Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2007-04-12 15:51:51 UTC |
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Update Date | 2022-03-07 02:49:29 UTC |
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HMDB ID | HMDB0005849 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4-Androstenediol |
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Description | 4-Androstenediol is a metabolite of testosterone. Conversely, the conversion of 4-androstenediol to testosterone has been demonstrated to occur in homogenates of hyperplastic human female adrenal glands. 4-Androstenediol is an anabolic agent that has been found in increased concentration in athletes suspected of doping. 4-Androstenediol has also been found in aqueous and solid nutritional supplements that are commercially available. Studies showing that non-hormonal supplements such as vitamins, minerals, and amino acids can contain anabolic androgenic steroids not declared on the labels of the products have been published. These undeclared substances (often prohormones of testosterone) can cause health risks to consumers and might lead to positive results in sports doping control. It has been demonstrated that 4-androstenediol taken by mouth is capable of producing in vivo increases in testosterone concentration in apparently healthy young men an women (PMID: 15808000 , 15103700 , 10638382 , 15370836 ). |
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Structure | [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[C@@H](O)CC[C@]12C InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,13-17,20-21H,3-10H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1 |
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Synonyms | Value | Source |
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Androst-4-ene-3beta,17beta-diol | Kegg | Androst-4-ene-3b,17b-diol | Generator | Androst-4-ene-3β,17β-diol | Generator | (3b,17b)-Androst-4-ene-3,17-diol | HMDB | 3b,17b-Dihydroxy-4-androstene | HMDB | 4-Androstene-3b,17b-diol | HMDB | Androst-4-en-3b,17b-diol | HMDB | D4-Androstene-3b,17b-diol | HMDB | (3beta,17beta)-Androst-4-ene-3,17-diol | HMDB | (3β,17β)-Androst-4-ene-3,17-diol | HMDB | 3beta,17beta-Dihydroxy-4-androstene | HMDB | 3β,17β-Dihydroxy-4-androstene | HMDB | 4-Androstenediol | HMDB |
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Chemical Formula | C19H30O2 |
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Average Molecular Weight | 290.4403 |
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Monoisotopic Molecular Weight | 290.224580204 |
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IUPAC Name | (1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol |
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Traditional Name | (1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol |
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CAS Registry Number | 1156-92-9 |
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SMILES | [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[C@@H](O)CC[C@]12C |
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InChI Identifier | InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,13-17,20-21H,3-10H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1 |
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InChI Key | BTTWKVFKBPAFDK-LOVVWNRFSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. |
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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 | Androstane steroids |
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Direct Parent | Androgens and derivatives |
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Alternative Parents | |
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Substituents | - Androgen-skeleton
- 17-hydroxysteroid
- 3-beta-hydroxysteroid
- Hydroxysteroid
- 3-hydroxysteroid
- 3-hydroxy-delta-4-steroid
- Delta-4-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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4-Androstenediol,1TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C | 2607.0 | Semi standard non polar | 33892256 | 4-Androstenediol,1TMS,isomer #2 | C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2O | 2591.2 | Semi standard non polar | 33892256 | 4-Androstenediol,2TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C | 2639.6 | Semi standard non polar | 33892256 | 4-Androstenediol,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CCC4=C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C | 2867.9 | Semi standard non polar | 33892256 | 4-Androstenediol,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 | 2851.4 | Semi standard non polar | 33892256 | 4-Androstenediol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 | 3164.6 | 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 - 4-Androstenediol GC-MS (Non-derivatized) - 70eV, Positive | splash10-03e9-0290000000-7d52fa98e687764c22a2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Androstenediol GC-MS (2 TMS) - 70eV, Positive | splash10-066r-3236900000-b524811a4353b5996ed1 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-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 - 4-Androstenediol 10V, Positive-QTOF | splash10-00dl-0090000000-f4b512d07e8fa29cf8be | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androstenediol 20V, Positive-QTOF | splash10-05fr-0290000000-7a460a768fecd3e1cea3 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androstenediol 40V, Positive-QTOF | splash10-01oy-3890000000-8177324a0ce9fde3f678 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androstenediol 10V, Negative-QTOF | splash10-000i-0090000000-7318adfbaee2ca1f4eef | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androstenediol 20V, Negative-QTOF | splash10-0079-0090000000-ea1dd5bd96f621180cc7 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androstenediol 40V, Negative-QTOF | splash10-0abc-1190000000-355691f711b0faad45c2 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androstenediol 10V, Negative-QTOF | splash10-000i-0090000000-c8c452fd99c6bb4f3631 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androstenediol 20V, Negative-QTOF | splash10-000i-0090000000-1ce9bb01eb35f26908c4 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androstenediol 40V, Negative-QTOF | splash10-000i-0090000000-f2f475ae4c62e877a9ba | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androstenediol 10V, Positive-QTOF | splash10-0006-0090000000-9de0edc3a8b815dd7071 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androstenediol 20V, Positive-QTOF | splash10-0abd-0940000000-d28d8b5f304b6ca1a699 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Androstenediol 40V, Positive-QTOF | splash10-0aos-2900000000-0737f10b02bfa62847f5 | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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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 | DB01526 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023781 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 120071 |
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KEGG Compound ID | C14210 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | 4-Androstenediol |
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METLIN ID | Not Available |
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PubChem Compound | 136297 |
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PDB ID | Not Available |
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ChEBI ID | 34386 |
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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 | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Thuyne WV, Delbeke FT: Validation of a GC-MS screening method for anabolizing agents in aqueous nutritional supplements. J Chromatogr Sci. 2005 Jan;43(1):2-6. [PubMed:15808000 ]
- Van Thuyne W, Delbeke FT: Validation of a GC-MS screening method for anabolizing agents in solid nutritional supplements. Biomed Chromatogr. 2004 Apr;18(3):155-9. [PubMed:15103700 ]
- Earnest CP, Olson MA, Broeder CE, Breuel KF, Beckham SG: In vivo 4-androstene-3,17-dione and 4-androstene-3 beta,17 beta-diol supplementation in young men. Eur J Appl Physiol. 2000 Feb;81(3):229-32. [PubMed:10638382 ]
- Parr MK, Geyer H, Reinhart U, Schanzer W: Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements. Food Addit Contam. 2004 Jul;21(7):632-40. [PubMed:15370836 ]
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