Dihydroandrosterone (BioDeep_00000027607)

 

Secondary id: BioDeep_00000015194, BioDeep_00000603881, BioDeep_00000637501

human metabolite Endogenous blood metabolite


代谢物信息卡片


(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol

化学式: C19H32O2 (292.24021719999996)
中文名称: 5a-雄甾烷-3a,17b-二醇
谱图信息: 最多检出来源 Homo sapiens(blood) 0.65%

分子结构信息

SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4O)C)O
InChI: InChI=1S/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17-,18-,19-/m0/s1

描述信息

Dihydroandrosterone is a major metabolite of testosterone. Dihydroandrosterone is the main steroid produced by the immature ovary; at puberty the synthesis of steroids shifts toward 4-ene-3-oxo steroids. testosterone 5a-reduced metabolites, including dihydrotestosterone are produced in the anterior pituitary and the central nervous system. Anabolic androgen steroid (AAS) are one of primary performance-enhancing substances abused by athletes. To defeat doping controls, athletes changed to take endogenous androgens from the application of synthetic AAS. testosterone was one candidate of endogenous androgens abused in sports. testosterone and its relevant steroids in urine is detected and monitored with GC/MS. The abuse of anabolic-androgenic steroids (AS) is a growing problem; however, the effects and mechanisms underlying their addictive effects are not well understood. (PMID: 17112575, 6243214, 491593, 491592) [HMDB]
Dihydroandrosterone is a major metabolite of testosterone. Dihydroandrosterone is the main steroid produced by the immature ovary; at puberty the synthesis of steroids shifts toward 4-ene-3-oxo steroids. testosterone 5a-reduced metabolites, including dihydrotestosterone are produced in the anterior pituitary and the central nervous system. Anabolic androgen steroid (AAS) are one of primary performance-enhancing substances abused by athletes. To defeat doping controls, athletes changed to take endogenous androgens from the application of synthetic AAS. testosterone was one candidate of endogenous androgens abused in sports. testosterone and its relevant steroids in urine is detected and monitored with GC/MS. The abuse of anabolic-androgenic steroids (AS) is a growing problem; however, the effects and mechanisms underlying their addictive effects are not well understood. (PMID: 17112575, 6243214, 491593, 491592).

同义名列表

20 个代谢物同义名

(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol; 5alpha-Androstane-3alpha,17beta-androstanediol; (3alpha,5alpha,17beta)-Androstane-3,17-diol; 3alpha,17beta-Dihydroxy-5alpha-androstane; 5alpha-Androstane-3alpha,17beta-diol; (3a,5a,17b)-Androstane-3,17-diol; (3Α,5α,17β)-androstane-3,17-diol; Etiocholane-3alpha,17beta-diol; 3Α,17β-dihydroxy-5α-androstane; 3a,17b-Dihydroxy-5a-androstane; 3a,5a-Tetrahydrotestosterone; 5a-Androstane-3a,17b-diol; 5Α-androstane-3α,17β-diol; Etiocholane-3a,17b-diol; Androstane-3a,17b-diol; Dihydroandrosterone; 3Α-androstanediol; 3a-Androstanediol; Hombreol; Adiol



数据库引用编号

15 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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)

3 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。



文献列表

  • K M McNamara, D T Harwood, U Simanainen, K A Walters, M Jimenez, D J Handelsman. Measurement of sex steroids in murine blood and reproductive tissues by liquid chromatography-tandem mass spectrometry. The Journal of steroid biochemistry and molecular biology. 2010 Aug; 121(3-5):611-8. doi: 10.1016/j.jsbmb.2010.02.001. [PMID: 20144714]
  • Mats Olsson, Lena Ekström, Jenny Schulze, Anders Kjellman, Olof Akre, Anders Rane, Ove Gustafsson. Radical prostatectomy: influence on serum and urinary androgen levels. The Prostate. 2010 Feb; 70(2):200-5. doi: 10.1002/pros.21053. [PMID: 19760638]
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  • Cheryl A Frye, Kassandra L Edinger, Edwin D Lephart, Alicia A Walf. 3alpha-androstanediol, but not testosterone, attenuates age-related decrements in cognitive, anxiety, and depressive behavior of male rats. Frontiers in aging neuroscience. 2010; 2(?):15. doi: 10.3389/fnagi.2010.00015. [PMID: 20552051]
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  • Hanna Pettersson, Johan Lundqvist, Ernst Oliw, Maria Norlin. CYP7B1-mediated metabolism of 5alpha-androstane-3alpha,17beta-diol (3alpha-Adiol): a novel pathway for potential regulation of the cellular levels of androgens and neurosteroids. Biochimica et biophysica acta. 2009 Dec; 1791(12):1206-15. doi: 10.1016/j.bbalip.2009.08.010. [PMID: 19732851]
  • L Di Luigi, P Sgrò, F Romanelli, M Mazzarino, F Donati, M C Braganò, S Bianchini, V Fierro, M Casasco, F Botrè, A Lenzi. Urinary and serum hormones profiles after testosterone enanthate administration in male hypogonadism: concerns on the detection of doping with testosterone in treated hypogonadal athletes. Journal of endocrinological investigation. 2009 May; 32(5):445-53. doi: 10.1007/bf03346484. [PMID: 19461217]
  • Tatsuya Higashi, Hiroyuki Yokoi, Yukiko Nagura, Tadashi Nishio, Kazutake Shimada. Studies on neurosteroids XXIV. Determination of neuroactive androgens, androsterone and 5alpha-androstane-3alpha,17beta-diol, in rat brain and serum using liquid chromatography-tandem mass spectrometry. Biomedical chromatography : BMC. 2008 Dec; 22(12):1434-41. doi: 10.1002/bmc.1078. [PMID: 18655222]
  • Ute Mareck, Hans Geyer, Georg Opfermann, Mario Thevis, Wilhelm Schänzer. Factors influencing the steroid profile in doping control analysis. Journal of mass spectrometry : JMS. 2008 Jul; 43(7):877-91. doi: 10.1002/jms.1457. [PMID: 18570179]
  • Thomas Piper, Ute Mareck, Hans Geyer, Ulrich Flenker, Mario Thevis, Petra Platen, Wilhelm Schänzer. Determination of 13C/12C ratios of endogenous urinary steroids: method validation, reference population and application to doping control purposes. Rapid communications in mass spectrometry : RCM. 2008 Jul; 22(14):2161-75. doi: 10.1002/rcm.3601. [PMID: 18536069]
  • Katryna Bogovich. The impact of unabated stimulation by human chorionic gonadotropin on the steroid hormone environment of pregnant rats and the spontaneous expression of ovarian cysts in female progeny. Endocrine. 2008 Apr; 33(2):152-64. doi: 10.1007/s12020-008-9072-z. [PMID: 18481228]
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  • Pierre-Gilles Blanchard, Van Luu-The. Differential androgen and estrogen substrates specificity in the mouse and primates type 12 17beta-hydroxysteroid dehydrogenase. The Journal of endocrinology. 2007 Aug; 194(2):449-55. doi: 10.1677/joe-07-0144. [PMID: 17641292]
  • Ann W Hsing, Frank Z Stanczyk, Alain Bélanger, Paul Schroeder, Lilly Chang, Roni T Falk, Thomas R Fears. Reproducibility of serum sex steroid assays in men by RIA and mass spectrometry. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2007 May; 16(5):1004-8. doi: 10.1158/1055-9965.epi-06-0792. [PMID: 17507629]
  • Mario Thevis, Hans Geyer, Ute Mareck, Ulrich Flenker, Wilhelm Schänzer. Doping-control analysis of the 5alpha-reductase inhibitor finasteride: determination of its influence on urinary steroid profiles and detection of its major urinary metabolite. Therapeutic drug monitoring. 2007 Apr; 29(2):236-47. doi: 10.1097/ftd.0b013e31803bb85d. [PMID: 17417080]
  • Peirong Hu, Min Zhang, Joseph L Napoli. Ontogeny of rdh9 (Crad3) expression: ablation causes changes in retinoid and steroid metabolizing enzymes, but RXR and androgen signaling seem normal. Biochimica et biophysica acta. 2007 Apr; 1770(4):694-705. doi: 10.1016/j.bbagen.2006.12.008. [PMID: 17270348]
  • A L Eriksson, M Lorentzon, D Mellström, L Vandenput, C Swanson, N Andersson, G L Hammond, J Jakobsson, A Rane, E S Orwoll, O Ljunggren, O Johnell, F Labrie, S H Windahl, C Ohlsson. SHBG gene promoter polymorphisms in men are associated with serum sex hormone-binding globulin, androgen and androgen metabolite levels, and hip bone mineral density. The Journal of clinical endocrinology and metabolism. 2006 Dec; 91(12):5029-37. doi: 10.1210/jc.2006-0679. [PMID: 16926255]
  • Sarah Chouinard, Georges Pelletier, Alain Bélanger, Olivier Barbier. Isoform-specific regulation of uridine diphosphate-glucuronosyltransferase 2B enzymes in the human prostate: differential consequences for androgen and bioactive lipid inactivation. Endocrinology. 2006 Nov; 147(11):5431-42. doi: 10.1210/en.2006-0229. [PMID: 16887906]
  • Tatsuya Higashi, Yasuaki Ninomiya, Naoko Iwaki, Akinori Yamauchi, Naoki Takayama, Kazutake Shimada. Studies on neurosteroids XVIII LC-MS analysis of changes in rat brain and serum testosterone levels induced by immobilization stress and ethanol administration. Steroids. 2006 Jul; 71(7):609-17. doi: 10.1016/j.steroids.2006.03.003. [PMID: 16620893]
  • Mahboubeh Papari-Zareei, Andrew Brandmaier, Richard J Auchus. Arginine 276 controls the directional preference of AKR1C9 (rat liver 3alpha-hydroxysteroid dehydrogenase) in human embryonic kidney 293 cells. Endocrinology. 2006 Apr; 147(4):1591-7. doi: 10.1210/en.2005-1141. [PMID: 16357042]
  • Doodipala S Reddy, Lata Venkatarangan, Benjamin Chien, Kumar Ramu. A high-performance liquid chromatography-tandem mass spectrometry assay of the androgenic neurosteroid 3alpha-androstanediol (5alpha-androstane-3alpha,17beta-diol) in plasma. Steroids. 2005 Dec; 70(13):879-85. doi: 10.1016/j.steroids.2005.05.007. [PMID: 16040068]
  • Madeline E Rhodes, Jayanth Talluri, Jacob P Harney, Cheryl A Frye. Ketogenic diet decreases circulating concentrations of neuroactive steroids of female rats. Epilepsy & behavior : E&B. 2005 Sep; 7(2):231-9. doi: 10.1016/j.yebeh.2005.05.025. [PMID: 16054440]
  • Véronique Bellemare, Frédérick Faucher, Rock Breton, Van Luu-The. Characterization of 17alpha-hydroxysteroid dehydrogenase activity (17alpha-HSD) and its involvement in the biosynthesis of epitestosterone. BMC biochemistry. 2005 Jul; 6(?):12. doi: 10.1186/1471-2091-6-12. [PMID: 16018803]
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  • Christophe Saudan, Norbert Baume, Patrice Mangin, Martial Saugy. Urinary analysis of 16(5alpha)-androsten-3alpha-ol by gas chromatography/combustion/isotope ratio mass spectrometry: implications in anti-doping analysis. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Oct; 810(1):157-64. doi: 10.1016/j.jchromb.2004.07.029. [PMID: 15358320]
  • Cheryl A Frye, Kassandra L Edinger, Angela M Seliga, JoAnna M Wawrzycki. 5alpha-reduced androgens may have actions in the hippocampus to enhance cognitive performance of male rats. Psychoneuroendocrinology. 2004 Sep; 29(8):1019-27. doi: 10.1016/j.psyneuen.2003.10.004. [PMID: 15219653]
  • Michael W Leihy, Geoffrey Shaw, Jean D Wilson, Marilyn B Renfree. Penile development is initiated in the tammar wallaby pouch young during the period when 5alpha-androstane-3alpha,17beta-diol is secreted by the testes. Endocrinology. 2004 Jul; 145(7):3346-52. doi: 10.1210/en.2004-0150. [PMID: 15059957]
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  • Tea Lanisnik Rizner, Hsueh K Lin, Trevor M Penning. Role of human type 3 3alpha-hydroxysteroid dehydrogenase (AKR1C2) in androgen metabolism of prostate cancer cells. Chemico-biological interactions. 2003 Feb; 143-144(?):401-9. doi: 10.1016/s0009-2797(02)00179-5. [PMID: 12604227]
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  • M W Leihy, G Shaw, J D Wilson, M B Renfree. Virilization of the urogenital sinus of the tammar wallaby is not unique to 5alpha-androstane-3alpha,17beta-diol. Molecular and cellular endocrinology. 2001 Jul; 181(1-2):111-5. doi: 10.1016/s0303-7207(01)00527-5. [PMID: 11476945]
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