Testosterone glucuronide (BioDeep_00001874143)

Main id: BioDeep_00000002701

 

natural product


代谢物信息卡片


17beta-hydroxyandrost-4-en-3-one 3-D-glucuronide

化学式: C25H36O8 (464.241)
中文名称: 睾酮β-D-葡糖苷酸
谱图信息: 最多检出来源 Homo sapiens(urine) 81.05%

分子结构信息

SMILES: CC12CCC3C(C1CCC2OC4C(C(C(C(O4)C(=O)O)O)O)O)CCC5=CC(=O)CCC35C
InChI: InChI=1S/C25H36O8/c1-24-9-7-13(26)11-12(24)3-4-14-15-5-6-17(25(15,2)10-8-16(14)24)32-23-20(29)18(27)19(28)21(33-23)22(30)31/h11,14-21,23,27-29H,3-10H2,1-2H3,(H,30,31)/t14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-/m0/s1

描述信息

A steroid glucosiduronic that is testosterone carrying a glucosiduronic acid residue at position 17.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

同义名列表

6 个代谢物同义名

17beta-hydroxyandrost-4-en-3-one 3-D-glucuronide; Testosterone 17beta-(beta-D-glucuronide); testosterone 17-glucosiduronic acid; Testosterone glucuronide; ST 19:2;O2;GlcA; Testosterone glucuronide



数据库引用编号

14 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)

9 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

  • Jenny Schulze, Kim Pettersson-Bohlin, John-Olof Thörngren, Lena Ekström. Re-evaluation of combined ((ES/EG)/(TS/TG)) ratio as a marker of testosterone intake in men. Drug testing and analysis. 2021 Aug; 13(8):1576-1579. doi: 10.1002/dta.3045. [PMID: 33864421]
  • R Wang, M F Hartmann, S A Wudy. Targeted LC-MS/MS analysis of steroid glucuronides in human urine. The Journal of steroid biochemistry and molecular biology. 2021 01; 205(?):105774. doi: 10.1016/j.jsbmb.2020.105774. [PMID: 33172831]
  • Haeyoung Zhang, Abdul Basit, Chris Wolford, Kuan-Fu Chen, Andrea Gaedigk, Yvonne S Lin, J Steven Leeder, Bhagwat Prasad. Normalized Testosterone Glucuronide as a Potential Urinary Biomarker for Highly Variable UGT2B17 in Children 7-18 Years. Clinical pharmacology and therapeutics. 2020 05; 107(5):1149-1158. doi: 10.1002/cpt.1764. [PMID: 31900930]
  • Hannah Colldén, Andreas Landin, Ville Wallenius, Erik Elebring, Lars Fändriks, Maria E Nilsson, Henrik Ryberg, Matti Poutanen, Klara Sjögren, Liesbeth Vandenput, Claes Ohlsson. The gut microbiota is a major regulator of androgen metabolism in intestinal contents. American journal of physiology. Endocrinology and metabolism. 2019 12; 317(6):E1182-E1192. doi: 10.1152/ajpendo.00338.2019. [PMID: 31689143]
  • M Lehtihet, A Andersson, A Börjesson, J Schulze, A Rane, M Ericsson, L Ekström. Codeine influences the serum and urinary profile of endogenous androgens but does not interact with the excretion rate of administered testosterone. Drug testing and analysis. 2018 Apr; 10(4):723-730. doi: 10.1002/dta.2301. [PMID: 28901724]
  • Eva Choong, Jenny J Schulze, Magnus Ericsson, Anders Rane, Lena Ekström. Discordant genotyping results using DNA isolated from anti-doping control urine samples. Drug testing and analysis. 2017 Jul; 9(7):994-1000. doi: 10.1002/dta.2103. [PMID: 27706926]
  • Emmanuel Strahm, Jenny E Mullen, Nina Gårevik, Magnus Ericsson, Jenny J Schulze, Anders Rane, Lena Ekström. Dose-dependent testosterone sensitivity of the steroidal passport and GC-C-IRMS analysis in relation to the UGT2B17 deletion polymorphism. Drug testing and analysis. 2015 Nov; 7(11-12):1063-70. doi: 10.1002/dta.1841. [PMID: 26198073]
  • Andreu Fabregat, Josep Marcos, Lorena Garrostas, Jordi Segura, Oscar J Pozo, Rosa Ventura. Evaluation of urinary excretion of androgens conjugated to cysteine in human pregnancy by mass spectrometry. The Journal of steroid biochemistry and molecular biology. 2014 Jan; 139(?):192-200. doi: 10.1016/j.jsbmb.2013.01.014. [PMID: 23410595]
  • Masato Okano, Toshihiko Ueda, Yasunori Nishitani, Hiroko Kano, Ayako Ikekita, Shinji Kageyama. UDP-glucuronosyltransferase 2B17 genotyping in Japanese athletes and evaluation of the current sports drug testing for detecting testosterone misuse. Drug testing and analysis. 2013 Mar; 5(3):166-81. doi: 10.1002/dta.1394. [PMID: 22887913]
  • S Medina, F Ferreres, C García-Viguera, M N Horcajada, J Orduna, M Savirón, G Zurek, J M Martínez-Sanz, J I Gil, A Gil-Izquierdo. Non-targeted metabolomic approach reveals urinary metabolites linked to steroid biosynthesis pathway after ingestion of citrus juice. Food chemistry. 2013 Jan; 136(2):938-46. doi: 10.1016/j.foodchem.2012.09.004. [PMID: 23122147]
  • Chun-Chi Wang, Jia-Ling Chen, Yen-Ling Chen, Hui-Ling Cheng, Shou-Mei Wu. A novel stacking method of repetitive large volume sample injection and sweeping MEKC for determination of androgenic steroids in urine. Analytica chimica acta. 2012 Sep; 744(?):99-104. doi: 10.1016/j.aca.2012.07.021. [PMID: 22935380]
  • Carl Jenkinson, Andrea Petroczi, Declan P Naughton. Red wine and component flavonoids inhibit UGT2B17 in vitro. Nutrition journal. 2012 Sep; 11(?):67. doi: 10.1186/1475-2891-11-67. [PMID: 22958586]
  • Carl Jenkinson, Andrea Petroczi, James Barker, Declan P Naughton. Dietary green and white teas suppress UDP-glucuronosyltransferase UGT2B17 mediated testosterone glucuronidation. Steroids. 2012 May; 77(6):691-5. doi: 10.1016/j.steroids.2012.02.023. [PMID: 22429924]
  • Serena Ambrosini, Sudhirkumar Shinde, Ersilia De Lorenzi, Borje Sellergren. Glucuronide directed molecularly imprinted solid-phase extraction: isolation of testosterone glucuronide from its parent drug in urine. The Analyst. 2012 Jan; 137(1):249-54. doi: 10.1039/c1an15606c. [PMID: 22034618]
  • Jenny J Schulze, John-Olof Thörngren, Mats Garle, Lena Ekström, Anders Rane. Androgen sulfation in healthy UDP-glucuronosyl transferase 2B17 enzyme-deficient men. The Journal of clinical endocrinology and metabolism. 2011 Nov; 96(11):3440-7. doi: 10.1210/jc.2011-0521. [PMID: 21849521]
  • Gushinder Kaur-Atwal, James C Reynolds, Christopher Mussell, Elodie Champarnaud, Tom W Knapman, Alison E Ashcroft, Gavin O'Connor, Steven D R Christie, Colin S Creaser. Determination of testosterone and epitestosterone glucuronides in urine by ultra performance liquid chromatography-ion mobility-mass spectrometry. The Analyst. 2011 Oct; 136(19):3911-6. doi: 10.1039/c1an15450h. [PMID: 21842047]
  • Lisa Yon, Brian Faulkner, Sumolya Kanchanapangka, Narongsak Chaiyabutr, Sompast Meepan, Bill Lasley. A safer method for studying hormone metabolism in an Asian elephant (Elephas maximus): accelerator mass spectrometry. Zoo biology. 2010 Nov; 29(6):760-6. doi: 10.1002/zoo.20309. [PMID: 20127658]
  • Nawed Deshmukh, Andrea Petróczi, James Barker, Andrea D Székely, Iltaf Hussain, Declan P Naughton. Potentially harmful advantage to athletes: a putative connection between UGT2B17 gene deletion polymorphism and renal disorders with prolonged use of anabolic androgenic steroids. Substance abuse treatment, prevention, and policy. 2010 Apr; 5(?):7. doi: 10.1186/1747-597x-5-7. [PMID: 20429943]
  • Shaik M Zakir, M Shukla, Zaka-Ur-Rab Simi, J Ahmad, Mahmood Sajid. Serum cortisol and testosterone levels in idiopathic central serous chorioretinopathy. Indian journal of ophthalmology. 2009 Nov; 57(6):419-22. doi: 10.4103/0301-4738.57143. [PMID: 19861741]
  • 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]
  • Jenny Jakobsson Schulze, Jonas Lundmark, Mats Garle, Lena Ekström, Pierre-Edouard Sottas, Anders Rane. Substantial advantage of a combined Bayesian and genotyping approach in testosterone doping tests. Steroids. 2009 Mar; 74(3):365-8. doi: 10.1016/j.steroids.2008.11.003. [PMID: 19056415]
  • Taina Sten, Ingo Bichlmaier, Tiia Kuuranne, Antti Leinonen, Jari Yli-Kauhaluoma, Moshe Finel. UDP-glucuronosyltransferases (UGTs) 2B7 and UGT2B17 display converse specificity in testosterone and epitestosterone glucuronidation, whereas UGT2A1 conjugates both androgens similarly. Drug metabolism and disposition: the biological fate of chemicals. 2009 Feb; 37(2):417-23. doi: 10.1124/dmd.108.024844. [PMID: 19022937]
  • Adam T Cawley, Graham J Trout, Rymantas Kazlauskas, Adrian V George. The detection of androstenedione abuse in sport: a mass spectrometry strategy to identify the 4-hydroxyandrostenedione metabolite. Rapid communications in mass spectrometry : RCM. 2008 Dec; 22(24):4147-57. doi: 10.1002/rcm.3826. [PMID: 19025884]
  • Borislav Starcevic, Anthony W Butch. Genetic variations in UDP-glucuronosyl transferase 2B17: implications for testosterone excretion profiling and doping control programs. Clinical chemistry. 2008 Dec; 54(12):1945-7. doi: 10.1373/clinchem.2008.110106. [PMID: 18927247]
  • Barbara Hauser, Doreen Schulz, Christophe Boesch, Tobias Deschner. Measuring urinary testosterone levels of the great apes--problems with enzymatic hydrolysis using Helix pomatia juice. General and comparative endocrinology. 2008 Aug; 158(1):77-86. doi: 10.1016/j.ygcen.2008.05.006. [PMID: 18639242]
  • Jenny Jakobsson Schulze, Jonas Lundmark, Mats Garle, Ilona Skilving, Lena Ekström, Anders Rane. Doping test results dependent on genotype of uridine diphospho-glucuronosyl transferase 2B17, the major enzyme for testosterone glucuronidation. The Journal of clinical endocrinology and metabolism. 2008 Jul; 93(7):2500-6. doi: 10.1210/jc.2008-0218. [PMID: 18334593]
  • Larry D Bowers. Testosterone doping: dealing with genetic differences in metabolism and excretion. The Journal of clinical endocrinology and metabolism. 2008 Jul; 93(7):2469-71. doi: 10.1210/jc.2008-0977. [PMID: 18617700]
  • Christophe Saudan, José M Entenza, Norbert Baume, Patrice Mangin, Martial Saugy. Short-term stability of testosterone and epitestosterone conjugates in urine samples: quantification by liquid chromatography-linear ion trap mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 Nov; 844(1):168-74. doi: 10.1016/j.jchromb.2006.07.010. [PMID: 16891159]
  • Norbert Baume, Christophe Saudan, Aurélien Desmarchelier, Emmanuel Strahm, Pierre-Edouard Sottas, Carlo Bagutti, Michel Cauderay, Yorck Olaf Schumacher, Patrice Mangin, Martial Saugy. Use of isotope ratio mass spectrometry to detect doping with oral testosterone undecanoate: inter-individual variability of 13C/12C ratio. Steroids. 2006 May; 71(5):364-70. doi: 10.1016/j.steroids.2005.11.004. [PMID: 16438998]
  • Emad A S Al-Dujaili. Development and validation of a simple and direct ELISA method for the determination of conjugated (glucuronide) and non-conjugated testosterone excretion in urine. Clinica chimica acta; international journal of clinical chemistry. 2006 Feb; 364(1-2):172-9. doi: 10.1016/j.cccn.2005.06.019. [PMID: 16098502]
  • C Jiménez, R de la Torre, J Segura, R Ventura. Stability studies of testosterone and epitestosterone glucuronides in urine. Rapid communications in mass spectrometry : RCM. 2006; 20(5):858-64. doi: 10.1002/rcm.2387. [PMID: 16470578]
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