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 02:49:00 UTC |
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HMDB ID | HMDB0000313 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 16b-Hydroxyestrone |
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Description | 16b-Hydroxyestrone is an aromatized C18 steroid with a 3-hydroxyl group and a 17-ketone, a major mammalian estrogen. It is converted from androstenedione directly, or from testosterone via estradiol. In humans, it is produced primarily by the cyclic ovaries, placenta, and the adipose tissue of men and postmenopausal women. |
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Structure | [H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3 InChI=1S/C18H22O3/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/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,18+/m1/s1 |
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Synonyms | Value | Source |
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(16beta)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-one | ChEBI | 16-Hydroxyestrone | ChEBI | 3,16-Dihydroxyestra-1,3,5(10)-trien-17-one | ChEBI | 3,16beta-Dihydroxy-estra-1,3,5(10)-trien-17-one | ChEBI | (16b)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-one | Generator | (16Β)-3,16-dihydroxyestra-1,3,5(10)-trien-17-one | Generator | 3,16b-Dihydroxy-estra-1,3,5(10)-trien-17-one | Generator | 3,16Β-dihydroxy-estra-1,3,5(10)-trien-17-one | Generator | 16alpha-Hydroxyestrone | HMDB | 16beta-Hydroxyestrone | HMDB | 3,16-Dihydroxy-estra-1,3,5(10)-trien-17-one | HMDB | 16 alpha-Hydroxyestrone | MeSH, HMDB | 16 beta-Hydroxyestrone | MeSH, HMDB | 16-alpha-Hydroxyestrone | MeSH, HMDB |
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Chemical Formula | C18H22O3 |
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Average Molecular Weight | 286.3655 |
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Monoisotopic Molecular Weight | 286.15689457 |
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IUPAC Name | (1S,10R,11S,13S,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one |
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Traditional Name | 16 α-hydroxyestrone |
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CAS Registry Number | 966-06-3 |
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SMILES | [H][C@@]12C[C@H](O)C(=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/C18H22O3/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/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,18+/m1/s1 |
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InChI Key | WPOCIZJTELRQMF-LFRCEIEQSA-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
- 16-beta-hydroxysteroid
- 16-hydroxysteroid
- Phenanthrene
- Tetralin
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Cyclic alcohol
- Secondary alcohol
- Ketone
- Carbonyl group
- Organooxygen compound
- Alcohol
- 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 | 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 | Not Available | 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 | |
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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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16b-Hydroxyestrone,1TMS,isomer #1 | C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1C[C@H](O[Si](C)(C)C)C2=O | 2768.0 | Semi standard non polar | 33892256 | 16b-Hydroxyestrone,1TMS,isomer #2 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@H](O)C2=O | 2786.1 | Semi standard non polar | 33892256 | 16b-Hydroxyestrone,1TMS,isomer #3 | C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1CC(O)=C2O[Si](C)(C)C | 2768.1 | Semi standard non polar | 33892256 | 16b-Hydroxyestrone,2TMS,isomer #1 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C[C@H](O[Si](C)(C)C)C2=O | 2875.1 | Semi standard non polar | 33892256 | 16b-Hydroxyestrone,2TMS,isomer #2 | C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C | 2779.4 | Semi standard non polar | 33892256 | 16b-Hydroxyestrone,2TMS,isomer #3 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC(O)=C2O[Si](C)(C)C | 2839.0 | Semi standard non polar | 33892256 | 16b-Hydroxyestrone,3TMS,isomer #1 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C | 2905.4 | Semi standard non polar | 33892256 | 16b-Hydroxyestrone,3TMS,isomer #1 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C | 2783.1 | Standard non polar | 33892256 | 16b-Hydroxyestrone,3TMS,isomer #1 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C | 2899.0 | Standard polar | 33892256 | 16b-Hydroxyestrone,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]2(C)C1=O | 3049.5 | Semi standard non polar | 33892256 | 16b-Hydroxyestrone,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)[C@@H](O)C[C@@H]12 | 3088.5 | Semi standard non polar | 33892256 | 16b-Hydroxyestrone,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]12C | 3043.6 | Semi standard non polar | 33892256 | 16b-Hydroxyestrone,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]12 | 3412.8 | Semi standard non polar | 33892256 | 16b-Hydroxyestrone,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]2C1 | 3287.1 | Semi standard non polar | 33892256 | 16b-Hydroxyestrone,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]12C | 3331.5 | Semi standard non polar | 33892256 | 16b-Hydroxyestrone,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@@H]3C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4CC[C@H]3[C@@H]2C1 | 3616.3 | Semi standard non polar | 33892256 | 16b-Hydroxyestrone,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@@H]3C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4CC[C@H]3[C@@H]2C1 | 3466.0 | Standard non polar | 33892256 | 16b-Hydroxyestrone,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@@H]3C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4CC[C@H]3[C@@H]2C1 | 3214.0 | Standard polar | 33892256 |
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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 - 16b-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ab9-2690000000-4da4066a9998d4bb7152 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (2 TMS) - 70eV, Positive | splash10-016r-3279600000-35209b189461208c9804 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16b-Hydroxyestrone GC-MS (TBDMS_2_3) - 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 - 16b-Hydroxyestrone 10V, Positive-QTOF | splash10-000i-0090000000-ea49b0e7c1a26f8807b3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 20V, Positive-QTOF | splash10-0ap0-0490000000-7a9632ca2f7369b28ad3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 40V, Positive-QTOF | splash10-0gb9-7980000000-f674402195ec376faeb7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 10V, Negative-QTOF | splash10-000i-0090000000-91f32a5e866ea149a4a4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 20V, Negative-QTOF | splash10-000i-0090000000-f8524ff8a5fae66251ad | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 40V, Negative-QTOF | splash10-02dl-1090000000-5ac386a35fc2bb3cc1f0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 10V, Positive-QTOF | splash10-000i-0090000000-8269f9806e3a6460adb9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 20V, Positive-QTOF | splash10-00ks-0590000000-2d8e09d2baef368efec1 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 40V, Positive-QTOF | splash10-00dj-0920000000-bce8e0246e58d9e59bbd | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 10V, Negative-QTOF | splash10-000i-0090000000-fcaf0435bbf678a207f7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 20V, Negative-QTOF | splash10-000i-0090000000-48bccddc063fe7e2f998 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16b-Hydroxyestrone 40V, Negative-QTOF | splash10-02di-0090000000-080f7d164203318ad338 | 2021-09-22 | Wishart Lab | View Spectrum |
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