3-Hydroxypregnan-20-one (BioDeep_00000173931)
Main id: BioDeep_00000014423
human metabolite blood metabolite
代谢物信息卡片
1-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}ethan-1-one
化学式: C21H34O2 (318.2558664)
中文名称:
谱图信息:
最多检出来源 () 0%
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
描述信息
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics
同义名列表
38 个代谢物同义名
1-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}ethan-1-one; 1-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}ethanone; Pregnanolone, (3beta, 5alpha, 8alpha, 17beta)-isomer; Pregnanolone, (3alpha, 5beta, 17-alpha)-isomer; Pregnanolone, (3beta, 5alpha, 17alpha)-isomer; Pregnanolone, (3beta, 5beta, 17alpha)-isomer; Pregnanolone, (3beta, 5beta,14beta)-isomer; alpha-Pregnan-20-one, 3 alpha-hydroxy-5; alpha-Hydroxy-5 alpha-pregnan-20-one, 3; beta-Pregnan-20-one, 3 alpha-hydroxy-5; 3 alpha-Hydroxy-5 alpha-pregnan-20-one; alpha-Hydroxy-5 beta-pregnan-20-one, 3; 3 alpha, 5 beta-Tetrahydroprogesterone; 3 alpha Hydroxy 5 alpha pregnan 20 one; 3 alpha, 5 beta Tetrahydroprogesterone; 3 alpha Hydroxy 5 beta pregnan 20 one; 3 alpha-Hydroxy-5 beta-pregnan-20-one; Pregnanolone, (3alpha,5alpha)-isomer; Pregnanolone, (3beta, 5alpha)-isomer; Pregnanolone, (3beta, 5beta)-isomer; 3beta Hydroxy 5alpha pregnan 20 one; Pregnanolone, (3alpha,5beta)-isomer; 3beta-hydroxy-5alpha-pregnan-20-one; beta-Ol-20-one, allopregnan-3; Pregnanolone, (3alpha)-isomer; Pregnanolone, (5alpha)-isomer; Pregnanolone, (3beta)-isomer; Allopregnan-3 beta-ol-20-one; Allopregnan 3 beta ol 20 one; allopregnan-3beta-ol-20-one; pregnan-3alpha-ol-20-one; Pregnan 3alpha ol 20 one; 3 Hydroxypregnan 20 one; 3-hydroxypregnan-20-one; Epipregnanolone; Pregnanolone; Sepranolone; Eltanolone
数据库引用编号
6 个数据库交叉引用编号
- PubChem: 262961
- HMDB: HMDB0245902
- MeSH: Pregnanolone
- chemspider: 230963
- RefMet: 3beta-Hydroxy-5alpha-pregnan-20-one
- PubChem: 92787
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。
文献列表
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Virologica Sinica.
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Journal of clinical psychopharmacology.
2017 Dec; 37(6):684-688. doi:
10.1097/jcp.0000000000000793. [PMID: 29045302] - David R Owen, Jinjiang Fan, Enrico Campioli, Sathvika Venugopal, Andrew Midzak, Edward Daly, Aline Harlay, Leeyah Issop, Vincenzo Libri, Dimitra Kalogiannopoulou, Eduardo Oliver, Enrique Gallego-Colon, Alessandro Colasanti, Les Huson, Eugenii A Rabiner, Puvan Suppiah, Charles Essagian, Paul M Matthews, Vassilios Papadopoulos. TSPO mutations in rats and a human polymorphism impair the rate of steroid synthesis.
The Biochemical journal.
2017 11; 474(23):3985-3999. doi:
10.1042/bcj20170648. [PMID: 29074640] - Maria Meyer, Laura I Garay, María Sol Kruse, Agustina Lara, Gisella Gargiulo-Monachelli, Michael Schumacher, Rachida Guennoun, Hector Coirini, Alejandro F De Nicola, Maria Claudia Gonzalez Deniselle. Protective effects of the neurosteroid allopregnanolone in a mouse model of spontaneous motoneuron degeneration.
The Journal of steroid biochemistry and molecular biology.
2017 11; 174(?):201-216. doi:
10.1016/j.jsbmb.2017.09.015. [PMID: 28951257] - Greer A Bennett, Hannah K Palliser, Julia C Shaw, Kerrin L Palazzi, David W Walker, Jonathan J Hirst. Maternal stress in pregnancy affects myelination and neurosteroid regulatory pathways in the guinea pig cerebellum.
Stress (Amsterdam, Netherlands).
2017 11; 20(6):580-588. doi:
10.1080/10253890.2017.1378637. [PMID: 28969480] - Antonio G Gomes de Mello Martins, Giuseppe Allegretta, Gerhard Unteregger, Jörg Haupenthal, Jens Eberhard, Michael Hoffmann, Jill A van der Zee, Kerstin Junker, Michael Stöckle, Rolf Müller, Rolf W Hartmann, Carsten-H Ohlmann. CYP17A1-independent production of the neurosteroid-derived 5α-pregnan-3β,6α-diol-20-one in androgen-responsive prostate cancer cell lines under serum starvation and inhibition by Abiraterone.
The Journal of steroid biochemistry and molecular biology.
2017 11; 174(?):183-191. doi:
10.1016/j.jsbmb.2017.09.006. [PMID: 28890368] - A L Cumberland, H K Palliser, P Rani, D W Walker, J J Hirst. Effects of combined IUGR and prenatal stress on the development of the hippocampus in a fetal guinea pig model.
Journal of developmental origins of health and disease.
2017 Oct; 8(5):584-596. doi:
10.1017/s2040174417000307. [PMID: 28502262] - Jeremiah P Jensen, Michelle A Nipper, Melinda L Helms, Matthew M Ford, John C Crabbe, David J Rossi, Deborah A Finn. Ethanol withdrawal-induced dysregulation of neurosteroid levels in plasma, cortex, and hippocampus in genetic animal models of high and low withdrawal.
Psychopharmacology.
2017 Sep; 234(18):2793-2811. doi:
10.1007/s00213-017-4671-0. [PMID: 28664280] - Maria Giuseppina Pisu, Giorgia Boero, Francesca Biggio, Anna Garau, Daniela Corda, Mauro Congiu, Alessandra Concas, Patrizia Porcu, Mariangela Serra. Juvenile social isolation affects maternal care in rats: involvement of allopregnanolone.
Psychopharmacology.
2017 Sep; 234(17):2587-2596. doi:
10.1007/s00213-017-4661-2. [PMID: 28623385] - Charlotte Hellgren, Erika Comasco, Alkistis Skalkidou, Inger Sundström-Poromaa. Allopregnanolone levels and depressive symptoms during pregnancy in relation to single nucleotide polymorphisms in the allopregnanolone synthesis pathway.
Hormones and behavior.
2017 08; 94(?):106-113. doi:
10.1016/j.yhbeh.2017.06.008. [PMID: 28666923] - Sabrina K Syan, Luciano Minuzzi, Dustin Costescu, Mara Smith, Olivia R Allega, Marg Coote, Geoffrey B C Hall, Benicio N Frey. Influence of endogenous estradiol, progesterone, allopregnanolone, and dehydroepiandrosterone sulfate on brain resting state functional connectivity across the menstrual cycle.
Fertility and sterility.
2017 05; 107(5):1246-1255.e4. doi:
10.1016/j.fertnstert.2017.03.021. [PMID: 28476183] - Anja Meyer, Andreas Wree, René Günther, Carsten Holzmann, Oliver Schmitt, Arndt Rolfs, Martin Witt. Increased Regenerative Capacity of the Olfactory Epithelium in Niemann-Pick Disease Type C1.
International journal of molecular sciences.
2017 Apr; 18(4):. doi:
10.3390/ijms18040777. [PMID: 28383485] - Matthew C Beattie, Antoniette M Maldonado-Devincci, Patrizia Porcu, Todd K O'Buckley, James B Daunais, Kathleen A Grant, A Leslie Morrow. Voluntary ethanol consumption reduces GABAergic neuroactive steroid (3α,5α)3-hydroxypregnan-20-one (3α,5α-THP) in the amygdala of the cynomolgus monkey.
Addiction biology.
2017 Mar; 22(2):318-330. doi:
10.1111/adb.12326. [PMID: 26625954] - Luana Lionetto, Fernando De Andrés, Matilde Capi, Martina Curto, Donata Sabato, Maurizio Simmaco, Paola Bossù, Eleonora Sacchinelli, Maria Donata Orfei, Federica Piras, Nerisa Banaj, Gianfranco Spalletta. LC-MS/MS simultaneous analysis of allopregnanolone, epiallopregnanolone, pregnanolone, dehydroepiandrosterone and dehydroepiandrosterone 3-sulfate in human plasma.
Bioanalysis.
2017 Mar; 9(6):527-539. doi:
10.4155/bio-2016-0262. [PMID: 28207286] - Yuyong Ke, Renaud Gonthier, Fernand Labrie. A sensitive and accurate LC-MS/MS assay with the derivatization of 1-Amino-4-methylpiperazine applied to serum allopregnanolone, pregnenolone and androsterone in pre- and postmenopausal women.
Steroids.
2017 02; 118(?):25-31. doi:
10.1016/j.steroids.2016.11.007. [PMID: 27913096] - Stefano Meletti, Chiara Lucchi, Giulia Monti, Giada Giovannini, Roberta Bedin, Tommaso Trenti, Cecilia Rustichelli, Giuseppe Biagini. Decreased allopregnanolone levels in cerebrospinal fluid obtained during status epilepticus.
Epilepsia.
2017 02; 58(2):e16-e20. doi:
10.1111/epi.13625. [PMID: 27888513] - Arif-Ullah Khan, Shamsher Ali, Anwarul-Hassan Gilani, Manzoor Ahmed, Muhammad Iqbal Choudhary. Antispasmodic, bronchodilator, vasorelaxant and cardiosuppressant effects of Buxus papillosa.
BMC complementary and alternative medicine.
2017 Jan; 17(1):54. doi:
10.1186/s12906-017-1558-x. [PMID: 28100216] - Narender Kumar, Jerôme Fagart, Philippe Liere, Scott J Mitchell, Alanah R Knibb, Isabelle Petit-Topin, Marion Rame, Martine El-Etr, Michael Schumacher, Jeremy J Lambert, Marie-Edith Rafestin-Oblin, Regine Sitruk-Ware. Nestorone® as a Novel Progestin for Nonoral Contraception: Structure-Activity Relationships and Brain Metabolism Studies.
Endocrinology.
2017 01; 158(1):170-182. doi:
10.1210/en.2016-1426. [PMID: 27824503] - Zhi-Kun Qiu, Jia-Li He, Xu Liu, Guan-Hua Zhang, Jia Zeng, Hong Nie, Yong-Gang Shen, Ji-Sheng Chen. The antidepressant-like activity of AC-5216, a ligand for 18KDa translocator protein (TSPO), in an animal model of diabetes mellitus.
Scientific reports.
2016 11; 6(?):37345. doi:
10.1038/srep37345. [PMID: 27886206] - Maria Claudia Gonzalez Deniselle, Philippe Liere, Antoine Pianos, Maria Meyer, Fanny Aprahamian, Annie Cambourg, Noelia P Di Giorgio, Michael Schumacher, Alejandro F De Nicola, Rachida Guennoun. Steroid Profiling in Male Wobbler Mouse, a Model of Amyotrophic Lateral Sclerosis.
Endocrinology.
2016 Nov; 157(11):4446-4460. doi:
10.1210/en.2016-1244. [PMID: 27571131] - Kristina M Deligiannidis, Aimee R Kroll-Desrosiers, Shunyan Mo, Hien P Nguyen, Abby Svenson, Nina Jaitly, Janet E Hall, Bruce A Barton, Anthony J Rothschild, Scott A Shaffer. Peripartum neuroactive steroid and γ-aminobutyric acid profiles in women at-risk for postpartum depression.
Psychoneuroendocrinology.
2016 08; 70(?):98-107. doi:
10.1016/j.psyneuen.2016.05.010. [PMID: 27209438] - Greer A Bennett, Hannah K Palliser, David Walker, Jonathan Hirst. Severity and timing: How prenatal stress exposure affects glial developmental, emotional behavioural and plasma neurosteroid responses in guinea pig offspring.
Psychoneuroendocrinology.
2016 08; 70(?):47-57. doi:
10.1016/j.psyneuen.2016.04.011. [PMID: 27155257] - Mary Kimmel, Makena Clive, Fiona Gispen, Jerry Guintivano, Tori Brown, Olivia Cox, Matthias W Beckmann, Johannes Kornhuber, Peter A Fasching, Lauren M Osborne, Elisabeth Binder, Jennifer L Payne, Zachary Kaminsky. Oxytocin receptor DNA methylation in postpartum depression.
Psychoneuroendocrinology.
2016 07; 69(?):150-60. doi:
10.1016/j.psyneuen.2016.04.008. [PMID: 27108164] - Li-Ming Zhang, Zhi-Kun Qiu, Xiao-Fei Chen, Nan Zhao, Hong-Xia Chen, Rui- Xue, You-Zhi Zhang, Ri-Fang Yang, Yun-Feng Li. Involvement of allopregnanolone in the anti-PTSD-like effects of AC-5216.
Journal of psychopharmacology (Oxford, England).
2016 05; 30(5):474-81. doi:
10.1177/0269881115625115. [PMID: 26783231] - M G Pisu, A Garau, G Boero, F Biggio, V Pibiri, R Dore, V Locci, E Paci, P Porcu, M Serra. Sex differences in the outcome of juvenile social isolation on HPA axis function in rats.
Neuroscience.
2016 Apr; 320(?):172-82. doi:
10.1016/j.neuroscience.2016.02.009. [PMID: 26868968] - Erin L Legacki, Elizabeth L Scholtz, Barry A Ball, Scott D Stanley, Trish Berger, Alan J Conley. The dynamic steroid landscape of equine pregnancy mapped by mass spectrometry.
Reproduction (Cambridge, England).
2016 Apr; 151(4):421-30. doi:
10.1530/rep-15-0547. [PMID: 26814209] - Pedro E Martinez, David R Rubinow, Lynnette K Nieman, Deloris E Koziol, A Leslie Morrow, Crystal E Schiller, Dahima Cintron, Karla D Thompson, Khursheed K Khine, Peter J Schmidt. 5α-Reductase Inhibition Prevents the Luteal Phase Increase in Plasma Allopregnanolone Levels and Mitigates Symptoms in Women with Premenstrual Dysphoric Disorder.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology.
2016 Mar; 41(4):1093-102. doi:
10.1038/npp.2015.246. [PMID: 26272051] - Verica Milivojevic, Helen C Fox, Mehmet Sofuoglu, Jonathan Covault, Rajita Sinha. Effects of progesterone stimulated allopregnanolone on craving and stress response in cocaine dependent men and women.
Psychoneuroendocrinology.
2016 Mar; 65(?):44-53. doi:
10.1016/j.psyneuen.2015.12.008. [PMID: 26716877] - Sahruh Turkmen, Alebtekin Ahangari, Torbjörn Bäckstrom. Roux-en-Y Gastric Bypass Surgery in Patients with Polycystic Ovary Syndrome and Metabolic Syndrome.
Obesity surgery.
2016 Jan; 26(1):111-8. doi:
10.1007/s11695-015-1729-0. [PMID: 25975201] - Zhuo-Wei Gao, Jing-Bin Huang, Qing Lin, Qiang Qin, Yao-Jun Liang, Lu Zhou, Min Luo. The effects of PK11195 on meningioma was associated with allopregnanolone biosynthesis, which was mediated by translocator protein 18 KDa.
Cancer biomarkers : section A of Disease markers.
2016; 16(1):65-9. doi:
10.3233/cbm-150541. [PMID: 26835706] - Helena Hedström, Torbjörn Bäckström, Marie Bixo, Sigrid Nyberg, Mingde Wang, Ida Gideonsson, Sahruh Turkmen. Women with polycystic ovary syndrome have elevated serum concentrations of and altered GABA(A) receptor sensitivity to allopregnanolone.
Clinical endocrinology.
2015 Nov; 83(5):643-50. doi:
10.1111/cen.12809. [PMID: 25929428] - Torbjörn Bäckström, Marie Bixo, Jessica Strömberg. GABAA Receptor-Modulating Steroids in Relation to Women's Behavioral Health.
Current psychiatry reports.
2015 Nov; 17(11):92. doi:
10.1007/s11920-015-0627-4. [PMID: 26396092] - Christopher D Schmoutz, Glenn F Guerin, Scott P Runyon, Suraj Dhungana, Nicholas E Goeders. A therapeutic combination of metyrapone and oxazepam increases brain levels of GABA-active neurosteroids and decreases cocaine self-administration in male rats.
Behavioural brain research.
2015 Sep; 291(?):108-111. doi:
10.1016/j.bbr.2015.05.019. [PMID: 26003946] - Rivka Ben Dor, Christine E Marx, Lawrence J Shampine, David R Rubinow, Peter J Schmidt. DHEA metabolism to the neurosteroid androsterone: a possible mechanism of DHEA's antidepressant action.
Psychopharmacology.
2015 Sep; 232(18):3375-83. doi:
10.1007/s00213-015-3991-1. [PMID: 26105109] - Zhi-Kun Qiu, Guan-Hua Zhang, Jia-Li He, Jian-Chun Ma, Jia Zeng, Dong Shen, Yong-Gang Shen, Ji-Sheng Chen, Cheng-Yong Liu. Free and Easy Wanderer Plus (FEWP) improves behavioral deficits in an animal model of post-traumatic stress disorder by stimulating allopregnanolone biosynthesis.
Neuroscience letters.
2015 Aug; 602(?):162-6. doi:
10.1016/j.neulet.2015.06.055. [PMID: 26160034] - H K Palliser, M A Kelleher, M Tolcos, D W Walker, J J Hirst. Effect of postnatal progesterone therapy following preterm birth on neurosteroid concentrations and cerebellar myelination in guinea pigs.
Journal of developmental origins of health and disease.
2015 Aug; 6(4):350-61. doi:
10.1017/s2040174415001075. [PMID: 25907069] - Giorgio Dimastrogiovanni, Denise Fernandes, Marta Bonastre, Cinta Porte. Progesterone is actively metabolized to 5α-pregnane-3,20-dione and 3β-hydroxy-5α-pregnan-20-one by the marine mussel Mytilus galloprovincialis.
Aquatic toxicology (Amsterdam, Netherlands).
2015 Aug; 165(?):93-100. doi:
10.1016/j.aquatox.2015.05.018. [PMID: 26026673] - M Pallarès, A Llidó, L Mòdol, M Vallée, S Darbra. Finasteride administration potentiates the disruption of prepulse inhibition induced by forced swim stress.
Behavioural brain research.
2015 Aug; 289(?):55-60. doi:
10.1016/j.bbr.2015.04.023. [PMID: 25913832] - Ken'ichi Yamaguchi. Evaluation for roles of neurosteroids in modulating forebrain mechanisms controlling vasopressin secretion and related phenomena in conscious rats.
Neuroscience research.
2015 Jun; 95(?):38-50. doi:
10.1016/j.neures.2015.01.002. [PMID: 25598212] - Zhi-Kun Qiu, Jia-Li He, Xu Liu, Sha Lai, Jian-Chun Ma, Jia Zeng, Yan Li, Hong-Wei Wu, Yong Chen, Yong-Gang Shen, Ji-Sheng Chen, Min Luo. The role of allopregnanolone in the anxiolytic-like effect of free and easy wanderer plus (FEWP), a polyherbal preparation.
Neuroscience letters.
2015 May; 595(?):94-8. doi:
10.1016/j.neulet.2015.03.039. [PMID: 25800108] - 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] - Mattia Sacchi, Daniel Balleza, Giulia Vena, Giulia Puia, Paolo Facci, Andrea Alessandrini. Effect of neurosteroids on a model lipid bilayer including cholesterol: An Atomic Force Microscopy study.
Biochimica et biophysica acta.
2015 May; 1848(5):1258-67. doi:
10.1016/j.bbamem.2015.01.002. [PMID: 25620773] - Daniel Balleza, Mattia Sacchi, Giulia Vena, Debora Galloni, Giulia Puia, Paolo Facci, Andrea Alessandrini. Effects of neurosteroids on a model membrane including cholesterol: A micropipette aspiration study.
Biochimica et biophysica acta.
2015 May; 1848(5):1268-76. doi:
10.1016/j.bbamem.2015.01.017. [PMID: 25660752] - Paula J Brunton, Marcio V Donadio, Song T Yao, Mike Greenwood, Jonathan R Seckl, David Murphy, John A Russell. 5α-Reduced neurosteroids sex-dependently reverse central prenatal programming of neuroendocrine stress responses in rats.
The Journal of neuroscience : the official journal of the Society for Neuroscience.
2015 Jan; 35(2):666-77. doi:
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PloS one.
2015; 10(6):e0128313. doi:
10.1371/journal.pone.0128313. [PMID: 26039057] - Jing-Yang Zhang, Yong-Xiang Wang. Gelsemium analgesia and the spinal glycine receptor/allopregnanolone pathway.
Fitoterapia.
2015 Jan; 100(?):35-43. doi:
10.1016/j.fitote.2014.11.002. [PMID: 25447163]