5alpha-androst-16-en-3-one (BioDeep_00001874408)
代谢物信息卡片
5alpha-androst-16-en-3-one
化学式: C19H28O (272.214)
中文名称: 雄烯酮, 5alpha-Androst-16-en-3-one
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC12CCC3C(C1CC=C2)CCC4C3(CCC(=O)C4)C
InChI: InChI=1S/C19H28O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13,15-17H,4-8,10-12H2,1-2H3/t13-,15-,16-,17-,18-,19-/m0/s1
描述信息
An androstanoid that is 5alpha-androst-16-ene substituted by an oxo group at position 3. It is a steroid pheromone found in high concentrations in the saliva of male pigs,.
同义名列表
数据库引用编号
5 个数据库交叉引用编号
- ChEBI: CHEBI:37894
- PubChem: 6852393
- ChEMBL: CHEMBL1309552
- CAS: 18339-16-7
- MetaboLights: MTBLC37894
分类词条
相关代谢途径
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
| 亚细胞结构定位 | 关联基因列表 |
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文献列表
- Christine Bone, Courtney Anderson, Yanping Lou, E J Squires. The characterization of androstenone transport in boar plasma.
The Journal of steroid biochemistry and molecular biology.
2019 01; 185(?):218-224. doi:
10.1016/j.jsbmb.2018.09.006. [PMID: 30205155] - L Huber, E J Squires, I B Mandell, C F M de Lange. Age at castration (surgical or immunological) impacts carcass characteristics and meat quality of male pigs.
Animal : an international journal of animal bioscience.
2018 Mar; 12(3):648-656. doi:
10.1017/s1751731117002063. [PMID: 28803576] - M van Son, R Agarwal, M P Kent, H Grove, E Grindflek, S Lien. Exploiting whole genome sequence data to fine map and characterize candidate genes within a quantitative trait loci region affecting androstenone on porcine chromosome 5.
Animal genetics.
2017 Dec; 48(6):653-659. doi:
10.1111/age.12615. [PMID: 29034488] - S P Parois, A Faoüen, N Le Floc'h, A Prunier. Influence of the inflammatory status of entire male pigs on their pubertal development and fat androstenone.
Animal : an international journal of animal bioscience.
2017 Jun; 11(6):1071-1077. doi:
10.1017/s1751731116002329. [PMID: 27832828] - C Brunius, J K Vidanarachchi, J Tomankova, K Lundström, K Andersson, G Zamaratskaia. Skatole metabolites in urine as a biological marker of pigs with enhanced hepatic metabolism.
Animal : an international journal of animal bioscience.
2016 Oct; 10(10):1734-40. doi:
10.1017/s1751731116000574. [PMID: 27080076] - J Wauters, J Vanden Bussche, K Verplanken, K M Bekaert, M Aluwé, A Van den Broeke, A Coussé, N Buys, L Vanhaecke. Development of a quantitative method for the simultaneous analysis of the boar taint compounds androstenone, skatole and indole in porcine serum and plasma by means of ultra-high performance liquid chromatography coupled to high resolution mass spectrometry.
Food chemistry.
2015 Nov; 187(?):120-9. doi:
10.1016/j.foodchem.2015.04.066. [PMID: 25977006] - A Van den Broeke, M Aluwé, S Janssens, J Wauters, L Vanhaecke, N Buys, S Millet, F A M Tuyttens. The effect of the MC4R gene on boar taint compounds, sexual maturity and behaviour in growing-finishing boars and gilts.
Animal : an international journal of animal bioscience.
2015 Oct; 9(10):1688-97. doi:
10.1017/s1751731115001135. [PMID: 26155873] - R Thomsen, S A Edwards, B B Jensen, T Rousing, J T Sørensen. Effect of faecal soiling on skatole and androstenone occurrence in organic entire male pigs.
Animal : an international journal of animal bioscience.
2015 Sep; 9(9):1587-96. doi:
10.1017/s1751731115000798. [PMID: 25990887] - S P Parois, A Prunier, M J Mercat, E Merlot, C Larzul. Genetic relationships between measures of sexual development, boar taint, health, and aggressiveness in pigs.
Journal of animal science.
2015 Aug; 93(8):3749-58. doi:
10.2527/jas.2014-8290. [PMID: 26440153] - Raffael Wesoly, Ina Jungbluth, Volker Stefanski, Ulrike Weiler. Pre-slaughter conditions influence skatole and androstenone in adipose tissue of boars.
Meat science.
2015 Jan; 99(?):60-7. doi:
10.1016/j.meatsci.2014.08.015. [PMID: 25282669] - Suzanne J Rowe, Burak Karacaören, Dirk-Jan de Koning, Boris Lukic, Nicola Hastings-Clark, Ingela Velander, Chris S Haley, Alan L Archibald. Analysis of the genetics of boar taint reveals both single SNPs and regional effects.
BMC genomics.
2014 Jun; 15(?):424. doi:
10.1186/1471-2164-15-424. [PMID: 24894739] - André M Hidalgo, John W M Bastiaansen, Barbara Harlizius, Hendrik-Jan Megens, Ole Madsen, Richard P M A Crooijmans, Martien A M Groenen. On the relationship between an Asian haplotype on chromosome 6 that reduces androstenone levels in boars and the differential expression of SULT2A1 in the testis.
BMC genetics.
2014 Jan; 15(?):4. doi:
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Doklady biological sciences : proceedings of the Academy of Sciences of the USSR, Biological sciences sections.
2013 Nov; 453(?):380-2. doi:
10.1134/s0012496613060173. [PMID: 24385176] - Asep Gunawan, Sudeep Sahadevan, Christiane Neuhoff, Christine Große-Brinkhaus, Ahmed Gad, Luc Frieden, Dawit Tesfaye, Ernst Tholen, Christian Looft, Muhammad Jasim Uddin, Karl Schellander, Mehmet Ulas Cinar. RNA deep sequencing reveals novel candidate genes and polymorphisms in boar testis and liver tissues with divergent androstenone levels.
PloS one.
2013; 8(5):e63259. doi:
10.1371/journal.pone.0063259. [PMID: 23696805] - Martin Krøyer Rasmussen, Carl Brunius, Bo Ekstrand, Galia Zamaratskaia. Expression of hepatic 3β-hydroxysteroid dehydrogenase and sulfotransferase 2A1 in entire and castrated male pigs.
Molecular biology reports.
2012 Aug; 39(8):7927-32. doi:
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Meat science.
2012 Aug; 91(4):396-401. doi:
10.1016/j.meatsci.2012.01.020. [PMID: 22353791] - Martin Krøyer Rasmussen, Carl Brunius, Galia Zamaratskaia, Bo Ekstrand. Feeding dried chicory root to pigs decrease androstenone accumulation in fat by increasing hepatic 3β hydroxysteroid dehydrogenase expression.
The Journal of steroid biochemistry and molecular biology.
2012 May; 130(1-2):90-5. doi:
10.1016/j.jsbmb.2012.01.003. [PMID: 22353548] - Carl Brunius, Galia Zamaratskaia, Kristina Andersson, Gang Chen, Mattias Norrby, Andrzej Madej, Kerstin Lundström. Early immunocastration of male pigs with Improvac(®) - effect on boar taint, hormones and reproductive organs.
Vaccine.
2011 Nov; 29(51):9514-20. doi:
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Animal : an international journal of animal bioscience.
2011 Sep; 5(11):1814-20. doi:
10.1017/s1751731111000838. [PMID: 22440422] - M K Rasmussen, G Zamaratskaia, B Ekstrand. Gender-related differences in cytochrome P450 in porcine liver--implication for activity, expression and inhibition by testicular steroids.
Reproduction in domestic animals = Zuchthygiene.
2011 Aug; 46(4):616-23. doi:
10.1111/j.1439-0531.2010.1714.x. [PMID: 21091800] - M Aluwé, K M Bekaert, F A M Tuyttens, L Vanhaecke, S De Smet, H F De Brabander, D L De Brabander, S Millet. Influence of soiling on boar taint in boars.
Meat science.
2011 Mar; 87(3):175-9. doi:
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Journal of animal science.
2011 Mar; 89(3):680-92. doi:
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Chemical senses.
2011 Jan; 36(1):9-17. doi:
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Theriogenology.
2010 Oct; 74(6):1088-98. doi:
10.1016/j.theriogenology.2010.05.006. [PMID: 20580070] - G Zamaratskaia, E J Squires. Biochemical, nutritional and genetic effects on boar taint in entire male pigs.
Animal : an international journal of animal bioscience.
2009 Nov; 3(11):1508-21. doi:
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Theriogenology.
2009 Sep; 72(5):672-80. doi:
10.1016/j.theriogenology.2009.04.025. [PMID: 19552946] - S Rottner, R Claus. Return of testicular function after vaccination of boars against GnRH: consequences on testes histology.
Animal : an international journal of animal bioscience.
2009 Sep; 3(9):1279-86. doi:
10.1017/s1751731109004844. [PMID: 22444904] - Maren Moe, Sigbjørn Lien, Torunn Aasmundstad, Theo H E Meuwissen, Marianne H S Hansen, Christian Bendixen, Eli Grindflek. Association between SNPs within candidate genes and compounds related to boar taint and reproduction.
BMC genetics.
2009 Jul; 10(?):32. doi:
10.1186/1471-2156-10-32. [PMID: 19575819] - Eva M Neuhaus, Weiyi Zhang, Lian Gelis, Ying Deng, Joachim Noldus, Hanns Hatt. Activation of an olfactory receptor inhibits proliferation of prostate cancer cells.
The Journal of biological chemistry.
2009 Jun; 284(24):16218-16225. doi:
10.1074/jbc.m109.012096. [PMID: 19389702] - Laurits Lydehøj Hansen, Sandra Stolzenbach, Jens Askov Jensen, Poul Henckel, Jens Hansen-Møller, Kostas Syriopoulos, Derek V Byrne. Effect of feeding fermentable fibre-rich feedstuffs on meat quality with emphasis on chemical and sensory boar taint in entire male and female pigs.
Meat science.
2008 Dec; 80(4):1165-73. doi:
10.1016/j.meatsci.2008.05.010. [PMID: 22063852] - K Lunde, B Egelandsdal, J Choinski, M Mielnik, A Flåtten, E Kubberød. Marinating as a technology to shift sensory thresholds in ready-to-eat entire male pork meat.
Meat science.
2008 Dec; 80(4):1264-72. doi:
10.1016/j.meatsci.2008.05.035. [PMID: 22063867] - C Pauly, P Spring, J V O'Doherty, S Ampuero Kragten, G Bee. Performances, meat quality and boar taint of castrates and entire male pigs fed a standard and a raw potato starch-enriched diet.
Animal : an international journal of animal bioscience.
2008 Nov; 2(11):1707-15. doi:
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Animal reproduction science.
2008 Oct; 108(1-2):37-48. doi:
10.1016/j.anireprosci.2007.07.001. [PMID: 17714891] - Maren Moe, Sigbjørn Lien, Christian Bendixen, Jakob Hedegaard, Henrik Hornshøj, Ingunn Berget, Theo H E Meuwissen, Eli Grindflek. Gene expression profiles in liver of pigs with extreme high and low levels of androstenone.
BMC veterinary research.
2008 Aug; 4(?):29. doi:
10.1186/1746-6148-4-29. [PMID: 18684314] - Galia Zamaratskaia, Ellen Dahl, Andrzej Madej, E James Squires, Oystein Andresen. Studies on 5alpha-androst-16-en-3-one binding to porcine serum, plasma and testicular cytosolic fraction and to human serum.
The Journal of steroid biochemistry and molecular biology.
2008 Jul; 111(1-2):24-8. doi:
10.1016/j.jsbmb.2008.02.010. [PMID: 18511263] - G Zamaratskaia, H K Andersson, G Chen, K Andersson, A Madej, K Lundström. Effect of a gonadotropin-releasing hormone vaccine (Improvac) on steroid hormones, boar taint compounds and performance in entire male pigs.
Reproduction in domestic animals = Zuchthygiene.
2008 Jun; 43(3):351-359. doi:
10.1111/j.1439-0531.2007.00914.x. [PMID: 18086253] - Erica J Reschly, Ni Ai, William J Welsh, Sean Ekins, Lee R Hagey, Matthew D Krasowski. Ligand specificity and evolution of liver X receptors.
The Journal of steroid biochemistry and molecular biology.
2008 May; 110(1-2):83-94. doi:
10.1016/j.jsbmb.2008.02.007. [PMID: 18395439] - G Zamaratskaia, Y Lou, J Peacock, L Rydhmer, H K Andersson, R K Juneja, G Chen, K Lundström, E J Squires. Effect of polymorphism in the porcine cytochrome b5 ( CYB5A) gene on androstenone and skatole concentrations and sexual development in Swedish pig populations.
Animal : an international journal of animal bioscience.
2008 Feb; 2(2):190-6. doi:
10.1017/s1751731107001103. [PMID: 22445012] - G Chen, E Bourneuf, S Marklund, G Zamaratskaia, A Madej, K Lundström. Gene expression of 3beta-hydroxysteroid dehydrogenase and 17beta-hydroxysteroid dehydrogenase in relation to androstenone, testosterone, and estrone sulphate in gonadally intact male and castrated pigs.
Journal of animal science.
2007 Oct; 85(10):2457-63. doi:
10.2527/jas.2007-0087. [PMID: 17609472] - G Zamaratskaia, Y Lou, G Chen, Ø Andresen, K Lundström, E J Squires. Effect of hCG stimulation on plasma androstenone concentrations and cytochrome b5 levels in testicular tissue.
Reproduction in domestic animals = Zuchthygiene.
2007 Feb; 42(1):105-8. doi:
10.1111/j.1439-0531.2006.00740.x. [PMID: 17214783] - P A Sinclair, W J Gilmore, Z Lin, Y Lou, E J Squires. Molecular cloning and regulation of porcine SULT2A1: relationship between SULT2A1 expression and sulfoconjugation of androstenone.
Journal of molecular endocrinology.
2006 Apr; 36(2):301-11. doi:
10.1677/jme.1.01847. [PMID: 16595701] - G Chen, G Zamaratskaia, A Madej, K Lundström. Effect of hCG administration on the relationship between testicular steroids and indolic compounds in fat and plasma in entire male pigs.
Meat science.
2006 Feb; 72(2):339-47. doi:
10.1016/j.meatsci.2005.08.004. [PMID: 22061563] - S Mikoshiba, H Takenaka, T Okumura, K Someya, M Ohdera. The suppressive effect of apricot kernel extract on 5alpha-Androst-16-en-3-one generated by microbial metabolism.
International journal of cosmetic science.
2006 Feb; 28(1):45-52. doi:
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Reproduction in domestic animals = Zuchthygiene.
2005 Dec; 40(6):500-6. doi:
10.1111/j.1439-0531.2005.00613.x. [PMID: 16324073] - G Zamaratskaia, A Madej, J Babol, Ej Squires, K Lundström. Free oestrone in adipose tissue and its relation to androstenone and skatole in entire male pigs.
Reproduction in domestic animals = Zuchthygiene.
2005 Apr; 40(2):156-60. doi:
10.1111/j.1439-0531.2005.00573.x. [PMID: 15819967] - P A Sinclair, E J Squires. Testicular sulfoconjugation of the 16-androstene steroids by hydroxysteroid sulfotransferase: its effect on the concentrations of 5alpha-androstenone in plasma and fat of the mature domestic boar.
Journal of animal science.
2005 Feb; 83(2):358-65. doi:
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Animal genetics.
2005 Feb; 36(1):14-22. doi:
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Reproduction in domestic animals = Zuchthygiene.
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The Journal of physiology.
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Meat science.
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Animal reproduction science.
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Journal of animal science.
2001 Oct; 79(10):2524-35. doi:
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2001 Jul; 79(7):1868-76. doi:
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Reproduction in domestic animals = Zuchthygiene.
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Journal of animal science.
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Reproduction, nutrition, developpement.
1983; 23(5):899-905. doi:
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Acta endocrinologica.
1982 Sep; 101(1):129-33. doi:
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Acta endocrinologica.
1982 Sep; 101(1):119-28. doi:
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Archiv fur experimentelle Veterinarmedizin.
1982; 36(5):739-50. doi:
NULL. [PMID: 7165458] - F R Fliess, H Kaiser, J Bergfeld. [Trials to eliminate the sex odor of growing boars through active immunization with an androstenone-protein conjugate].
Archiv fur experimentelle Veterinarmedizin.
1980; 34(2):227-33. doi:
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Acta veterinaria Scandinavica.
1980; 21(3):451-3. doi:
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Experientia.
1979 Dec; 35(12):1674-5. doi:
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The Biochemical journal.
1974 Nov; 144(2):347-52. doi:
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