3a-Hydroxy-5b-pregnane-20-one (BioDeep_00000028302)

 

Secondary id: BioDeep_00000002965, BioDeep_00000055252, BioDeep_00000864738

human metabolite Endogenous blood metabolite


代谢物信息卡片


1-[(2S,5R,7R,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one

化学式: C21H34O2 (318.2559)
中文名称: 孕烷醇酮
谱图信息: 最多检出来源 Homo sapiens(otcml) 24.6%

分子结构信息

SMILES: CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
InChI: InChI=1S/C21H34O2/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/h14-19,23H,4-12H2,1-3H3/t14-,15-,16+,17-,18+,19+,20+,21-/m1/s1

描述信息

3alpha-Hydroxy-5beta-pregnane-20-one is an intermediate in C21-Steroid hormone metabolism. 3alpha-Hydroxy-5beta-pregnane-20-one is converted from 5beta-Pregnane-3,20-dione via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50). It is then converted to Pregnanediol via the enzyme 3alpha(or 20beta)-hydroxysteroid dehydrogenase (EC 1.1.1.53). [HMDB]
3alpha-Hydroxy-5beta-pregnane-20-one is an intermediate in C21-Steroid hormone metabolism. 3alpha-Hydroxy-5beta-pregnane-20-one is converted from 5beta-Pregnane-3,20-dione via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50). It is then converted to Pregnanediol via the enzyme 3alpha(or 20beta)-hydroxysteroid dehydrogenase (EC 1.1.1.53).
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics
C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent

同义名列表

5 个代谢物同义名

1-[(2S,5R,7R,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one; 3alpha-Hydroxy-5beta-pregnane-20-one; 3a-Hydroxy-5b-pregnane-20-one; Pregnanolone; Pregnanolone



数据库引用编号

20 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

35 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(34)

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

  • Julia V Bukanova, Elena I Solntseva, Vladimir G Skrebitsky. Factors promoting the release of picrotoxin from the trap in the GABA(A) receptor pore. Neurochemistry international. 2024 May; 175(?):105703. doi: 10.1016/j.neuint.2024.105703. [PMID: 38395151]
  • Shaimaa Nasr Amin, Sherif Ahmed Shaltout, Walaa Bayoumie El Gazzar, Noha Samir Abdel Latif, Ghadah Nazar Al-Jussani, Yasmeen Jamal Alabdallat, Khaled Anwer Albakri, Dalia Azmy Elberry. Impact of NMDA receptors block versus GABA-A receptors modulation on synaptic plasticity and brain electrical activity in metabolic syndrome. Advances in medical sciences. 2024 Mar; 69(1):176-189. doi: 10.1016/j.advms.2024.03.008. [PMID: 38561071]
  • Meiyue Dong, Yanyan Wang, Ping Li, Zinuo Chen, Varada Anirudhan, Qinghua Cui, Lijun Rong, Ruikun Du. Allopregnanolone targets nucleoprotein as a novel influenza virus inhibitor. Virologica Sinica. 2023 Dec; 38(6):931-939. doi: 10.1016/j.virs.2023.09.003. [PMID: 37741571]
  • Hao Zhang, Mingqi Qiao, Dongmei Gao, Jieqiong Wang, Chunyan Sun, Ya Sun, Yang Zhang, Huayuan Liu, Zhen Zhang, Mingzhou Gao. Shuyu capsule alleviates premenstrual depression via allopregnanolone metabolic pathway targeting GABA (A) receptors δ subunit in the hippocampus. Asian journal of psychiatry. 2023 Oct; 90(?):103800. doi: 10.1016/j.ajp.2023.103800. [PMID: 37898099]
  • Ya Sun, Mingzhou Gao, Dongmei Gao, Dan Chen, Jieqiong Wang. Allopregnanolone-mediated GABAA-Rα4 function in amygdala and hippocampus of PMDD liver qi-invasion syndrome model rats. Aging. 2023 Feb; 15(?):. doi: 10.18632/aging.204541. [PMID: 36842096]
  • Veronica Antipova, Lisa-Marie Steinhoff, Carsten Holzmann, Arndt Rolfs, Carlos Junior Hempel, Martin Witt, Andreas Wree. Organ Weights in NPC1 Mutant Mice Partly Normalized by Various Pharmacological Treatment Approaches. International journal of molecular sciences. 2022 Dec; 24(1):. doi: 10.3390/ijms24010573. [PMID: 36614015]
  • Mingzhou Gao, Hao Zhang, Ya Sun, Zhan Gao, Chunyan Sun, Fengqin Wei, Dongmei Gao. Gabrb2 knock-out mice exhibit double-directed PMDD-like symptoms: GABAAR subunits, neurotransmitter metabolism disruption, and allopregnanolone binding. Aging. 2022 10; 14(20):8437-8447. doi: 10.18632/aging.204351. [PMID: 36287173]
  • Johanna Molin, Eszter Vanky, Tone S Løvvik, Eva Dehlin, Marie Bixo. Gestational weight gain, appetite regulating hormones, and metformin treatment in polycystic ovary syndrome: A longitudinal, placebo-controlled study. BJOG : an international journal of obstetrics and gynaecology. 2022 06; 129(7):1112-1121. doi: 10.1111/1471-0528.17042. [PMID: 34865304]
  • Irene Vuu, Edward E Patterson, Chun-Yi Wu, Dorota Zolkowska, Ilo E Leppik, Michael A Rogawski, Gregory A Worrell, Vaclav Kremen, James C Cloyd, Lisa D Coles. Intravenous and Intramuscular Allopregnanolone for Early Treatment of Status Epilepticus: Pharmacokinetics, Pharmacodynamics, and Safety in Dogs. The Journal of pharmacology and experimental therapeutics. 2022 02; 380(2):104-113. doi: 10.1124/jpet.121.000736. [PMID: 34862270]
  • Torbjörn Bäckström, Roshni Das, Marie Bixo. Positive GABAA receptor modulating steroids and their antagonists: Implications for clinical treatments. Journal of neuroendocrinology. 2022 02; 34(2):e13013. doi: 10.1111/jne.13013. [PMID: 34337790]
  • Silvia Diviccaro, Valentina Caputi, Lucia Cioffi, Silvia Giatti, Joshua M Lyte, Donatella Caruso, Siobhain M O'Mahony, Roberto Cosimo Melcangi. Exploring the Impact of the Microbiome on Neuroactive Steroid Levels in Germ-Free Animals. International journal of molecular sciences. 2021 Nov; 22(22):. doi: 10.3390/ijms222212551. [PMID: 34830433]
  • Gabrielle K Crombie, Hannah K Palliser, Julia C Shaw, Deborah M Hodgson, David W Walker, Jonathan J Hirst. Neurosteroid-based intervention using Ganaxolone and Emapunil for improving stress-induced myelination deficits and neurobehavioural disorders. Psychoneuroendocrinology. 2021 11; 133(?):105423. doi: 10.1016/j.psyneuen.2021.105423. [PMID: 34601389]
  • G Mayne, E De Bloois, D Dabelea, U Christians. Development and validation of an LC-MS/MS assay for the quantification of allopregnanolone and its progesterone-derived isomers, precursors, and cortisol/cortisone in pregnancy. Analytical and bioanalytical chemistry. 2021 Sep; 413(21):5427-5438. doi: 10.1007/s00216-021-03523-0. [PMID: 34279681]
  • Bo Qian, Zeng Zen, Zhaoxuan Zheng, Chengqiang Wang, Jiale Song. A preliminary study on the mechanism of the neurosteroid-mediated ionotropic receptor dysfunction in neurodevelopmental toxicity induced by decabromodiphenyl ether. Ecotoxicology and environmental safety. 2021 Jul; 217(?):112198. doi: 10.1016/j.ecoenv.2021.112198. [PMID: 33862428]
  • Donna Elizabeth Sunny, Elke Hammer, Till Ittermann, Elisabeth Luise Krüger, Stephanie Hübner, Michaela Friederike Hartmann, Stefan Alexander Wudy, Uwe Völker, Matthias Heckmann. Fetal Zone Steroids and Estrogen Show Sex Specific Effects on Oligodendrocyte Precursor Cells in Response to Oxidative Damage. International journal of molecular sciences. 2021 Jun; 22(12):. doi: 10.3390/ijms22126586. [PMID: 34205405]
  • Melanie H Jacobson, Cheryl R Stein, Mengling Liu, Marra G Ackerman, Jennifer K Blakemore, Sara E Long, Graziano Pinna, Raquel Romay-Tallon, Kurunthachalam Kannan, Hongkai Zhu, Leonardo Trasande. Prenatal Exposure to Bisphenols and Phthalates and Postpartum Depression: The Role of Neurosteroid Hormone Disruption. The Journal of clinical endocrinology and metabolism. 2021 06; 106(7):1887-1899. doi: 10.1210/clinem/dgab199. [PMID: 33792735]
  • Sahruh Turkmen, Torbjörn Bäckström, Yvonne Kangas Flodin, Marie Bixo. Neurosteroid involvement in threatened preterm labour. Endocrinology, diabetes & metabolism. 2021 04; 4(2):e00216. doi: 10.1002/edm2.216. [PMID: 33855217]
  • 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]
  • Valérie Jolivel, Susana Brun, Fabien Binamé, Jérémie Benyounes, Omar Taleb, Dominique Bagnard, Jérôme De Sèze, Christine Patte-Mensah, Ayikoe-Guy Mensah-Nyagan. Microglial Cell Morphology and Phagocytic Activity Are Critically Regulated by the Neurosteroid Allopregnanolone: A Possible Role in Neuroprotection. Cells. 2021 03; 10(3):. doi: 10.3390/cells10030698. [PMID: 33801063]
  • Giorgia Boero, Ryan E Tyler, Caroline A Todd, Todd K O'Buckley, Irina Balan, Joyce Besheer, A Leslie Morrow. (3α,5α)3-hydroxypregnan-20-one (3α,5α-THP) regulation of hypothalamic and extrahypothalamic corticotropin releasing factor (CRF): Sexual dimorphism and brain region specificity in Sprague Dawley rats. Neuropharmacology. 2021 03; 186(?):108463. doi: 10.1016/j.neuropharm.2021.108463. [PMID: 33460689]
  • Gabrielle K Crombie, Hannah K Palliser, Julia C Shaw, Deborah M Hodgson, David W Walker, Jonathan J Hirst. Effects of prenatal stress on behavioural and neurodevelopmental outcomes are altered by maternal separation in the neonatal period. Psychoneuroendocrinology. 2021 02; 124(?):105060. doi: 10.1016/j.psyneuen.2020.105060. [PMID: 33333379]
  • Leila Chew, Kevin L Sun, Wenchao Sun, Zhe Wang, Jayakumar Rajadas, Ryan E Flores, Emily Arnold, Booil Jo, Lawrence K Fung. Association of serum allopregnanolone with restricted and repetitive behaviors in adult males with autism. Psychoneuroendocrinology. 2021 01; 123(?):105039. doi: 10.1016/j.psyneuen.2020.105039. [PMID: 33161257]
  • 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]
  • Michael Schumacher, Philippe Liere, Abdelmoumen Ghoumari. Progesterone and fetal-neonatal neuroprotection. Best practice & research. Clinical obstetrics & gynaecology. 2020 Nov; 69(?):50-61. doi: 10.1016/j.bpobgyn.2020.09.001. [PMID: 33039311]
  • Cecilia Rustichelli, Elisa Bellei, Stefania Bergamini, Emanuela Monari, Carlo Baraldi, Flavia Lo Castro, Aldo Tomasi, Anna Ferrari. Serum levels of allopregnanolone, progesterone and testosterone in menstrually-related and postmenopausal migraine: A cross-sectional study. Cephalalgia : an international journal of headache. 2020 10; 40(12):1355-1362. doi: 10.1177/0333102420937742. [PMID: 32588652]
  • Eileen E Parks, Sreemathi Logan, Alexander Yeganeh, Julie A Farley, Daniel B Owen, William E Sonntag. Interleukin 6 reduces allopregnanolone synthesis in the brain and contributes to age-related cognitive decline in mice. Journal of lipid research. 2020 10; 61(10):1308-1319. doi: 10.1194/jlr.ra119000479. [PMID: 32669383]
  • Antonella Rosario Ramona Cáceres, Adriana Soledad Vega Orozco, Ricardo Jorge Cabrera, Myriam Raquel Laconi. "Rapid actions of the neurosteroid allopregnanolone on ovarian and hypothalamic steroidogenesis: Central and peripheral modulation". Journal of neuroendocrinology. 2020 03; 32(3):e12836. doi: 10.1111/jne.12836. [PMID: 32062869]
  • Chao Shang, Ying Guo, Jun-Qi Yao, Xin-Xin Fang, Li-Jun Sun, Xiang-Yun Jiang, Zhen-Chun Ding, Yu-Hua Ran, Heng-Lin Wang, Li-Ming Zhang, Yun-Feng Li. Rapid anti-PTSD-like activity of the TSPO agonist YL-IPA08: Emphasis on brain GABA, neurosteroids and HPA axis function. Behavioural brain research. 2020 02; 379(?):112320. doi: 10.1016/j.bbr.2019.112320. [PMID: 31669345]
  • Allison Kimball, Laura E Dichtel, Maren B Nyer, David Mischoulon, Lauren B Fisher, Cristina Cusin, Christina M Dording, Nhi-Ha Trinh, Albert Yeung, Melanie S Haines, Joshua C Sung, Graziano Pinna, Ann M Rasmusson, Linda L Carpenter, Maurizio Fava, Anne Klibanski, Karen Klahr Miller. The allopregnanolone to progesterone ratio across the menstrual cycle and in menopause. Psychoneuroendocrinology. 2020 02; 112(?):104512. doi: 10.1016/j.psyneuen.2019.104512. [PMID: 31780185]
  • Tomasz Misztal, Patrycja Młotkowska, Elżbieta Marciniak, Anna Misztal. Allopregnanolone reduces neuroendocrine response to acute stressful stimuli in sheep. The Journal of endocrinology. 2020 01; 244(1):201-211. doi: 10.1530/joe-19-0376. [PMID: 31600724]
  • Tian Wang, Jia Yao, Shuhua Chen, Zisu Mao, Roberta Diaz Brinton. Allopregnanolone Reverses Bioenergetic Deficits in Female Triple Transgenic Alzheimer's Mouse Model. Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics. 2020 01; 17(1):178-188. doi: 10.1007/s13311-019-00793-6. [PMID: 31664643]
  • Li Ren, Qing Song, Yunhuan Liu, Lihua Zhang, Zhiming Hao, Wenke Feng. Probiotic Lactobacillus rhamnosus GG prevents progesterone metabolite epiallaopregnanolone sulfate-induced hepatic bile acid accumulation and liver injury. Biochemical and biophysical research communications. 2019 11; 520(1):67-72. doi: 10.1016/j.bbrc.2019.09.103. [PMID: 31575408]
  • Wei Zheng, Dong-Bin Cai, Wei Zheng, Kang Sim, Gabor S Ungvari, Xiao-Jiang Peng, Yu-Ping Ning, Gang Wang, Yu-Tao Xiang. Brexanolone for postpartum depression: A meta-analysis of randomized controlled studies. Psychiatry research. 2019 09; 279(?):83-89. doi: 10.1016/j.psychres.2019.07.006. [PMID: 31323375]
  • Anna-Maria Neßlauer, Anne Gläser, Markus Gräler, Robby Engelmann, Brigitte Müller-Hilke, Marcus Frank, Christine Burstein, Arndt Rolfs, John Neidhardt, Andreas Wree, Martin Witt, Anja U Bräuer. A therapy with miglustat, 2-hydroxypropyl-ß-cyclodextrin and allopregnanolone restores splenic cholesterol homeostasis in Niemann-pick disease type C1. Lipids in health and disease. 2019 Jun; 18(1):146. doi: 10.1186/s12944-019-1088-2. [PMID: 31248418]
  • Zhiyi Yu, David C Chiara, Pavel Y Savechenkov, Karol S Bruzik, Jonathan B Cohen. A photoreactive analog of allopregnanolone enables identification of steroid-binding sites in a nicotinic acetylcholine receptor. The Journal of biological chemistry. 2019 05; 294(19):7892-7903. doi: 10.1074/jbc.ra118.007172. [PMID: 30923128]
  • Eleonora Napoli, Andrea Schneider, Jun Yi Wang, Aditi Trivedi, Nika Roa Carrillo, Flora Tassone, Michael Rogawski, Randi J Hagerman, Cecilia Giulivi. Allopregnanolone Treatment Improves Plasma Metabolomic Profile Associated with GABA Metabolism in Fragile X-Associated Tremor/Ataxia Syndrome: a Pilot Study. Molecular neurobiology. 2019 May; 56(5):3702-3713. doi: 10.1007/s12035-018-1330-3. [PMID: 30187385]
  • Doodipala Samba Reddy, Chase Matthew Carver, Bryan Clossen, Xin Wu. Extrasynaptic γ-aminobutyric acid type A receptor-mediated sex differences in the antiseizure activity of neurosteroids in status epilepticus and complex partial seizures. Epilepsia. 2019 04; 60(4):730-743. doi: 10.1111/epi.14693. [PMID: 30895610]
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