Androstenediol (BioDeep_00000637494)

Main id: BioDeep_00000005470

 


代谢物信息卡片


Androst-5-ene-3beta,17beta-diol

化学式: C19H30O2 (290.224568)
中文名称: 5-雄烯二醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@H](O)CC[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O)C1
InChI: InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1

描述信息

A 3beta-hydroxy-Delta(5)-steroid that is 3beta-hydroxyandrost-5-ene carrying an additional hydroxy group at position 17beta.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D045930 - Anabolic Agents
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C2360 - Anabolic Steroid

同义名列表

4 个代谢物同义名

Androst-5-ene-3beta,17beta-diol; Androstenediol; androst-5-en-3beta,17beta-diol; ST 19:1;O2



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(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)

2 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

  • Benedikt A Gasser, Samuel F Buerki, Johann Kurz, Markus G Mohaupt. Hyperandrogenism? Increased 17, 20-Lyase Activity? A Metanalysis and Systematic Review of Altered Androgens in Boys and Girls with Autism. International journal of molecular sciences. 2021 Nov; 22(22):. doi: 10.3390/ijms222212324. [PMID: 34830216]
  • Takako Kawakita, Toshiyuki Yasui, Kanako Yoshida, Sumika Matsui, Takeshi Iwasa. Correlations of androstenediol with reproductive hormones and cortisol according to stages during the menopausal transition in Japanese women. The Journal of steroid biochemistry and molecular biology. 2021 11; 214(?):106009. doi: 10.1016/j.jsbmb.2021.106009. [PMID: 34571175]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Haruka Tanabe, Hitoshi Mutai, Daimei Sasayama, Hidehiko Sasamoto, Yoshimichi Miyashiro, Nobuhiro Sugiyama, Shinsuke Washizuka. Sex differences in serum levels of 5α-androstane-3β, 17β-diol, and androstenediol in the young adults: A liquid chromatography-tandem mass spectrometry study. PloS one. 2021; 16(12):e0261440. doi: 10.1371/journal.pone.0261440. [PMID: 34910781]
  • Joanne F Dorgan, Seungyoun Jung, Cher M Dallal, Min Zhan, Christina A Stennett, Yuji Zhang, Richard L Eckert, Linda G Snetselaar, Linda Van Horn. Alcohol consumption and serum metabolite concentrations in young women. Cancer causes & control : CCC. 2020 Feb; 31(2):113-126. doi: 10.1007/s10552-019-01256-1. [PMID: 31828464]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Satoshi Endo, Namiki Miyagi, Toshiyuki Matsunaga, Akira Ikari. Rabbit dehydrogenase/reductase SDR family member 11 (DHRS11): Its identity with acetohexamide reductase with broad substrate specificity and inhibitor sensitivity, different from human DHRS11. Chemico-biological interactions. 2019 May; 305(?):12-20. doi: 10.1016/j.cbi.2019.03.026. [PMID: 30926317]
  • Michael E Baker, Richard Lathe. The promiscuous estrogen receptor: Evolution of physiological estrogens and response to phytochemicals and endocrine disruptors. The Journal of steroid biochemistry and molecular biology. 2018 11; 184(?):29-37. doi: 10.1016/j.jsbmb.2018.07.001. [PMID: 30009950]
  • Yann Neuzillet, Jean-Pierre Raynaud, Camélia Radulescu, Jean Fiet, Franck Giton, Jean-François Dreyfus, Tarek P Ghoneim, Thierry Lebret, Henry Botto. Sexual steroids in serum and prostatic tissue of human non-cancerous prostate (STERPROSER trial). The Prostate. 2017 Nov; 77(15):1512-1519. doi: 10.1002/pros.23429. [PMID: 28905453]
  • Tianzhu Zang, Daniel Tamae, Clementina Mesaros, Qingqing Wang, Meng Huang, Ian A Blair, Trevor M Penning. Simultaneous quantitation of nine hydroxy-androgens and their conjugates in human serum by stable isotope dilution liquid chromatography electrospray ionization tandem mass spectrometry. The Journal of steroid biochemistry and molecular biology. 2017 01; 165(Pt B):342-355. doi: 10.1016/j.jsbmb.2016.08.001. [PMID: 27531846]
  • Juilee Rege, Shigehiro Karashima, Antonio M Lerario, Joshua M Smith, Richard J Auchus, Josephine Z Kasa-Vubu, Hironobu Sasano, Yasuhiro Nakamura, Perrin C White, William E Rainey. Age-dependent Increases in Adrenal Cytochrome b5 and Serum 5-Androstenediol-3-sulfate. The Journal of clinical endocrinology and metabolism. 2016 12; 101(12):4585-4593. doi: 10.1210/jc.2016-2864. [PMID: 27623070]
  • Yuyong Ke, Jonathan Bertin, Renaud Gonthier, Jean-Nicolas Simard, Fernand Labrie. A sensitive, simple and robust LC-MS/MS method for the simultaneous quantification of seven androgen- and estrogen-related steroids in postmenopausal serum. The Journal of steroid biochemistry and molecular biology. 2014 Oct; 144 Pt B(?):523-34. doi: 10.1016/j.jsbmb.2014.08.015. [PMID: 25158021]
  • Mario V Tartagni, Hala Alrasheed, Gianluca R Damiani, Monica Montagnani, Maria A De Salvia, Giovanni De Pergola, Massimo Tartagni, Giuseppe Loverro. Intermittent low-dose finasteride administration is effective for treatment of hirsutism in adolescent girls: a pilot study. Journal of pediatric and adolescent gynecology. 2014 Jun; 27(3):161-5. doi: 10.1016/j.jpag.2013.09.010. [PMID: 24559619]
  • Alan J Conley, Frank Z Stanczyk, John H Morrison, Pawel Borowicz, Kurt Benirschke, Nancy A Gee, Bill L Lasley. Modulation of higher-primate adrenal androgen secretion with estrogen-alone or estrogen-plus-progesterone intervention. Menopause (New York, N.Y.). 2013 Mar; 20(3):322-8. doi: 10.1097/gme.0b013e318273a070. [PMID: 23435030]
  • Johan Lundqvist, Maria Norlin. Effects of CYP7B1-related steroids on androgen receptor activation in different cell lines. Biochimica et biophysica acta. 2012 Jul; 1821(7):973-9. doi: 10.1016/j.bbalip.2012.03.007. [PMID: 22484622]
  • 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]
  • 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]
  • Maria Florencia Quiroga, Matias Tomas Angerami, Natalia Santucci, Diego Ameri, Jose Luis Francos, Jorge Wallach, Omar Sued, Pedro Cahn, Horacio Salomón, Oscar Bottasso. Dynamics of adrenal steroids are related to variations in Th1 and Treg populations during Mycobacterium tuberculosis infection in HIV positive persons. PloS one. 2012; 7(3):e33061. doi: 10.1371/journal.pone.0033061. [PMID: 22431997]
  • Frank Giton, Jean Fiet, Jean-Nicolas Cornu, Olivier Cussenot, Alain Bélanger, Saîk Urien, Alejandro Oliva, Pascal Blanchet, Luc Multigner. Serum sex steroids measured in middle-aged European and African-Caribbean men by gas chromatography-mass spectrometry. European journal of endocrinology. 2011 Dec; 165(6):917-24. doi: 10.1530/eje-11-0551. [PMID: 21951700]
  • Eva C Bonefeld-Jorgensen, Manhai Long, Rossana Bossi, Pierre Ayotte, Gert Asmund, Tanja Krüger, Mandana Ghisari, Gert Mulvad, Peder Kern, Peter Nzulumiki, Eric Dewailly. Perfluorinated compounds are related to breast cancer risk in Greenlandic Inuit: a case control study. Environmental health : a global access science source. 2011 Oct; 10(?):88. doi: 10.1186/1476-069x-10-88. [PMID: 21978366]
  • Vishal Gupta. Mineralocorticoid hypertension. Indian journal of endocrinology and metabolism. 2011 Oct; 15 Suppl 4(?):S298-312. doi: 10.4103/2230-8210.86972. [PMID: 22145132]
  • Naoko Honma, Shigehira Saji, Makiko Hirose, Shin-ichiro Horiguchi, Katsumasa Kuroi, Shin-ichi Hayashi, Toshiaki Utsumi, Nobuhiro Harada. Sex steroid hormones in pairs of tumor and serum from breast cancer patients and pathobiological role of androstene-3β, 17β-diol. Cancer science. 2011 Oct; 102(10):1848-54. doi: 10.1111/j.1349-7006.2011.02018.x. [PMID: 21707867]
  • Man Ho Choi, Ju-Yeon Moon, Sung-Hee Cho, Bong Chul Chung, Eun Jig Lee. Metabolic alteration of urinary steroids in pre- and post-menopausal women, and men with papillary thyroid carcinoma. BMC cancer. 2011 Aug; 11(?):342. doi: 10.1186/1471-2407-11-342. [PMID: 21824401]
  • Ulf Brunnemer, Christian Zeckey, Frank Hildebrand, Michael Frink, Philipp Mommsen, Martijn van Griensven, Hagen Andruszkow, Christian Krettek, Tanja Barkhausen. Androstenediol exerts salutary effects on chemokine response after trauma-hemorrhage and sepsis in mice. Journal of orthopaedic trauma. 2011 Aug; 25(8):511-5. doi: 10.1097/bot.0b013e3182251044. [PMID: 21738064]
  • Juliana C Monteiro, Marcos L M Gomes, Tatiana C Tomiosso, Wilson R Nakagaki, Mariana M Sbervelheri, Danilo L Ferrucci, Edson R Pimentel, Heidi Dolder. More resistant tendons obtained from the association of Heteropterys aphrodisiaca and endurance training. BMC complementary and alternative medicine. 2011 Jun; 11(?):51. doi: 10.1186/1472-6882-11-51. [PMID: 21711561]
  • Juliann G Kiang, Neil G Agravante, Joan T Smith, Phillip D Bowman. 17-DMAG diminishes hemorrhage-induced small intestine injury by elevating Bcl-2 protein and inhibiting iNOS pathway, TNF-α increase, and caspase-3 activation. Cell & bioscience. 2011 Jun; 1(1):21. doi: 10.1186/2045-3701-1-21. [PMID: 21711488]
  • Adam T Cawley, Graham J Trout, Rymantas Kazlauskas, Adrian V George. The potential of urinary androstdiene markers to identify 4-androstenediol (4-ADIOL) administration in athletes. Forensic science international. 2011 May; 208(1-3):129-38. doi: 10.1016/j.forsciint.2010.11.016. [PMID: 21177052]
  • David C Muller, Graham G Giles, Julie Bassett, Howard A Morris, John T Manning, John L Hopper, Dallas R English, Gianluca Severi. Second to fourth digit ratio (2D:4D) and concentrations of circulating sex hormones in adulthood. Reproductive biology and endocrinology : RB&E. 2011 Apr; 9(?):57. doi: 10.1186/1477-7827-9-57. [PMID: 21521531]
  • S J Stanway, C Palmieri, F Z Stanczyk, E J Folkerd, M Dowsett, R Ward, R C Coombes, M J Reed, A Purohit. Effect of tamoxifen or anastrozole on steroid sulfatase activity and serum androgen concentrations in postmenopausal women with breast cancer. Anticancer research. 2011 Apr; 31(4):1367-72. doi: . [PMID: 21508387]
  • Fernand Labrie, Céline Martel, John Balser. Wide distribution of the serum dehydroepiandrosterone and sex steroid levels in postmenopausal women: role of the ovary?. Menopause (New York, N.Y.). 2011 Jan; 18(1):30-43. doi: 10.1097/gme.0b013e3181e195a6. [PMID: 20683211]
  • Tulsidas G Shrivastav, Shail K Chaube, Kiran P Kariya, Payal Kumari, Rita Singh, Dinesh Kumar. Influence of different homologous and heterologous combinations of antibodies and enzyme conjugates of dehydroepiandrostosterone on the sensitivity and specificity of DHEA ELISA. Journal of immunoassay & immunochemistry. 2011; 32(2):114-27. doi: 10.1080/15321819.2010.543221. [PMID: 21391048]
  • Martin Hill, Jana Zárubová, Petr Marusič, Jana Vrbíková, Marta Velíková, Radmila Kancheva, Lyudmila Kancheva, Jana Kubátová, Michaela Dušková, Ludmila Zamrazilová, Hana Kazihnitková, Kateřina Simůnková, Luboslav Stárka. Effects of valproate and carbamazepine monotherapy on neuroactive steroids, their precursors and metabolites in adult men with epilepsy. The Journal of steroid biochemistry and molecular biology. 2010 Oct; 122(4):239-52. doi: 10.1016/j.jsbmb.2010.06.003. [PMID: 20541012]
  • Rosemary Basson, Lori A Brotto, A John Petkau, Fernand Labrie. Role of androgens in women's sexual dysfunction. Menopause (New York, N.Y.). 2010 Sep; 17(5):962-71. doi: 10.1097/gme.0b013e3181d59765. [PMID: 20539247]
  • T Kwok, C Ohlsson, L Vandenput, N Tang, Y F Zhang, B Tomlinson, P C Leung. ACE inhibitor use was associated with lower serum dehydroepiandrosterone concentrations in older men. Clinica chimica acta; international journal of clinical chemistry. 2010 Aug; 411(15-16):1122-5. doi: 10.1016/j.cca.2010.04.011. [PMID: 20403346]
  • Jie Hu, Zhonghua Zhang, Wen-Jun Shen, Salman Azhar. Cellular cholesterol delivery, intracellular processing and utilization for biosynthesis of steroid hormones. Nutrition & metabolism. 2010 Jun; 7(?):47. doi: 10.1186/1743-7075-7-47. [PMID: 20515451]
  • Kazutaka Narimoto, Atsushi Mizokami, Kouji Izumi, Shinya Mihara, Kiyoshi Sawada, Toshiaki Sugata, Masayoshi Shimamura, Kimiomi Miyazaki, Akio Nishino, Mikio Namiki. Adrenal androgen levels as predictors of outcome in castration-resistant prostate cancer patients treated with combined androgen blockade using flutamide as a second-line anti-androgen. International journal of urology : official journal of the Japanese Urological Association. 2010 Apr; 17(4):337-45. doi: 10.1111/j.1442-2042.2010.02473.x. [PMID: 20202011]
  • Fay Warnock, Kevin McElwee, Rubo J Seo, Sean McIsaac, Danielle Seim, Tatiana Ramirez-Aponte, Karine An Macritchie, Allan H Young. Measuring cortisol and DHEA in fingernails: a pilot study. Neuropsychiatric disease and treatment. 2010 Feb; 6(?):1-7. doi: 10.2147/ndt.s8307. [PMID: 20169040]
  • N Prakash, Kumar M Vijay, U Sunilchandra, Bh Pavithra, A Pawar. Evaluation of Testicular Toxicity Following Short-term Exposure to Cypermethrin in Albino Mice. Toxicology international. 2010 Jan; 17(1):18-21. doi: 10.4103/0971-6580.68344. [PMID: 21042468]
  • Ilse Becue, Christof Van Poucke, Jeroen C W Rijk, Toine F H Bovee, Michel Nielen, Carlos Van Peteghem. Investigation of urinary steroid metabolites in calf urine after oral and intramuscular administration of DHEA. Analytical and bioanalytical chemistry. 2010 Jan; 396(2):799-808. doi: 10.1007/s00216-009-3265-z. [PMID: 19915825]
  • Ze-Hua Liu, Yoshinori Kanjo, Satoshi Mizutani. Urinary excretion rates of natural estrogens and androgens from humans, and their occurrence and fate in the environment: a review. The Science of the total environment. 2009 Sep; 407(18):4975-85. doi: 10.1016/j.scitotenv.2009.06.001. [PMID: 19559467]
  • Thomas Remer, Friedrich Manz, Michaela F Hartmann, Eckhard Schoenau, Stefan A Wudy. Prepubertal healthy children's urinary androstenediol predicts diaphyseal bone strength in late puberty. The Journal of clinical endocrinology and metabolism. 2009 Feb; 94(2):575-8. doi: 10.1210/jc.2008-1375. [PMID: 19001521]
  • Mary E Turyk, Victoria W Persky, Pamela Imm, Lynda Knobeloch, Robert Chatterton, Henry A Anderson. Hormone disruption by PBDEs in adult male sport fish consumers. Environmental health perspectives. 2008 Dec; 116(12):1635-41. doi: 10.1289/ehp.11707. [PMID: 19079713]
  • Barbara Hauser, Doreen Schulz, Christophe Boesch, Tobias Deschner. Measuring urinary testosterone levels of the great apes--problems with enzymatic hydrolysis using Helix pomatia juice. General and comparative endocrinology. 2008 Aug; 158(1):77-86. doi: 10.1016/j.ygcen.2008.05.006. [PMID: 18639242]
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  • Louise Berger, Mohamed El-Alfy, Fernand Labrie. Effects of intravaginal dehydroepiandrosterone on vaginal histomorphology, sex steroid receptor expression and cell proliferation in the rat. The Journal of steroid biochemistry and molecular biology. 2008 Mar; 109(1-2):67-80. doi: 10.1016/j.jsbmb.2007.09.023. [PMID: 18242978]
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  • László Szalay, Tomoharu Shimizu, Takao Suzuki, Ya-Ching Hsieh, Mashkoor A Choudhry, Martin G Schwacha, Kirby I Bland, Irshad H Chaudry. Androstenediol administration after trauma-hemorrhage attenuates inflammatory response, reduces organ damage, and improves survival following sepsis. American journal of physiology. Gastrointestinal and liver physiology. 2006 Aug; 291(2):G260-6. doi: 10.1152/ajpgi.00390.2005. [PMID: 16574990]
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  • Gregory A Brown, Drew McKenzie. Acute resistance exercise does not change the hormonal response to sublingual androstenediol intake. European journal of applied physiology. 2006 Jul; 97(4):404-12. doi: 10.1007/s00421-006-0194-9. [PMID: 16636857]
  • Tomoharu Shimizu, László Szalay, Ya-Ching Hsieh, Takao Suzuki, Mashkoor A Choudhry, Kirby I Bland, Irshad H Chaudry. A role of PPAR-gamma in androstenediol-mediated salutary effects on cardiac function following trauma-hemorrhage. Annals of surgery. 2006 Jul; 244(1):131-8. doi: 10.1097/01.sla.0000217709.00863.82. [PMID: 16794398]
  • Patience Browne, Alan J Conley, Terry Spraker, Rolf R Ream, Bill L Lasley. Sex steroid concentrations and localization of steroidogenic enzyme expression in free-ranging female northern fur seals (Callorhinus ursinus). General and comparative endocrinology. 2006 Jun; 147(2):175-83. doi: 10.1016/j.ygcen.2005.12.019. [PMID: 16473352]
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