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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 | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 53-16-7 |
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SMILES | Not Available |
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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 | Not Available |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | - Cell membrane
- Cytoplasm
- Endoplasmic reticulum
- Membrane
- Mitochondria
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Biospecimen Locations | - Blood
- Kidney
- Liver
- Milk
- Placenta
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.000269 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 0.0018 uM | Not Specified | Not Specified | Normal | | details | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.00003699 +/- 0.000003699 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.000125 +/- 0.000009986 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.00003366 - 0.00007471 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.000206 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.0000155 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.0000211 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.0000755 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.0000100 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.0000292 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.00008507 +/- 0.00001110 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.00008877 +/- 0.000007397 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.000118 +/- 0.000003699 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.000137 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.000163 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.000248 +/- 0.000007397 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.00002922 +/- 0.000002589 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.00167 +/- 0.000244 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.00468 +/- 0.000141 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.000565 +/- 0.000222 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.000522 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.000766 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.000692 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.00186 - 0.00209 uM | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.00259 uM | Not Specified | Not Specified | Treated with estradiol benzoate and progesterone | | details | Blood | Detected and Quantified | 0.00707 uM | Not Specified | Not Specified | Treated with estradiol benzoate | | details |
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External Links |
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HMDB ID | HMDB0000145 |
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DrugBank ID | DB00655 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB012798 |
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KNApSAcK ID | C00003663 |
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Chemspider ID | 5660 |
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KEGG Compound ID | C00468 |
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BioCyc ID | Not Available |
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BiGG ID | 35059 |
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Wikipedia Link | Estrone |
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METLIN ID | 264 |
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PubChem Compound | 5870 |
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PDB ID | Not Available |
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ChEBI ID | 17263 |
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References |
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Synthesis Reference | Kocovsky, Paved; Baines, Richard S. Synthesis of estrone via a thallium(III)-mediated fragmentation of a 19-hydroxyandrost-5-ene precursor. Tetrahedron Letters (1993), 34(38), 6139-40. |
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Material Safety Data Sheet (MSDS) | Not Available |
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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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