Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 05:55:25 UTC |
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Update Date | 2016-11-09 01:21:20 UTC |
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Accession Number | CHEM035607 |
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Identification |
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Common Name | 19-Oxotestosterone |
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Class | Small Molecule |
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Description | 19-Oxotestosterone 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. 19-Oxotestosterone exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 19-Oxotestosterone participates in a number of enzymatic reactions, within cattle. In particular, 19-Oxotestosterone can be converted into estradiol and formic acid through its interaction with the enzyme cytochrome P450 19A1. In addition, 19-Oxotestosterone can be biosynthesized from 19-hydroxytestosterone; which is catalyzed by the enzyme cytochrome P450 19A1. In cattle, 19-oxotestosterone is involved in the metabolic pathway called the androgen and estrogen metabolism pathway. |
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Contaminant Sources | |
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Not Available |
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Chemical Formula | C19H28O2 |
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Average Molecular Mass | 288.424 g/mol |
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Monoisotopic Mass | 288.209 g/mol |
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CAS Registry Number | 4075-13-2 |
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IUPAC Name | (1S,2S,10S,11S,14S,15S)-14-hydroxy-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-2-carbaldehyde |
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Traditional Name | 19-oxotestosterone |
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SMILES | [H][C@@]1(O)CC[C@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])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-WXJALIKYSA-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
- 19-oxosteroid
- 3-oxo-delta-4-steroid
- 3-oxosteroid
- 17-hydroxysteroid
- Oxosteroid
- Hydroxysteroid
- Delta-4-steroid
- Cyclohexenone
- Cyclic alcohol
- Cyclic ketone
- Secondary alcohol
- Ketone
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Aldehyde
- 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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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-1190000000-38a46782f3a05e410638 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0592-2169000000-be11c2989577a025bceb | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f79-0095000000-f1b4c5073a1a349142cd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ktr-0191000000-787c331104e02697f82e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052r-4290000000-c3ebd3f84fc5f2a0f1ad | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0039000000-fcbe7a10b70f243584ca | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ue9-0098000000-88bd42d7a3c0ee3d7238 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05fs-0090000000-e5ab8ef14971dd3b053a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0029000000-ab4e4333433d95463751 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-0190000000-58b8fdd5c28b55834da9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0aba-0900000000-a07aa8a9e25f2da78867 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0019000000-e1aa2d5a1d9cdeff04e6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0pi0-0093000000-1d8018c21ff4c38691c5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ab9-0290000000-794f96d5ceb67c29f858 | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0003959 |
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FooDB ID | FDB030283 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | 19-OXO-TESTOSTERONE |
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METLIN ID | 6991 |
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PDB ID | Not Available |
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Wikipedia Link | Not Available |
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Chemspider ID | 13628409 |
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ChEBI ID | 75308 |
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PubChem Compound ID | 7048589 |
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Kegg Compound ID | C05295 |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. Benson, Harvey Douglas; Grunwell, Joyce Francis; Johnston, John O'Neal; Petrow, Vladimir. Compositions for inducing an estrogenic response. Belg. (1977), 32 pp. | 2. Handelsman DJ: Clinical review: The rationale for banning human chorionic gonadotropin and estrogen blockers in sport. J Clin Endocrinol Metab. 2006 May;91(5):1646-53. Epub 2006 Feb 14. | 3. Mazer N, Fisher D, Fischer J, Cosgrove M, Bell D, Eilers B: Transfer of transdermally applied testosterone to clothing: a comparison of a testosterone patch versus a testosterone gel. J Sex Med. 2005 Mar;2(2):227-34. | 4. Pasqualotto FF, Lucon AM, de Goes PM, Sobreiro BP, Hallak J, Pasqualotto EB, Arap S: Relationship between the number of veins ligated in a varicocelectomy with testicular volume, hormonal levels and semen parameters outcome. J Assist Reprod Genet. 2005 Jun;22(6):245-9. | 5. Schaap LA, Pluijm SM, Smit JH, van Schoor NM, Visser M, Gooren LJ, Lips P: The association of sex hormone levels with poor mobility, low muscle strength and incidence of falls among older men and women. Clin Endocrinol (Oxf). 2005 Aug;63(2):152-60. | 6. Huang I, Jones J, Khorram O: Human seminal plasma nitric oxide: correlation with sperm morphology and testosterone. Med Sci Monit. 2006 Mar;12(3):CR103-6. Epub 2006 Feb 23. | 7. Ahtiainen JP, Pakarinen A, Alen M, Kraemer WJ, Hakkinen K: Short vs. long rest period between the sets in hypertrophic resistance training: influence on muscle strength, size, and hormonal adaptations in trained men. J Strength Cond Res. 2005 Aug;19(3):572-82. | 8. Tan U: Testosterone and somatosensory evoked potentials from right and left posterior tibial nerves in right-handed young adults. Int J Neurosci. 1990 Dec;55(2-4):161-70. | 9. Fejes I, Koloszar S, Szollosi J, Zavaczki Z, Pal A: Is semen quality affected by male body fat distribution? Andrologia. 2005 Oct;37(5):155-9. | 10. Jarow JP, Zirkin BR: The androgen microenvironment of the human testis and hormonal control of spermatogenesis. Ann N Y Acad Sci. 2005 Dec;1061:208-20. | 11. Klimek M, Pabian W, Tomaszewska B, Kolodziejczyk J: Levels of plasma ACTH in men from infertile couples. Neuro Endocrinol Lett. 2005 Aug;26(4):347-50. | 12. Fournier P, Boissier S, Filleur S, Guglielmi J, Cabon F, Colombel M, Clezardin P: Bisphosphonates inhibit angiogenesis in vitro and testosterone-stimulated vascular regrowth in the ventral prostate in castrated rats. Cancer Res. 2002 Nov 15;62(22):6538-44. | 13. Dicker A, Ryden M, Naslund E, Muehlen IE, Wiren M, Lafontan M, Arner P: Effect of testosterone on lipolysis in human pre-adipocytes from different fat depots. Diabetologia. 2004 Mar;47(3):420-428. doi: 10.1007/s00125-003-1324-0. Epub 2004 Jan 30. | 14. Sipila S, Heikkinen E, Cheng S, Suominen H, Saari P, Kovanen V, Alen M, Rantanen T: Endogenous hormones, muscle strength, and risk of fall-related fractures in older women. J Gerontol A Biol Sci Med Sci. 2006 Jan;61(1):92-6. | 15. Ferrando AA, Sheffield-Moore M, Wolf SE, Herndon DN, Wolfe RR: Testosterone administration in severe burns ameliorates muscle catabolism. Crit Care Med. 2001 Oct;29(10):1936-42. | 16. Martinez-Riera A, Santolaria-Fernandez F, Gonzalez Reimers E, Milena A, Gomez-Sirvent JL, Rodriguez-Moreno F, Gonzalez-Martin I, Rodriguez-Rodriguez E: Alcoholic hypogonadism: hormonal response to clomiphene. Alcohol. 1995 Nov-Dec;12(6):581-7. | 17. Ebert T, Jockenhovel F, Morales A, Shabsigh R: The current status of therapy for symptomatic late-onset hypogonadism with transdermal testosterone gel. Eur Urol. 2005 Feb;47(2):137-46. | 18. Shores MM, Matsumoto AM, Sloan KL, Kivlahan DR: Low serum testosterone and mortality in male veterans. Arch Intern Med. 2006 Aug 14-28;166(15):1660-5. | 19. Bhasin S, Cunningham GR, Hayes FJ, Matsumoto AM, Snyder PJ, Swerdloff RS, Montori VM: Testosterone therapy in adult men with androgen deficiency syndromes: an endocrine society clinical practice guideline. J Clin Endocrinol Metab. 2006 Jun;91(6):1995-2010. Epub 2006 May 23. | 20. Jarow JP, Wright WW, Brown TR, Yan X, Zirkin BR: Bioactivity of androgens within the testes and serum of normal men. J Androl. 2005 May-Jun;26(3):343-8. | 21. Lottrup G, Andersson AM, Leffers H, Mortensen GK, Toppari J, Skakkebaek NE, Main KM: Possible impact of phthalates on infant reproductive health. Int J Androl. 2006 Feb;29(1):172-80; discussion 181-5. | 22. https://www.ncbi.nlm.nih.gov/pubmed/?term=2317517 | 23. https://www.ncbi.nlm.nih.gov/pubmed/?term=2363692 | 24. https://www.ncbi.nlm.nih.gov/pubmed/?term=3857612 |
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