Ethylene dimethanesulfonate (BioDeep_00000178899)

   

human metabolite blood metabolite


代谢物信息卡片


2-(methanesulfonyloxy)ethyl methanesulfonate

化学式: C4H10O6S2 (217.9919)
中文名称:
谱图信息: 最多检出来源 Mus musculus(blood) 100%

分子结构信息

SMILES: CS(=O)(=O)OCCOS(=O)(=O)C
InChI: InChI=1S/C4H10O6S2/c1-11(5,6)9-3-4-10-12(2,7)8/h3-4H2,1-2H3

描述信息

同义名列表

15 个代谢物同义名

2-(methanesulfonyloxy)ethyl methanesulfonate; 1,2-Ethanediol, 1,2-dimethanesulfonate; 1,2-Bis(methanesulfonyloxy)ethane; 1,2-Ethanediyl dimethanesulfonate; Ethylene dimethanesulphonic acid; Ethylene dimethanesulfonic acid; Ethane 1,2-dimethanesulfonate; Ethylene dimethanesulphonate; Ethylene dimethane sulfonate; Ethylene dimethanesulfonate; Ethane dimethane sulfonate; Ethane dimethanesulphonate; Ethane dimethyl sulfonate; Ethane dimethanesulfonate; 1,2-Bis(mesyloxy)ethane



数据库引用编号

6 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)

1 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


文献列表

  • Huitao Li, Qiqi Zhu, Songxue Wang, Tongliang Huang, Xiaoheng Li, Chaobo Ni, Yinghui Fang, Linxi Li, Qingquan Lian, Ren-Shan Ge. Paraquat exposure delays stem/progenitor Leydig cell regeneration in the adult rat testis. Chemosphere. 2019 Sep; 231(?):60-71. doi: 10.1016/j.chemosphere.2019.05.104. [PMID: 31128353]
  • Chaobo Ni, Yinghui Fang, Xiuxiu Chen, Keyang Wu, Huitao Li, Yiyan Wang, Lin Zhenkun, Qingquan Lian, Ren-Shan Ge. Stem Leydig cell regeneration in the adult rat testis is inhibited after a short-term triphenyltin exposure. Toxicology letters. 2019 May; 306(?):80-89. doi: 10.1016/j.toxlet.2019.02.010. [PMID: 30772500]
  • Yue Duan, Yiyan Wang, Xiaoheng Li, Jiaying Mo, Xiaoling Guo, Chao Li, Mengyan Tu, Fei Ge, Wenwen Zheng, Jing Lin, Ren-Shan Ge. Fibroblast growth factor 16 stimulates proliferation but blocks differentiation of rat stem Leydig cells during regeneration. Journal of cellular and molecular medicine. 2019 04; 23(4):2632-2644. doi: 10.1111/jcmm.14157. [PMID: 30672118]
  • Dibyendu Dutta, In Park, Hiwot Guililat, Samuel Sang, Arpita Talapatra, Barkha Singhal, Nathaniel C Mills. Testosterone regulates granzyme K expression in rat testes. Endocrine regulations. 2017 Oct; 51(4):193-204. doi: 10.1515/enr-2017-0020. [PMID: 29232193]
  • Min Zhang, Jiancheng Wang, Chunhua Deng, Mei Hua Jiang, Xin Feng, Kai Xia, Weiqiang Li, Xingqiang Lai, Haipeng Xiao, Ren-Shan Ge, Yong Gao, Andy Peng Xiang. Transplanted human p75-positive stem Leydig cells replace disrupted Leydig cells for testosterone production. Cell death & disease. 2017 10; 8(10):e3123. doi: 10.1038/cddis.2017.531. [PMID: 29022899]
  • Xiaolong Wu, Xiaoling Guo, Huang Wang, Songyi Zhou, Lili Li, Xiaomin Chen, Guimin Wang, Jianpeng Liu, Hong-Shan Ge, Ren-Shan Ge. A brief exposure to cadmium impairs Leydig cell regeneration in the adult rat testis. Scientific reports. 2017 07; 7(1):6337. doi: 10.1038/s41598-017-06870-0. [PMID: 28740105]
  • Haolin Chen, Jingjing Guo, Renshan Ge, Qingquan Lian, Vassilios Papadopoulos, Barry R Zirkin. Steroidogenic fate of the Leydig cells that repopulate the testes of young and aged Brown Norway rats after elimination of the preexisting Leydig cells. Experimental gerontology. 2015 Dec; 72(?):8-15. doi: 10.1016/j.exger.2015.08.014. [PMID: 26335619]
  • M V T Lobo, M I Arenas, L Huerta, S Sacristán, M Pérez-Crespo, A Gutiérrez-Adán, J J Díaz-Gil, M A Lasunción, A Martín-Hidalgo. Liver growth factor induces testicular regeneration in EDS-treated rats and increases protein levels of class B scavenger receptors. American journal of physiology. Endocrinology and metabolism. 2015 Jan; 308(2):E111-21. doi: 10.1152/ajpendo.00329.2014. [PMID: 25389365]
  • Bingbing Chen, Dongxin Chen, Zheli Jiang, Jingyang Li, Shiwen Liu, Yaoyao Dong, Wenwen Yao, Benson Akingbemi, Renshan Ge, Xiaokun Li. Effects of estradiol and methoxychlor on Leydig cell regeneration in the adult rat testis. International journal of molecular sciences. 2014 May; 15(5):7812-26. doi: 10.3390/ijms15057812. [PMID: 24806340]
  • Xue Ma, Lu-Gang Huang, Qiang Dong. [Effects of ethane dimethane sulfonate on fetal Leydig cells in neonatal rats]. Beijing da xue xue bao. Yi xue ban = Journal of Peking University. Health sciences. 2013 Oct; 45(5):770-3. doi: NULL. [PMID: 24136276]
  • Jingjing Guo, Xing-Wang Li, Yong Liang, Yufei Ge, Xiaomin Chen, Qing-Quan Lian, Ren-Shan Ge. The increased number of Leydig cells by di(2-ethylhexyl) phthalate comes from the differentiation of stem cells into Leydig cell lineage in the adult rat testis. Toxicology. 2013 Apr; 306(?):9-15. doi: 10.1016/j.tox.2013.01.021. [PMID: 23391632]
  • Zoltan Erdos, Kara Pearson, Michael Goedken, Karsten Menzel, Frank D Sistare, Warren E Glaab, Louise Parks Saldutti. Inhibin B response to testicular toxicants hexachlorophene, ethane dimethane sulfonate, di-(n-butyl)-phthalate, nitrofurazone, DL-ethionine, 17-alpha ethinylestradiol, 2,5-hexanedione, or carbendazim following short-term dosing in male rats. Birth defects research. Part B, Developmental and reproductive toxicology. 2013 Feb; 98(1):41-53. doi: 10.1002/bdrb.21035. [PMID: 23348767]
  • Xing-Wang Li, Yong Liang, Ying Su, Haiyun Deng, Xiao-Heng Li, Jingjing Guo, Qing-Quan Lian, Ren-Shan Ge. Adverse effects of di-(2-ethylhexyl) phthalate on Leydig cell regeneration in the adult rat testis. Toxicology letters. 2012 Nov; 215(2):84-91. doi: 10.1016/j.toxlet.2012.10.001. [PMID: 23064086]
  • Liang Jiang, Longbiao Guo, Hua Jiang, Dali Zeng, Jiang Hu, Liwen Wu, Jian Liu, Zhenyu Gao, Qian Qian. Genetic analysis and fine-mapping of a dwarfing with withered leaf-tip mutant in rice. Journal of genetics and genomics = Yi chuan xue bao. 2008 Dec; 35(12):715-21. doi: 10.1016/s1673-8527(08)60226-x. [PMID: 19103426]
  • Mariana Bakalska, Nina Atanassova, Yvetta Koeva, Boycho Nikolov, Michail Davidoff. Induction of male germ cell apoptosis by testosterone withdrawal after ethane dimethanesulfonate treatment in adult rats. Endocrine regulations. 2004 Sep; 38(3):103-10. doi: NULL. [PMID: 15693288]
  • F F G Rommerts, L Kühne, G W A van Cappellen, D M Stocco, S R King, A Jankowska. Specific dose-dependent effects of ethane 1,2-dimethanesulfonate in rat and mouse Leydig cells and non-steroidogenic cells on programmed cell death. The Journal of endocrinology. 2004 Apr; 181(1):169-78. doi: 10.1677/joe.0.1810169. [PMID: 15072577]
  • Antonio Salva, Matthew P Hardy, Xiu-feng Wu, Chantal M Sottas, David T MacLaughlin, Patricia K Donahoe, Mary M Lee. Müllerian-inhibiting substance inhibits rat Leydig cell regeneration after ethylene dimethanesulphonate ablation. Biology of reproduction. 2004 Mar; 70(3):600-7. doi: 10.1095/biolreprod.103.021550. [PMID: 14585814]
  • Dana K Tarka-Leeds, Juan D Suarez, Naomi L Roberts, John M Rogers, Matthew P Hardy, Gary R Klinefelter. Gestational exposure to ethane dimethanesulfonate permanently alters reproductive competence in the CD-1 mouse. Biology of reproduction. 2003 Sep; 69(3):959-67. doi: 10.1095/biolreprod.103.017343. [PMID: 12748126]
  • S Ariyaratne, I Kim, N Mills, I Mason, C Mendis-Handagama. Effects of ethane dimethane sulfonate on the functional structure of the adult rat testis. Archives of andrology. 2003 Jul; 49(4):313-26. doi: 10.1080/01485010390204922. [PMID: 12851034]
  • V Sriraman, M R Sairam, A J Rao. Evaluation of relative roles of LH and FSH in regulation of differentiation of Leydig cells using an ethane 1,2-dimethylsulfonate-treated adult rat model. The Journal of endocrinology. 2003 Jan; 176(1):151-61. doi: 10.1677/joe.0.1760151. [PMID: 12525259]
  • B Plećas, V P Pesić, D Mirković, N Majkić-Singh, M Hristić, T Solarović. Opposite effects of dexamethasone and ACTH on the adrenal cortex response to ethane dimethanesulphonate (EDS). Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie. 2001 Apr; 53(1):31-4. doi: 10.1078/0940-2993-00163. [PMID: 11370731]
  • I Woolveridge, M F Taylor, F F Rommerts, I D Morris. Apoptosis related gene products in differentiated and tumorigenic rat Leydig cells and following regression induced by the cytotoxin ethane dimethanesulphonate. International journal of andrology. 2001 Feb; 24(1):56-64. doi: 10.1046/j.1365-2605.2001.00265.x. [PMID: 11168651]
  • D W Onyango, E O Wang, D Oduor-Okelo, G Werner. Early testicular response to intraperitoneal administration of ethane dimethanesulphonate (EDS) in the goat (Capra hircus). Journal of submicroscopic cytology and pathology. 2001 Jan; 33(1-2):117-24. doi: ". [PMID: 11686392]
  • S Minucci, G De Rienzo, R Di Sena, G Cobellis, R Meccariello, R Pierantoni, S Fasano. Effects of multiple injections of ethane 1,2-dimethane sulphonate (EDS) on the frog, Rana esculenta, testicular activity. The Journal of experimental zoology. 2000 Oct; 287(5):384-93. doi: 10.1002/1097-010x(20001001)287:5<384::aid-jez6>3.0.co;2-i. [PMID: 10980496]
  • H B Ariyaratne, N Mills, J I Mason, S M Mendis-Handagama. Effects of thyroid hormone on Leydig cell regeneration in the adult rat following ethane dimethane sulphonate treatment. Biology of reproduction. 2000 Oct; 63(4):1115-23. doi: 10.1095/biolreprod63.4.1115. [PMID: 10993834]
  • M Tena-Sempere, J Kero, A Rannikko, W Yan, I Huhtaniemi. The pattern of inhibin/activin alpha- and betaB-subunit messenger ribonucleic acid expression in rat testis after selective Leydig cell destruction by ethylene dimethane sulfonate. Endocrinology. 1999 Dec; 140(12):5761-70. doi: 10.1210/endo.140.12.7193. [PMID: 10579342]
  • R Sumathi, V Sriraman, B S Kurkalli, F F Rommerts, A J Rao. Ethane dimethylsulphonate selectively destroys Leydig cells in the adult bonnet monkeys (Macaca radiata). Asian journal of andrology. 1999 Sep; 1(3):115-20. doi: NULL. [PMID: 11250777]
  • M Tena-Sempere, J Kero, A Rannikko, I Huhtaniemi. Experimental cryptorchidism induces a change in the pattern of expression of LH receptor mRNA in rat testis after selective Leydig cell destruction by ethylene dimethane sulfonate. The Journal of endocrinology. 1999 Apr; 161(1):131-41. doi: 10.1677/joe.0.1610131. [PMID: 10194537]
  • B Plećas, A Glavaski, M Hristić, T Solarović. Ventral prostate structure and serum testosterone levels after chronic treatment with isoproterenol in adult rats with different androgen status. Archives of andrology. 1998 May; 40(3):225-36. doi: 10.3109/01485019808987946. [PMID: 9583360]
  • M Koga, H Tanaka, K Yomogida, J Tsuchida, K Uchida, M Kitamura, S Sakoda, K Matsumiya, A Okuyama, Y Nishimune. Expression of selenoprotein-P messenger ribonucleic acid in the rat testis. Biology of reproduction. 1998 Jan; 58(1):261-5. doi: 10.1095/biolreprod58.1.261. [PMID: 9472950]
  • M Tena-Sempere, A Rannikko, J Kero, F P Zhang, I T Huhtaniemi. Molecular mechanisms of reappearance of luteinizing hormone receptor expression and function in rat testis after selective Leydig cell destruction by ethylene dimethane sulfonate. Endocrinology. 1997 Aug; 138(8):3340-8. doi: 10.1210/endo.138.8.5325. [PMID: 9231786]
  • M Miyano, Y Ito, S Fujihira, T Matsuo, H Ueno, H Mori. Restoration of Leydig cells after repeated administration of ethane dimethanesulfonate in adult rats. Pathology international. 1997 Jul; 47(7):478-88. doi: 10.1111/j.1440-1827.1997.tb04527.x. [PMID: 9234387]
  • R L Sprando, B R Zirkin. Is Leydig cell steroidogenic function affected by the germ cell content of the seminiferous tubules?. Journal of andrology. 1997 Jul; 18(4):424-30. doi: NULL. [PMID: 9283956]
  • B Plećas, A Glavaski, V Savić, M Hristić, D Durić, T Solarović. Effects of ethane dimethanesulfonate on the structure of adult male rat adrenal cortex. Pharmacological research. 1997 Jun; 35(6):541-6. doi: 10.1006/phrs.1997.0186. [PMID: 9356206]
  • G R Klinefelter, J W Laskey, J Ferrell, J D Suarez, N L Roberts. Discriminant analysis indicates a single sperm protein (SP22) is predictive of fertility following exposure to epididymal toxicants. Journal of andrology. 1997 Mar; 18(2):139-50. doi: NULL. [PMID: 9154508]
  • J N Rao, L Debeljuk, A Bartke, Y P Gao, J F Wilber, P Feng. The detection of thyrotropin-releasing hormone (TRH) and TRH receptor gene expression in Siberian hamster testes. Peptides. 1997; 18(8):1217-22. doi: 10.1016/s0196-9781(97)00183-6. [PMID: 9396064]
  • H Chen, I Huhtaniemi, B R Zirkin. Depletion and repopulation of Leydig cells in the testes of aging brown Norway rats. Endocrinology. 1996 Aug; 137(8):3447-52. doi: 10.1210/endo.137.8.8754773. [PMID: 8754773]
  • J J Montagne, A Ladram, D Grouselle, P Nicolas, M Bulant. Identification and cellular localization of thyrotropin-releasing hormone-related peptides in rat testis. Endocrinology. 1996 Jan; 137(1):185-91. doi: 10.1210/endo.137.1.8536611. [PMID: 8536611]
  • S Minucci, S Fasano, C Marmorino, P Chieffi, R Pierantoni. Ethane 1,2-dimethane sulfonate effects on the testis of the lizard, Podarcis s. sicula Raf: morphological and hormonal changes. General and comparative endocrinology. 1995 Mar; 97(3):273-82. doi: 10.1006/gcen.1995.1027. [PMID: 7789742]
  • L E Gray, G Klinefelter, W Kelce, J Laskey, J Ostby, L Ewing. Hamster Leydig cells are less sensitive to ethane dimethanesulfonate when compared to rat Leydig cells both in vivo and in vitro. Toxicology and applied pharmacology. 1995 Feb; 130(2):248-56. doi: 10.1006/taap.1995.1030. [PMID: 7871538]
  • B Yan, D Yang, M Brady, A Parkinson. Rat testicular carboxylesterase: cloning, cellular localization, and relationship to liver hydrolase A. Archives of biochemistry and biophysics. 1995 Feb; 316(2):899-908. doi: 10.1006/abbi.1995.1121. [PMID: 7864649]
  • L S Holst, A M Hoffmann, H Mulder, F Sundler, C Holm, A Bergh, G Fredrikson. Localization of hormone-sensitive lipase to rat Sertoli cells and its expression in developing and degenerating testes. FEBS letters. 1994 Nov; 355(2):125-30. doi: 10.1016/0014-5793(94)01185-0. [PMID: 7982484]
  • M P Hedger, S Hettiarachchi. Measurement of immunoglobulin G levels in adult rat testicular interstitial fluid and serum. Journal of andrology. 1994 Nov; 15(6):583-90. doi: NULL. [PMID: 7721660]
  • M Tena-Sempere, F P Zhang, I Huhtaniemi. Persistent expression of a truncated form of the luteinizing hormone receptor messenger ribonucleic acid in the rat testis after selective Leydig cell destruction by ethylene dimethane sulfonate. Endocrinology. 1994 Sep; 135(3):1018-24. doi: 10.1210/endo.135.3.8070344. [PMID: 8070344]
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  • G R Klinefelter, J W Laskey, W R Kelce, J Ferrell, N L Roberts, J D Suarez, V Slott. Chloroethylmethanesulfonate-induced effects on the epididymis seem unrelated to altered Leydig cell function. Biology of reproduction. 1994 Jul; 51(1):82-91. doi: 10.1095/biolreprod51.1.82. [PMID: 7918878]
  • G R Klinefelter, J W Laskey, S D Perreault, J Ferrell, S Jeffay, J Suarez, N Roberts. The ethane dimethanesulfonate-induced decrease in the fertilizing ability of cauda epididymal sperm is independent of the testis. Journal of andrology. 1994 Jul; 15(4):318-27. doi: NULL. [PMID: 7982800]
  • T Matikainen, J Toppari, K K Vihko, I Huhtaniemi. Effects of recombinant human FSH in immature hypophysectomized male rats: evidence for Leydig cell-mediated action on spermatogenesis. The Journal of endocrinology. 1994 Jun; 141(3):449-57. doi: 10.1677/joe.0.1410449. [PMID: 8071643]
  • J W Laskey, G R Klinefelter, W R Kelce, L L Ewing. Effects of ethane dimethanesulfonate (EDS) on adult and immature rabbit Leydig cells: comparison with EDS-treated rat Leydig cells. Biology of reproduction. 1994 May; 50(5):1151-60. doi: 10.1095/biolreprod50.5.1151. [PMID: 8025172]
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  • G R Klinefelter, N L Roberts, J D Suarez. Direct effects of ethane dimethanesulphonate on epididymal function in adult rats. An in vitro demonstration. Journal of andrology. 1992 Sep; 13(5):409-21. doi: NULL. [PMID: 1331010]
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  • D F Cameron, K Whittington, R E Schultz, H P Selawry. Successful islet/abdominal testis transplantation does not require Leydig cells. Transplantation. 1990 Oct; 50(4):649-53. doi: 10.1097/00007890-199010000-00024. [PMID: 2171164]
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  • G Edwards, H Jackson, I D Morris. Testicular endocrine effects of alkane methanesulphonates related to the Leydig cell cytotoxic compound, EDS. Cancer chemotherapy and pharmacology. 1990; 26(1):19-25. doi: 10.1007/bf02940288. [PMID: 2157553]
  • R Schulz, F Paris, P Lembke, V Blüm. Testosterone immunoreactivity in the seminiferous epithelium of rat testis: effect of treatment with ethane dimethanesulfonate. The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society. 1989 Nov; 37(11):1667-73. doi: 10.1177/37.11.2553802. [PMID: 2553802]
  • K J Teerds, D G De Rooij, F F Rommerts, R van den Hurk, C J Wensing. Stimulation of the proliferation and differentiation of Leydig cell precursors after the destruction of existing Leydig cells with ethane dimethyl sulphonate (EDS) can take place in the absence of LH. Journal of andrology. 1989 Nov; 10(6):472-7. doi: 10.1002/j.1939-4640.1989.tb00143.x. [PMID: 2559907]
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