Estrone
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Basic Info
| Common Name | Estrone(F05495) |
| 2D Structure | |
| Description | Estrone, one of the major mammalian estrogens, is an aromatized C18 steroid with a 3-hydroxyl group and a 17-ketone. It is produced in vivo from androstenedione or from testosterone via estradiol. It is produced primarily in the ovaries, placenta, and in peripheral tissues (especially adipose tissue) through conversion of adrostenedione. Estrone may be further metabolized to 16-alpha-hydroxyestrone, which may be reduced to estriol by estradiol dehydrogenase. |
| FRCD ID | F05495 |
| CAS Number | 53-16-7 |
| PubChem CID | 5870 |
| Formula | C18H22O2 |
| IUPAC Name | (8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one |
| InChI Key | DNXHEGUUPJUMQT-CBZIJGRNSA-N |
| InChI | InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1 |
| Canonical SMILES | CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)O |
| Isomeric SMILES | C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O |
| Wikipedia | Estrone |
| Synonyms |
folliculin
estrone
53-16-7
OESTRONE
Theelin
estrovarin
Estrugenone
follicular hormone
Kestrone
Estron
|
| 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 - Hydroxysteroid - 17-oxosteroid - Oxosteroid - Phenanthrene - Tetralin - 1-hydroxy-2-unsubstituted benzenoid - Benzenoid - Ketone - Carbonyl group - Organooxygen compound - Hydrocarbon derivative - Organic oxide - 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 | 270.372 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 418 |
| Monoisotopic Mass | 270.162 |
| Exact Mass | 270.162 |
| XLogP | 3.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 20 |
| Defined Atom Stereocenter Count | 4 |
| 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+ | 0.9529 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8934 |
| P-glycoprotein Substrate | Substrate | 0.6001 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9066 |
| Non-inhibitor | 0.8882 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7300 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7882 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6624 |
| CYP450 2D6 Substrate | Non-substrate | 0.9116 |
| CYP450 3A4 Substrate | Substrate | 0.7290 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9017 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9353 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9599 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8954 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8681 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8711 |
| Inhibitor | 0.5459 | |
| AMES Toxicity | Non AMES toxic | 0.9268 |
| Carcinogens | Non-carcinogens | 0.8917 |
| Fish Toxicity | High FHMT | 0.9902 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9741 |
| Honey Bee Toxicity | High HBT | 0.6917 |
| Biodegradation | Not ready biodegradable | 0.9717 |
| Acute Oral Toxicity | III | 0.7811 |
| Carcinogenicity (Three-class) | Non-required | 0.3609 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.9094 | LogS |
| Caco-2 Permeability | 1.7823 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9267 | LD50, mol/kg |
| Fish Toxicity | -0.2012 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.5378 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Occurrence, impact variables and potential risk of PPCPs and pesticides in adrinking water reservoir and related drinking water treatment plants in theYangtze Estuary. | Environ Sci Process Impacts | 2018 Jul 18 | 29900462 |
| Contaminants of emerging concern in surface waters in Barbados, West Indies. | Environ Monit Assess | 2017 Nov 14 | 29138943 |
| Relationships between POPs, biometrics and circulating steroids in male polarbears (Ursus maritimus) from Svalbard. | Environ Pollut | 2017 Nov | 28710978 |
| 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 |
| Metabonomic analysis of the protective effect of quercetin on the toxicity induced by mixture of organophosphate pesticides in rat urine. | Hum Exp Toxicol | 2017 May | 27251765 |
| Environmental impact of estrogens on human, animal and plant life: A criticalreview. | Environ Int | 2017 Feb | 28040262 |
| Contamination with bacterial zoonotic pathogen genes in U.S. streams influenced by varying types of animal agriculture. | Sci Total Environ | 2016 Sep 1 | 27139306 |
| Simultaneous determination of estrogens and progestogens in honey using highperformance liquid chromatography-tandem mass spectrometry. | J Pharm Biomed Anal | 2016 Nov 30 | 27616008 |
| Simultaneous attenuation of pharmaceuticals, organic matter, and nutrients inwastewater effluent through managed aquifer recharge: Batch and column studies. | Chemosphere | 2016 Jan | 26559901 |
| Effect of dietary estrogens from bovine milk on blood hormone levels andreproductive organs in mice. | J Dairy Sci | 2016 Aug | 27265162 |
| 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 |
| Hydroxylated polychlorinated biphenyls decrease circulating steroids in femalepolar bears (Ursus maritimus). | Environ Res | 2015 Apr | 25725300 |
| A preliminary risk assessment of potential exposure to naturally occurringestrogens from Beijing (China) market milk products. | Food Chem Toxicol | 2014 Sep | 24910459 |
| High cortisol and cortisone levels are associated with breast milk dioxin concentrations in Vietnamese women. | Eur J Endocrinol | 2014 Jan | 24123093 |
| Effects of single pesticides and binary pesticide mixtures on estrone production in H295R cells. | Arch Toxicol | 2013 Dec | 23708528 |
| 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 |
| Bisphenol A and estrone-induced developmental effects in early chick embryos. | Environ Toxicol | 2012 Jan | 21702074 |
| Uptake of natural and synthetic estrogens by maize seedlings. | J Agric Food Chem | 2012 Aug 29 | 22816790 |
| Catechol metabolites of zeranol and 17β-estradiol: a comparative in vitro study on the induction of oxidative DNA damage and methylation by catechol-O-methyltransferase. | Toxicol Lett | 2012 Apr 5 | 22285433 |
| Effect of a low fat versus a low carbohydrate weight loss dietary intervention onbiomarkers of long term survival in breast cancer patients ('CHOICE'): studyprotocol. | BMC Cancer | 2011 Jul 6 | 21733177 |
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:
- 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:
- 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:
- 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 ]