Record Information |
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Version | 2.0 |
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Creation Date | 2014-09-11 05:14:33 UTC |
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Update Date | 2014-12-24 20:26:56 UTC |
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Accession Number | T3D4746 |
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Identification |
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Common Name | Estrone |
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Class | Small Molecule |
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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. |
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Compound Type | - Animal Toxin
- Anti-Menopausal Agent
- Drug
- Estrogen
- Food Toxin
- Metabolite
- Natural Compound
- Organic Compound
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Chemical Structure | |
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Synonyms | Synonym | (+)-Estrone | 1,3,5(10)-Estratrien-3-ol-17-one | 3-Hydroxy-1,3,5(10)-estratrien-17-one | 3-Hydroxy-17-keto-estra-1,3,5-triene | 3-Hydroxyestra-1,3,5(10)-trien-17-one | 3-Hydroxyestra-1,3,5(10)-triene-17-one | 3-Hydroxyoestra-1,3,5(10)-trien-17-one | D1,3,5(10)-Estratrien-3-ol-17-one | Estrona | Estronum | follicular hormone | Folliculin | Oestrone |
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Chemical Formula | C18H22O2 |
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Average Molecular Mass | 270.366 g/mol |
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Monoisotopic Mass | 270.162 g/mol |
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CAS Registry Number | 53-16-7 |
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IUPAC Name | (1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one |
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Traditional Name | (1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one |
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SMILES | [H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O)C=C3CC[C@@]21[H] |
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InChI Identifier | 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 |
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InChI Key | InChIKey=DNXHEGUUPJUMQT-CBZIJGRNSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Estrane steroids |
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Direct Parent | Estrogens and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homopolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | - Cytoplasm
- Endoplasmic reticulum
- Extracellular
- Membrane
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Biofluid Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 260.2°C | Boiling Point | 154°C | Solubility | 30 mg/L (at 25°C) | LogP | 3.13 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-05ox-3951000000-8bc438f505b3cf49b21f | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) | splash10-003u-4942000000-a72ea34d85d9d524c247 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) | splash10-0019-8931000000-aad9803af812c7c40f53 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00di-2940000000-2d417e7ecb4a8b87b817 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00di-0980000000-5b293db89a0f2efeb784 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-05ox-3951000000-8bc438f505b3cf49b21f | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-003u-4942000000-a72ea34d85d9d524c247 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0019-8931000000-aad9803af812c7c40f53 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0adl-1970000000-871531490fb22b8fe12f | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-009t-1093000000-a8d755d13e3b819514c8 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00di-0190000000-071e67516e11357ff64e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a4j-4910000000-20e059a7c508ba492af3 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-067i-9700000000-9ff5214f08822f238fa9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-00di-2940000000-3b9744c27d6a3d2eff6e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0ukc-2690000000-7afb48e267c7b334213b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-014i-0690000000-a76244de959b06ec896e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a59-0910000000-4a1bc1cbc90c3e5281e6 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a59-0900000000-0830d4ad43804976f508 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0udi-0390000000-41440e74b3f0b5f365d7 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0udi-0390000000-fdc0255246e3a9013d0a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0a59-2910000000-fc5173d435c3c7fc603c | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-00di-0390000000-25cecb1c4785e7bffd56 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0pb9-0930000000-d947dbed0baa600d21a1 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0190000000-38b40bed2e5c895d292f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0pc0-0920000000-391eea72f6dda0eaa3c2 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 45V, Negative | splash10-0159-0900000000-350b322964f2315bf505 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-014i-0690000000-277d92852a8f35c82f11 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0002-0910000000-db57c4d24dab84acfe27 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 60V, Negative | splash10-014i-0900000000-61f2965f743c194d4628 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0190000000-64cf013a5b0ad5e8bf56 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00fr-0590000000-40418c285df2157226dc | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fb9-6980000000-724c68b368fbe3d38f5e | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0090000000-6778bd7122813b501c1e | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0090000000-0f2e0b96bc30b346c581 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0f9i-1090000000-9ccbd9f351dd1f8e52cb | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-00di-2930000000-c99df908474247066a2b | JSpectraViewer | MoNA | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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Toxicity Profile |
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Route of Exposure | 43% |
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Mechanism of Toxicity | Estrogens enter the cells of responsive tissues (e.g. female organs, breasts, hypothalamus, pituitary) where they interact with estrogen receptors. Hormone-bound estrogen receptors dimerize, translocate to the nucleus of cells and bind to estrogen response elements (ERE) of genes. Binding to ERE alters the transcription rate of affected genes. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) release from the anterior pituitary. |
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Metabolism | Hepatic.
Half Life: 19 hours |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | For management of perimenopausal and postmenopausal symptoms. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Symptoms of overdose include nausea and vomiting. Estrogen related side effects include nausea, breast tenderness, fluid retention and edema, headaches and/or migraines, chloasma and poor contact lens fit. Estrogen hormone deficiency is associated with breakthrough bleeding, hypomenorrhea, irritability, depression and menopausal symptoms. Withdrawal bleeds may occur in females. |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB00655 |
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HMDB ID | HMDB00145 |
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PubChem Compound ID | 5870 |
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ChEMBL ID | CHEMBL1405 |
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ChemSpider ID | 5660 |
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KEGG ID | C00468 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 17263 |
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BioCyc ID | ESTRONE |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | J3Z |
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ACToR ID | Not Available |
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Wikipedia Link | Estrone |
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References |
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Synthesis Reference | Seiichi Takano, Kunio Ogasawara, “Method for producing (+)-estrone derivatives.” U.S. Patent US5424462, issued January, 1965. |
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MSDS | Link |
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General References | - Miyoshi Y, Tanji Y, Taguchi T, Tamaki Y, Noguchi S: Association of serum estrone levels with estrogen receptor-positive breast cancer risk in postmenopausal Japanese women. Clin Cancer Res. 2003 Jun;9(6):2229-33. [12796390 ]
- Kajta M, Lason W, Bien E, Marszal M: Neuroprotective effects of estrone on NMDA-induced toxicity in primary cultures of rat cortical neurons are independent of estrogen receptors. Pol J Pharmacol. 2002 Nov-Dec;54(6):727-9. [12866733 ]
- Czernik PJ, Little JM, Barone GW, Raufman JP, Radominska-Pandya A: Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa. Drug Metab Dispos. 2000 Oct;28(10):1210-6. [10997942 ]
- Pfeiffer E, Graf E, Gerstner S, Metzler M: Stimulation of estradiol glucuronidation: a protective mechanism against estradiol-mediated carcinogenesis? Mol Nutr Food Res. 2006 Apr;50(4-5):385-9. [16598814 ]
- Kuhl H, Wiegratz I: Can 19-nortestosterone derivatives be aromatized in the liver of adult humans? Are there clinical implications? Climacteric. 2007 Aug;10(4):344-53. [17653961 ]
- Parker WH, Broder MS, Liu Z, Shoupe D, Farquhar C, Berek JS: Ovarian conservation at the time of hysterectomy for benign disease. Clin Obstet Gynecol. 2007 Jun;50(2):354-61. [17513923 ]
- Stanway SJ, Delavault P, Purohit A, Woo LW, Thurieau C, Potter BV, Reed MJ: Steroid sulfatase: a new target for the endocrine therapy of breast cancer. Oncologist. 2007 Apr;12(4):370-4. [17470679 ]
- Ito K: Hormone replacement therapy and cancers: the biological roles of estrogen and progestin in tumorigenesis are different between the endometrium and breast. Tohoku J Exp Med. 2007 May;212(1):1-12. [17464097 ]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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