Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:49:01 UTC |
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HMDB ID | HMDB0000372 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 16-Oxoestrone |
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Description | Estrone (also oestrone) is an estrogenic hormone secreted by the ovary. Its molecular formula is C18H22O2. estrone has a melting point of 254.5 degrees Celsius. estrone is one of the three estrogens, which also include estriol and estradiol. estrone is the least prevalent of the three hormones, estradiol being prevalent almost always in a female body, estriol being prevalent primarily during pregnancy. estrone sulfate is relevant to health and disease due to its conversion to estrone sulfate, a long-lived derivative of estrone. estrone sulfate acts as a pool of estrone which can be converted as needed to the more active estradiol. |
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Structure | C[C@]12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(=O)C2=O InChI=1S/C18H20O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-15,19H,2,4,6-7,9H2,1H3/t13?,14?,15?,18-/m0/s1 |
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Synonyms | Value | Source |
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16-Ketoestrone | HMDB | 3-Hydroxy-1,3,5(10)-estratriene-16,17-dione | HMDB |
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Chemical Formula | C18H20O3 |
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Average Molecular Weight | 284.3496 |
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Monoisotopic Molecular Weight | 284.141244506 |
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IUPAC Name | (15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-13,14-dione |
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Traditional Name | (15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-13,14-dione |
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CAS Registry Number | 1228-73-5 |
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SMILES | C[C@]12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(=O)C2=O |
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InChI Identifier | InChI=1S/C18H20O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-15,19H,2,4,6-7,9H2,1H3/t13?,14?,15?,18-/m0/s1 |
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InChI Key | ANPHVANSJXDRTP-VLVBFLKRSA-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
- 16-oxosteroid
- 17-oxosteroid
- Oxosteroid
- Phenanthrene
- Tetralin
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Ketone
- Cyclic 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 | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 231 - 235 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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16-Oxoestrone,1TMS,isomer #1 | C[C@]12CCC3C4=CC=C(O[Si](C)(C)C)C=C4CCC3C1CC(=O)C2=O | 2840.0 | Semi standard non polar | 33892256 | 16-Oxoestrone,1TMS,isomer #2 | C[C@]12CCC3C4=CC=C(O)C=C4CCC3C1C=C(O[Si](C)(C)C)C2=O | 2786.0 | Semi standard non polar | 33892256 | 16-Oxoestrone,2TMS,isomer #1 | C[C@]12CCC3C4=CC=C(O[Si](C)(C)C)C=C4CCC3C1C=C(O[Si](C)(C)C)C2=O | 2821.2 | Semi standard non polar | 33892256 | 16-Oxoestrone,2TMS,isomer #1 | C[C@]12CCC3C4=CC=C(O[Si](C)(C)C)C=C4CCC3C1C=C(O[Si](C)(C)C)C2=O | 2729.0 | Standard non polar | 33892256 | 16-Oxoestrone,2TMS,isomer #1 | C[C@]12CCC3C4=CC=C(O[Si](C)(C)C)C=C4CCC3C1C=C(O[Si](C)(C)C)C2=O | 3087.1 | Standard polar | 33892256 | 16-Oxoestrone,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CCC1C2CC[C@]2(C)C(=O)C(=O)CC12 | 3080.5 | Semi standard non polar | 33892256 | 16-Oxoestrone,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC2C3CCC4=CC(O)=CC=C4C3CC[C@]2(C)C1=O | 3074.9 | Semi standard non polar | 33892256 | 16-Oxoestrone,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3CC[C@]2(C)C1=O | 3343.8 | Semi standard non polar | 33892256 | 16-Oxoestrone,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3CC[C@]2(C)C1=O | 3181.7 | Standard non polar | 33892256 | 16-Oxoestrone,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3CC[C@]2(C)C1=O | 3317.1 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - 16-Oxoestrone GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ab9-0970000000-c33450029c2a510fb1dd | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Oxoestrone GC-MS (1 TMS) - 70eV, Positive | splash10-0032-1095000000-28ce684570c9033f6ecb | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Oxoestrone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Oxoestrone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Oxoestrone GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Oxoestrone GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Oxoestrone GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Oxoestrone 10V, Positive-QTOF | splash10-000i-0090000000-6d759bc421714d0d2920 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Oxoestrone 20V, Positive-QTOF | splash10-0a4r-0390000000-d8c66380533ac80c418f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Oxoestrone 40V, Positive-QTOF | splash10-0gdi-7980000000-4a05c980006c31f9644c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Oxoestrone 10V, Negative-QTOF | splash10-001i-0090000000-71415abfa8ce5bdff3d3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Oxoestrone 20V, Negative-QTOF | splash10-001i-0090000000-66dbf6c2ee8a27f150f2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Oxoestrone 40V, Negative-QTOF | splash10-0gdi-1090000000-dd632ccd4b6912edb4b7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Oxoestrone 10V, Negative-QTOF | splash10-001i-0090000000-78a425e25a58a7330ede | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Oxoestrone 20V, Negative-QTOF | splash10-001i-0090000000-ea975f2e73cc3dfd69ff | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Oxoestrone 40V, Negative-QTOF | splash10-01sl-0390000000-45c573c062efce8ba045 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Oxoestrone 10V, Positive-QTOF | splash10-000i-0090000000-5bc7bcd7c5f268094120 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Oxoestrone 20V, Positive-QTOF | splash10-004r-0590000000-13c3647f4ba51b6998ee | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Oxoestrone 40V, Positive-QTOF | splash10-004i-1790000000-7983b1aed115bbdf442d | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Extracellular
- Membrane (predicted from logP)
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Biospecimen Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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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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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB021991 |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | C14441 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | 16-Ketoestrone |
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METLIN ID | 5361 |
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PubChem Compound | 53477688 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | uffman, Max N. 16-Keto estrogens. (1950), US 2522178 19500912 CAN 45:6349 AN 1951:6349 |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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