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 | HMDB0000406 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 16-Ketoestradiol |
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Description | 16-Ketoestradiol is found in the estrogen patch. The estrogen patch is a delivery system for estradiol used as hormone replacement therapy to treat the symptoms of menopause, such as hot flashes and vaginal dryness, and to prevent osteoporosis. Originally marketed as Vivelle (Novartis), it was discontinued in 2003 and reintroduced in a smaller form as Vivelle-Dot. Although the estrogen is given transdermally rather than in the standard oral tablets, the estrogen patch carries similar risks and benefits as more conventional forms of estrogen-only hormone replacement therapy. |
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Structure | [H][C@@]12CC(=O)[C@H](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/h3,5,8,13-15,17,19,21H,2,4,6-7,9H2,1H3/t13-,14-,15+,17+,18+/m1/s1 |
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Synonyms | Value | Source |
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16-oxo-17beta-Estradiol | Kegg | 16-oxo-17b-Estradiol | Generator | 16-oxo-17Β-estradiol | Generator | 1,3,5(10)-Estratriene-3,17b-diol-16-one | HMDB | 16-Keto-17b-estradiol | HMDB | 16-Oxoestradiol | HMDB | 16-Oxoestradiol-17b | HMDB | 3,17b-Dihydroxyestra-1,3,5(10)-trien-16-one | HMDB | 16-Ketoestradiol, (17beta)-isomer, 4-(14)C-labeled | HMDB | 16-Ketoestradiol, (17alpha)-isomer | HMDB | (17beta)-3,17-Dihydroxyestra-1,3,5(10)-trien-16-one | 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,14R,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-13-one |
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Traditional Name | 16-ketoestradiol |
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CAS Registry Number | 566-75-6 |
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SMILES | [H][C@@]12CC(=O)[C@H](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/h3,5,8,13-15,17,19,21H,2,4,6-7,9H2,1H3/t13-,14-,15+,17+,18+/m1/s1 |
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InChI Key | KJDGFQJCHFJTRH-YONAWACDSA-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
- Oxosteroid
- 17-hydroxysteroid
- Phenanthrene
- Tetralin
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Cyclic alcohol
- Secondary alcohol
- Ketone
- Cyclic 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 | | 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-Ketoestradiol,1TMS,isomer #1 | C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1CC(=O)[C@@H]2O[Si](C)(C)C | 2832.6 | Semi standard non polar | 33892256 | 16-Ketoestradiol,1TMS,isomer #2 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC(=O)[C@@H]2O | 2823.5 | Semi standard non polar | 33892256 | 16-Ketoestradiol,1TMS,isomer #3 | C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1CC(O[Si](C)(C)C)=C2O | 2764.1 | Semi standard non polar | 33892256 | 16-Ketoestradiol,1TMS,isomer #4 | C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2O | 2734.5 | Semi standard non polar | 33892256 | 16-Ketoestradiol,2TMS,isomer #1 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC(=O)[C@@H]2O[Si](C)(C)C | 2904.1 | Semi standard non polar | 33892256 | 16-Ketoestradiol,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 | 16-Ketoestradiol,2TMS,isomer #3 | C[C@]12CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C | 2749.9 | Semi standard non polar | 33892256 | 16-Ketoestradiol,2TMS,isomer #4 | 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 | 2845.2 | Semi standard non polar | 33892256 | 16-Ketoestradiol,2TMS,isomer #5 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2O | 2762.3 | Semi standard non polar | 33892256 | 16-Ketoestradiol,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 | 16-Ketoestradiol,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 | 16-Ketoestradiol,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 | 16-Ketoestradiol,3TMS,isomer #2 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C | 2836.6 | Semi standard non polar | 33892256 | 16-Ketoestradiol,3TMS,isomer #2 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C | 2748.6 | Standard non polar | 33892256 | 16-Ketoestradiol,3TMS,isomer #2 | C[C@]12CC[C@@H]3C4=CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C | 2890.0 | Standard polar | 33892256 | 16-Ketoestradiol,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@H]1C(=O)C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@@]21C | 3108.2 | Semi standard non polar | 33892256 | 16-Ketoestradiol,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC(=O)[C@@H]2O | 3110.8 | Semi standard non polar | 33892256 | 16-Ketoestradiol,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=C(O)[C@@]2(C)CC[C@@H]3C4=CC=C(O)C=C4CC[C@H]3[C@@H]2C1 | 3044.1 | Semi standard non polar | 33892256 | 16-Ketoestradiol,1TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1=C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]2(C)[C@H]1O | 2996.5 | Semi standard non polar | 33892256 | 16-Ketoestradiol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC(=O)[C@@H]2O[Si](C)(C)C(C)(C)C | 3432.7 | Semi standard non polar | 33892256 | 16-Ketoestradiol,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 | 16-Ketoestradiol,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=C[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C | 3234.6 | Semi standard non polar | 33892256 | 16-Ketoestradiol,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1=C(O)[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 | 3320.0 | Semi standard non polar | 33892256 | 16-Ketoestradiol,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)OC1=C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]2(C)[C@H]1O | 3261.6 | Semi standard non polar | 33892256 | 16-Ketoestradiol,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 | 16-Ketoestradiol,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 | 16-Ketoestradiol,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 | 16-Ketoestradiol,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C | 3549.5 | Semi standard non polar | 33892256 | 16-Ketoestradiol,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C | 3366.3 | Standard non polar | 33892256 | 16-Ketoestradiol,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=C[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C | 3197.7 | 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-Ketoestradiol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ab9-2890000000-32071d38f05cd2ca0c9b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (2 TMS) - 70eV, Positive | splash10-01dj-1196500000-273f84f940ea3f0838d0 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TMS_2_4) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TMS_2_5) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TBDMS_1_4) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TBDMS_2_4) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 16-Ketoestradiol GC-MS (TBDMS_2_5) - 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-Ketoestradiol 10V, Positive-QTOF | splash10-000i-0090000000-55a266ba34ecf6bdfd11 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Ketoestradiol 20V, Positive-QTOF | splash10-0a4i-0390000000-ffb77059d15a727397bb | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Ketoestradiol 40V, Positive-QTOF | splash10-0gb9-5690000000-c133890ef184dc5ec585 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Ketoestradiol 10V, Negative-QTOF | splash10-000i-0090000000-f86f24db58f0d8c36621 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Ketoestradiol 20V, Negative-QTOF | splash10-000i-0090000000-a4dfb2cdc949c3369ad4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Ketoestradiol 40V, Negative-QTOF | splash10-02bf-2090000000-ce1f2fe2172e07fbffc6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Ketoestradiol 10V, Positive-QTOF | splash10-000i-0090000000-ed97c93b7e7537d3f95c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Ketoestradiol 20V, Positive-QTOF | splash10-00n0-0590000000-4aa6f11d398258fe6ed6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Ketoestradiol 40V, Positive-QTOF | splash10-00fs-0930000000-15b323540fb6bb7af8e7 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Ketoestradiol 10V, Negative-QTOF | splash10-000i-0090000000-fcaf0435bbf678a207f7 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Ketoestradiol 20V, Negative-QTOF | splash10-000i-0090000000-555b35bd0b896dc0c574 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 16-Ketoestradiol 40V, Negative-QTOF | splash10-004i-0090000000-d8910a82c7c88f5cf2bb | 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 | Not Available |
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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 | FDB022022 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 59791 |
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KEGG Compound ID | C14383 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | 16-Ketoestradiol |
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METLIN ID | 5395 |
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PubChem Compound | 66417 |
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PDB ID | Not Available |
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ChEBI ID | 1150238 |
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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 | Tong, Zhengshou; Gan, Guizhi; Li, Lu. Syntheses of 16-substituted estradiol derivatives. Yiyao Gongye (1984), (8), 14-17. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
- Xu X, Veenstra TD, Fox SD, Roman JM, Issaq HJ, Falk R, Saavedra JE, Keefer LK, Ziegler RG: Measuring fifteen endogenous estrogens simultaneously in human urine by high-performance liquid chromatography-mass spectrometry. Anal Chem. 2005 Oct 15;77(20):6646-54. [PubMed:16223252 ]
- Xu X, Keefer LK, Waterhouse DJ, Saavedra JE, Veenstra TD, Ziegler RG: Measuring seven endogenous ketolic estrogens simultaneously in human urine by high-performance liquid chromatography-mass spectrometry. Anal Chem. 2004 Oct 1;76(19):5829-36. [PubMed:15456304 ]
- Weiss PA, Esterbauer HE, Scherr F: [Excretion of estriol, estetrol, 16-epi-estriol, 16-keto-estradiol and 16-hydroxyestrone in the 24-hour urine of pregnant women in the last trimester]. Endokrinologie. 1975 Aug;65(3):254-65. [PubMed:1222727 ]
- Xu X, Duncan AM, Merz-Demlow BE, Phipps WR, Kurzer MS: Menstrual cycle effects on urinary estrogen metabolites. J Clin Endocrinol Metab. 1999 Nov;84(11):3914-8. [PubMed:10566628 ]
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