Adrenosterone (BioDeep_00000003080)

 

Secondary id: BioDeep_00000405684

human metabolite Endogenous


代谢物信息卡片


(1S,2R,10S,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14,17-trione

化学式: C19H24O3 (300.1725354)
中文名称: 肾上腺甾酮
谱图信息: 最多检出来源 Viridiplantae(plant) 0.17%

Reviewed

Last reviewed on 2024-08-14.

Cite this Page

Adrenosterone. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/adrenosterone (retrieved 2024-11-08) (BioDeep RN: BioDeep_00000003080). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC12CC(=O)C3C(CCC4=CC(=O)CCC43C)C1CCC2=O
InChI: InChI=1S/C19H24O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-14,17H,3-8,10H2,1-2H3

描述信息

Adrenosterone is a steroid hormone with weak androgenic effect. It was first isolated in 1936 from the adrenal cortex by Tadeus Reichstein at the Pharmaceutical Institute in the University of Basel. Originally, adrenosterone was called Reichsteins substance G.(Wikipedia). Andrenosterone is created from androst-4-ene-3,17-dione by the work of two enzymes, CYP11B (E1.14.15.4) and 11beta-hydroxysteroid dehydrogenase [EC:1.1.1.146].
Adrenosterone is a steroid hormone with weak androgenic effect. It was first isolated in 1936 from the adrenal cortex by Tadeus Reichstein at the Pharmaceutical Institute in the University of Basel. Originally, adrenosterone was called Reichsteins substance G.
Adrenosterone ((+)-Adrenosterone) is a competitive hydroxysteroid (11-beta) dehydrogenase 1 (HSD11β1) inhibitor. Adrenosterone is a steroid hormone with weak androgenic effect. Adrenosterone is a dietary supplement that can decrease fat and increase muscle mass. Adrenosterone acts as a suppressor of metastatic progression of human cancer cells[1][2][3].

同义名列表

17 个代谢物同义名

(1S,2R,10S,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14,17-trione; 2,15-dimethyltetracyclo[8.7.0.0<2,7>.0<11,15>]heptadec-6-ene-5,14,17-trione; 11-Oxoandrost-4-ene-3,17-dione; Androst-4-ene-3,11,17-trione; 4-Androstene-3,11,17-trione; 4-Androsten-3,11,17-trione; Adrenosterone, 3H-labeled; 11-Oxy-4-androstenedione; Reichsteins substance G; 11-keto-androstenedione; 11-Ketoandrostenedione; 11-Oxoandrostenedione; Andrenosterone; Adrenosterone; NSC 12166; 11-oxo; (+)-Adrenosterone



数据库引用编号

17 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

6 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(6)

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

  • Marina A Skiba, Robin J Bell, Rakibul M Islam, David J Handelsman, Reena Desai, Susan R Davis. Androgens During the Reproductive Years: What Is Normal for Women?. The Journal of clinical endocrinology and metabolism. 2019 11; 104(11):5382-5392. doi: 10.1210/jc.2019-01357. [PMID: 31390028]
  • Michael W O'Reilly, Punith Kempegowda, Carl Jenkinson, Angela E Taylor, Jonathan L Quanson, Karl-Heinz Storbeck, Wiebke Arlt. 11-Oxygenated C19 Steroids Are the Predominant Androgens in Polycystic Ovary Syndrome. The Journal of clinical endocrinology and metabolism. 2017 03; 102(3):840-848. doi: 10.1210/jc.2016-3285. [PMID: 27901631]
  • Lance Brooker, Adam Cawley, Ray Kazlauskas, Catrin Goebel, Adrian George. Carbon isotope ratio analysis of endogenous glucocorticoid urinary metabolites after cortisone acetate and adrenosterone administration for doping control. Drug testing and analysis. 2012 Dec; 4(12):951-61. doi: 10.1002/dta.1403. [PMID: 22987608]
  • Ying-Yong Zhao, Jing Liu, Xian-Long Cheng, Xu Bai, Rui-Chao Lin. Urinary metabonomics study on biochemical changes in an experimental model of chronic renal failure by adenine based on UPLC Q-TOF/MS. Clinica chimica acta; international journal of clinical chemistry. 2012 Mar; 413(5-6):642-9. doi: 10.1016/j.cca.2011.12.014. [PMID: 22227165]
  • Yasuto Kido, Pär Matsson, Kathleen M Giacomini. Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. Journal of medicinal chemistry. 2011 Jul; 54(13):4548-58. doi: 10.1021/jm2001629. [PMID: 21599003]
  • Peter T Vedell, Karen L Svenson, Gary A Churchill. Stochastic variation of transcript abundance in C57BL/6J mice. BMC genomics. 2011 Mar; 12(?):167. doi: 10.1186/1471-2164-12-167. [PMID: 21450099]
  • Lance Brooker, Maria Kristina Parr, Adam Cawley, Ulrich Flenker, Christopher Howe, Rymantas Kazlauskas, Wilhelm Schänzer, Adrian George. Development of criteria for the detection of adrenosterone administration by gas chromatography-mass spectrometry and gas chromatography-combustion-isotope ratio mass spectrometry for doping control. Drug testing and analysis. 2009 Nov; 1(11-12):587-95. doi: 10.1002/dta.108. [PMID: 20355175]
  • Ignasi Forné, María J Agulleiro, Esther Asensio, Joaquín Abián, Joan Cerdà. 2-D DIGE analysis of Senegalese sole (Solea senegalensis) testis proteome in wild-caught and hormone-treated F1 fish. Proteomics. 2009 Apr; 9(8):2171-81. doi: 10.1002/pmic.200800696. [PMID: 19322785]
  • Anna Hellqvist, Monika Schmitz, Bertil Borg. Effects of castration and androgen-treatment on the expression of FSH-beta and LH-beta in the three-spine stickleback, gasterosteus aculeatus--feedback differences mediating the photoperiodic maturation response?. General and comparative endocrinology. 2008 Sep; 158(2):178-82. doi: 10.1016/j.ygcen.2008.07.004. [PMID: 18664367]
  • Maria J Agulleiro, Alexander P Scott, Neil Duncan, Constantinos C Mylonas, Joan Cerdà. Treatment of GnRHa-implanted Senegalese sole (Solea senegalensis) with 11-ketoandrostenedione stimulates spermatogenesis and increases sperm motility. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology. 2007 Aug; 147(4):885-92. doi: 10.1016/j.cbpa.2007.02.008. [PMID: 17360211]
  • H J Th Goos, D Consten. Stress adaptation, cortisol and pubertal development in the male common carp, Cyprinus carpio. Molecular and cellular endocrinology. 2002 Nov; 197(1-2):105-16. doi: 10.1016/s0303-7207(02)00284-8. [PMID: 12431803]
  • C A Manire, L E Rasmussen, T S Gross. Serum steroid hormones including 11-ketotestosterone, 11-ketoandrostenedione, and dihydroprogesterone in juvenile and adult bonnethead sharks, Sphyrna tiburo. The Journal of experimental zoology. 1999 Oct; 284(5):595-603. doi: 10.1002/(sici)1097-010x(19991001)284:5<595::aid-jez15>3.0.co;2-6. [PMID: 10469997]
  • B Borg, E Antonopoulou, I Mayer, E Andersson, I Berglund, P Swanson. Effects of gonadectomy and androgen treatments on pituitary and plasma levels of gonadotropins in mature male Atlantic salmon, Salmo salar, parr--positive feedback control of both gonadotropins. Biology of reproduction. 1998 Mar; 58(3):814-20. doi: 10.1095/biolreprod58.3.814. [PMID: 9510971]
  • I Mayer, M Rand-Weaver, B Borg. Effects of gonadectomy and steroids on plasma and pituitary levels of somatolactin in Atlantic salmon, Salmo salar. General and comparative endocrinology. 1998 Feb; 109(2):223-31. doi: 10.1006/gcen.1997.7015. [PMID: 9473366]
  • I Mayer, N R Liley, B Borg. Stimulation of spawning behavior in castrated rainbow trout (Oncorhynchus mykiss) by 17 alpha,20 beta-dihydroxy-4-pregnen-3-one, but not by 11-ketoandrostenedione. Hormones and behavior. 1994 Jun; 28(2):181-90. doi: 10.1006/hbeh.1994.1015. [PMID: 7927284]
  • R Schulz, V Blüm. Extragonadal 17 beta-hydroxysteroid dehydrogenase activity in rainbow trout. General and comparative endocrinology. 1991 May; 82(2):197-205. doi: 10.1016/0016-6480(91)90184-8. [PMID: 1649780]
  • I Mayer, B Borg, R Schulz. Seasonal changes in and effect of castration/androgen replacement on the plasma levels of five androgens in the male three-spined stickleback, Gasterosteus aculeatus L. General and comparative endocrinology. 1990 Jul; 79(1):23-30. doi: 10.1016/0016-6480(90)90084-y. [PMID: 2354778]
  • I Mayer, B Borg, R Schulz. Conversion of 11-ketoandrostenedione to 11-ketotestosterone by blood cells of six fish species. General and comparative endocrinology. 1990 Jan; 77(1):70-4. doi: 10.1016/0016-6480(90)90207-3. [PMID: 2295425]
  • R Schulz. In vitro metabolism of steroid hormones in the liver and in blood cells of male rainbow trout (Salmo gairdneri Richardson). General and comparative endocrinology. 1986 Nov; 64(2):312-9. doi: 10.1016/0016-6480(86)90019-5. [PMID: 3557096]
  • R Schlaghecke, H K Kley, H L Krüskemper. The measurement of 4-androstene-3, 11, 17-trione (11-oxo-androstenedione) by radioimmunoassay in human plasma. Steroids. 1984 Jul; 44(1):23-33. doi: 10.1016/s0039-128x(84)80013-6. [PMID: 6100340]
  • D E Kime, M Hyder. The effect of temperature and gonadotropin on testicular steroidogenesis in Sarotherodon (Tilapia) mossambicus in vitro. General and comparative endocrinology. 1983 Apr; 50(1):105-15. doi: 10.1016/0016-6480(83)90247-2. [PMID: 6852519]
  • K SCHUBERT, K WEHRBERGER, G FRANKENBERG. [ISOLATION OF ADRENOSTERONE FROM THE URINE IN MEN AND WOMEN]. Acta biologica et medica Germanica. 1964; 13(?):809-11. doi: NULL. [PMID: 14308712]