Estradiol
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Basic Info
| Common Name | Estradiol(F05482) |
| 2D Structure | |
| Description | Generally refers to the 17-beta-isomer of estradiol, an aromatized C18 steroid with hydroxyl group at 3-beta- and 17-beta-position. Estradiol-17-beta is the most potent form of mammalian estrogenic steroids. In humans, it is produced primarily by the cyclic ovaries and the placenta. It is also produced by the adipose tissue of men and postmenopausal women. The 17-alpha-isomer of estradiol binds weakly to estrogen receptors (receptors, estrogen) and exhibits little estrogenic activity in estrogen-responsive tissues. Various isomers can be synthesized. |
| FRCD ID | F05482 |
| CAS Number | 50-28-2 |
| PubChem CID | 5757 |
| Formula | C18H24O2 |
| IUPAC Name | (8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol |
| InChI Key | VOXZDWNPVJITMN-ZBRFXRBCSA-N |
| InChI | InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1 |
| Canonical SMILES | CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4)O |
| Isomeric SMILES | C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)O |
| Wikipedia | Estradiol |
| Synonyms |
beta-Estradiol
Oestradiol
estradiol
17beta-Estradiol
50-28-2
Dihydrofolliculin
Estrace
Ovocyclin
progynon
Dihydrotheelin
|
| Classifies |
Illegal Additives
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Steroids and steroid derivatives |
| Subclass | Estrane steroids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Estrogens and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic homopolycyclic compounds |
| Substituents | Estrogen-skeleton - 17-hydroxysteroid - Hydroxysteroid - 3-hydroxysteroid - Phenanthrene - Tetralin - 1-hydroxy-2-unsubstituted benzenoid - Benzenoid - Cyclic alcohol - Secondary alcohol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aromatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 272.388 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 382 |
| Monoisotopic Mass | 272.178 |
| Exact Mass | 272.178 |
| XLogP | 4 |
| Formal Charge | 0 |
| Heavy Atom Count | 20 |
| Defined Atom Stereocenter Count | 5 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8917 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8867 |
| P-glycoprotein Substrate | Substrate | 0.7058 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9147 |
| Non-inhibitor | 0.9403 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8008 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7239 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7270 |
| CYP450 2D6 Substrate | Non-substrate | 0.8010 |
| CYP450 3A4 Substrate | Substrate | 0.7132 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9106 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9390 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9574 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9025 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7887 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8647 |
| Inhibitor | 0.6624 | |
| AMES Toxicity | Non AMES toxic | 0.9198 |
| Carcinogens | Non-carcinogens | 0.8829 |
| Fish Toxicity | High FHMT | 0.9823 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9902 |
| Honey Bee Toxicity | High HBT | 0.6720 |
| Biodegradation | Not ready biodegradable | 0.9746 |
| Acute Oral Toxicity | III | 0.8307 |
| Carcinogenicity (Three-class) | Danger | 0.5801 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.7778 | LogS |
| Caco-2 Permeability | 1.3905 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2272 | LD50, mol/kg |
| Fish Toxicity | 0.2691 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.7916 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Impact of low-dose chronic exposure to bisphenol A and its analogue bisphenol B, bisphenol F and bisphenol S on hypothalamo-pituitary-testicular activities in adult rats: A focus on the possible hormonal mode of action. | Food Chem Toxicol | 2018 Nov | 30120946 |
| Endocrine disrupting potency of organic pollutant mixtures isolated fromcommercial fish oil evaluated in yeast-based bioassays. | PLoS One | 2018 May 22 | 29787602 |
| Combined treatment with Dendrobium candidum and black tea extract promotesosteoprotective activity in ovariectomized estrogen deficient rats and osteoclastformation. | Life Sci | 2018 May 1 | 29544757 |
| The effects of the botanical estrogen, isoliquiritigenin on delayed spatialalternation. | Neurotoxicol Teratol | 2018 Mar - Apr | 29408209 |
| Effect of 17β-estradiol on milk production, hormone secretion, and mammary gland gene expression in dairy cows. | J Dairy Sci | 2018 Mar | 29274969 |
| Efficacy of using previously used controlled internal drug release (CIDR) insert on the reproductive performance, hormone profiles and economic measures of sheep. | Reprod Domest Anim | 2018 Jun 12 | 29892981 |
| Prenatal exposure to zearalenone disrupts reproductive potential and development via hormone-related genes in male rats. | Food Chem Toxicol | 2018 Jun | 29627501 |
| An overview of Jatropha curcas meal-induced productive and reproductive toxicity in Japanese quail: Potential mechanisms and heat detoxification. | Theriogenology | 2018 Jun | 29554603 |
| Molecular and biochemical evidence on the role of Zearalenone in rat polycysticovary. | Toxicon | 2018 Jul 25 | 30055260 |
| Fluorescent microarray for multiplexed quantification of environmental contaminants in seawater samples. | Talanta | 2018 Jul 1 | 29674074 |
| Ameliorative effect of ginseng extract on phthalate and bisphenol A reprotoxicity during pregnancy in rats. | Environ Sci Pollut Res Int | 2018 Jul | 29777495 |
| Licorice root components mimic estrogens in an object location task but not anobject recognition task. | Horm Behav | 2018 Jul | 29920269 |
| Consequences of a double hit of stress during the perinatal period and midlife infemale rats: Mismatch or cumulative effect? | Psychoneuroendocrinology | 2018 Jul | 29689422 |
| Egg deposition of maternal testosterone is primarily controlled by thepreovulatory peak of luteinizing hormone in Japanese quail. | Gen Comp Endocrinol | 2018 Jan 15 | 28495270 |
| Prenatal exposure to di(2-ethylhexyl) phthalate disrupts ovarian function in atransgenerational manner in female mice. | Biol Reprod | 2018 Jan 1 | 29165555 |
| Prenatal dioxin exposure estimated from dioxins in breast milk and sex hormone levels in umbilical cord blood in Vietnamese newborn infants. | Sci Total Environ | 2018 Feb 15 | 29751436 |
| Reproductive and endocrine-disrupting toxicity of Microcystis aeruginosa in female zebrafish. | Chemosphere | 2018 Feb | 29112878 |
| Accumulation of steroid hormones in the eggshells of Japanese quail (Coturnixcoturnix japonica). | Gen Comp Endocrinol | 2018 Apr 1 | 29174486 |
| Bovine teeth as a novel matrix for the control of the food chain: liquidchromatography-tandem mass spectrometry detection of treatments withprednisolone, dexamethasone, estradiol, nandrolone and seven β2-agonists. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2017Jan | 27845609 |
| The effect of HT-2 toxin on ovarian steroidogenesis and its response to IGF-I, leptin and ghrelin in rabbits. | Physiol Res | 2017 Sep 22 | 28937260 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Monoamine transmembrane transporter activity
- Specific Function:
- Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A3
- Uniprot ID:
- Q01959
- Molecular Weight:
- 68494.255 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial membrane potential and cellular respiration upon stimulation by progesterone.
- Gene Name:
- PGR
- Uniprot ID:
- P06401
- Molecular Weight:
- 98979.96 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
- Gene Name:
- CYP2C18
- Uniprot ID:
- P33260
- Molecular Weight:
- 55710.075 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth. Involved in chromatin remodeling. May play a negative role in adipogenesis through the regulation of lipolytic and antilipogenic genes expression.
- Gene Name:
- NR3C1
- Uniprot ID:
- P04150
- Molecular Weight:
- 85658.57 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]