Pregnenolone sulfate (BioDeep_00000019615)

Secondary id: BioDeep_00000012045, BioDeep_00000415744

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Volatile Flavor Compounds

代谢物信息卡片

[(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid

化学式: C21H32O5S (396.1970342)
中文名称: 硫化孕烯醇酮
谱图信息: 最多检出来源 Homo sapiens(blood) 0.08%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Pregnenolone sulfate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/pregnenolone_sulfate (retrieved 2024-11-24) (BioDeep RN: BioDeep_00000019615). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OS(=O)(=O)O)C)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)/t15-,16-,17+,18-,19-,20-,21+/m0/s1

描述信息

Pregnenolone sulfate is a sulfated version of the steroid hormone known as pregnenolone. Pregnenolone sulfate belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. Pregnenolone sulfate is a neurosteroid found in the brain and central nervous system. Pregnenolone sulfate is a metabolite synthesized from pregnenolone via sulfation. It is known to have cognitive and memory-enhancing, antidepressant, anxiogenic, and proconvulsant effects (PMID: 21094889). As a neurosteroid, pregnenolone sulfate modulates a variety of ion channels, transporters, and enzymes. Interestingly, as a sulfated steroid, pregnenolone sulfate is not the final- or waste-product of pregnenolone being sulfated via a phase II metabolism reaction and renally excreted, as one would presume from pharmacology textbook knowledge. Pregnenolone sulfate is also the source and thereby the starting point for subsequent steroid synthesis pathways. Recently, pregnenolone sulfate has been shown to not only be a modulator of ion channels, but it is also an activating ion channel ligand (PMID: 24084011).
Pregnenolone sulfate, a neurosteroid, is a metabolite of Pregnenolone. It is found in the brain and central nervous system. [HMDB]
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

26 个代谢物同义名

[(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid; [(1S,2R,10S,11S,14S,15S)-14-Acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulphonic acid; [(1S,2R,10S,11S,14S,15S)-14-Acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulphonate; [(1S,2R,10S,11S,14S,15S)-14-Acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulfonate; Pregn-5-en-20-on-3b-yl sulfuric acid; Pregn-5-en-20-on-3b-yl sulfurate; Pregn-5-en-20-one-3b-yl sulphate; Pregn-5-en-20-one-3b-yl sulfate; Pregnenolone hydrogen sulphate; Pregnenolone hydrogen sulfate; 5-Pregnen-3b-sulphate-20-one; Pregnenolone sulphuric acid; 5-Pregnen-3b-sulfate-20-one; Pregnenolone sulfuric acid; Pregnenolone monosulphate; Pregnenolone monosulfate; Pregnenolone 3b-sulphate; Pregnenolone 3b-sulfate; Pregnenolone 3-sulphate; Pregnenolone 3-sulfate; Pregnenolone sulphate; pregnenolone sulfate; CHEMBL141573; Pregnenolone sulfate; 3β-Hydroxy-5-pregnen-20-one monosulfate; 3beta-Hydroxypregn-5-en-20-one sulfate

数据库引用编号

19 个数据库交叉引用编号

ChEBI: CHEBI:35420
KEGG: C18044
PubChem: 20845972
PubChem: 105074
PubChem: 4903
HMDB: HMDB0000774
ChEMBL: CHEMBL1179605
Wikipedia: Pregnenolone sulfate
foodb: FDB022235
chemspider: 17216005
CAS: 1247-64-9
PMhub: MS000026316
PubChem: 96024264
LipidMAPS: LMST05020014
PDB-CCD: A8W
NIKKAJI: J468.821J
RefMet: Pregnenolone sulfate
medchemexpress: HY-B1739
KNApSAcK: 35420

分类词条

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)

2 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]
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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]
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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]
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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]
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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]
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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]
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