| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:20:08 UTC |
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| Update Date | 2020-06-04 20:40:27 UTC |
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| BMDB ID | BMDB0000145 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Estrone |
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| Description | Estrone, also known as folliculin or estrovarin, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, estrone is considered to be a steroid lipid molecule. Estrone is a drug which is used for management of perimenopausal and postmenopausal symptoms. Estrone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Estrone exists in all living organisms, ranging from bacteria to humans. Estrone participates in a number of enzymatic reactions, within cattle. In particular, Estrone and phosphoadenosine phosphosulfate can be converted into estrone sulfate and adenosine 3',5'-diphosphate through the action of the enzyme estrogen sulfotransferase. In addition, Estrone can be converted into 2-hydroxyestrone; which is mediated by the enzyme cytochrome P450 1A1. In cattle, estrone is involved in the metabolic pathway called the estrone metabolism pathway. Estrone is a potentially toxic compound. |
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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 | HMDB | | Hyrex brand OF estrone | HMDB | | Estrone, (9 beta)-isomer | HMDB | | Estrovarin | HMDB | | Kestrone | HMDB | | Wehgen | HMDB | | Estrone, (8 alpha)-isomer | HMDB | | Hauck brand OF estrone | HMDB | | Unigen | HMDB | | Vortech brand OF estrone | HMDB |
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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[8.7.0.0^{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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| 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 | 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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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cell membrane
- Cytoplasm
- Endoplasmic reticulum
- Membrane
- Mitochondria
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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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| General References | - Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3. [PubMed:512140 ]
- Malekinejad H, Scherpenisse P, Bergwerff AA: Naturally occurring estrogens in processed milk and in raw milk (from gestated cows). J Agric Food Chem. 2006 Dec 27;54(26):9785-91. doi: 10.1021/jf061972e. [PubMed:17177502 ]
- Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637. [PubMed:17852390 ]
- Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16. [PubMed:18412364 ]
- Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. [PubMed:19679050 ]
- Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947. [PubMed:20494161 ]
- Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024. Epub 2010 May 25. [PubMed:20541211 ]
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