Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-08-13 21:47:21 UTC |
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Update Date | 2022-03-07 02:49:21 UTC |
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HMDB ID | HMDB0004590 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 19-Nor-5-androstenediol |
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Description | 19-Nor-5-androstenediol is an androgen steroid that has been found to be part of nutritional supplements that are commercialized as nandrolone-free. Some reports regarding nandrolone-positive cases have been related to intake of some of these supplements. Nandrolone is the most frequently abused substance in doping control because it does not convert to estrogens and does not have and androgenic side effects. For this reason, one the major metabolites of nandrolone, 19-norandrosterone (19-NA) have been used as determinants for doping of nandrolone. However, there are situations where the occurrence of nandrolone metabolites is a phenomenon not necessarily associated with doping: a) in human ovarian follicular fluid is a possible intermediate in the multistep enzymatic conversion of androgen to estrogen, b) during the course of pregnancy, 19-NA increases in urine, c) human chorionic gonadotropin (hCG) also stimulates 19-NA excretion in urine, d) exercise has been shown to affect the urinary excretion of nandrolone metabolites such as 19-NA, e) 19-NA is a minor metabolite of oral contraceptives such as norethisterone. Furthermore, 19-NA is the main urinary metabolite of 19-Nor-5-androstenediol. Nevertheless, the prevalence of nandrolone abuse is evident; internationally, 212 cases were found in 1995 and 232 cases were found in 1996. From 1998 to 2001, nandrolone-positive findings reported by the IOC-accredited laboratories ranged from 0.17% to 0.65%. (PMID: 15902981 ). |
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Structure | [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CC[C@H](O)CC3=CC[C@@]21[H] InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2,12-17,19-20H,3-10H2,1H3/t12-,13-,14+,15+,16-,17-,18-/m0/s1 |
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Synonyms | Value | Source |
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(3b,17b)-Estr-5-ene-3,17-diol | HMDB | 19-Nor-5-androstene-3b,17b-diol | HMDB | D5-Estrene-3b,17b-diol | HMDB | Estr-5-ene-3b,17b-diol | HMDB |
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Chemical Formula | C18H28O2 |
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Average Molecular Weight | 276.4137 |
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Monoisotopic Molecular Weight | 276.20893014 |
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IUPAC Name | (1S,2R,5S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol |
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Traditional Name | estr-5-ene-3b,17b-diol |
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CAS Registry Number | 25975-59-1 |
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SMILES | [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CC[C@H](O)CC3=CC[C@@]21[H] |
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InChI Identifier | InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2,12-17,19-20H,3-10H2,1H3/t12-,13-,14+,15+,16-,17-,18-/m0/s1 |
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InChI Key | VVUQRXPUVKXAIO-XFUVECHXSA-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
- 17-hydroxysteroid
- 3-beta-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- Hydroxysteroid
- 3-hydroxysteroid
- 3-hydroxy-delta-5-steroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic 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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19-Nor-5-androstenediol,1TMS,isomer #1 | C[C@]12CC[C@@H]3[C@H]4CC[C@H](O)CC4=CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C | 2577.2 | Semi standard non polar | 33892256 | 19-Nor-5-androstenediol,1TMS,isomer #2 | C[C@]12CC[C@@H]3[C@H]4CC[C@H](O[Si](C)(C)C)CC4=CC[C@H]3[C@@H]1CC[C@@H]2O | 2559.9 | Semi standard non polar | 33892256 | 19-Nor-5-androstenediol,2TMS,isomer #1 | C[C@]12CC[C@@H]3[C@H]4CC[C@H](O[Si](C)(C)C)CC4=CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C | 2628.3 | Semi standard non polar | 33892256 | 19-Nor-5-androstenediol,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@@H]4[C@H]3CC[C@]12C | 2847.3 | Semi standard non polar | 33892256 | 19-Nor-5-androstenediol,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2C(=CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]32)C1 | 2836.6 | Semi standard non polar | 33892256 | 19-Nor-5-androstenediol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2C(=CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]32)C1 | 3160.5 | Semi standard non 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 - 19-Nor-5-androstenediol GC-MS (Non-derivatized) - 70eV, Positive | splash10-00l2-1290000000-79238caefbd6e0af9fc1 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 19-Nor-5-androstenediol GC-MS (2 TMS) - 70eV, Positive | splash10-0pbc-2459400000-7d6e6c42cd032bc15b6e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 19-Nor-5-androstenediol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 19-Nor-5-androstenediol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | 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 - 19-Nor-5-androstenediol 10V, Positive-QTOF | splash10-0a6r-0090000000-66417865401a6cc4ed73 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19-Nor-5-androstenediol 20V, Positive-QTOF | splash10-0a6u-0390000000-fc88f23ca19917ba5ca7 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19-Nor-5-androstenediol 40V, Positive-QTOF | splash10-116u-4960000000-b6217c11cfb8521467d5 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19-Nor-5-androstenediol 10V, Negative-QTOF | splash10-004i-0090000000-05890200ad907aeac469 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19-Nor-5-androstenediol 20V, Negative-QTOF | splash10-056r-0090000000-00a4168224d02e623f06 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19-Nor-5-androstenediol 40V, Negative-QTOF | splash10-0a6v-1190000000-d6ecf02c9469e90cd10f | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19-Nor-5-androstenediol 10V, Negative-QTOF | splash10-004i-0090000000-4d3066b364d5c97a28e0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19-Nor-5-androstenediol 20V, Negative-QTOF | splash10-004i-0090000000-4d3066b364d5c97a28e0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19-Nor-5-androstenediol 40V, Negative-QTOF | splash10-05i0-0090000000-98cee4d9f284b4d6e284 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19-Nor-5-androstenediol 10V, Positive-QTOF | splash10-056r-0090000000-0e3410f9e3c2e1ab03ea | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19-Nor-5-androstenediol 20V, Positive-QTOF | splash10-0ke9-0790000000-d665b12002fc950bdbaa | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 19-Nor-5-androstenediol 40V, Positive-QTOF | splash10-00os-2910000000-b45eff9beefb3ad91a4c | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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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 | DB01455 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023379 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 8075901 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | 19-Nor-5-androstenediol |
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METLIN ID | Not Available |
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PubChem Compound | 9900246 |
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PDB ID | Not Available |
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ChEBI ID | 529214 |
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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 | Hartman, John A. The preparation of four 3,17b-dihydroxyestrenes. Journal of the American Chemical Society (1955), 77 5151-4. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Tseng YL, Kuo FH, Sun KH: Quantification and profiling of 19-norandrosterone and 19-noretiocholanolone in human urine after consumption of a nutritional supplement and norsteroids. J Anal Toxicol. 2005 Mar;29(2):124-34. [PubMed:15902981 ]
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