5beta-Pregnane-3,20-dione (BioDeep_00000893780)

   

human metabolite blood metabolite


代谢物信息卡片


14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one

化学式: C21H32O2 (316.2402)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 1.82%

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

描述信息

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

同义名列表

3 个代谢物同义名

14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one; 5beta-pregnane-3,20-dione; Pregnane 3,20 dione



数据库引用编号

5 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。

亚细胞结构定位 关联基因列表


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]
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  • 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]
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  • 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]
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  • 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]
  • 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]
  • 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]
  • 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]
  • M Cabeza, R Miranda. Increased synthesis of cholesterol stearate in flanking organ from gonadectomized female hamsters treated with progesterone and 5 alpha-dihydroprogesterone. Proceedings of the Western Pharmacology Society. 1997; 40(?):87-9. doi: ". [PMID: 9436221]
  • S Chantilis, R Dombroski, C H Shackleton, M L Casey, P C MacDonald. Metabolism of 5 alpha-dihydroprogesterone in women and men: 3 beta- and 3 alpha-,6 alpha-dihydroxy-5 alpha-pregnan-20-ones are major urinary metabolites. The Journal of clinical endocrinology and metabolism. 1996 Oct; 81(10):3644-9. doi: 10.1210/jcem.81.10.8855816. [PMID: 8855816]
  • W E Schutzer, J L Kerby, D W Holtan. Differential effect of trilostane on the progestin milieu in the pregnant mare. Journal of reproduction and fertility. 1996 Jul; 107(2):241-8. doi: 10.1530/jrf.0.1070241. [PMID: 8882291]
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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]
  • L Milewich, B B Mendonca, I Arnhold, A M Wallace, M D Donaldson, J D Wilson, D W Russell. Women with steroid 5 alpha-reductase 2 deficiency have normal concentrations of plasma 5 alpha-dihydroprogesterone during the luteal phase. The Journal of clinical endocrinology and metabolism. 1995 Nov; 80(11):3136-9. doi: 10.1210/jcem.80.11.7593415. [PMID: 7593415]
  • D L Cheney, D Uzunov, E Costa, A Guidotti. Gas chromatographic-mass fragmentographic quantitation of 3 alpha-hydroxy-5 alpha-pregnan-20-one (allopregnanolone) and its precursors in blood and brain of adrenalectomized and castrated rats. The Journal of neuroscience : the official journal of the Society for Neuroscience. 1995 Jun; 15(6):4641-50. doi: . [PMID: 7790929]
  • 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]
  • M Hamon, S W Clarke, E Houghton, A L Fowden, M Silver, P D Rossdale, J C Ousey, R B Heap. Production of 5 alpha-dihydroprogesterone during late pregnancy in the mare. Journal of reproduction and fertility. Supplement. 1991; 44(?):529-35. doi: NULL. [PMID: 1795296]
  • S O Mack, M C Lorence, S Andersson, J I Mason. Expression of cytochrome P-450(17) alpha, 3 beta-hydroxysteroid dehydrogenase/delta 5----4-isomerase, and steroid 5 alpha-reductase in rat H540 Leydig tumor cells. Molecular and cellular endocrinology. 1990 Dec; 74(3):R11-7. doi: 10.1016/0303-7207(90)90231-v. [PMID: 2095353]
  • 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 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, 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]
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