pregnenolone sulfate (BioDeep_00000415744)

Main id: BioDeep_00000019615

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(3beta)-3-(sulfooxy)pregn-5-en-20-one

化学式: C21H32O5S (396.1970342)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1C[C@H](OS(O)(=O)=O)CC2=CC[C@]3([H])[C@@]([H])([C@]21C)CC[C@]1([C@]3(CC[C@@H]1C(=O)C)[H])C
InChI: InChI=1S/C21H32O5S/c1-13(22)17-6-7-18-16-5-4-14-12-15(26-27(23,24)25)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19H,5-12H2,1-3H3,(H,23,24,25)

描述信息

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
Pregnenolone monosulfate (3β-Hydroxy-5-pregnen-20-one monosulfate) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone monosulfate acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone monosulfate can protect the brain from cannabis intoxication[1][2]. Pregnenolone monosulfate is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3].
Pregnenolone monosulfate (3β-Hydroxy-5-pregnen-20-one monosulfate) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone monosulfate acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone monosulfate can protect the brain from cannabis intoxication[1][2]. Pregnenolone monosulfate is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3].

同义名列表

8 个代谢物同义名

pregnenolone sulfate; (3beta)-3-(sulfooxy)pregn-5-en-20-one; 20-oxopregn-5-en-3beta-yl sulfate; 5-pregnen-3beta-ol-20-one sulfate; ST 21:2;O2;S; 3β-Hydroxy-5-pregnen-20-one monosulfate; Pregnenolone monosulfate; 3beta-Hydroxypregn-5-en-20-one sulfate



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

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。



文献列表

  • Ádám Horváth, Anita Steib, Andrea Nehr-Majoros, Boglárka Kántás, Ágnes Király, Márk Racskó, Balázs István Tóth, Eszter Szánti-Pintér, Eva Kudová, Rita Skoda-Földes, Zsuzsanna Helyes, Éva Szőke. Anti-Nociceptive Effects of Sphingomyelinase and Methyl-Beta-Cyclodextrin in the Icilin-Induced Mouse Pain Model. International journal of molecular sciences. 2024 Apr; 25(9):. doi: 10.3390/ijms25094637. [PMID: 38731855]
  • Alexander Becker, Claudia Götz, Mathias Montenarh, Stephan E Philipp. Control of TRPM3 Ion Channels by Protein Kinase CK2-Mediated Phosphorylation in Pancreatic β-Cells of the Line INS-1. International journal of molecular sciences. 2021 Dec; 22(23):. doi: 10.3390/ijms222313133. [PMID: 34884938]
  • Cecilia Rustichelli, Elisa Bellei, Stefania Bergamini, Emanuela Monari, Flavia Lo Castro, Carlo Baraldi, Aldo Tomasi, Anna Ferrari. Comparison of pregnenolone sulfate, pregnanolone and estradiol levels between patients with menstrually-related migraine and controls: an exploratory study. The journal of headache and pain. 2021 Mar; 22(1):13. doi: 10.1186/s10194-021-01231-9. [PMID: 33757421]
  • Jude Prah, Ali Winters, Kiran Chaudhari, Jessica Hersh, Ran Liu, Shao-Hua Yang. Cholesterol sulfate alters astrocyte metabolism and provides protection against oxidative stress. Brain research. 2019 11; 1723(?):146378. doi: 10.1016/j.brainres.2019.146378. [PMID: 31425677]
  • Steven J Kleene, Brian J Siroky, Julio A Landero-Figueroa, Bradley P Dixon, Nolan W Pachciarz, Lu Lu, Nancy K Kleene. The TRPP2-dependent channel of renal primary cilia also requires TRPM3. PloS one. 2019; 14(3):e0214053. doi: 10.1371/journal.pone.0214053. [PMID: 30883612]
  • Nadia Berkane, Philippe Liere, Guillaume Lefevre, Nadia Alfaidy, Roland Abi Nahed, Jessica Vincent, Jean-Paul Oudinet, Antoine Pianos, Annie Cambourg, Patrick Rozenberg, Pierre Galichon, Alexandra Rousseau, Tabassome Simon, Michael Schumacher, Nathalie Chabbert-Buffet, Alexandre Hertig. Abnormal steroidogenesis and aromatase activity in preeclampsia. Placenta. 2018 09; 69(?):40-49. doi: 10.1016/j.placenta.2018.07.004. [PMID: 30213483]
  • Juilee Rege, Aya T Nanba, Richard J Auchus, Jianwei Ren, Hwei-Ming Peng, William E Rainey, Adina F Turcu. Adrenocorticotropin Acutely Regulates Pregnenolone Sulfate Production by the Human Adrenal In Vivo and In Vitro. The Journal of clinical endocrinology and metabolism. 2018 01; 103(1):320-327. doi: 10.1210/jc.2017-01525. [PMID: 29126147]
  • Nadja Mannowetz, Melissa R Miller, Polina V Lishko. Regulation of the sperm calcium channel CatSper by endogenous steroids and plant triterpenoids. Proceedings of the National Academy of Sciences of the United States of America. 2017 05; 114(22):5743-5748. doi: 10.1073/pnas.1700367114. [PMID: 28507119]
  • Alberto Sánchez-Guijo, Jens Neunzig, Adrian Gerber, Vinzenz Oji, Michaela F Hartmann, Hans-Christian Schuppe, Heiko Traupe, Rita Bernhardt, Stefan A Wudy. Role of steroid sulfatase in steroid homeostasis and characterization of the sulfated steroid pathway: Evidence from steroid sulfatase deficiency. Molecular and cellular endocrinology. 2016 12; 437(?):142-153. doi: 10.1016/j.mce.2016.08.019. [PMID: 27531568]
  • Juilee Rege, Shigehiro Karashima, Antonio M Lerario, Joshua M Smith, Richard J Auchus, Josephine Z Kasa-Vubu, Hironobu Sasano, Yasuhiro Nakamura, Perrin C White, William E Rainey. Age-dependent Increases in Adrenal Cytochrome b5 and Serum 5-Androstenediol-3-sulfate. The Journal of clinical endocrinology and metabolism. 2016 12; 101(12):4585-4593. doi: 10.1210/jc.2016-2864. [PMID: 27623070]
  • Eun-Jin Kang, So-Hye Hong, Jae-Eon Lee, Seung Chul Kim, Hoe-Saeng Yang, Pyong In Yi, Sang-Myeong Lee, Beum-Soo An. Pregnenolone sulfate regulates prolactin production in the rat pituitary. The Journal of endocrinology. 2016 09; 230(3):339-46. doi: 10.1530/joe-16-0088. [PMID: 27507676]
  • Kunitoshi Uchida, Lusine Demirkhanyan, Swapna Asuthkar, Alejandro Cohen, Makoto Tominaga, Eleonora Zakharian. Stimulation-dependent gating of TRPM3 channel in planar lipid bilayers. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2016 Mar; 30(3):1306-16. doi: 10.1096/fj.15-281576. [PMID: 26655382]
  • Divyan A Chopra, Daniel T Monaghan, Shashank M Dravid. Bidirectional Effect of Pregnenolone Sulfate on GluN1/GluN2A N-Methyl-D-Aspartate Receptor Gating Depending on Extracellular Calcium and Intracellular Milieu. Molecular pharmacology. 2015 Oct; 88(4):650-9. doi: 10.1124/mol.115.100396. [PMID: 26162866]
  • Balázs I Tóth, Maik Konrad, Debapriya Ghosh, Florian Mohr, Christian R Halaszovich, Michael G Leitner, Joris Vriens, Johannes Oberwinkler, Thomas Voets. Regulation of the transient receptor potential channel TRPM3 by phosphoinositides. The Journal of general physiology. 2015 Jul; 146(1):51-63. doi: 10.1085/jgp.201411339. [PMID: 26123194]
  • Alain Y Dury, Yuyong Ke, Renaud Gonthier, Maxim Isabelle, Jean-Nicolas Simard, Fernand Labrie. Validated LC-MS/MS simultaneous assay of five sex steroid/neurosteroid-related sulfates in human serum. The Journal of steroid biochemistry and molecular biology. 2015 May; 149(?):1-10. doi: 10.1016/j.jsbmb.2015.01.006. [PMID: 25595042]
  • P Wong, Y Sze, C C R Chang, J Lee, X Zhang. Pregnenolone sulfate normalizes schizophrenia-like behaviors in dopamine transporter knockout mice through the AKT/GSK3β pathway. Translational psychiatry. 2015 Mar; 5(?):e528. doi: 10.1038/tp.2015.21. [PMID: 25781227]
  • G Y Son, Y M Yang, W S Park, I Chang, D M Shin. Hypotonic stress induces RANKL via transient receptor potential melastatin 3 (TRPM3) and vaniloid 4 (TRPV4) in human PDL cells. Journal of dental research. 2015 Mar; 94(3):473-81. doi: 10.1177/0022034514567196. [PMID: 25595364]
  • Fadia El Bitar, Johann Meunier, Vanessa Villard, Marion Alméras, Kathiresan Krishnan, Douglas F Covey, Tangui Maurice, Yvette Akwa. Neuroprotection by the synthetic neurosteroid enantiomers ent-PREGS and ent-DHEAS against Aβ₂₅₋₃₅ peptide-induced toxicity in vitro and in vivo in mice. Psychopharmacology. 2014 Sep; 231(17):3293-3312. doi: 10.1007/s00213-014-3435-3. [PMID: 24481566]
  • G Schuler, Y Dezhkam, L Bingsohn, B Hoffmann, K Failing, C E Galuska, M F Hartmann, A Sánchez-Guijo, S A Wudy. Free and sulfated steroids secretion in postpubertal boars (Sus scrofa domestica). Reproduction (Cambridge, England). 2014 Sep; 148(3):303-14. doi: 10.1530/rep-14-0193. [PMID: 24961601]
  • Yeranddy A Alpizar, Alicia Sanchez, Ahmed Radwan, Islam Radwan, Thomas Voets, Karel Talavera. Lack of correlation between the amplitudes of TRP channel-mediated responses to weak and strong stimuli in intracellular Ca(2+) imaging experiments. Cell calcium. 2013 Nov; 54(5):362-74. doi: 10.1016/j.ceca.2013.08.005. [PMID: 24079971]
  • Sònia Darbra, Laura Mòdol, Marc Pallarès. Allopregnanolone infused into the dorsal (CA1) hippocampus increases prepulse inhibition of startle response in Wistar rats. Psychoneuroendocrinology. 2012 Apr; 37(4):581-5. doi: 10.1016/j.psyneuen.2011.08.002. [PMID: 21871738]
  • Jobin Mathew, Savitha Balakrishnan, Sherin Antony, Pretty Mary Abraham, C S Paulose. Decreased GABA receptor in the cerebral cortex of epileptic rats: effect of Bacopa monnieri and Bacoside-A. Journal of biomedical science. 2012 Feb; 19(?):25. doi: 10.1186/1423-0127-19-25. [PMID: 22364254]
  • Marc Freichel, Julia Almering, Volodymyr Tsvilovskyy. The Role of TRP Proteins in Mast Cells. Frontiers in immunology. 2012; 3(?):150. doi: 10.3389/fimmu.2012.00150. [PMID: 22701456]
  • R Kancheva, M Hill, Z Novák, J Chrastina, L Kancheva, L Stárka. Neuroactive steroids in periphery and cerebrospinal fluid. Neuroscience. 2011 Sep; 191(?):22-7. doi: 10.1016/j.neuroscience.2011.05.054. [PMID: 21641969]
  • Joris Vriens, Grzegorz Owsianik, Thomas Hofmann, Stephan E Philipp, Julia Stab, Xiaodi Chen, Melissa Benoit, Fenqin Xue, Annelies Janssens, Sara Kerselaers, Johannes Oberwinkler, Rudi Vennekens, Thomas Gudermann, Bernd Nilius, Thomas Voets. TRPM3 is a nociceptor channel involved in the detection of noxious heat. Neuron. 2011 May; 70(3):482-94. doi: 10.1016/j.neuron.2011.02.051. [PMID: 21555074]
  • Patrizia Porcu, Todd K O'Buckley, Soomin C Song, Jo Lynne Harenza, Lu Lu, Xusheng Wang, Robert W Williams, Michael F Miles, A Leslie Morrow. Genetic analysis of the neurosteroid deoxycorticosterone and its relation to alcohol phenotypes: identification of QTLs and downstream gene regulation. PloS one. 2011 Apr; 6(4):e18405. doi: 10.1371/journal.pone.0018405. [PMID: 21494628]
  • Sachar Lambert, Anna Drews, Oleksandr Rizun, Thomas F J Wagner, Annette Lis, Stefanie Mannebach, Sandra Plant, Melanie Portz, Marcel Meissner, Stephan E Philipp, Johannes Oberwinkler. Transient receptor potential melastatin 1 (TRPM1) is an ion-conducting plasma membrane channel inhibited by zinc ions. The Journal of biological chemistry. 2011 Apr; 286(14):12221-33. doi: 10.1074/jbc.m110.202945. [PMID: 21278253]
  • Y Majeed, M S Amer, A K Agarwal, L McKeown, K E Porter, D J O'Regan, J Naylor, C W G Fishwick, K Muraki, D J Beech. Stereo-selective inhibition of transient receptor potential TRPC5 cation channels by neuroactive steroids. British journal of pharmacology. 2011 Apr; 162(7):1509-20. doi: 10.1111/j.1476-5381.2010.01136.x. [PMID: 21108630]
  • Sabine I Mayer, Isabelle Müller, Stefanie Mannebach, Takeshi Endo, Gerald Thiel. Signal transduction of pregnenolone sulfate in insulinoma cells: activation of Egr-1 expression involving TRPM3, voltage-gated calcium channels, ERK, and ternary complex factors. The Journal of biological chemistry. 2011 Mar; 286(12):10084-96. doi: 10.1074/jbc.m110.202697. [PMID: 21257751]
  • Minoru Takase, Shogo Haraguchi, Itaru Hasunuma, Sakae Kikuyama, Kazuyoshi Tsutsui. Expression of cytochrome P450 side-chain cleavage enzyme mRNA and production of pregnenolone in the brain of the red-bellied newt Cynops pyrrhogaster. General and comparative endocrinology. 2011 Feb; 170(3):468-74. doi: 10.1016/j.ygcen.2010.10.019. [PMID: 21050853]
  • Andrew Chao, Barney A Schlinger, Luke Remage-Healey. Combined liquid and solid-phase extraction improves quantification of brain estrogen content. Frontiers in neuroanatomy. 2011; 5(?):57. doi: 10.3389/fnana.2011.00057. [PMID: 21909323]
  • Matthew D Taves, Chunqi Ma, Sarah A Heimovics, Colin J Saldanha, Kiran K Soma. Measurement of steroid concentrations in brain tissue: methodological considerations. Frontiers in endocrinology. 2011; 2(?):39. doi: 10.3389/fendo.2011.00039. [PMID: 22654806]
  • Georges Rammouz, Laurent Lecanu, Vassilios Papadopoulos. Oxidative Stress-Mediated Brain Dehydroepiandrosterone (DHEA) Formation in Alzheimer's Disease Diagnosis. Frontiers in endocrinology. 2011; 2(?):69. doi: 10.3389/fendo.2011.00069. [PMID: 22654823]
  • Matthew D Taves, Kim L Schmidt, Ilan M Ruhr, Katarzyna Kapusta, Nora H Prior, Kiran K Soma. Steroid concentrations in plasma, whole blood and brain: effects of saline perfusion to remove blood contamination from brain. PloS one. 2010 Dec; 5(12):e15727. doi: 10.1371/journal.pone.0015727. [PMID: 21206751]
  • Fang Fang, Whitney V Christian, Sadie G Gorman, Mei Cui, Jiaoti Huang, Kim Tieu, Nazzareno Ballatori. Neurosteroid transport by the organic solute transporter OSTα-OSTβ. Journal of neurochemistry. 2010 Oct; 115(1):220-33. doi: 10.1111/j.1471-4159.2010.06920.x. [PMID: 20649839]
  • Malin Gingnell, Erika Comasco, Lars Oreland, Mats Fredrikson, Inger Sundström-Poromaa. Neuroticism-related personality traits are related to symptom severity in patients with premenstrual dysphoric disorder and to the serotonin transporter gene-linked polymorphism 5-HTTPLPR. Archives of women's mental health. 2010 Oct; 13(5):417-23. doi: 10.1007/s00737-010-0164-4. [PMID: 20440524]
  • Thomas F J Wagner, Anna Drews, Sabine Loch, Florian Mohr, Stephan E Philipp, Sachar Lambert, Johannes Oberwinkler. TRPM3 channels provide a regulated influx pathway for zinc in pancreatic beta cells. Pflugers Archiv : European journal of physiology. 2010 Sep; 460(4):755-65. doi: 10.1007/s00424-010-0838-9. [PMID: 20401728]
  • Jacqueline Naylor, Jing Li, Carol J Milligan, Fanning Zeng, Piruthivi Sukumar, Bing Hou, Alicia Sedo, Nadira Yuldasheva, Yasser Majeed, Dhananjay Beri, Shan Jiang, Victoria A L Seymour, Lynn McKeown, Bhaskar Kumar, Christian Harteneck, David O'Regan, Stephen B Wheatcroft, Mark T Kearney, Clare Jones, Karen E Porter, David J Beech. Pregnenolone sulphate- and cholesterol-regulated TRPM3 channels coupled to vascular smooth muscle secretion and contraction. Circulation research. 2010 May; 106(9):1507-15. doi: 10.1161/circresaha.110.219329. [PMID: 20360246]
  • M Hill, J Vrbíková, J Zárubová, H Vceláková, M Dusková, R Kancheva, J Kubátová, L Stárka. Sulphates of 3beta-hydroxy-5-ene steroids in women with epilepsy. Prague medical report. 2010; 111(2):111-26. doi: NULL. [PMID: 20654001]
  • S Chi, W Cai, P Liu, Z Zhang, X Chen, L Gao, J Qi, L Bi, L Chen, Z Qi. Baifuzi reduces transient ischemic brain damage through an interaction with the STREX domain of BKCa channels. Cell death & disease. 2010; 1(?):e13. doi: 10.1038/cddis.2009.10. [PMID: 21364615]
  • Julie Espallergues, Laurent Givalois, Jamal Temsamani, Claude Laruelle, Tangui Maurice. The 3beta-hydroxysteroid dehydrogenase inhibitor trilostane shows antidepressant properties in mice. Psychoneuroendocrinology. 2009 Jun; 34(5):644-59. doi: 10.1016/j.psyneuen.2008.11.003. [PMID: 19117688]
  • Milan Meloun, Martin Hill, Helena Vceláková-Havlíková. Minimizing the effects of multicollinearity in the polynomial regression of age relationships and sex differences in serum levels of pregnenolone sulfate in healthy subjects. Clinical chemistry and laboratory medicine. 2009; 47(4):464-70. doi: 10.1515/cclm.2009.104. [PMID: 19278363]
  • Melissa Runge-Morris, Thomas A Kocarek. Regulation of sulfotransferase and UDP-glucuronosyltransferase gene expression by the PPARs. PPAR research. 2009; 2009(?):728941. doi: 10.1155/2009/728941. [PMID: 19680455]
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  • Helena Vceláková, Martin Hill, Oldrich Lapcík, Antonín Parízek. Determination of 17alpha-hydroxypregnenolone sulfate and its application in diagnostics. Steroids. 2007 Apr; 72(4):323-7. doi: 10.1016/j.steroids.2006.11.026. [PMID: 17298837]
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