7a-Hydroxydehydroepiandrosterone (BioDeep_00000012046)

 

Secondary id: BioDeep_00001869039

human metabolite Endogenous


代谢物信息卡片


(1S,2R,5S,9S,10R,11S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one

化学式: C19H28O3 (304.2038338)
中文名称: 7-羟基去氢表雄酮
谱图信息: 最多检出来源 Anoectochilus roxburghii(viridiplantae) 28.23%

分子结构信息

SMILES: CC12CCC3C(C(O)C=C4CC(O)CCC43C)C1CCC2=O
InChI: InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-15,17,20-21H,3-9H2,1-2H3/t12-,13-,14-,15+,17-,18-,19-/m0/s1

描述信息

7a-Hydroxydehydroepiandrosterone is a major metabolite of dehydroepiandrosterone (DHEA), which is is 7alpha-hydroxylated by the cytochrome P450 7B1 (EC 1.14.13.100, 25-hydroxycholesterol 7alpha-hydroxylase, CYP7B1) in the human brain and liver microsomes. Exposure to the proinflammatory cytokines TNFalpha, IL-1alpha, IL-1beta, and IL-17 increases CYP7B activity in synovial tissue. Increased CYP7B activity leads to higher levels of the DHEA metabolite 7alpha-OH-DHEA in synovial fluid, which may contribute to the maintenance of the chronic inflammation observed in rheumatoid arthritis patients. The glucocorticoid dhydrocorticosterone inhibits the conversion of DHEA to 7a-Hydroxydehydroepiandrosterone. The total levels of 7a-Hydroxydehydroepiandrosterone are increased in serum of patients with Alzheimers disease. (PMID: 17467270, 15751070, 12667489, 9520908) [HMDB]
7a-Hydroxydehydroepiandrosterone is a major metabolite of dehydroepiandrosterone (DHEA), which is is 7alpha-hydroxylated by the cytochrome P450 7B1 (EC 1.14.13.100, 25-hydroxycholesterol 7alpha-hydroxylase, CYP7B1) in the human brain and liver microsomes. Exposure to the proinflammatory cytokines TNFalpha, IL-1alpha, IL-1beta, and IL-17 increases CYP7B activity in synovial tissue. Increased CYP7B activity leads to higher levels of the DHEA metabolite 7alpha-OH-DHEA in synovial fluid, which may contribute to the maintenance of the chronic inflammation observed in rheumatoid arthritis patients. The glucocorticoid dhydrocorticosterone inhibits the conversion of DHEA to 7a-Hydroxydehydroepiandrosterone. The total levels of 7a-Hydroxydehydroepiandrosterone are increased in serum of patients with Alzheimers disease. (PMID: 17467270, 15751070, 12667489, 9520908).
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

同义名列表

34 个代谢物同义名

(1S,2R,5S,9S,10R,11S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one; 7-Hydroxydehydroepiandrosterone, (3beta,7beta)-isomer; (3beta,7alpha)-3,7-Dihydroxyandrost-5-en-17-one; 7-Hydroxydehydroepiandrosterone, (3beta)-isomer; 3beta,7alpha-Dihydroxy-5-androstene-17-one; 3beta,7alpha-Dihydroxyandrost-5-en-17-one; (3b,7a)-3,7-Dihydroxy-androst-5-en-17-one; (3b,7a)-3,7-Dihydroxyandrost-5-en-17-one; (3Β,7α)-3,7-dihydroxyandrost-5-en-17-one; 7-alpha-Hydroxydehydroepiandrosterone; 7 alpha-Hydroxydehydroepiandrosterone; (-)-7a-Hydroxydehydroepiandrosterone; 7alpha-Hydroxydehydroepiandrosterone; 3Β,7α-dihydroxy-5-androstene-17-one; 3b,7a-Dihydroxy-androst-5-en-17-one; 3b,7a-Dihydroxy-5-androstene-17-one; 7beta-Hydroxydehydroepiandrosterone; 3Β,7α-dihydroxyandrost-5-en-17-one; 3b,7a-Dihydroxy-5-androsten-17-one; 3b,7a-Dihydroxyandrost-5-en-17-one; 7a-Hydroxydehydroisoandrosterone; 7a-Hydroxydehydroepiandrosterone; 7-Hydroxydehydroepiandrosterone; 7alpha-Hydroxy-dhea; 7|A-Hydroxy DHEA; 7a-Hydroxy-dhea; 7Α-hydroxy-dhea; 7-alpha-OH-DHEA; 7alpha-OH-DHEA; 7beta-OH-DHEA; 7-a-OH-DHEA; 7Α-OH-dhea; 7β-oh-dhea; 7a-OH-DHEA



数据库引用编号

14 个数据库交叉引用编号

分类词条

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代谢反应

0 个相关的代谢反应过程信息。

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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。

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文献列表

  • Stefano DE Luca, Eleonora Amante, Cristian Fiori, Giorgio Alleva, Eugenio Alladio, Federico Marini, Diletta Garrou, Matteo Manfredi, Daniele Amparore, Enrico Checcucci, Serena Pruner, Alberto Salomone, Roberto M Scarpa, Marco Vincenti, Francesco Porpiglia. Prospective evaluation of urinary steroids and prostate carcinoma-induced deviation: preliminary results. Minerva urology and nephrology. 2021 02; 73(1):98-106. doi: 10.23736/s2724-6051.19.03529-x. [PMID: 31833333]
  • K Adamcová, L Kolátorová, T Chlupáčová, M Šimková, H Jandíková, A Pařízek, L Stárka, M Dušková. Changes to fetal steroidogenesis caused by maternal smoking. Physiological research. 2017 09; 66(Suppl 3):S375-S386. doi: 10.33549/physiolres.933728. [PMID: 28948822]
  • L Máčová, M Bičíková, H Zamrazilová, M Hill, H Kazihnitková, B Sedláčková, L Stárka. Reduced levels of circulating 7alpha-hydroxy-dehydroepiandrosterone in treated adolescent obese patients. Physiological research. 2014; 63(1):95-101. doi: 10.33549/physiolres.932540. [PMID: 24182335]
  • Marie Bicikova, Richard Hampl, Martin Hill, Daniela Ripova, Pavel Mohr, Zdenek Putz. Neuro- and immunomodulatory steroids and other biochemical markers in drug-naive schizophrenia patients and the effect of treatment with atypical antipsychotics. Neuro endocrinology letters. 2011; 32(2):141-7. doi: . [PMID: 21552193]
  • Hanna Pettersson, Lisa Holmberg, Magnus Axelson, Maria Norlin. CYP7B1-mediated metabolism of dehydroepiandrosterone and 5alpha-androstane-3beta,17beta-diol--potential role(s) for estrogen signaling. The FEBS journal. 2008 Apr; 275(8):1778-89. doi: 10.1111/j.1742-4658.2008.06336.x. [PMID: 18331353]
  • John Dulos, Monique A J van der Vleuten, Annemieke Kavelaars, Cobi J Heijnen, Annemieke M Boots. CYP7B expression and activity in fibroblast-like synoviocytes from patients with rheumatoid arthritis: regulation by proinflammatory cytokines. Arthritis and rheumatism. 2005 Mar; 52(3):770-8. doi: 10.1002/art.20950. [PMID: 15751070]
  • Luboslav Stárka, Richard Hampl, Miroslav Hanus, Michaela Matousková, Martin Hill. Plasma levels of 7-hydroxymetabolites of dehydroepiandrosterone in healthy Central European aging men. Clinical chemistry and laboratory medicine. 2005; 43(11):1218-22. doi: 10.1515/cclm.2005.211. [PMID: 16232089]
  • Marie Bicíková, Daniela Rípová, Martin Hill, Roman Jirák, Helena Havlíková, Jaroslava Tallová, Richard Hampl. Plasma levels of 7-hydroxylated dehydroepiandrosterone (DHEA) metabolites and selected amino-thiols as discriminatory tools of Alzheimer's disease and vascular dementia. Clinical chemistry and laboratory medicine. 2004 May; 42(5):518-24. doi: 10.1515/cclm.2004.088. [PMID: 15202788]
  • Marie-Agnès Pelissier, Catherine Trap, Marie-Irène Malewiak, Robert Morfin. Antioxidant effects of dehydroepiandrosterone and 7alpha-hydroxy-dehydroepiandrosterone in the rat colon, intestine and liver. Steroids. 2004 Feb; 69(2):137-44. doi: 10.1016/j.steroids.2003.12.006. [PMID: 15013692]
  • Ivan Sterzl, Richard Hampl, Martin Hill, Pavlína Hrdá, Petr Matucha. Immunomodulatory cytokines in human seminal plasma correlate with immunomodulatory steroids. Steroids. 2003 Oct; 68(9):725-31. doi: 10.1016/s0039-128x(03)00114-4. [PMID: 14625004]
  • Boaz Robinzon, Kristy K Michael, Sharon L Ripp, Stephen J Winters, Russell A Prough. Glucocorticoids inhibit interconversion of 7-hydroxy and 7-oxo metabolites of dehydroepiandrosterone: a role for 11beta-hydroxysteroid dehydrogenases?. Archives of biochemistry and biophysics. 2003 Apr; 412(2):251-8. doi: 10.1016/s0003-9861(03)00056-0. [PMID: 12667489]
  • Richard Hampl, Michal Pohanka, Martin Hill, Luboslav Stárka. The content of four immunomodulatory steroids and major androgens in human semen. The Journal of steroid biochemistry and molecular biology. 2003 Feb; 84(2-3):307-16. doi: 10.1016/s0960-0760(03)00044-x. [PMID: 12711017]
  • Michal Pohanka, Richard Hampl, Ivan Sterzl, Luboslav Stárka. Steroid hormones in human semen with particular respect to dehydroepiandrosterone and its immunomodulatory metabolites. Endocrine regulations. 2002 Jun; 36(2):79-86. doi: . [PMID: 12207557]
  • M Hill, O Lapcík, H Havlíková, R Morfin, R Hampl. 7-Hydroxydehydroepiandrosterone epimers in human serum and saliva. Comparison of gas chromatography-mass spectrometry and radioimmunoassay. Journal of chromatography. A. 2001 Nov; 935(1-2):297-307. doi: 10.1016/s0021-9673(01)01106-2. [PMID: 11762781]
  • O Lapcík, R Hampl, M Hill, L Stárka. Immunoassay of 7-hydroxysteroids: 2. Radioimmunoassay of 7alpha-hydroxy-dehydroepiandrosterone. The Journal of steroid biochemistry and molecular biology. 1999 Dec; 71(5-6):231-7. doi: 10.1016/s0960-0760(99)00145-4. [PMID: 10704912]
  • S Attal-Khémis, V Dalmeyda, J L Michot, M Roudier, R Morfin. Increased total 7 alpha-hydroxy-dehydroepiandrosterone in serum of patients with Alzheimer's disease. The journals of gerontology. Series A, Biological sciences and medical sciences. 1998 Mar; 53(2):B125-32. doi: 10.1093/gerona/53a.2.b125. [PMID: 9520908]
  • S Attal-Khémis, V Dalmeyda, R Morfin. Change of 7alpha-hydroxy-dehydroepiandrosterone levels in serum of mice treated by cytochrome P450-modifying agents. Life sciences. 1998; 63(17):1543-53. doi: 10.1016/s0024-3205(98)00421-4. [PMID: 9808065]
  • B H Mason, I M Holdaway, S J Skinner, R G Kay. The relationship of urinary and plasma androgens to steroid receptors and menopausal status in breast cancer patients and their influence on survival. Breast cancer research and treatment. 1994; 32(2):203-12. doi: 10.1007/bf00665771. [PMID: 7865850]
  • S J Skinner, I M Holdaway, B H Mason, R A Couch, R G Kay. Estrogen receptor status, adrenal androgens and 7 alpha-hydroxydehydroepiandrosterone in breast cancer patients. European journal of cancer & clinical oncology. 1984 Oct; 20(10):1227-31. doi: 10.1016/0277-5379(84)90251-7. [PMID: 6237915]
  • S J Skinner, R A Couch, S Thambyah, R J Dobbs, S M Jordan, B Mason, R G Kay. The relationship of plasma 7 alpha-hydroxy dehydroepiandrosterone to disease stage and adrenal androgens in breast cancer patients. European journal of cancer. 1980 Feb; 16(2):223-8. doi: 10.1016/0014-2964(80)90154-1. [PMID: 6445272]
  • L STARKA, J SULCOVA, K SILINK. [Urinary excretion of 7-hydroxydehydroepiandrosterone sulfate]. Clinica chimica acta; international journal of clinical chemistry. 1962 May; 7(?):309-16. doi: 10.1016/0009-8981(62)90029-3. [PMID: 13916329]