Estriol
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Basic Info
| Common Name | Estriol(F05514) |
| 2D Structure | |
| Description | A hydroxylated metabolite of estradiol or estrone that has a hydroxyl group at C3-beta, 16-alpha, and 17-beta position. Estriol is a major urinary estrogen. During pregnancy, large amount of estriol is produced by the placenta. Isomers with inversion of the hydroxyl group or groups are called epiestriol. Though estriol is used as part of the primarily North American phenomenon of bioidentical hormone replacement therapy, it is not approved for use by the FDA or Health Canada. It is however available in the United States by prescription filled only by compounding pharmacies. It has also been approved and marketed throughout Europe and Asia for approximately 40 years for the treatment of post-menopausal hot flashes. |
| FRCD ID | F05514 |
| CAS Number | 50-27-1 |
| PubChem CID | 5756 |
| Formula | C18H24O3 |
| IUPAC Name | (8R,9S,13S,14S,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol |
| InChI Key | PROQIPRRNZUXQM-ZXXIGWHRSA-N |
| InChI | InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1 |
| Canonical SMILES | CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O |
| Isomeric SMILES | C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)O |
| Wikipedia | Estriol |
| Synonyms |
50-27-1
estriol
Oestriol
Estratriol
Ovestin
Ovestrion
Trihydroxyestrin
Destriol
Tridestrin
Aacifemine
|
| Classifies |
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 - 3-hydroxysteroid - 17-hydroxysteroid - 16-hydroxysteroid - 16-alpha-hydroxysteroid - Hydroxysteroid - Phenanthrene - Tetralin - 1-hydroxy-2-unsubstituted benzenoid - Benzenoid - Cyclic alcohol - Secondary alcohol - 1,2-diol - Polyol - Organooxygen compound - Hydrocarbon derivative - Alcohol - Organic oxygen compound - 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 | 288.387 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| Complexity | 411 |
| Monoisotopic Mass | 288.173 |
| Exact Mass | 288.173 |
| XLogP | 2.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 21 |
| Defined Atom Stereocenter Count | 6 |
| 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+ | 0.7057 |
| Human Intestinal Absorption | HIA+ | 0.9966 |
| Caco-2 Permeability | Caco2+ | 0.7591 |
| P-glycoprotein Substrate | Substrate | 0.7862 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9208 |
| Non-inhibitor | 0.9805 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8619 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7869 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7536 |
| CYP450 2D6 Substrate | Non-substrate | 0.7993 |
| CYP450 3A4 Substrate | Substrate | 0.6892 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6618 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9399 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9619 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7086 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8932 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9152 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9480 |
| Inhibitor | 0.7684 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.9147 |
| Fish Toxicity | High FHMT | 0.9940 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9972 |
| Honey Bee Toxicity | High HBT | 0.6452 |
| Biodegradation | Not ready biodegradable | 0.9811 |
| Acute Oral Toxicity | III | 0.5947 |
| Carcinogenicity (Three-class) | Danger | 0.3846 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.8878 | LogS |
| Caco-2 Permeability | 0.7160 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9758 | LD50, mol/kg |
| Fish Toxicity | 0.5279 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.7032 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Multiresidue determination of estrogens in different dairy products by ultra-high-performance liquid chromatography triple quadrupole mass spectrometry. | J Chromatogr A | 2017 May 5 | 28363417 |
| Modifications of Western-type diet regarding protein, fat and sucrose levels asmodulators of steroid metabolism and activity in liver. | J Steroid Biochem Mol Biol | 2017 Jan | 27471150 |
| Environmental impact of estrogens on human, animal and plant life: A criticalreview. | Environ Int | 2017 Feb | 28040262 |
| Determination of naturally occurring estrogenic hormones in cow's and riverbuffalo's meat by HPLC-FLD method. | J Food Drug Anal | 2016 Jul | 28911549 |
| A first screening and risk assessment of pharmaceuticals and additives inpersonal care products in waste water, sludge, recipient water and sediment from Faroe Islands, Iceland and Greenland. | Sci Total Environ | 2016 Aug 15 | 27092417 |
| Qualitative/Chemical Analyses of Ankaferd Hemostat and Its Antioxidant Content inSynthetic Gastric Fluids. | Biomed Res Int | 2016 | 26925418 |
| Development of a method for the analysis of hormones and pharmaceuticals inearthworms by quick, easy, cheap, effective, rugged and safe (QuEChERS)extraction followed by liquid chromatography-tandem mass spectrometry (LC-MS/MS). | Anal Bioanal Chem | 2015 Oct | 26302963 |
| Evaluation of the combination of a dispersive liquid-liquid microextraction method with micellar electrokinetic chromatography coupled to mass spectrometry for the determination of estrogenic compounds in milk and yogurt. | Electrophoresis | 2015 Feb | 25394185 |
| A preliminary risk assessment of potential exposure to naturally occurringestrogens from Beijing (China) market milk products. | Food Chem Toxicol | 2014 Sep | 24910459 |
| [Estrogens determination of livestock dung based on UE-SPE-HPLC/FLD]. | Ying Yong Sheng Tai Xue Bao | 2013 Nov | 24564161 |
| Synthesis of molecularly imprinted polymer using attapulgite as matrix byultrasonic irradiation for simultaneous on-line solid phase extraction and highperformance liquid chromatography determination of four estrogens. | J Chromatogr A | 2012 Mar 16 | 22318004 |
| Probiotics for the treatment of bacterial vaginosis. | Cochrane Database Syst Rev | 2009 Oct 7 | 19821358 |
| Degradation of estrogenic hormones in a silt loam soil. | J Agric Food Chem | 2008 Oct 8 | 18778070 |
| A gas chromatographic/mass spectrometric screening, confirmation, andquantification method for estrogenic compounds. | Biomed Environ Mass Spectrom | 1988 Jan 1 | 3349206 |
Targets
- 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:
- 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:
- 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 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 ]