Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-05-22 20:04:38 UTC |
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Update Date | 2021-09-14 15:40:23 UTC |
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HMDB ID | HMDB0006259 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 6beta-Hydroxytestosterone |
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Description | 6beta-Hydroxytestosterone, also known as 4-androsten-6b,17b-diol-3-one, 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. Thus, 6beta-hydroxytestosterone is considered to be a steroid. Based on a literature review a significant number of articles have been published on 6beta-Hydroxytestosterone. |
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Structure | [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)C2=CC(=O)CC[C@]12C InChI=1S/C19H28O3/c1-18-7-5-11(20)9-15(18)16(21)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h9,12-14,16-17,21-22H,3-8,10H2,1-2H3/t12-,13-,14-,16+,17-,18+,19-/m0/s1 |
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Synonyms | Value | Source |
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(6beta,17beta)-6,17-Dihydroxyandrost-4-en-3-one | ChEBI | 4-Androsten-6beta,17beta-diol-3-one | ChEBI | 6beta,17beta-Dihydroxy-4-androsten-3-one | ChEBI | 6beta,17beta-Dihydroxyandrost-4-en-3-one | ChEBI | (6b,17b)-6,17-Dihydroxyandrost-4-en-3-one | Generator | (6Β,17β)-6,17-dihydroxyandrost-4-en-3-one | Generator | 4-Androsten-6b,17b-diol-3-one | Generator | 4-Androsten-6β,17β-diol-3-one | Generator | 6b,17b-Dihydroxy-4-androsten-3-one | Generator | 6Β,17β-dihydroxy-4-androsten-3-one | Generator | 6b,17b-Dihydroxyandrost-4-en-3-one | Generator | 6Β,17β-dihydroxyandrost-4-en-3-one | Generator | 6b-Hydroxytestosterone | Generator | 6Β-hydroxytestosterone | Generator | 6 beta-Hydroxytestosterone | MeSH | 6 beta-Hydroxytestosterone, (17beta)-isomer | MeSH | 6 beta-Hydroxytestosterone, (6alpha,17beta)-isomer | MeSH | 6 beta Hydroxy testosterone | HMDB | 6,17-Dihydroxy-(6b,17b)-androst-4-en-3-one | HMDB | 6,17-Dihydroxy-(6beta,17beta)-androst-4-en-3-one | HMDB | 6,17-Dihydroxyandrost-4-en-3-one (acd/name 4.0) | HMDB |
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Chemical Formula | C19H28O3 |
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Average Molecular Weight | 304.4238 |
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Monoisotopic Molecular Weight | 304.203844762 |
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IUPAC Name | (1S,2R,8R,10R,11S,14S,15S)-8,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one |
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Traditional Name | 6β-hydroxytestosterone |
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CAS Registry Number | 62-99-7 |
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SMILES | [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)C2=CC(=O)CC[C@]12C |
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InChI Identifier | InChI=1S/C19H28O3/c1-18-7-5-11(20)9-15(18)16(21)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h9,12-14,16-17,21-22H,3-8,10H2,1-2H3/t12-,13-,14-,16+,17-,18+,19-/m0/s1 |
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InChI Key | XSEGWEUVSZRCBC-ZVBLRVHNSA-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
- 3-oxo-delta-4-steroid
- 3-oxosteroid
- 17-hydroxysteroid
- Oxosteroid
- 6-hydroxysteroid
- Hydroxysteroid
- Delta-4-steroid
- Cyclohexenone
- Cyclic alcohol
- Cyclic ketone
- Secondary alcohol
- Ketone
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- 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 | 172 °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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6beta-Hydroxytestosterone,1TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](C[C@@H](O)C4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C | 2884.3 | Semi standard non polar | 33892256 | 6beta-Hydroxytestosterone,1TMS,isomer #2 | C[C@]12CC[C@H]3[C@@H](C[C@@H](O[Si](C)(C)C)C4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2O | 2871.5 | Semi standard non polar | 33892256 | 6beta-Hydroxytestosterone,1TMS,isomer #3 | C[C@]12CC[C@H]3[C@@H](C[C@@H](O)C4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@H]2O | 2776.8 | Semi standard non polar | 33892256 | 6beta-Hydroxytestosterone,2TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](C[C@@H](O[Si](C)(C)C)C4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C | 2835.4 | Semi standard non polar | 33892256 | 6beta-Hydroxytestosterone,2TMS,isomer #2 | C[C@]12CC[C@H]3[C@@H](C[C@@H](O)C4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C | 2787.6 | Semi standard non polar | 33892256 | 6beta-Hydroxytestosterone,2TMS,isomer #3 | C[C@]12CC[C@H]3[C@@H](C[C@@H](O[Si](C)(C)C)C4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@H]2O | 2747.9 | Semi standard non polar | 33892256 | 6beta-Hydroxytestosterone,3TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](C[C@@H](O[Si](C)(C)C)C4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C | 2729.4 | Semi standard non polar | 33892256 | 6beta-Hydroxytestosterone,3TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](C[C@@H](O[Si](C)(C)C)C4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C | 2789.1 | Standard non polar | 33892256 | 6beta-Hydroxytestosterone,3TMS,isomer #1 | C[C@]12CC[C@H]3[C@@H](C[C@@H](O[Si](C)(C)C)C4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C | 3081.3 | Standard polar | 33892256 | 6beta-Hydroxytestosterone,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 3134.3 | Semi standard non polar | 33892256 | 6beta-Hydroxytestosterone,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H]3CC[C@H](O)[C@@]3(C)CC[C@@H]2[C@@]2(C)CCC(=O)C=C12 | 3104.6 | Semi standard non polar | 33892256 | 6beta-Hydroxytestosterone,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)[C@H](O)C[C@H]1[C@@H]3CC[C@H](O)[C@@]3(C)CC[C@@H]12 | 3061.3 | Semi standard non polar | 33892256 | 6beta-Hydroxytestosterone,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | 3306.8 | Semi standard non polar | 33892256 | 6beta-Hydroxytestosterone,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)[C@H](O)C[C@H]1[C@@H]3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12 | 3321.9 | Semi standard non polar | 33892256 | 6beta-Hydroxytestosterone,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@@H]3CC[C@H](O)[C@@]3(C)CC[C@@H]12 | 3236.8 | Semi standard non polar | 33892256 | 6beta-Hydroxytestosterone,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@@H]3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12 | 3454.9 | Semi standard non polar | 33892256 | 6beta-Hydroxytestosterone,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@@H]3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12 | 3423.0 | Standard non polar | 33892256 | 6beta-Hydroxytestosterone,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@@H]3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12 | 3396.0 | 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 - 6beta-Hydroxytestosterone GC-MS (Non-derivatized) - 70eV, Positive | splash10-002r-0490000000-fbce40562e85113343e0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6beta-Hydroxytestosterone GC-MS (2 TMS) - 70eV, Positive | splash10-001i-3201900000-19a880626afdcb624da4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6beta-Hydroxytestosterone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6beta-Hydroxytestosterone 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 - 6beta-Hydroxytestosterone 10V, Positive-QTOF | splash10-00kr-0092000000-489bed8773fcd0c13de6 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6beta-Hydroxytestosterone 20V, Positive-QTOF | splash10-00kr-0090000000-f07fc698e115a5f1c7cb | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6beta-Hydroxytestosterone 40V, Positive-QTOF | splash10-0pvl-3490000000-3c10f54e817114fb8e5a | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6beta-Hydroxytestosterone 10V, Negative-QTOF | splash10-0udi-0049000000-2030860ac7b87d34beb0 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6beta-Hydroxytestosterone 20V, Negative-QTOF | splash10-0udr-0097000000-0f7ab0e063794ee5cfd2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6beta-Hydroxytestosterone 40V, Negative-QTOF | splash10-00dr-1190000000-d45875a741e3ea1e7526 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6beta-Hydroxytestosterone 10V, Positive-QTOF | splash10-0a4i-0019000000-9b79f62ea088c74b3a3d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6beta-Hydroxytestosterone 20V, Positive-QTOF | splash10-0a6r-1794000000-57b269ff6c81d8c47be7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6beta-Hydroxytestosterone 40V, Positive-QTOF | splash10-0a4i-3910000000-eed8482fba4fd9079a6f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6beta-Hydroxytestosterone 10V, Negative-QTOF | splash10-0udi-0009000000-93986d59045cc7fce551 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6beta-Hydroxytestosterone 20V, Negative-QTOF | splash10-0udi-0009000000-93986d59045cc7fce551 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6beta-Hydroxytestosterone 40V, Negative-QTOF | splash10-0gbi-0092000000-1bd122937767d0574fc2 | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
- Endoplasmic reticulum
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Normal | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | 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 | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023864 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 18558308 |
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KEGG Compound ID | C14497 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 18603089 |
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PDB ID | Not Available |
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ChEBI ID | 34477 |
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Food Biomarker Ontology | Not Available |
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VMH ID | 6HTSTSTERONE |
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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 | Furuta Takashi; Suzuki Atsushi; Matsuzawa Mitsuhiro; Shibasaki Hiromi; Kasuya Yasuji Syntheses of stable isotope-labeled 6 beta-hydroxycortisol, 6 beta-hydroxycortisone, and 6 beta-hydroxytestosterone. Steroids (2003), 68(7-8), 693-703. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Testino SA Jr, Ozarowski J, Thurston AW, Arrendale RF, Patonay G: Determination of testosterone and 6beta-hydroxytestosterone by gas chromatography-selected ion monitoring-mass spectrometry for the characterization of cytochrome p450 3A activity. J Chromatogr B Biomed Sci Appl. 1999 Oct 29;734(1):73-81. [PubMed:10574192 ]
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