Tetrahydrodeoxycorticosterone (BioDeep_00000009526)

 

Secondary id: BioDeep_00000598641

human metabolite Endogenous blood metabolite


代谢物信息卡片


2-hydroxy-1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one

化学式: C21H34O3 (334.25078140000005)
中文名称: 3alpha,21-二羟基-5alpha-孕甾-20-酮, 四氢11-脱氧皮质酮
谱图信息: 最多检出来源 Homo sapiens(feces) 0.03%

分子结构信息

SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4C(=O)CO)C)O
InChI: InChI=1S/C21H34O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13-18,22-23H,3-12H2,1-2H3/t13-,14+,15-,16-,17-,18+,20-,21-/m0/s1

描述信息

The neurosteroid allotetrahydrodeoxycorticosterone (THDOC) is an allosteric modulator of the GABA(A) receptor. Although the role of THDOC within the brain is undefined, recent studies indicate that stress induces THDOC to levels that can activate GABA(A) receptors. These results might have significant implications for human stress-sensitive conditions such as epilepsy, post-traumatic stress disorder and depression. (PMID 12628349) [HMDB]
The neurosteroid allotetrahydrodeoxycorticosterone (THDOC) is an allosteric modulator of the GABA(A) receptor. Although the role of THDOC within the brain is undefined, recent studies indicate that stress induces THDOC to levels that can activate GABA(A) receptors. These results might have significant implications for human stress-sensitive conditions such as epilepsy, post-traumatic stress disorder and depression. (PMID 12628349).
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics
D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014151 - Anti-Anxiety Agents
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
D018377 - Neurotransmitter Agents > D000081227 - Neurosteroids
3α,21-Dihydroxy-5α-pregnan-20-one (THDOC), an endogenous neurosteroid, is a positive modulator of GABAA receptors. 3α,21-Dihydroxy-5α-pregnan-20-one potentiates neuronal response to low concentrations of GABA at α4β1δ GABAA receptors in vitro.

同义名列表

27 个代谢物同义名

2-hydroxy-1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one; Tetrahydrodeoxycorticosterone, (3alpha,5alpha)-isomer; Tetrahydrodeoxycorticosterone, (3beta,5alpha)-isomer; 3 beta,5 alpha-Tetrahydrodeoxycorticosterone; 3 alpha,5 beta-Tetrahydrodeoxycorticosterone; 3 alpha,21-Dihydroxy-5 beta-pregnan-20-one; 3alpha,21-dihydroxy-5alpha-pregnane-20-one; 3alpha,21-Dihydroxy-5alpha-pregnan-20-one; 3alpha,21-dihydroxy-5beta-pregnan-20-one; 5alpha-Pregnane-3alpha,21-diol-20-one; 5alpha-Pregnan-3alpha,21-diol-20-one; Deoxycorticosterone-21-aminopropane; 3Α,21-dihydroxy-5α-pregnan-20-one; Allotetrahydrodeoxycorticosterone; Tetrahydro-11-deoxycorticosterone; 3a,21-Dihydroxy-5a-pregnan-20-one; Tetrahydrodesoxycorticosterone; Tetrahydrodeoxycorticosterone; 3,21-Dihydroxypregnan-20-one; 21-hydroxyallopregnanolone; Pregnane-3,21-diol-20-one; 5-alpha-THDOC; 5alpha-THDOC; ST 21:1;O3; 5a-THDOC; 5Α-thdoc; THDOC



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

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

  • 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]
  • 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]
  • Vivien Zell, Pierre-Éric Juif, Ulrike Hanesch, Pierrick Poisbeau, Fernand Anton, Pascal Darbon. Corticosterone analgesia is mediated by the spinal production of neuroactive metabolites that enhance GABAergic inhibitory transmission on dorsal horn rat neurons. The European journal of neuroscience. 2015 Feb; 41(3):390-7. doi: 10.1111/ejn.12796. [PMID: 25427854]
  • Emily P McQuarrie, E Marie Freel, Patrick B Mark, Robert Fraser, Rajan K Patel, Henry G Dargie, John M C Connell, Alan G Jardine. Urinary corticosteroid excretion predicts left ventricular mass and proteinuria in chronic kidney disease. Clinical science (London, England : 1979). 2012 Sep; 123(5):285-94. doi: 10.1042/cs20120015. [PMID: 22397469]
  • Marco Bortolato, Paola Devoto, Paola Roncada, Roberto Frau, Giovanna Flore, Pierluigi Saba, Giuseppa Pistritto, Alessio Soggiu, Salvatore Pisanu, Agata Zappala, Maria Serafina Ristaldi, Maria Tattoli, Vincenzo Cuomo, Francesco Marrosu, Maria Luisa Barbaccia. Isolation rearing-induced reduction of brain 5α-reductase expression: relevance to dopaminergic impairments. Neuropharmacology. 2011 Jun; 60(7-8):1301-8. doi: 10.1016/j.neuropharm.2011.01.013. [PMID: 21256141]
  • Ruotian Jiang, Akiko Miyamoto, Adeline Martz, Alexandre Specht, Hitoshi Ishibashi, Marie Kueny-Stotz, Stefan Chassaing, Raymond Brouillard, Lia Prado de Carvalho, Maurice Goeldner, Junichi Nabekura, Mogens Nielsen, Thomas Grutter. Retrochalcone derivatives are positive allosteric modulators at synaptic and extrasynaptic GABA(A) receptors in vitro. British journal of pharmacology. 2011 Mar; 162(6):1326-39. doi: 10.1111/j.1476-5381.2010.01142.x. [PMID: 21133889]
  • Kevin N Boyd, Sandeep Kumar, Todd K O'Buckley, A Leslie Morrow. Chronic ethanol exposure produces tolerance to elevations in neuroactive steroids: mechanisms and reversal by exogenous ACTH. Journal of neurochemistry. 2010 Oct; 115(1):142-52. doi: 10.1111/j.1471-4159.2010.06904.x. [PMID: 20633208]
  • Cheryl A Frye, Alicia A Walf, Jason J Paris. Conjugated equine estrogen, with medroxyprogesterone acetate, enhances formation of 5alpha-reduced progestogens and reduces anxiety-like behavior of middle-aged rats. Behavioural pharmacology. 2010 Sep; 21(5-6):530-9. doi: 10.1097/fbp.0b013e32833e0a23. [PMID: 20679892]
  • Cheryl A Frye, Carolyn J Koonce, Alicia A Walf. Mnemonic effects of progesterone to mice require formation of 3alpha,5alpha-THP. Neuroreport. 2010 Jun; 21(8):590-5. doi: 10.1097/wnr.0b013e32833a7e14. [PMID: 20431492]
  • Cornelius Schüle, Thomas C Baghai, Flavia di Michele, Daniela Eser, Augusto Pasini, Elena Romeo, Rainer Rupprecht. Mirtazapine does not influence tetrahydrodeoxycorticosterone levels in depressed patients. The world journal of biological psychiatry : the official journal of the World Federation of Societies of Biological Psychiatry. 2010 Mar; 11(2 Pt 2):308-13. doi: 10.3109/15622970701639429. [PMID: 20218794]
  • Patrizia Porcu, Todd K O'Buckley, Sarah E Alward, Soomin C Song, Kathleen A Grant, Harriet de Wit, A Leslie Morrow. Differential effects of ethanol on serum GABAergic 3alpha,5alpha/3alpha,5beta neuroactive steroids in mice, rats, cynomolgus monkeys, and humans. Alcoholism, clinical and experimental research. 2010 Mar; 34(3):432-42. doi: 10.1111/j.1530-0277.2009.01123.x. [PMID: 20028362]
  • Pratap Meera, Richard W Olsen, Thomas S Otis, Martin Wallner. Etomidate, propofol and the neurosteroid THDOC increase the GABA efficacy of recombinant alpha4beta3delta and alpha4beta3 GABA A receptors expressed in HEK cells. Neuropharmacology. 2009 Jan; 56(1):155-60. doi: 10.1016/j.neuropharm.2008.08.011. [PMID: 18778723]
  • Maria Giuseppina Pisu, Maria Cristina Mostallino, Riccardo Dore, Maria Luisa Mura, Elisabetta Maciocco, Emilio Russo, Giovambattista De Sarro, Mariangela Serra. Neuroactive steroids and GABAA receptor plasticity in the brain of the WAG/Rij rat, a model of absence epilepsy. Journal of neurochemistry. 2008 Sep; 106(6):2502-14. doi: 10.1111/j.1471-4159.2008.05538.x. [PMID: 18624910]
  • Antonella Tuveri, Anna Maria Paoletti, Marisa Orrù, Gian Benedetto B Melis, Maria Francesca Marotto, Pierina Zedda, Francesco Marrosu, Cristiana Sogliano, Carla Marra, Giovanni Biggio, Alessandra Concas. Reduced serum level of THDOC, an anticonvulsant steroid, in women with perimenstrual catamenial epilepsy. Epilepsia. 2008 Jul; 49(7):1221-9. doi: 10.1111/j.1528-1167.2008.01555.x. [PMID: 18325018]
  • M D Womack, S Pyner, R Barrett-Jolley. Inhibition by alpha-tetrahydrodeoxycorticosterone (THDOC) of pre-sympathetic parvocellular neurones in the paraventricular nucleus of rat hypothalamus. British journal of pharmacology. 2006 Nov; 149(5):600-7. doi: 10.1038/sj.bjp.0706911. [PMID: 17001301]
  • L R G Nieminen, K K Makino, N Mehta, M Virkkunen, H Y Kim, J R Hibbeln. Relationship between omega-3 fatty acids and plasma neuroactive steroids in alcoholism, depression and controls. Prostaglandins, leukotrienes, and essential fatty acids. 2006 Oct; 75(4-5):309-14. doi: 10.1016/j.plefa.2006.07.012. [PMID: 16959481]
  • Maria Carolina Hardoy, Mariangela Serra, Mauro Giovanni Carta, Paolo Contu, Maria Giuseppina Pisu, Giovanni Biggio. Increased neuroactive steroid concentrations in women with bipolar disorder or major depressive disorder. Journal of clinical psychopharmacology. 2006 Aug; 26(4):379-84. doi: 10.1097/01.jcp.0000229483.52955.ec. [PMID: 16855455]
  • Francesca Biggio, Giorgio Gorini, Stefania Caria, Luca Murru, Maria Cristina Mostallino, Enrico Sanna, Paolo Follesa. Plastic neuronal changes in GABA(A) receptor gene expression induced by progesterone metabolites: in vitro molecular and functional studies. Pharmacology, biochemistry, and behavior. 2006 Aug; 84(4):545-54. doi: 10.1016/j.pbb.2006.07.002. [PMID: 16914187]
  • Rahul T Khisti, Kevin N Boyd, Sandeep Kumar, A Leslie Morrow. Systemic ethanol administration elevates deoxycorticosterone levels and chronic ethanol exposure attenuates this response. Brain research. 2005 Jul; 1049(1):104-11. doi: 10.1016/j.brainres.2005.05.007. [PMID: 15936001]
  • Francesca Brambilla, Carmen Mellado, Alessandra Alciati, Maria Giuseppina Pisu, Robert H Purdy, Stefano Zanone, Giulia Perini, Mariangela Serra, Mariarosa Serra, Giovanni Biggio. Plasma concentrations of anxiolytic neuroactive steroids in men with panic disorder. Psychiatry research. 2005 Jun; 135(3):185-90. doi: 10.1016/j.psychres.2004.11.009. [PMID: 15996752]
  • Daniela Eser, Flavia di Michele, Peter Zwanzger, Augusto Pasini, Thomas C Baghai, Cornelius Schüle, Rainer Rupprecht, Elena Romeo. Panic induction with cholecystokinin-tetrapeptide (CCK-4) Increases plasma concentrations of the neuroactive steroid 3alpha, 5alpha tetrahydrodeoxycorticosterone (3alpha, 5alpha-THDOC) in healthy volunteers. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2005 Jan; 30(1):192-5. doi: 10.1038/sj.npp.1300572. [PMID: 15467707]
  • Gianfranco Spalletta, Elena Romeo, Giuseppina Bonaviri, Giorgio Bernardi, Carlo Caltagirone, Flavia di Michele. Preliminary evidence for an association between aggressive and hostile behaviour and 3alpha,5alpha-tetrahydroprogesterone plasma levels in schizophrenia. Journal of psychiatry & neuroscience : JPN. 2005 Jan; 30(1):49-52. doi: NULL. [PMID: 15644998]
  • Palmiero Monteleone, Michele Fabrazzo, Mariangela Serra, Alfonso Tortorella, M Giuseppina Pisu, Giovanni Biggio, Mario Maj. Long-term treatment with clozapine does not affect morning circulating levels of allopregnanolone and THDOC in patients with schizophrenia: a preliminary study. Journal of clinical psychopharmacology. 2004 Aug; 24(4):437-40. doi: 10.1097/01.jcp.0000130552.78501.1a. [PMID: 15232336]
  • Laura E O'Dell, Ahmed A Alomary, Monique Vallée, George F Koob, Robert L Fitzgerald, Robert H Purdy. Ethanol-induced increases in neuroactive steroids in the rat brain and plasma are absent in adrenalectomized and gonadectomized rats. European journal of pharmacology. 2004 Jan; 484(2-3):241-7. doi: 10.1016/j.ejphar.2003.11.031. [PMID: 14744609]
  • Francesca Brambilla, Giovanni Biggio, Maria Giuseppina Pisu, Robert H Purdy, Gilberto Gerra, Amir Zaimovich, Mariangela Serra. Plasma concentrations of anxiolytic neurosteroids in men with normal anxiety scores: a correlation analysis. Neuropsychobiology. 2004; 50(1):6-9. doi: 10.1159/000077934. [PMID: 15179013]
  • Matt T Bianchi, Robert L Macdonald. Neurosteroids shift partial agonist activation of GABA(A) receptor channels from low- to high-efficacy gating patterns. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2003 Nov; 23(34):10934-43. doi: 10.1523/jneurosci.23-34-10934.2003. [PMID: 14645489]
  • Cheryl Frye, Angela Seliga. Effects of olanzapine infusions to the ventral tegmental area on lordosis and midbrain 3alpha,5alpha-THP concentrations in rats. Psychopharmacology. 2003 Nov; 170(2):132-9. doi: 10.1007/s00213-003-1523-x. [PMID: 12845413]
  • Francesca Brambilla, Giovanni Biggio, Maria Giuseppina Pisu, Laura Bellodi, Giampaolo Perna, Vesna Bogdanovich-Djukic, Robert H Purdy, Mariangela Serra. Neurosteroid secretion in panic disorder. Psychiatry research. 2003 May; 118(2):107-16. doi: 10.1016/s0165-1781(03)00077-5. [PMID: 12798975]
  • John J Peluso, G Fernandez, A Pappalardo, B A White. Membrane-initiated events account for progesterone's ability to regulate intracellular free calcium levels and inhibit rat granulosa cell mitosis. Biology of reproduction. 2002 Aug; 67(2):379-85. doi: 10.1095/biolreprod67.2.379. [PMID: 12135870]
  • Doodipala S Reddy. The clinical potentials of endogenous neurosteroids. Drugs of today (Barcelona, Spain : 1998). 2002 Jul; 38(7):465-85. doi: 10.1358/dot.2002.38.7.820115. [PMID: 12582464]
  • Mariangela Serra, M Giuseppina Pisul, Laura Dazzi, Robert H Purdy, Giovanni Biggio. Prevention of the stress-induced increase in the concentration of neuroactive steroids in rat brain by long-term administration of mirtazapine but not of fluoxetine. Journal of psychopharmacology (Oxford, England). 2002 Jun; 16(2):133-8. doi: 10.1177/026988110201600203. [PMID: 12095071]
  • Doodipala S Reddy, Michael A Rogawski. Stress-induced deoxycorticosterone-derived neurosteroids modulate GABA(A) receptor function and seizure susceptibility. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2002 May; 22(9):3795-805. doi: 20026274. [PMID: 11978855]
  • Giuseppe Trapani, Laura Dazzi, Maria Giuseppina Pisu, Antonia Reho, Emanuele Seu, Giovanni Biggio. A rapid method for obtaining finasteride, a 5alpha-reductase inhibitor, from commercial tablets. Brain research. Brain research protocols. 2002 Apr; 9(2):130-4. doi: 10.1016/s1385-299x(02)00146-0. [PMID: 12034332]
  • Kai M Wohlfarth, Matt T Bianchi, Robert L Macdonald. Enhanced neurosteroid potentiation of ternary GABA(A) receptors containing the delta subunit. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2002 Mar; 22(5):1541-9. doi: 10.1523/jneurosci.22-05-01541.2002. [PMID: 11880484]
  • M L Barbaccia, D Affricano, R H Purdy, E Maciocco, F Spiga, G Biggio. Clozapine, but not haloperidol, increases brain concentrations of neuroactive steroids in the rat. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2001 Oct; 25(4):489-97. doi: 10.1016/s0893-133x(01)00254-8. [PMID: 11557162]
  • M L Barbaccia, M Serra, R H Purdy, G Biggio. Stress and neuroactive steroids. International review of neurobiology. 2001; 46(?):243-72. doi: 10.1016/s0074-7742(01)46065-x. [PMID: 11599302]
  • C A Frye, S M Petralia, M E Rhodes. Estrous cycle and sex differences in performance on anxiety tasks coincide with increases in hippocampal progesterone and 3alpha,5alpha-THP. Pharmacology, biochemistry, and behavior. 2000 Nov; 67(3):587-96. doi: 10.1016/s0091-3057(00)00392-0. [PMID: 11164090]
  • M Serra, M G Pisu, M Littera, G Papi, E Sanna, F Tuveri, L Usala, R H Purdy, G Biggio. Social isolation-induced decreases in both the abundance of neuroactive steroids and GABA(A) receptor function in rat brain. Journal of neurochemistry. 2000 Aug; 75(2):732-40. doi: 10.1046/j.1471-4159.2000.0750732.x. [PMID: 10899949]
  • A Ströhle, A Pasini, E Romeo, B Hermann, G Spalletta, F di Michele, F Holsboer, R Rupprecht. Fluoxetine decreases concentrations of 3 alpha, 5 alpha-tetrahydrodeoxycorticosterone (THDOC) in major depression. Journal of psychiatric research. 2000 May; 34(3):183-6. doi: 10.1016/s0022-3956(00)00006-6. [PMID: 10867112]
  • G Trapani, M Franco, A Latrofa, L Ricciardi, A Carotti, M Serra, E Sanna, G Biggio, G Liso. Novel 2-phenylimidazo[1,2-a]pyridine derivatives as potent and selective ligands for peripheral benzodiazepine receptors: synthesis, binding affinity, and in vivo studies. Journal of medicinal chemistry. 1999 Sep; 42(19):3934-41. doi: 10.1021/jm991035g. [PMID: 10508441]
  • A Ströhle, E Romeo, B Hermann, A Pasini, G Spalletta, F di Michele, F Holsboer, R Rupprecht. Concentrations of 3 alpha-reduced neuroactive steroids and their precursors in plasma of patients with major depression and after clinical recovery. Biological psychiatry. 1999 Feb; 45(3):274-7. doi: 10.1016/s0006-3223(98)00328-x. [PMID: 10023501]
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