5α-Dihydroprogesterone (BioDeep_00001867973)

Main id: BioDeep_00000637533

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


5alpha-pregnane-3,20-dione

化学式: C21H32O2 (316.24021719999996)
中文名称: 二氢黄体酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(=O)C4)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/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1

描述信息

A C21-steroid hormone that is 5alpha-pregnane substituted by oxo groups at positions 3 and 20. It is a metabolite of progestrone.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
5a-Pregnane-3,20-dione is the endogenous progesterone metabolite.

同义名列表

4 个代谢物同义名

5alpha-pregnane-3,20-dione; 5α-Dihydroprogesterone; 5a-Pregnane-3,20-dione; 5alpha-Pregnane-3,20-dione



数据库引用编号

15 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

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)

17 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

  • 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]
  • S L Pineles, Y I Nillni, G Pinna, J Irvine, A Webb, K A Arditte Hall, R Hauger, M W Miller, P A Resick, S P Orr, A M Rasmusson. PTSD in women is associated with a block in conversion of progesterone to the GABAergic neurosteroids allopregnanolone and pregnanolone measured in plasma. Psychoneuroendocrinology. 2018 07; 93(?):133-141. doi: 10.1016/j.psyneuen.2018.04.024. [PMID: 29727810]
  • John P Wiebe, Kevin J Pawlak, Arthur Kwok. Mechanism of action of the breast cancer-promoter hormone, 5α-dihydroprogesterone (5αP), involves plasma membrane-associated receptors and MAPK activation. The Journal of steroid biochemistry and molecular biology. 2016 Jan; 155(Pt A):166-76. doi: 10.1016/j.jsbmb.2015.10.021. [PMID: 26519986]
  • Miguel Debono, Ashwini Mallappa, Verena Gounden, Aikaterini A Nella, Robert F Harrison, Christopher A Crutchfield, Peter S Backlund, Steven J Soldin, Richard J Ross, Deborah P Merke. Hormonal circadian rhythms in patients with congenital adrenal hyperplasia: identifying optimal monitoring times and novel disease biomarkers. European journal of endocrinology. 2015 Dec; 173(6):727-37. doi: 10.1530/eje-15-0064. [PMID: 26340969]
  • John P Wiebe, Martin A Rivas, Maria F Mercogliano, Patricia V Elizalde, Roxana Schillaci. Progesterone-induced stimulation of mammary tumorigenesis is due to the progesterone metabolite, 5α-dihydroprogesterone (5αP) and can be suppressed by the 5α-reductase inhibitor, finasteride. The Journal of steroid biochemistry and molecular biology. 2015 May; 149(?):27-34. doi: 10.1016/j.jsbmb.2015.01.004. [PMID: 25595041]
  • John P Wiebe, Guihua Zhang, Ian Welch, Heather-Anne T Cadieux-Pitre. Progesterone metabolites regulate induction, growth, and suppression of estrogen- and progesterone receptor-negative human breast cell tumors. Breast cancer research : BCR. 2013 May; 15(3):R38. doi: 10.1186/bcr3422. [PMID: 25927181]
  • Carolyn J Koonce, Alicia A Walf, Cheryl A Frye. Type 1 5α-reductase may be required for estrous cycle changes in affective behaviors of female mice. Behavioural brain research. 2012 Jan; 226(2):376-80. doi: 10.1016/j.bbr.2011.09.028. [PMID: 21946309]
  • M Dušková, K Simůnková, M Hill, M Velíková, J Kubátová, L Kancheva, H Kazihnitková, H Hruškovičová, H Pospíšilová, B Rácz, M Salátová, V Cirmanová, E Králíková, L Stárka, A Pařízek. Chronic cigarette smoking alters circulating sex hormones and neuroactive steroids in premenopausal women. Physiological research. 2012; 61(1):97-111. doi: 10.33549/physiolres.932164. [PMID: 22188108]
  • Itsuki Adachi, Satoshi Kusuda, Hitomi Kawai, Megumi Ohazama, Atsushi Taniguchi, Natsuko Kondo, Masato Yoshihara, Ryuta Okuda, Tatsuya Ishikawa, Iwai Kanda, Osamu Doi. Fecal progestagens to detect and monitor pregnancy in captive female cheetahs (Acinonyx jubatus). The Journal of reproduction and development. 2011 Apr; 57(2):262-6. doi: 10.1262/jrd.10-057t. [PMID: 21242656]
  • Ronald W Irwin, Jun Ming Wang, Shuhua Chen, Roberta Diaz Brinton. Neuroregenerative mechanisms of allopregnanolone in Alzheimer's disease. Frontiers in endocrinology. 2011; 2(?):117. doi: 10.3389/fendo.2011.00117. [PMID: 22654847]
  • I Adachi, S Kusuda, E Nagao, Y Taira, M Asano, T Tsubota, O Doi. Fecal steroid metabolites and reproductive monitoring in a female Tsushima leopard cat (Prionailurus bengalensis euptilurus). Theriogenology. 2010 Nov; 74(8):1499-503. doi: 10.1016/j.theriogenology.2010.04.031. [PMID: 20615533]
  • Cheryl A Frye, Danielle C Llaneza. Corticosteroid and neurosteroid dysregulation in an animal model of autism, BTBR mice. Physiology & behavior. 2010 Jun; 100(3):264-7. doi: 10.1016/j.physbeh.2010.03.005. [PMID: 20298706]
  • K M Tripp, M Dubois, P Delahaut, J P Verstegen. Detection and identification of plasma progesterone metabolites in the female Florida manatee (Trichechus manatus latirostris) using GC/MS/MS. Theriogenology. 2009 Aug; 72(3):365-71. doi: 10.1016/j.theriogenology.2009.03.004. [PMID: 19464047]
  • Laura A Jansen, Lindsey D Peugh, Jeffrey G Ojemann. GABA(A) receptor properties in catastrophic infantile epilepsy. Epilepsy research. 2008 Oct; 81(2-3):188-97. doi: 10.1016/j.eplepsyres.2008.05.011. [PMID: 18650066]
  • Martin Hill, David Cibula, Helena Havlíková, Lyudmila Kancheva, Tomás Fait, Radmila Kancheva, Antonín Parízek, Luboslav Stárka. Circulating levels of pregnanolone isomers during the third trimester of human pregnancy. The Journal of steroid biochemistry and molecular biology. 2007 Jun; 105(1-5):166-75. doi: 10.1016/j.jsbmb.2006.10.010. [PMID: 17583491]
  • D Meffre, A Pianos, P Liere, B Eychenne, A Cambourg, M Schumacher, D G Stein, R Guennoun. Steroid profiling in brain and plasma of male and pseudopregnant female rats after traumatic brain injury: analysis by gas chromatography/mass spectrometry. Endocrinology. 2007 May; 148(5):2505-17. doi: 10.1210/en.2006-1678. [PMID: 17303653]
  • Tatsuya Higashi, Akihiro Nagahama, Norihiro Otomi, Kazutake Shimada. Studies on neurosteroids XIX. Development and validation of liquid chromatography-tandem mass spectrometric method for determination of 5alpha-reduced pregnane-type neurosteroids in rat brain and serum. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 Apr; 848(2):188-99. doi: 10.1016/j.jchromb.2006.10.036. [PMID: 17085081]
  • George Wittemyer, André Ganswindt, Keith Hodges. The impact of ecological variability on the reproductive endocrinology of wild female African elephants. Hormones and behavior. 2007 Mar; 51(3):346-54. doi: 10.1016/j.yhbeh.2006.12.013. [PMID: 17320085]
  • Iratxe Ciriza, Paloma Carrero, Cheryl A Frye, Luis M Garcia-Segura. Reduced metabolites mediate neuroprotective effects of progesterone in the adult rat hippocampus. The synthetic progestin medroxyprogesterone acetate (Provera) is not neuroprotective. Journal of neurobiology. 2006 Aug; 66(9):916-28. doi: 10.1002/neu.20293. [PMID: 16758493]
  • Sabina Luchetti, Flavia di Michele, Elena Romeo, Livia Brusa, Giorgio Bernardi, Brian J Cummings, Patrizia Longone. Comparative non-radioactive RT-PCR assay: an approach to study the neurosteroids biosynthetic pathway in humans. Journal of neuroscience methods. 2006 Jun; 153(2):290-8. doi: 10.1016/j.jneumeth.2005.11.005. [PMID: 16378642]
  • F Labombarda, A Pianos, P Liere, B Eychenne, S Gonzalez, A Cambourg, A F De Nicola, M Schumacher, R Guennoun. Injury elicited increase in spinal cord neurosteroid content analyzed by gas chromatography mass spectrometry. Endocrinology. 2006 Apr; 147(4):1847-59. doi: 10.1210/en.2005-0955. [PMID: 16396987]
  • C Schüle, E Romeo, D P Uzunov, D Eser, F di Michele, T C Baghai, A Pasini, M Schwarz, H Kempter, R Rupprecht. Influence of mirtazapine on plasma concentrations of neuroactive steroids in major depression and on 3alpha-hydroxysteroid dehydrogenase activity. Molecular psychiatry. 2006 Mar; 11(3):261-72. doi: 10.1038/sj.mp.4001782. [PMID: 16344854]
  • Marc Verleye, Yvette Akwa, Philippe Liere, Nathalie Ladurelle, Antoine Pianos, Bernard Eychenne, Michael Schumacher, Jean-Marie Gillardin. The anxiolytic etifoxine activates the peripheral benzodiazepine receptor and increases the neurosteroid levels in rat brain. Pharmacology, biochemistry, and behavior. 2005 Dec; 82(4):712-20. doi: 10.1016/j.pbb.2005.11.013. [PMID: 16388839]
  • K J Pawlak, G Zhang, J P Wiebe. Membrane 5alpha-pregnane-3,20-dione (5alphaP) receptors in MCF-7 and MCF-10A breast cancer cells are up-regulated by estradiol and 5alphaP and down-regulated by the progesterone metabolites, 3alpha-dihydroprogesterone and 20alpha-dihydroprogesterone, with associated changes in cell proliferation and detachment. The Journal of steroid biochemistry and molecular biology. 2005 Nov; 97(3):278-88. doi: 10.1016/j.jsbmb.2005.05.014. [PMID: 16154741]
  • Susan E Gilbert Evans, Lori E Ross, Edward M Sellers, Robert H Purdy, Myroslava K Romach. 3alpha-reduced neuroactive steroids and their precursors during pregnancy and the postpartum period. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology. 2005 Nov; 21(5):268-79. doi: 10.1080/09513590500361747. [PMID: 16373246]
  • Véronique Bellemare, Frédérick Faucher, Rock Breton, Van Luu-The. Characterization of 17alpha-hydroxysteroid dehydrogenase activity (17alpha-HSD) and its involvement in the biosynthesis of epitestosterone. BMC biochemistry. 2005 Jul; 6(?):12. doi: 10.1186/1471-2091-6-12. [PMID: 16018803]
  • Penelope M Sheehan, Gregory E Rice, Eric K Moses, Shaun P Brennecke. 5 Beta-dihydroprogesterone and steroid 5 beta-reductase decrease in association with human parturition at term. Molecular human reproduction. 2005 Jul; 11(7):495-501. doi: 10.1093/molehr/gah201. [PMID: 16123077]
  • Thomas C Baghai, Flavia di Michele, Cornelius Schüle, Daniela Eser, Peter Zwanzger, Augusto Pasini, Elena Romeo, Rainer Rupprecht. Plasma concentrations of neuroactive steroids before and after electroconvulsive therapy in major depression. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2005 Jun; 30(6):1181-6. doi: 10.1038/sj.npp.1300684. [PMID: 15702138]
  • J P Wiebe, M J Lewis, V Cialacu, K J Pawlak, G Zhang. The role of progesterone metabolites in breast cancer: potential for new diagnostics and therapeutics. The Journal of steroid biochemistry and molecular biology. 2005 Feb; 93(2-5):201-8. doi: 10.1016/j.jsbmb.2004.12.003. [PMID: 15860263]
  • Madeline E Rhodes, Cheryl A Frye. Progestins in the hippocampus of female rats have antiseizure effects in a pentylenetetrazole seizure model. Epilepsia. 2004 Dec; 45(12):1531-8. doi: 10.1111/j.0013-9580.2004.16504.x. [PMID: 15571511]
  • Phuong N Nguyen, Saraid S Billiards, David W Walker, Jonathan J Hirst. Changes in 5alpha-pregnane steroids and neurosteroidogenic enzyme expression in fetal sheep with umbilicoplacental embolization. Pediatric research. 2003 Dec; 54(6):840-7. doi: 10.1203/01.pdr.0000088066.47755.36. [PMID: 12930920]
  • F di Michele, P Longone, E Romeo, S Lucchetti, L Brusa, M Pierantozzi, A Bassi, G Bernardi, P Stanzione. Decreased plasma and cerebrospinal fluid content of neuroactive steroids in Parkinson's disease. Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology. 2003 Oct; 24(3):172-3. doi: 10.1007/s10072-003-0115-1. [PMID: 14598072]
  • Allon Nechmad, Rachel Maayan, Baruch Spivak, Edward Ramadan, Michael Poyurovsky, Abraham Weizman. Brain neurosteroid changes after paroxetine administration in mice. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology. 2003 Oct; 13(5):327-32. doi: 10.1016/s0924-977x(03)00015-4. [PMID: 12957330]
  • Rahul T Khisti, Margaret J VanDoren, Todd O'Buckley, A Leslie Morrow. Neuroactive steroid 3 alpha-hydroxy-5 alpha-pregnan-20-one modulates ethanol-induced loss of righting reflex in rats. Brain research. 2003 Aug; 980(2):255-65. doi: 10.1016/s0006-8993(03)02978-0. [PMID: 12867266]
  • J C Thiéry, P Robel, S Canepa, B Delaleu, V Gayrard, N Picard-Hagen, B Malpaux. Passage of progesterone into the brain changes with photoperiod in the ewe. The European journal of neuroscience. 2003 Aug; 18(4):895-901. doi: 10.1046/j.1460-9568.2003.02796.x. [PMID: 12925015]
  • Jean D Wilson, Michael W Leihy, Geoffrey Shaw, Marilyn B Renfree. Androgen physiology: unsolved problems at the millennium. Molecular and cellular endocrinology. 2002 Dec; 198(1-2):1-5. doi: 10.1016/s0303-7207(02)00362-3. [PMID: 12573808]
  • B E Pearson Murphy, S I Steinberg, F Y Hu, C M Allison. Neuroactive ring A-reduced metabolites of progesterone in human plasma during pregnancy: elevated levels of 5 alpha-dihydroprogesterone in depressed patients during the latter half of pregnancy. The Journal of clinical endocrinology and metabolism. 2001 Dec; 86(12):5981-7. doi: 10.1210/jcem.86.12.8122. [PMID: 11739473]
  • C A Frye, J M Vongher. Progesterone and 3alpha,5alpha-THP enhance sexual receptivity in mice. Behavioral neuroscience. 2001 Oct; 115(5):1118-28. doi: 10.1037/0735-7044.115.5.1118. [PMID: 11584925]
  • S Kirkman, E D Wallace, R J van Aarde, H C Potgieter. Steroidogenic correlates of pregnancy in the rock hyrax (Procavia capensis). Life sciences. 2001 Mar; 68(18):2061-72. doi: 10.1016/s0024-3205(01)00999-7. [PMID: 11324711]
  • P J Weiler, J P Wiebe. Plasma membrane receptors for the cancer-regulating progesterone metabolites, 5alpha-pregnane-3,20-dione and 3alpha-hydroxy-4-pregnen-20-one in MCF-7 breast cancer cells. Biochemical and biophysical research communications. 2000 Jun; 272(3):731-7. doi: 10.1006/bbrc.2000.2847. [PMID: 10860824]
  • M Fiess, M Heistermann, J K Hodges. Patterns of urinary and fecal steroid excretion during the ovarian cycle and pregnancy in the African elephant (Loxodonta africana). General and comparative endocrinology. 1999 Jul; 115(1):76-89. doi: 10.1006/gcen.1999.7287. [PMID: 10375466]
  • M D Greyling, M Ford, H C Potgieter, R J van Aarde. Influence of gestation on uterine endometrial steroid receptor concentrations in the African elephant, Loxodonta africana. Biology of reproduction. 1998 Jan; 58(1):60-4. doi: 10.1095/biolreprod58.1.60. [PMID: 9472923]
  • R A Dombroski, M L Casey, P C MacDonald. 5-Alpha-dihydroprogesterone formation in human placenta from 5alpha-pregnan-3beta/alpha-ol-20-ones and 5-pregnan-3beta-yl-20-one sulfate. The Journal of steroid biochemistry and molecular biology. 1997 Sep; 63(1-3):155-63. doi: 10.1016/s0960-0760(97)00058-7. [PMID: 9449217]
  • C Corpéchot, B E Collins, M P Carey, A Tsouros, P Robel, J P Fry. Brain neurosteroids during the mouse oestrous cycle. Brain research. 1997 Aug; 766(1-2):276-80. doi: 10.1016/s0006-8993(97)00749-x. [PMID: 9359616]
  • M Bixo, A Andersson, B Winblad, R H Purdy, T Bäckström. Progesterone, 5alpha-pregnane-3,20-dione and 3alpha-hydroxy-5alpha-pregnane-20-one in specific regions of the human female brain in different endocrine states. Brain research. 1997 Aug; 764(1-2):173-8. doi: 10.1016/s0006-8993(97)00455-1. [PMID: 9295207]
  • M Löfgren, T Bäckström. High progesterone is related to effective human labor. Study of serum progesterone and 5alpha-pregnane-3,20-dione in normal and abnormal deliveries. Acta obstetricia et gynecologica Scandinavica. 1997 May; 76(5):423-30. doi: 10.3109/00016349709047823. [PMID: 9197444]
  • J K Hodges, M Heistermann, A Beard, R J van Aarde. Concentrations of progesterone and the 5 alpha-reduced progestins, 5 alpha-pregnane-3,20-dione and 3 alpha-hydroxy-5 alpha-pregnan-20-one, in luteal tissue and circulating blood and their relationship to luteal function in the African elephant, Loxodonta africana. Biology of reproduction. 1997 Mar; 56(3):640-6. doi: 10.1095/biolreprod56.3.640. [PMID: 9047008]
  • H H Meyer, K Jewgenow, J K Hodges. Binding activity of 5alpha-reduced gestagens to the progestin receptor from African elephant (Loxodonta africana). General and comparative endocrinology. 1997 Feb; 105(2):164-7. doi: 10.1006/gcen.1996.6813. [PMID: 9038248]
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  • M Wang, L Seippel, R H Purdy, T Bãckström. Relationship between symptom severity and steroid variation in women with premenstrual syndrome: study on serum pregnenolone, pregnenolone sulfate, 5 alpha-pregnane-3,20-dione and 3 alpha-hydroxy-5 alpha-pregnan-20-one. The Journal of clinical endocrinology and metabolism. 1996 Mar; 81(3):1076-82. doi: 10.1210/jcem.81.3.8772579. [PMID: 8772579]
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  • R A Dombroski, M L Casey, P C MacDonald. The metabolic disposition of plasma 5 alpha-dihydroprogesterone (5 alpha-pregnane-3,20-dione) in women and men. The Journal of clinical endocrinology and metabolism. 1993 Oct; 77(4):944-8. doi: 10.1210/jcem.77.4.8408469. [PMID: 8408469]
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  • M Löfgren, J Holst, T Bäckström. Effects in vitro of progesterone and two 5 alpha-reduced progestins, 5 alpha-pregnane-3,20-dione and 5 alpha-pregnane-3 alpha-ol-20-one, on contracting human myometrium at term. Acta obstetricia et gynecologica Scandinavica. 1992 Jan; 71(1):28-33. doi: 10.3109/00016349209007943. [PMID: 1315093]
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  • M Bixo, T Bäckström. Regional distribution of progesterone and 5 alpha-pregnane-3,20-dione in rat brain during progesterone-induced 'anesthesia'. Psychoneuroendocrinology. 1990; 15(2):159-62. doi: 10.1016/0306-4530(90)90025-5. [PMID: 2359812]
  • M Löfgren, T Bäckström. Serum concentrations of progesterone and 5 alpha-pregnane-3,20-dione during labor and early post partum. Acta obstetricia et gynecologica Scandinavica. 1990; 69(2):123-6. doi: 10.3109/00016349009006156. [PMID: 2386015]
  • M Löfgren, T Bäckström, I Joelsson. Decrease in serum concentration of 5 alpha-pregnane-3,20-dione prior to spontaneous labor. Acta obstetricia et gynecologica Scandinavica. 1988; 67(5):467-70. doi: 10.3109/00016348809004262. [PMID: 3218466]
  • S Landgren, J Aasly, T Bäckström, B Dubrovsky, E Danielsson. The effect of progesterone and its metabolites on the interictal epileptiform discharge in the cat's cerebral cortex. Acta physiologica Scandinavica. 1987 Sep; 131(1):33-42. doi: 10.1111/j.1748-1716.1987.tb08202.x. [PMID: 3673611]
  • T Bäckström, A Andersson, D T Baird, G Selstam. The human corpus luteum secretes 5 alpha-pregnane-3,20-dione. Acta endocrinologica. 1986 Jan; 111(1):116-21. doi: 10.1530/acta.0.1110116. [PMID: 3946101]
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