Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-04-12 20:18:38 UTC |
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Update Date | 2021-09-14 15:40:10 UTC |
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HMDB ID | HMDB0006012 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Epimetendiol |
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Description | Epimetendiol is one of the major urinary metabolites of the anabolic androgenic compound metandienone. Anabolic-androgenic steroids such as metandienone are some of the most frequently detected drugs in amateur and professional sports. Doping control laboratories have developed numerous assays enabling the determination of administered drugs and/or their metabolic products that allow retrospectives with respect to pharmacokinetics and excretion profiles of steroids and their metabolites. Metandienone misuse can be detected by high resolution mass spectrometry for a prolonged period after stopping the intake of metandienone. Androgenic anabolic steroids are defined as natural, synthetic or semi-synthetic drugs chemicals derived from testosterone, used with the aim to improve physical performance by increasing both muscle strength and mass. Despite their reported toxicological effects on the cardiovascular, hepatic and neuro-endocrine systems, the AAS have been extensively used in sports activities. The use of anabolic steroids was banned by the International Olympic Committee for the first time at the Olympic Games in Montreal in 1976. Androgenic anabolic steroids (AAS) are defined as natural, synthetic or semi-synthetic drugs chemicals derived from testosterone, used with the aim to improve physical performance by increasing both muscle strength and mass. Despite their reported toxicological effects on the cardiovascular, hepatic and neuro-endocrine systems, the AAS have been extensively used in sports activities. (PMID: 16804957 , 10595716 , 10506840 , 1089834 , 14085300 , 14141174 , 3279830 , 4231505 , 4361633 , 4592844 , 4612989 , 4896687 , 4907221 , 4942579 , 6394898 ). |
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Structure | [H][C@@]12CC[C@@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2(C)C[C@H](O)C=C[C@]12C InChI=1S/C21H34O2/c1-18-9-6-15-16(19(18,2)10-5-14(22)13-18)7-11-20(3)17(15)8-12-21(20,4)23/h5,10,14-17,22-23H,6-9,11-13H2,1-4H3/t14-,15-,16+,17+,18-,19-,20+,21-/m1/s1 |
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Synonyms | Value | Source |
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(3a,5b,17a)-17-Methyl-androst-1-ene-3,17-diol | HMDB | 17-Epimetendiol | HMDB | 17b-Methyl-5b-androst-1-ene-3a,17a-diol | HMDB |
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Chemical Formula | C21H34O2 |
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Average Molecular Weight | 318.4935 |
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Monoisotopic Molecular Weight | 318.255880332 |
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IUPAC Name | (1S,2R,5S,7R,10R,11S,14R,15S)-2,7,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-ene-5,14-diol |
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Traditional Name | (1S,2R,5S,7R,10R,11S,14R,15S)-2,7,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-ene-5,14-diol |
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CAS Registry Number | 132830-78-5 |
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SMILES | [H][C@@]12CC[C@@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2(C)C[C@H](O)C=C[C@]12C |
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InChI Identifier | InChI=1S/C21H34O2/c1-18-9-6-15-16(19(18,2)10-5-14(22)13-18)7-11-20(3)17(15)8-12-21(20,4)23/h5,10,14-17,22-23H,6-9,11-13H2,1-4H3/t14-,15-,16+,17+,18-,19-,20+,21-/m1/s1 |
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InChI Key | NZDUEHZAWOAARB-BWTDTTKRSA-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-alpha-hydroxysteroid
- Hydroxysteroid
- 3-hydroxysteroid
- 3-hydroxy-delta-1-steroid
- Delta-1-steroid
- Tertiary alcohol
- 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 | Not Available |
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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 | |
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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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Epimetendiol,1TMS,isomer #1 | C[C@]12C=C[C@@H](O)C[C@@]1(C)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@@]2(C)O[Si](C)(C)C | 2680.3 | Semi standard non polar | 33892256 | Epimetendiol,1TMS,isomer #2 | C[C@]12CC[C@H]3[C@@H](CC[C@]4(C)C[C@H](O[Si](C)(C)C)C=C[C@]34C)[C@@H]1CC[C@@]2(C)O | 2656.8 | Semi standard non polar | 33892256 | Epimetendiol,2TMS,isomer #1 | C[C@]12C=C[C@@H](O[Si](C)(C)C)C[C@@]1(C)CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@@]2(C)O[Si](C)(C)C | 2667.6 | Semi standard non polar | 33892256 | Epimetendiol,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@]1(C)CC[C@H]2[C@@H]3CC[C@]4(C)C[C@H](O)C=C[C@]4(C)[C@H]3CC[C@@]21C | 2928.5 | Semi standard non polar | 33892256 | Epimetendiol,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@@H]1C=C[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@@]4(C)O)[C@@H]3CC[C@]2(C)C1 | 2933.2 | Semi standard non polar | 33892256 | Epimetendiol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@@H]1C=C[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@@]4(C)O[Si](C)(C)C(C)(C)C)[C@@H]3CC[C@]2(C)C1 | 3199.0 | Semi standard non polar | 33892256 |
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General References | - Kokkonen J, Leinonen A, Tuominen J, Seppala T: Comparison of sensitivity between gas chromatography-low-resolution mass spectrometry and gas chromatography-high-resolution mass spectrometry for determining metandienone metabolites in urine. J Chromatogr B Biomed Sci Appl. 1999 Nov 12;734(2):179-89. [PubMed:10595716 ]
- Schanzer W, Geyer H, Fussholler G, Halatcheva N, Kohler M, Parr MK, Guddat S, Thomas A, Thevis M: Mass spectrometric identification and characterization of a new long-term metabolite of metandienone in human urine. Rapid Commun Mass Spectrom. 2006;20(15):2252-8. [PubMed:16804957 ]
- Habscheid W, Abele U, Dahm HH: [Severe cholestasis with kidney failure from anabolic steroids in a body builder]. Dtsch Med Wochenschr. 1999 Sep 10;124(36):1029-32. [PubMed:10506840 ]
- Fedorov IV: [Biochemical changes in skeletal muscles during hypokinesia and possible means for counteracting them]. Kosm Biol Aviakosm Med. 1975 Jan-Feb;9(1):3-8. [PubMed:1089834 ]
- LARON Z, GITTER S: ANABOLIC STEROIDS: THEIR CLINICAL USE AND SPECIFIC DANGERS IN PEDIATRICS. Clin Pediatr (Phila). 1963 Nov;2:594-600. [PubMed:14085300 ]
- TAINTER ML, ARNOLD A, BEYLER AL, POTTS GO, ROTH CH: ANABOLIC STEROIDS IN THE MANAGEMENT OF THE DIABETIC PATIENT. N Y State J Med. 1964 Apr 15;64:1001-9. [PubMed:14141174 ]
- Pope HG Jr, Katz DL: Affective and psychotic symptoms associated with anabolic steroid use. Am J Psychiatry. 1988 Apr;145(4):487-90. [PubMed:3279830 ]
- Moldawer M: Anabolic agents: clinical efficacy versus side effects. J Am Med Womens Assoc. 1968 Apr;23(4):352-69. [PubMed:4231505 ]
- Herbst AL: Exogenous hormones in pregnancy. Clin Obstet Gynecol. 1973 Dec;16(4):37-50. [PubMed:4361633 ]
- Hirst AE Jr, Gore I: Marfan's syndrome: a review. Prog Cardiovasc Dis. 1973 Sep-Oct;16(2):187-98. [PubMed:4592844 ]
- Adigamov LF, Nesterin MF: [Metabolism of hormonal growth stimulants and chemical methods for determining them (a review of the literature)]. Vopr Pitan. 1973 Nov-Dec;(6):43-50. [PubMed:4612989 ]
- Zharov EI, Segal' RG: [Use of anabolic hormones for the treatment of cardiovascular patients]. Kardiologiia. 1969 Jan;9(1):144-53. [PubMed:4896687 ]
- Marks V, Salmols E: [Glucagon mediated insulin release in man]. Acta Diabetol Lat. 1968 Oct;5 Suppl 1:285-308. [PubMed:4907221 ]
- Mossor-Ostrowska J: [Anabolic steroids in the treatment of liver diseases]. Pol Tyg Lek. 1971 Aug 9;26(32):1248-51. [PubMed:4942579 ]
- Badalian LO, Temin PA, Mukhin KIu: [Treatment problems using anabolic steroids in progressive muscular dystrophy]. Klin Med (Mosk). 1984 Nov;62(11):23-9. [PubMed:6394898 ]
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