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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2019-01-11 19:14:50 UTC |
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HMDB ID | HMDB0000628 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Epitestosterone |
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Description | The 17-alpha isomer of testosterone, derived from pregnenolone via the delta5-steroid pathway, and via 5-androstene-3-beta,17-alpha-diol. Epitestosterone acts as an antiandrogen in various target tissues. The ratio between testosterone/epitestosterone is used to monitor anabolic drug abuse. |
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Structure | |
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Synonyms | Value | Source |
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Epi-testosterone | ChEBI | 17-Epitestosterone | HMDB | 17a-cis-Testosterone | HMDB | cis-Testosterone | HMDB | Isotestosterone | HMDB | 17-alpha-Testosterone | MeSH | 17 alpha Testosterone | MeSH |
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Chemical Formula | C19H28O2 |
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Average Molecular Weight | 288.4244 |
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Monoisotopic Molecular Weight | 288.20893014 |
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IUPAC Name | (1S,2R,10R,11S,14R,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one |
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Traditional Name | epitestosterone |
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CAS Registry Number | 481-30-1 |
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SMILES | [H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C |
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InChI Identifier | InChI=1S/C19H28O2/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/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17+,18-,19-/m0/s1 |
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InChI Key | MUMGGOZAMZWBJJ-KZYORJDKSA-N |
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Chemical Taxonomy |
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Description | This compound 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
- Hydroxysteroid
- Oxosteroid
- 17-hydroxysteroid
- Delta-4-steroid
- Cyclohexenone
- Cyclic alcohol
- Secondary alcohol
- Ketone
- Cyclic ketone
- Organooxygen compound
- Alcohol
- Carbonyl group
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- 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 | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental 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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Predicted Properties | |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-006t-1940000000-716f44b32e61cf34c7b4 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-006t-1940000000-716f44b32e61cf34c7b4 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-004i-3910000000-d6ace9b7f8aff4dd46d0 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-053u-1920200000-db3504f562c54e6e1bbb | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) | splash10-004l-3910000000-b43cd1ee268a855c8aa0 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) | splash10-004l-3910000000-356ddfa8ddf8e551278d | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0597-7920000000-dde7fba02fcbcec2d665 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-05fs-4920000000-ccd839134de79f179f9e | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00ds-0950000000-c65fc8043083ad93d169 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-004i-3910000000-d6ace9b7f8aff4dd46d0 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-053u-1920200000-db3504f562c54e6e1bbb | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-004l-3910000000-b43cd1ee268a855c8aa0 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-004l-3910000000-356ddfa8ddf8e551278d | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-074i-0390000000-09e2a725ebd92c93dc88 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-000t-1119000000-bf66038b9de80f6b8aab | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-0090000000-e1af5f6bcaf571731a2b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-052b-7900000000-581eb9c19ccb29ebac52 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-052b-9300000000-37c235bd069ce0c93813 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0690-0190000000-d4814fdc14f2b2818eb2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0fk9-1690000000-b39908a52b06c7853085 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00dr-0190000000-4b469479ef097f60ed90 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dr-0390000000-8bebba5f70c72e80b630 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-5890000000-46ba5a59d051001f2a63 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-3c963477109db1f6b39e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0090000000-87d4a2534cd39e8c54a8 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0abc-1190000000-abbd0808a06f67c1f6fc | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-00dv-5940000000-5e22fba0c369374c75df | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | - Extracellular
- Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | - Adrenal Gland
- Gonads
- Prostate
- Testes
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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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Blood | Detected and Quantified | 0.00132 +/- 0.00008 uM | Adult (>18 years old) | Male | Eugonadism | | details | Blood | Detected and Quantified | 0.00068 +/- 0.00004 uM | Adult (>18 years old) | Male | Hypogonadism | | details |
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Associated Disorders and Diseases |
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Disease References | Hypogonadism |
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- Kicman AT, Coutts SB, Cowan DA, Handelsman DJ, Howe CJ, Burring S, Wu FC: Adrenal and gonadal contributions to urinary excretion and plasma concentration of epitestosterone in men--effect of adrenal stimulation and implications for detection of testosterone abuse. Clin Endocrinol (Oxf). 1999 May;50(5):661-8. [PubMed:10468933 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB07768 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB021799 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 9789 |
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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 | Epitestosterone |
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METLIN ID | 5601 |
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PubChem Compound | 10204 |
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PDB ID | FFA |
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ChEBI ID | 42534 |
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References |
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Synthesis Reference | Alvarez, Francisco. Steroids. CCXLIX. A new synthesis of epitestosterone from pregnenolone acetate via nitrosation. Steroids (1963), 2(4), 393-8. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Falk O, Palonek E, Bjorkhem I: Effect of ethanol on the ratio between testosterone and epitestosterone in urine. Clin Chem. 1988 Jul;34(7):1462-4. [PubMed:3390919 ]
- Kicman AT, Oftebro H, Walker C, Norman N, Cowan DA: Potential use of ketoconazole in a dynamic endocrine test to differentiate between biological outliers and testosterone use by athletes. Clin Chem. 1993 Sep;39(9):1798-803. [PubMed:8375050 ]
- Riondino G, Strollo F: [Age-dependent changes in epitestosterone urinary excretion in man]. Boll Soc Ital Biol Sper. 1981 Nov 30;57(22):2215-21. [PubMed:7326107 ]
- Starka L: Epitestosterone. J Steroid Biochem Mol Biol. 2003 Oct;87(1):27-34. [PubMed:14630088 ]
- Marenich LP: [Effect of chorionic gonadotropin on the urinary excretion of testosterone and other androgens in healthy men and those with coronary arteriosclerosis]. Kardiologiia. 1979 Jun;19(6):76-9. [PubMed:156806 ]
- Aguilera R, Hatton CK, Catlin DH: Detection of epitestosterone doping by isotope ratio mass spectrometry. Clin Chem. 2002;48(4):629-36. [PubMed:11901061 ]
- Bicikova M, Hampl R, Hill M, Starka L: Inhibition of steroid 17 alpha-hydroxylase and C17,20-lyase in the human testis by epitestosterone. J Steroid Biochem Mol Biol. 1993 Oct;46(4):515-8. [PubMed:8217882 ]
- Havlikova H, Hill M, Hampl R, Starka L: Sex- and age-related changes in epitestosterone in relation to pregnenolone sulfate and testosterone in normal subjects. J Clin Endocrinol Metab. 2002 May;87(5):2225-31. [PubMed:11994368 ]
- Yamamoto Y, Peric-Golia P, Osawa Y, Kirdani RY, Sanberg AA: Androgen metabolism in sheep. Steroids. 1978 Oct;32(3):373-88. [PubMed:715826 ]
- Kicman AT, Coutts SB, Cowan DA, Handelsman DJ, Howe CJ, Burring S, Wu FC: Adrenal and gonadal contributions to urinary excretion and plasma concentration of epitestosterone in men--effect of adrenal stimulation and implications for detection of testosterone abuse. Clin Endocrinol (Oxf). 1999 May;50(5):661-8. [PubMed:10468933 ]
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