5a-androstane (BioDeep_00000004713)

 

Secondary id: BioDeep_00000637502, BioDeep_00000862599


代谢物信息卡片


5alpha-androstane

化学式: C19H32 (260.2503872)
中文名称: 5-ALPHA-雄烷
谱图信息: 最多检出来源 Viridiplantae(plant) 91.67%

分子结构信息

SMILES: CC12CCCC1C1CCC3CCCCC3(C)C1CC2
InChI: InChI=1S/C19H32/c1-18-11-5-7-16(18)15-9-8-14-6-3-4-12-19(14,2)17(15)10-13-18/h14-17H,3-13H2,1-2H3/t14-,15+,16+,17+,18+,19+/m1/s1

描述信息

The 5alpha-stereoisomer of androstane.

同义名列表

3 个代谢物同义名

5alpha-androstane; 5a-androstane; 5-|A-ANDROSTANE



数据库引用编号

12 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)

0 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

  • Shahad W Kattan, Mohamed S Nafie, Gamal A Elmgeed, Walla Alelwani, Muhammad Badar, Mohamed A Tantawy. Molecular docking, anti-proliferative activity and induction of apoptosis in human liver cancer cells treated with androstane derivatives: Implication of PI3K/AKT/mTOR pathway. The Journal of steroid biochemistry and molecular biology. 2020 04; 198(?):105604. doi: 10.1016/j.jsbmb.2020.105604. [PMID: 31982513]
  • Neus Fabregat-Cabello, Stéphanie D Peeters, Tugba Yilmaz, Étienne Cavalier, Caroline M Le Goff. Establishment of reference intervals for serum concentrations of androstanediol glucuronide by a newly developed LC-MS/MS method. Steroids. 2019 03; 143(?):62-66. doi: 10.1016/j.steroids.2018.12.008. [PMID: 30625341]
  • Jingzhu Wang, Yi He, Xin Liu, Zhiyong Yang, Wenning Yang. Steroid profile and IRMS analysis of musk administration for doping control. Drug testing and analysis. 2017 Nov; 9(11-12):1779-1787. doi: 10.1002/dta.2293. [PMID: 28842970]
  • Hsin-Chou Yang, Shih-Kai Chu, Chieh-Liang Huang, Hsiang-Wei Kuo, Sheng-Chang Wang, Sheng-Wen Liu, Ing-Kang Ho, Yu-Li Liu. Genome-Wide Pharmacogenomic Study on Methadone Maintenance Treatment Identifies SNP rs17180299 and Multiple Haplotypes on CYP2B6, SPON1, and GSG1L Associated with Plasma Concentrations of Methadone R- and S-enantiomers in Heroin-Dependent Patients. PLoS genetics. 2016 Mar; 12(3):e1005910. doi: 10.1371/journal.pgen.1005910. [PMID: 27010727]
  • Wei Liu, Lan Zhang, Liangbiao Fan, Zian Lin, Yimin Cai, Zhenyi Wei, Guonan Chen. An improved hollow fiber solvent-stir bar microextraction for the preconcentration of anabolic steroids in biological matrix with determination by gas chromatography-mass spectrometry. Journal of chromatography. A. 2012 Apr; 1233(?):1-7. doi: 10.1016/j.chroma.2012.01.064. [PMID: 22386059]
  • Tamra E Meyer, Lisa W Chu, Qizhai Li, Kai Yu, Philip S Rosenberg, Idan Menashe, Anand P Chokkalingam, Sabah M Quraishi, Wen-Yi Huang, Jocelyn M Weiss, Rudolf Kaaks, Richard B Hayes, Stephen J Chanock, Ann W Hsing. The association between inflammation-related genes and serum androgen levels in men: the prostate, lung, colorectal, and ovarian study. The Prostate. 2012 Jan; 72(1):65-71. doi: 10.1002/pros.21407. [PMID: 21520164]
  • Magdalena M Przybycien-Szymanska, Roberta A Gillespie, Toni R Pak. 17β-Estradiol is required for the sexually dimorphic effects of repeated binge-pattern alcohol exposure on the HPA axis during adolescence. PloS one. 2012; 7(2):e32263. doi: 10.1371/journal.pone.0032263. [PMID: 22384198]
  • Neelima Dhingra, T R Bhardwaj, Neeraj Mehta, Tapas Mukhopadhyay, Ashok Kumar, Manoj Kumar. Synthesis, antiproliferative activity, acute toxicity and assessment of the antiandrogenic activities of new androstane derivatives. Archives of pharmacal research. 2011 Jul; 34(7):1055-63. doi: 10.1007/s12272-011-0702-2. [PMID: 21811911]
  • Cheryl A Frye, Kassandra L Edinger, Edwin D Lephart, Alicia A Walf. 3alpha-androstanediol, but not testosterone, attenuates age-related decrements in cognitive, anxiety, and depressive behavior of male rats. Frontiers in aging neuroscience. 2010; 2(?):15. doi: 10.3389/fnagi.2010.00015. [PMID: 20552051]
  • Rodrigo Aguilera, Thomas E Chapman, Henrique Pereira, Giselle C Oliveira, Renata P Illanes, Telma F Fernandes, Débora A Azevedo, Francisco Aquino Neto. Drug testing data from the 2007 Pan American Games: delta13C values of urinary androsterone, etiocholanolone and androstanediols determined by GC/C/IRMS. The Journal of steroid biochemistry and molecular biology. 2009 Jul; 115(3-5):107-14. doi: 10.1016/j.jsbmb.2009.03.012. [PMID: 19428237]
  • Sigrun B Kjøtrød, Arne Sunde, Vidar von Düring, Sven M Carlsen. Possible metformin effect on adrenal androgens during pretreatment and IVF cycle in women with polycystic ovary syndrome. Fertility and sterility. 2009 Feb; 91(2):500-8. doi: 10.1016/j.fertnstert.2007.11.069. [PMID: 18304542]
  • Alan R Kristal, Jeannette M Schenk, YoonJu Song, Kathryn B Arnold, Marian L Neuhouser, Phyllis J Goodman, Daniel W Lin, Frank Z Stanczyk, Ian M Thompson. Serum steroid and sex hormone-binding globulin concentrations and the risk of incident benign prostatic hyperplasia: results from the prostate cancer prevention trial. American journal of epidemiology. 2008 Dec; 168(12):1416-24. doi: 10.1093/aje/kwn272. [PMID: 18945688]
  • Lisa W Chu, Yong Zhu, Kai Yu, Tongzhang Zheng, Anand P Chokkalingam, Frank Z Stanczyk, Yu-Tang Gao, Ann W Hsing. Correlation between circadian gene variants and serum levels of sex steroids and insulin-like growth factor-I. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2008 Nov; 17(11):3268-73. doi: 10.1158/1055-9965.epi-08-0073. [PMID: 18990770]
  • Fru Angwafor, Mark L Anderson. An open label, dose response study to determine the effect of a dietary supplement on dihydrotestosterone, testosterone and estradiol levels in healthy males. Journal of the International Society of Sports Nutrition. 2008 Aug; 5(?):12. doi: 10.1186/1550-2783-5-12. [PMID: 18700016]
  • Cheryl A Frye, Kassandra Edinger, Kanako Sumida. Androgen administration to aged male mice increases anti-anxiety behavior and enhances cognitive performance. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2008 Apr; 33(5):1049-61. doi: 10.1038/sj.npp.1301498. [PMID: 17625503]
  • I Roglio, R Bianchi, S Giatti, G Cavaletti, D Caruso, S Scurati, D Crippa, L M Garcia-Segura, F Camozzi, G Lauria, R C Melcangi. Testosterone derivatives are neuroprotective agents in experimental diabetic neuropathy. Cellular and molecular life sciences : CMLS. 2007 May; 64(9):1158-68. doi: 10.1007/s00018-007-7002-5. [PMID: 17417742]
  • M Julie Thornton, Louisa D Nelson, Anthony H Taylor, M Pattie Birch, Ian Laing, Andrew G Messenger. The modulation of aromatase and estrogen receptor alpha in cultured human dermal papilla cells by dexamethasone: a novel mechanism for selective action of estrogen via estrogen receptor beta?. The Journal of investigative dermatology. 2006 Sep; 126(9):2010-8. doi: 10.1038/sj.jid.5700344. [PMID: 16691199]
  • Emma Maldonado, Vita E Alvarado, Fernando R Torres, Mahinda Martínez, Ana L Pérez-Castorena. Androstane and withanolides from Physalis cinerascens. Planta medica. 2005 Jun; 71(6):548-53. doi: 10.1055/s-2005-864157. [PMID: 15971127]
  • N Charlotte Onland-Moret, Carla H van Gils, Mark Roest, Diederick E Grobbee, Petra H M Peeters. Cyp17, urinary sex steroid levels and breast cancer risk in postmenopausal women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2005 Apr; 14(4):815-20. doi: 10.1158/1055-9965.epi-04-0197. [PMID: 15824149]
  • Trent D Lund, Daniel J Munson, Megan E Haldy, Robert J Handa. Dihydrotestosterone may inhibit hypothalamo-pituitary-adrenal activity by acting through estrogen receptor in the male mouse. Neuroscience letters. 2004 Jul; 365(1):43-7. doi: 10.1016/j.neulet.2004.04.035. [PMID: 15234470]
  • Alexa Greube, Karin Müller, Edda Töpfer-Petersen, Andreas Herrmann, Peter Müller. Interaction of fibronectin type II proteins with membranes: the stallion seminal plasma protein SP-1/2. Biochemistry. 2004 Jan; 43(2):464-72. doi: 10.1021/bi035647l. [PMID: 14717601]
  • N C Onland-Moret, R Kaaks, P A H van Noord, S Rinaldi, T Key, D E Grobbee, P H M Peeters. Urinary endogenous sex hormone levels and the risk of postmenopausal breast cancer. British journal of cancer. 2003 May; 88(9):1394-9. doi: 10.1038/sj.bjc.6600890. [PMID: 12778067]
  • S Rinaldi, C N Moret, R Kaaks, C Biessy, M S Kurzer, H Déchaud, P H M Peeters, P A H van Noord. Reproducibility over time of measurements of androgens, estrogens and hydroxy estrogens in urine samples from post-menopausal women. European journal of epidemiology. 2003; 18(5):417-24. doi: 10.1023/a:1024209122412. [PMID: 12889688]
  • 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]
  • Peter Müller, Andreas Herrmann. Rapid transbilayer movement of spin-labeled steroids in human erythrocytes and in liposomes. Biophysical journal. 2002 Mar; 82(3):1418-28. doi: 10.1016/s0006-3495(02)75496-9. [PMID: 11867457]
  • Nathan J Cherrington, Dylan P Hartley, Ning Li, David R Johnson, Curtis D Klaassen. Organ distribution of multidrug resistance proteins 1, 2, and 3 (Mrp1, 2, and 3) mRNA and hepatic induction of Mrp3 by constitutive androstane receptor activators in rats. The Journal of pharmacology and experimental therapeutics. 2002 Jan; 300(1):97-104. doi: 10.1124/jpet.300.1.97. [PMID: 11752103]
  • F Abe, T Yamauchi. An androstane bioside and 3'-thiazolidinone derivatives of doubly-linked cardenolide glycosides from the roots of Asclepias tuberosa. Chemical & pharmaceutical bulletin. 2000 Jul; 48(7):991-3. doi: 10.1248/cpb.48.991. [PMID: 10923828]
  • ". Progestins: present and future. The Journal of steroid biochemistry and molecular biology. 1996 Dec; 59(5-6):357-63. doi: 10.1016/s0960-0760(96)00183-5. [PMID: 9010340]
  • W K Subczynski, W E Antholine, J S Hyde, A Kusumi. Microimmiscibility and three-dimensional dynamic structures of phosphatidylcholine-cholesterol membranes: translational diffusion of a copper complex in the membrane. Biochemistry. 1990 Aug; 29(34):7936-45. doi: 10.1021/bi00486a023. [PMID: 2261449]
  • E E BAULIEU, P MAUVAIS-JARVIS. STUDIES ON TESTOSTERONE METABOLISM. I. CONVERSION OF TESTOSTERONE-17-ALPHA-3H TO 5-ALPHA- AND 5-BETA-ANDROSTANE-3-ALPHA, 17-BETA-DEOL-17-ALPHA-3H: A NEW '17-BETA-HYDROXYL PATHWAY'. The Journal of biological chemistry. 1964 May; 239(?):1569-77. doi: NULL. [PMID: 14189896]
  • E E BAULIEU. [METABOLISM AND CONJUGATION OF 3 XI-HYDROXY-5 XI-H-ANDROSTANE-17-ONE]. Annales d'endocrinologie. 1963 Sep; 24(?):801-13. doi: NULL. [PMID: 14092340]
  • P D KLIMSTRA, R E COUNSELL. HYPOCHOLESTEROLEMIC AGENTS. II. 2BETA-HALO-5ALPHA-ANDROSTANE DERIVATIVES. Journal of medicinal and pharmaceutical chemistry. 1962 Nov; 5(?):1216-24. doi: ". [PMID: 14056454]
  • E E BAULIEU. [Ester sulfates of steroid hormones. Isolation and characterization in urines of the ester sulfate of 5 beta-androstane 3 alpha-ol-17-one after administration of 5 beta-androstane 3 alpha-ol 17 one (etiocholanolone) to a child]. Comptes rendus hebdomadaires des seances de l'Academie des sciences. 1960 Jun; 250(?):4219-21. doi: NULL. [PMID: 13797694]
  • E E BAULIEU. [Sulfate esters of steroid hormones; isolation and characterization of 5 alpha-androstane-3 beta-o1-17-one sulfate in human urine after administration of 5 alpha-androstane-3 beta o1-17-one]. Comptes rendus hebdomadaires des seances de l'Academie des sciences. 1959 Jun; 248(24):3493-4. doi: NULL. [PMID: 13671771]
  • R V BROOKS, W KLYNE. Steroids of pregnant mare's urine. V. Identification of two androstane-3:16-diols; the structure of uranolone. The Biochemical journal. 1957 Apr; 65(4):663-8. doi: 10.1042/bj0650663. [PMID: 13426081]
  • B R CARROLL, D I HAMM, C D KOCHAKIAN. Reduction of androstane-3, 17-dione by liver homogenates. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 1956 Dec; 93(3):493-6. doi: 10.3181/00379727-93-22795. [PMID: 13389498]
  • H L MASON, E J KEPIER. Isolation of steroids from the urine of patients with adrenal cortical tumors and adrenal cortical hyperplasia; a new 17-ketosteroid, androstane-3 (alpha) 11-diol-17-one. The Journal of biological chemistry. 1945; 161(?):235-57. doi: NULL. [PMID: 21005731]