Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2018-02-21 20:56:59 UTC |
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HMDB ID | HMDB0000145 |
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Secondary Accession Numbers | - HMDB0004449
- HMDB00145
- HMDB04449
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Metabolite Identification |
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Common Name | Estrone |
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Description | Estrone is a major mammalian estrogen. The conversion of the natural C19 steroids, testosterone and androstenedione into estrone is dependent on a complex key reaction catalyzed by the cytochrome P450 aromatase (EC 1.14.14.1, unspecific monooxygenase), which is expressed in many tissues of the adult human (e.g. ovary, fat tissue), but not in the liver. The ovaries after menopause continue to produce androstenedione and testosterone in significant amounts and these androgens are converted in fat, muscle, and skin into estrone. When women between the ages of 45 and 64 years have prophylactic oophorectomy (when hysterectomy is performed for benign disease to prevent the development of ovarian cancer), evidence suggests that oophorectomy increases the subsequent risk of coronary heart disease (CHD) and osteoporosis. Whereas 14,000 women die of ovarian cancer every year nearly 490,000 women die of heart disease and 48,000 women die within 1 year after hip fracture. Therefore, the decision to perform prophylactic oophorectomy should be approached with great caution for the majority of women who are at low risk of developing ovarian cancer. Steroid sulfatase (EC 3.1.6.2, STS) hydrolyzes steroid sulfates, such as estrone sulfate to estrone which can be converted to steroids with potent estrogenic properties, that is, estradiol; STS activity is much higher in breast tumors and high levels of STS mRNA expression in tumors are associated with a poor prognosis. The biological roles of estrogens in tumorigenesis are certainly different between the endometrium and breast, although both are considered "estrogen-dependent tissues". 17beta-hydroxysteroid dehydrogenases (EC 1.1.1.62, 17-HSDs) are enzymes involved in the formation of active sex steroids. estrone is interconverted by two enzymes 17-HSD types. Type 1 converts estrone to estradiol and Type 2 catalyzes the reverse reaction. (PMID: 17653961 , 17513923 , 17470679 , 17464097 ). |
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Structure | |
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Synonyms | Value | Source |
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3-Hydroxy-1,3,5(10)-estratrien-17-one | ChEBI | Follicular hormone | ChEBI | Folliculin | ChEBI | Oestrone | ChEBI | (+)-Estrone | HMDB | 1,3,5(10)-Estratrien-3-ol-17-one | HMDB | 3-Hydroxy-17-keto-estra-1,3,5-triene | HMDB | 3-Hydroxyestra-1,3,5(10)-trien-17-one | HMDB | 3-Hydroxyestra-1,3,5(10)-triene-17-one | HMDB | 3-Hydroxyoestra-1,3,5(10)-trien-17-one | HMDB | D1,3,5(10)-Estratrien-3-ol-17-one | HMDB | Estrone, (+-)-isomer | MeSH | Hyrex brand OF estrone | MeSH | Estrone, (9 beta)-isomer | MeSH | Estrovarin | MeSH | Kestrone | MeSH | Wehgen | MeSH | Estrone, (8 alpha)-isomer | MeSH | Hauck brand OF estrone | MeSH | Unigen | MeSH | Vortech brand OF estrone | MeSH |
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Chemical Formula | C18H22O2 |
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Average Molecular Weight | 270.3661 |
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Monoisotopic Molecular Weight | 270.161979948 |
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IUPAC Name | (1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one |
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Traditional Name | estrone |
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CAS Registry Number | 53-16-7 |
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SMILES | [H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 |
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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 | DNXHEGUUPJUMQT-CBZIJGRNSA-N |
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Chemical Taxonomy |
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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. |
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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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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 258 - 260 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.03 mg/mL | Not Available | LogP | 3.13 | HANSCH,C ET AL. (1995) |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-05ox-3951000000-8bc438f505b3cf49b21f | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) | splash10-003u-4942000000-a72ea34d85d9d524c247 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) | splash10-0019-8931000000-aad9803af812c7c40f53 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00di-2940000000-2d417e7ecb4a8b87b817 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00di-0980000000-5b293db89a0f2efeb784 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-05ox-3951000000-8bc438f505b3cf49b21f | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-003u-4942000000-a72ea34d85d9d524c247 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0019-8931000000-aad9803af812c7c40f53 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0adl-1970000000-871531490fb22b8fe12f | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-009t-1093000000-a8d755d13e3b819514c8 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00di-0190000000-071e67516e11357ff64e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a4j-4910000000-20e059a7c508ba492af3 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-067i-9700000000-9ff5214f08822f238fa9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-00di-2940000000-3b9744c27d6a3d2eff6e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0ukc-2690000000-7afb48e267c7b334213b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-014i-0690000000-a76244de959b06ec896e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a59-0910000000-4a1bc1cbc90c3e5281e6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a59-0900000000-0830d4ad43804976f508 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0udi-0390000000-41440e74b3f0b5f365d7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0udi-0390000000-fdc0255246e3a9013d0a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0a59-2910000000-fc5173d435c3c7fc603c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-00di-0390000000-25cecb1c4785e7bffd56 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0190000000-64cf013a5b0ad5e8bf56 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00fr-0590000000-40418c285df2157226dc | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fb9-6980000000-724c68b368fbe3d38f5e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0090000000-6778bd7122813b501c1e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0090000000-0f2e0b96bc30b346c581 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0f9i-1090000000-9ccbd9f351dd1f8e52cb | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-00di-2930000000-c99df908474247066a2b | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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Disease References | Menstrual cycle |
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- (). The Merck Manual, 17th ed. Mark H. Beers, MD, Robert Berkow, MD, eds. Whitehouse Station, NJ: Merck Research Labs, 1999.. .
| Aromatase deficiency |
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- Mullis PE, Yoshimura N, Kuhlmann B, Lippuner K, Jaeger P, Harada H: Aromatase deficiency in a female who is compound heterozygote for two new point mutations in the P450arom gene: impact of estrogens on hypergonadotropic hypogonadism, multicystic ovaries, and bone densitometry in childhood. J Clin Endocrinol Metab. 1997 Jun;82(6):1739-45. doi: 10.1210/jcem.82.6.3994. [PubMed:9177373 ]
| X-linked ichthyosis |
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- Lykkesfeldt G, Bennett P, Lykkesfeldt AE, Micic S, Moller S, Svenstrup B: Abnormal androgen and oestrogen metabolism in men with steroid sulphatase deficiency and recessive X-linked ichthyosis. Clin Endocrinol (Oxf). 1985 Oct;23(4):385-93. [PubMed:3864567 ]
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General References | - 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. [PubMed:16598814 ]
- 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. [PubMed:10997942 ]
- 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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:17464097 ]
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