Equine estrogens differentially prevent neuronal cell death induced by glutamate.

Journal: Journal of the Society for Gynecologic Investigation 20030701

Title: Contribution of conserved amino acids at the dimeric interface to the conformational stability and the structural integrity of the active site in ketosteroid isomerase from Pseudomonas putida biotype B.

Journal: Journal of biochemistry 20030701

Title: Conformations of stereoisomeric base adducts to 4-hydroxyequilenin.

Journal: Chemical research in toxicology 20030601

Title: Effect of halogenated substituents on the metabolism and estrogenic effects of the equine estrogen, equilenin.

Journal: Chemical research in toxicology 20030601

Title: Catechol estrogen 4-hydroxyequilenin is a substrate and an inhibitor of catechol-O-methyltransferase.

Journal: Chemical research in toxicology 20030501

Title: Investigations into the biosynthetic pathways for classical and ring B-unsaturated oestrogens in equine placental preparations and allantochorionic tissues.

Journal: The Journal of steroid biochemistry and molecular biology 20021101

Title: Inhibition of cellular enzymes by equine catechol estrogens in human breast cancer cells: specificity for glutathione S-transferase P1-1.

Journal: Chemical research in toxicology 20020701

Title: Conformational analysis of a 4-hydroxyequilenin Guanine adduct using density functional theory.

Journal: Chemical research in toxicology 20020501

Title: Oxidative DNA damage induced by equine estrogen metabolites: role of estrogen receptor alpha.

Journal: Chemical research in toxicology 20020401

Title: Cytotoxicity of estradiol, equilin, equilenin, and their derivatives on Chinese hamster V79 cells.

Journal: Drug and chemical toxicology 20020201

Title: Equine estrogen metabolite 4-hydroxyequilenin induces DNA damage in the rat mammary tissues: formation of single-strand breaks, apurinic sites, stable adducts, and oxidized bases.

Journal: Chemical research in toxicology 20011201

Title: Regulation of human apolipoprotein A-I gene expression by equine estrogens.

Journal: Journal of lipid research 20011101

Title: Reversed-phase liquid chromatographic method for estrogen determination in equine biological samples.

Journal: Journal of chromatographic science 20010901

Title: Metabolism of equilenin in MCF-7 and MDA-MB-231 human breast cancer cells.

Journal: Chemical research in toxicology 20010501

Title: Folding mechanism of ketosteroid isomerase from Comamonas testosteroni.

Journal: Biochemistry 20010424

Title: Structural and functional consequences of inactivation of human glutathione S-transferase P1-1 mediated by the catechol metabolite of equine estrogens, 4-hydroxyequilenin.

Journal: Biochemistry 20010417

Title: Equilenin-2'-deoxynucleoside adducts: analysis with nano-liquid chromatography coupled to nano-electrospray tandem mass spectrometry.

Journal: Journal of mass spectrometry : JMS 20010301

Title: Evidence that a metabolite of equine estrogens, 4-hydroxyequilenin, induces cellular transformation in vitro.

Journal: Chemical research in toxicology 20010101

Title: Simultaneous azo-coupling method for an estrogen sulfatase in human tissues.

Journal: Histochemistry 19830101

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