Pregnenolone (BioDeep_00000001411)

 

Secondary id: BioDeep_00000398996, BioDeep_00000861171

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product Volatile Flavor Compounds


代谢物信息卡片


1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone

化学式: C21H32O2 (316.24021719999996)
中文名称: 孕烯醇酮
谱图信息: 最多检出来源 Homo sapiens(blood) 0.02%

分子结构信息

SMILES: CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
InChI: InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3

描述信息

Pregnenolone is a derivative of cholesterol, the product of cytochrome P450 side-chain cleavage (EC 1.14.15.6, CYP11A1. This reaction consists of three consecutive monooxygenations, a 22-hydroxylation, a 20-hydroxylation, and the cleavage of the C20-C22 bond, yielding pregnenolone. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. This reaction occurs in steroid hormone-producing tissues such as the adrenal cortex, corpus luteum, and placenta. The most notable difference between the placenta and other steroidogenic tissues is that electron supply to CYP11A1 limits the rate at which cholesterol is converted into pregnenolone in the placenta. The limiting component for electron delivery to CYP11A1 is the concentration of adrenodoxin reductase in the mitochondrial matrix which is insufficient to maintain the adrenodoxin pool in a fully reduced state. Pregnenolone is also a neurosteroid, and is produced in the spinal cord; CYP11A1 is the key enzyme catalyzing the conversion of cholesterol into pregnenolone, the rate-limiting step in the biosynthesis of all classes of steroids, and has been localized in sensory networks of the spinal cord dorsal horn. In the adrenal glomerulosa cell, angiotensin II, one of the major physiological regulators of mineralocorticoid synthesis, appears to affect most of the cholesterol transfer to the mitochondrial outer membrane and many steps in the transport to the inner membrane. Thus, it exerts a powerful control over the use of cholesterol for aldosterone production (PMID: 17222962, 15823613, 16632873, 15134809).
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
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Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3].
Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3].

同义名列表

31 个代谢物同义名

1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone; 1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one; 1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone; (3BETA)-3-HYDROXYPREGN-5-en-20-one; 3β-Hydroxy-5-pregnen-20-one; (3b)-3-hydroxy-Pregn-5-en-20-one; 3β-Hydroxypregn-5-en-20-one; (3Β)-3-hydroxypregn-5-en-20-one; (3b)-3-HYDROXYPREGN-5-en-20-one; 3beta-hydroxypregn-5-en-20-one; 5-Pregnen-3β-ol-20-one; 3Β-hydroxypregn-5-en-20-one; 3b-Hydroxypregn-5-en-20-one; 5-Pregnen-3-beta-ol-20-one; 3-Hydroxypregn-5-en-20-one; 5 Pregnen 3 beta ol 20 one; 5-Pregnen-3beta-ol-20-one; Pregn-5-ene-3b-ol-20-one; Pregn-5-en-3b-ol-20-one; 5-Pregnen-3β-ol-20-one; 5-Pregnen-3b-ol-20-one; Pregnenolone; Skinostelon; Pregnolon; Regnosone; Pregnetan; Pregneton; Prenolon; Natolone; 3β-Hydroxy-5-pregnen-20-one; Pregnenolone



数据库引用编号

26 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(16)

BioCyc(1)

PlantCyc(0)

代谢反应

152 个相关的代谢反应过程信息。

Reactome(141)

BioCyc(5)

WikiPathways(5)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(1)

PathBank(0)

PharmGKB(0)

141 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]
  • Fu-Rong Xu, Zhen-Hong Wei, Xiao-Xia Xu, Xiao-Gang Zhang, Chao-Jun Wei, Xiao-Ming Qi, Yong-Hong Li, Xiao-Ling Gao, Yu Wu. The hypothalamic steroidogenic pathway mediates susceptibility to inflammation-evoked depression in female mice. Journal of neuroinflammation. 2023 Dec; 20(1):293. doi: 10.1186/s12974-023-02976-7. [PMID: 38062440]
  • Maritta Kunert, Chloe Langley, Rosalind Lucier, Kerstin Ploss, Carlos E Rodríguez López, Delia A Serna Guerrero, Eva Rothe, Sarah E O'Connor, Prashant D Sonawane. Promiscuous CYP87A enzyme activity initiates cardenolide biosynthesis in plants. Nature plants. 2023 Sep; ?(?):. doi: 10.1038/s41477-023-01515-9. [PMID: 37723202]
  • Yiqin Lin, Yingle Chen, Jingyang Zeng, Shunyuan Li. Nodakenetin Alleviates Inflammatory Pain Hypersensitivity by Suppressing NF-κB Signal Pathway. Neuroimmunomodulation. 2022; 29(4):486-492. doi: 10.1159/000525690. [PMID: 35995035]
  • 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, Emanuela Monari, Rossella Avallone, Elisa Bellei, Stefania Bergamini, Aldo Tomasi, Anna Ferrari. Dehydroepiandrosterone sulfate, dehydroepiandrosterone, 5α-dihydroprogesterone and pregnenolone in women with migraine: Analysis of serum levels and correlation with age, migraine years and frequency. Journal of pharmaceutical and biomedical analysis. 2021 Nov; 206(?):114388. doi: 10.1016/j.jpba.2021.114388. [PMID: 34597839]
  • Britton Trabert, Ashley M Geczik, Doug C Bauer, Diana S M Buist, Jane A Cauley, Roni T Falk, Gretchen L Gierach, Trisha F Hue, James V Lacey, Andrea Z LaCroix, Kara A Michels, Jeffrey A Tice, Xia Xu, Louise A Brinton, Cher M Dallal. Association of Endogenous Pregnenolone, Progesterone, and Related Metabolites with Risk of Endometrial and Ovarian Cancers in Postmenopausal Women: The B∼FIT Cohort. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2021 11; 30(11):2030-2037. doi: 10.1158/1055-9965.epi-21-0669. [PMID: 34465588]
  • K Rehm, A K Hankele, S E Ulbrich, L Bigler. Simultaneous quantification of progestogens in plasma and serum by UHPLC-HRMS employing multiplexed targeted single ion monitoring. Talanta. 2021 Sep; 232(?):122358. doi: 10.1016/j.talanta.2021.122358. [PMID: 34074386]
  • Johanna Ruhnau, Stephanie Hübner, Donna Sunny, Till Ittermann, Michaela F Hartmann, Jan De Lafollie, Stefan A Wudy, Matthias Heckmann. Impact of Gestational and Postmenstrual Age on Excretion of Fetal Zone Steroids in Preterm Infants Determined by Gas Chromatography-Mass Spectrometry. The Journal of clinical endocrinology and metabolism. 2021 08; 106(9):e3725-e3738. doi: 10.1210/clinem/dgab194. [PMID: 33822093]
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  • Li Yu, Miao Liu, Zhenxin Wang, Te Liu, Suying Liu, Beili Wang, Baishen Pan, Xi Dong, Wei Guo. Correlation between steroid levels in follicular fluid and hormone synthesis related substances in its exosomes and embryo quality in patients with polycystic ovary syndrome. Reproductive biology and endocrinology : RB&E. 2021 May; 19(1):74. doi: 10.1186/s12958-021-00749-6. [PMID: 34001150]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • 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]
  • Yilin Liu, Ilia G Denisov, Stephen G Sligar, James R Kincaid. Substrate-Specific Allosteric Effects on the Enhancement of CYP17A1 Lyase Efficiency by Cytochrome b5. Journal of the American Chemical Society. 2021 03; 143(10):3729-3733. doi: 10.1021/jacs.1c00581. [PMID: 33656879]
  • Melina A Pagotto, María L Roldán, Sara M Molinas, Trinidad Raices, Gerardo B Pisani, Omar P Pignataro, Liliana A Monasterolo. Impairment of renal steroidogenesis at the onset of diabetes. Molecular and cellular endocrinology. 2021 03; 524(?):111170. doi: 10.1016/j.mce.2021.111170. [PMID: 33482284]
  • Graziano Pinna. Sex and COVID-19: A Protective Role for Reproductive Steroids. Trends in endocrinology and metabolism: TEM. 2021 01; 32(1):3-6. doi: 10.1016/j.tem.2020.11.004. [PMID: 33229187]
  • Kristina M Deligiannidis, Aimee R Kroll-Desrosiers, Yanglan Tan, Michelle L Dubuke, Scott A Shaffer. Longitudinal proneuroactive and neuroactive steroid profiles in medication-free women with, without and at-risk for perinatal depression: A liquid chromatography-tandem mass spectrometry analysis. Psychoneuroendocrinology. 2020 11; 121(?):104827. doi: 10.1016/j.psyneuen.2020.104827. [PMID: 32828068]
  • Y V Faletrov, K A Gilep, A S Falchevskaya, M S Horetski, J V Panada, E V Andrievskaya, E V Rudaya, N S Frolova, A Brzostek, R Plocinska, V M Shkumatov. [In silico modeling of izoniazid-steroid conjugates interactions with cytochromes P450 of mycobacteria and their bioconversion in vitro by the cells]. Biomeditsinskaia khimiia. 2020 Sep; 66(5):378-385. doi: 10.18097/pbmc20206605378. [PMID: 33140731]
  • Mathijs Drummen, Lea Tischmann, Blandine Gatta-Cherifi, Daniela Cota, Isabelle Matias, Anne Raben, Tanja Adam, Margriet Westerterp-Plantenga. Role of Endocannabinoids in Energy-Balance Regulation in Participants in the Postobese State-a PREVIEW Study. The Journal of clinical endocrinology and metabolism. 2020 07; 105(7):. doi: 10.1210/clinem/dgaa193. [PMID: 32333763]
  • Jeffrey M McManus, Nima Sharifi. Structure-dependent retention of steroid hormones by common laboratory materials. The Journal of steroid biochemistry and molecular biology. 2020 04; 198(?):105572. doi: 10.1016/j.jsbmb.2019.105572. [PMID: 31883923]
  • Wenqi Jin, Rui Ma, Lu Zhai, Xiaohao Xu, Tingting Lou, Qingxia Huang, Jing Wang, Daqing Zhao, Xiangyan Li, Liwei Sun. Ginsenoside Rd attenuates ACTH-induced corticosterone secretion by blocking the MC2R-cAMP/PKA/CREB pathway in Y1 mouse adrenocortical cells. Life sciences. 2020 Mar; 245(?):117337. doi: 10.1016/j.lfs.2020.117337. [PMID: 31972205]
  • Natasja G J Costermans, Nicoline M Soede, Marco Blokland, Frederike van Tricht, Jaap Keijer, Bas Kemp, Katja J Teerds. Steroid profile of porcine follicular fluid and blood serum: Relation with follicular development. Physiological reports. 2019 12; 7(24):e14320. doi: 10.14814/phy2.14320. [PMID: 31883224]
  • Jingjing Jiang, Xue Liu, Xiaotian Liu, Zhongyan Tian, Haiqing Zhang, Xinling Qian, Zhicheng Luo, Dandan Wei, Shuna Jin, Chongjian Wang, Zhenxing Mao. The effect of progesterone and pregnenolone on diabetes status in Chinese rural population: a dose-response analysis from Henan Rural Cohort. European journal of endocrinology. 2019 Dec; 181(6):603-614. doi: 10.1530/eje-19-0352. [PMID: 31581126]
  • 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]
  • Bingyan Cao, Chunxiu Gong, Di Wu, Xuejun Liang, Wenjing Li, Min Liu, Chang Su, Miao Qin, Xi Meng, Liya Wei. A cross-sectional survey of adrenal steroid hormones among overweight/obese boys according to puberty stage. BMC pediatrics. 2019 11; 19(1):414. doi: 10.1186/s12887-019-1755-5. [PMID: 31690265]
  • Hiroshi Miura, Tatsuya Yamazaki, Motohiro Kikuchi, Minoru Sakaguchi. Plasma steroid hormone concentrations and their relationships in Suffolk ewes during gestation and parturition. Animal science journal = Nihon chikusan Gakkaiho. 2019 Nov; 90(11):1426-1431. doi: 10.1111/asj.13286. [PMID: 31486265]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Ruben Vanholme, Lisa Sundin, Keletso Carol Seetso, Hoon Kim, Xinyu Liu, Jin Li, Barbara De Meester, Lennart Hoengenaert, Geert Goeminne, Kris Morreel, Jurgen Haustraete, Huei-Hsuan Tsai, Wolfgang Schmidt, Bartel Vanholme, John Ralph, Wout Boerjan. COSY catalyses trans-cis isomerization and lactonization in the biosynthesis of coumarins. Nature plants. 2019 10; 5(10):1066-1075. doi: 10.1038/s41477-019-0510-0. [PMID: 31501530]
  • L I Velikanova, Z R Shafigullina, N V Vorokhobina, E V Malevanaya. Gas Chromatography-Mass Spectrometry Analysis of Urinary Steroid Metabolomics for Detection of Early Signs of Adrenal Neoplasm Malignancy in Patients with Cushing's Syndrome. Bulletin of experimental biology and medicine. 2019 Sep; 167(5):676-680. doi: 10.1007/s10517-019-04597-8. [PMID: 31630306]
  • Monica Aleman, Patrick M McCue, Munashe Chigerwe, John E Madigan. Plasma concentrations of steroid precursors, steroids, neuroactive steroids, and neurosteroids in healthy neonatal foals from birth to 7 days of age. Journal of veterinary internal medicine. 2019 Sep; 33(5):2286-2293. doi: 10.1111/jvim.15618. [PMID: 31489708]
  • Marika Matousova, Radko Soucek, Eva Tloustova, Barbora Slavikova, Hana Chodounska, Helena Mertlikova-Kaiserova, Eva Kudova. Pregn-5-en-3β-ol and androst-5-en-3β-ol dicarboxylic acid esters as potential therapeutics for NMDA hypofunction: In vitro safety assessment and plasma stability. Steroids. 2019 07; 147(?):4-9. doi: 10.1016/j.steroids.2018.09.012. [PMID: 30296546]
  • Philippe Liere, Charlotte A Cornil, Marie Pierre de Bournonville, Antoine Pianos, Matthieu Keller, Michael Schumacher, Jacques Balthazart. Steroid profiles in quail brain and serum: Sex and regional differences and effects of castration with steroid replacement. Journal of neuroendocrinology. 2019 02; 31(2):e12681. doi: 10.1111/jne.12681. [PMID: 30585662]
  • 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]
  • Jeffrey M McManus, Kelsey Bohn, Mohammad Alyamani, Yoon-Mi Chung, Eric A Klein, Nima Sharifi. Rapid and structure-specific cellular uptake of selected steroids. PloS one. 2019; 14(10):e0224081. doi: 10.1371/journal.pone.0224081. [PMID: 31622417]
  • Vitória Müller, Bruna R Curcio, Ramiro E Toribio, Lorena S Feijó, Luciana A Borba, Igor F Canisso, Carlos E W Nogueira. Cortisol, progesterone, 17αOHprogesterone, and pregnenolone in foals born from mare's hormone-treated for experimentally induced ascending placentitis. Theriogenology. 2019 Jan; 123(?):139-144. doi: 10.1016/j.theriogenology.2018.06.024. [PMID: 30308389]
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  • Dongdong Liang, Zhaofei Fan, Yuxia Zou, Xungang Tan, Zhihao Wu, Shuang Jiao, Jun Li, Peijun Zhang, Feng You. Characteristics of Cyp11a during Gonad Differentiation of the Olive Flounder Paralichthys olivaceus. International journal of molecular sciences. 2018 Sep; 19(9):. doi: 10.3390/ijms19092641. [PMID: 30200601]
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