Epiandrosterone (BioDeep_00000398248)

Main id: BioDeep_00000014335

Secondary id: BioDeep_00000604112

natural product PANOMIX_OTCML-2023 BioNovoGene_Lab2019


代谢物信息卡片


Epiandrosterone

化学式: C19H30O2 (290.224568)
中文名称: 表雄酮, 表雄甾酮, 表雄甾酮, 表雄甾酮
谱图信息: 最多检出来源 Homo sapiens(feces) 1.12%

分子结构信息

SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4=O)C)O
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/h12-16,20H,3-11H2,1-2H3

描述信息

A 3beta-hydroxy steroid that is (5alpha)-androstane substituted by a beta-hydroxy group at position 3 and an oxo group at position 17.
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.312
Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong.
Epiandrosterone is a steroid hormone with weak androgenic activity. Epiandrosterone is naturally produced by the enzyme 5α-reductase from the adrenal hormone DHEA.

同义名列表

4 个代谢物同义名

Epiandrosterone; 3β-Androsterone; trans-Androsterone; iso-Androsterone



数据库引用编号

42 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。



文献列表

  • K Schuh, S Häussler, H Sadri, C Prehn, J Lintelmann, J Adamski, C Koch, D Frieten, M H Ghaffari, G Dusel, H Sauerwein. Blood and adipose tissue steroid metabolomics and mRNA expression of steroidogenic enzymes in periparturient dairy cows differing in body condition. Scientific reports. 2022 02; 12(1):2297. doi: 10.1038/s41598-022-06014-z. [PMID: 35145150]
  • Thomas Piper, Nadine Haenelt, Gregor Fusshöller, Hans Geyer, Mario Thevis. Sensitive detection of testosterone and testosterone prohormone administrations based on urinary concentrations and carbon isotope ratios of androsterone and etiocholanolone. Drug testing and analysis. 2021 Nov; 13(11-12):1835-1851. doi: 10.1002/dta.3168. [PMID: 34648228]
  • Margarita Suárez, Kamil Makowski, Reinier Lemos, Luis Almagro, Hortensia Rodríguez, María Ángeles Herranz, Dolores Molero, Orlando Ortiz, Enrique Maroto, Fernando Albericio, Yasujiro Murata, Nazario Martín. An Androsterone-H2 @C60 hybrid: Synthesis, Properties and Molecular Docking Simulations with SARS-Cov-2. ChemPlusChem. 2021 07; 86(7):972-981. doi: 10.1002/cplu.202000770. [PMID: 33540487]
  • Jen-Tsan Chi, Pao-Hwa Lin, Vladimir Tolstikov, Taofik Oyekunle, Gloria C G Alvarado, Adela Ramirez-Torres, Emily Y Chen, Valerie Bussberg, Bo Chi, Bennett Greenwood, Rangaprasad Sarangarajan, Niven R Narain, Michael A Kiebish, Stephen J Freedland. The influence of low-carbohydrate diets on the metabolic response to androgen-deprivation therapy in prostate cancer. The Prostate. 2021 07; 81(10):618-628. doi: 10.1002/pros.24136. [PMID: 33949711]
  • Mahmoud Khatib A A Al-Ruweidi, Fatma Hassan Ali, Samar Shurbaji, Anton Popelka, Huseyin C Yalcin. Dexamethasone and transdehydroandrosterone significantly reduce pulmonary epithelial cell injuries associated with mechanical ventilation. Journal of applied physiology (Bethesda, Md. : 1985). 2021 04; 130(4):1143-1151. doi: 10.1152/japplphysiol.00574.2020. [PMID: 33600286]
  • Loredana Iannella, Cristiana Colamonici, Davide Curcio, Francesco Botrè, Xavier de la Torre. Detecting the abuse of 19-norsteroids in doping controls: A new gas chromatography coupled to isotope ratio mass spectrometry method for the analysis of 19-norandrosterone and 19-noretiocholanolone. Drug testing and analysis. 2021 Apr; 13(4):770-784. doi: 10.1002/dta.2985. [PMID: 33242373]
  • R Wang, M F Hartmann, S A Wudy. Targeted LC-MS/MS analysis of steroid glucuronides in human urine. The Journal of steroid biochemistry and molecular biology. 2021 01; 205(?):105774. doi: 10.1016/j.jsbmb.2020.105774. [PMID: 33172831]
  • Dayamin Martinez-Brito, Maria Laura Notarianni, Michele Iannone, Xavier de la Torre, Francesco Botrè. Validation of steroid sulfates deconjugation for metabolic studies. Application to human urine samples. Journal of pharmacological and toxicological methods. 2020 Nov; 106(?):106938. doi: 10.1016/j.vascn.2020.106938. [PMID: 33080389]
  • Laurie De Wilde, Pieter Van Renterghem, Peter Van Eenoo, Michaël Polet. Development and validation of a fast gas chromatography combustion isotope ratio mass spectrometry method for the detection of epiandrosterone sulfate in urine. Drug testing and analysis. 2020 Aug; 12(8):1006-1018. doi: 10.1002/dta.2801. [PMID: 32267625]
  • Britton Trabert, Kara A Michels, Garnet L Anderson, Louise A Brinton, Roni T Falk, Ashley M Geczik, Holly R Harris, Kathy Pan, Ruth M Pfeiffer, Lihong Qi, Thomas Rohan, Nicolas Wentzensen, Xia Xu. Circulating androgens and postmenopausal ovarian cancer risk in the Women's Health Initiative Observational Study. International journal of cancer. 2019 10; 145(8):2051-2060. doi: 10.1002/ijc.32157. [PMID: 30684389]
  • Markus H Drag, Lisette J A Kogelman, Hanne Maribo, Lene Meinert, Preben D Thomsen, Haja N Kadarmideen. Characterization of eQTLs associated with androstenone by RNA sequencing in porcine testis. Physiological genomics. 2019 Oct; 51(10):488-499. doi: 10.1152/physiolgenomics.00125.2018. [PMID: 31373884]
  • Sook Wah Yee, Adrian Stecula, Huan-Chieh Chien, Ling Zou, Elena V Feofanova, Marjolein van Borselen, Kit Wun Kathy Cheung, Noha A Yousri, Karsten Suhre, Jason M Kinchen, Eric Boerwinkle, Roshanak Irannejad, Bing Yu, Kathleen M Giacomini. Unraveling the functional role of the orphan solute carrier, SLC22A24 in the transport of steroid conjugates through metabolomic and genome-wide association studies. PLoS genetics. 2019 09; 15(9):e1008208. doi: 10.1371/journal.pgen.1008208. [PMID: 31553721]
  • Francisco Cortés-Benítez, Jenny Roy, Martin Perreault, René Maltais, Donald Poirier. A- and D-Ring Structural Modifications of an Androsterone Derivative Inhibiting 17β-Hydroxysteroid Dehydrogenase Type 3: Chemical Synthesis and Structure-Activity Relationships. Journal of medicinal chemistry. 2019 08; 62(15):7070-7088. doi: 10.1021/acs.jmedchem.9b00624. [PMID: 31268309]
  • Xavier de la Torre, Daniel Jardines, Davide Curcio, Cristiana Colamonici, Francesco Botrè. Isotope ratio mass spectrometry in antidoping analysis: The use of endogenous reference compounds. Rapid communications in mass spectrometry : RCM. 2019 Mar; 33(6):579-586. doi: 10.1002/rcm.8377. [PMID: 30589473]
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  • J Vitku, L Kolatorova, C Ricco, C Ferroud, O Hennebert, T Skodova, J Heracek, L Starka. The quantitation of 7beta-hydroxy-epiandrosterone in the plasma and seminal plasma of men with different degrees of fertility. Physiological research. 2018 11; 67(Suppl 3):S511-S519. doi: 10.33549/physiolres.933963. [PMID: 30484677]
  • Sergi Coll, Xavier Matabosch, Lorena Garrostas, Nuria Monfort, Clara Perez-Maña, Nieves Pizarro, Julián A Mateus, Mohammed Ezzel, Rafael de la Torre, Rosa Ventura. The effect of tea consumption on the steroid profile. Drug testing and analysis. 2018 Sep; 10(9):1438-1447. doi: 10.1002/dta.2392. [PMID: 29659189]
  • Heidi Laderoute, Christine Bone, E James Squires. The sulfoconjugation of androstenone and dehydroepiandrosterone by human and porcine sulfotransferase enzymes. Steroids. 2018 08; 136(?):8-16. doi: 10.1016/j.steroids.2018.05.010. [PMID: 29792900]
  • Luboslav Stárka, Martin Hill, Lucie Kolatorova, Michaela Dušková. Androst-5-ene-3β,7α/β,17β-triols, their plasma levels and dependence on the hypothalamic-pituitary-adrenal axis. Steroids. 2018 06; 134(?):88-95. doi: 10.1016/j.steroids.2018.02.005. [PMID: 29477344]
  • Sasha Savkovic, Sarina Lim, Veena Jayadev, Ann Conway, Leo Turner, Douglas Curtis, Catrin Goebel, David J Handelsman. Urine and Serum Sex Steroid Profile in Testosterone-Treated Transgender and Hypogonadal and Healthy Control Men. The Journal of clinical endocrinology and metabolism. 2018 06; 103(6):2277-2283. doi: 10.1210/jc.2018-00054. [PMID: 29584875]
  • Takahiro Maeda, Eiji Kikuchi, Masanori Hasegawa, Keiko Homma, Yota Yasumizu, Seiya Hattori, Takeo Kosaka, Kazunobu Shinoda, Akira Miyajima, Mototsugu Oya. Change of the 5α/5β ratio of urinary steroid metabolites in benign prostatic hyperplasia patients treated with dutasteride. Clinical biochemistry. 2018 May; 55(?):36-41. doi: 10.1016/j.clinbiochem.2018.03.021. [PMID: 29608891]
  • Clemens Kamrath, Lisa Wettstaedt, Claudia Boettcher, Michaela F Hartmann, Stefan A Wudy. Androgen excess is due to elevated 11-oxygenated androgens in treated children with congenital adrenal hyperplasia. The Journal of steroid biochemistry and molecular biology. 2018 04; 178(?):221-228. doi: 10.1016/j.jsbmb.2017.12.016. [PMID: 29277706]
  • Yuyong Ke, Alain Bélanger, Jean-Nicolas Simard, Renaud Gonthier, Céline Martel, Mario Vaillancourt, Fernand Labrie. Concentration range of serum sex steroids in normal postmenopausal women and those with diagnosis of vulvovaginal atrophy. Menopause (New York, N.Y.). 2018 03; 25(3):293-300. doi: 10.1097/gme.0000000000000993. [PMID: 29206779]
  • Brittany L Mason, Erin Van Enkevort, Francesca Filbey, Christine E Marx, John Park, Alyson Nakamura, Prabha Sunderajan, E Sherwood Brown. Neurosteroid Levels in Patients With Bipolar Disorder and a History of Cannabis Use Disorders. Journal of clinical psychopharmacology. 2017 Dec; 37(6):684-688. doi: 10.1097/jcp.0000000000000793. [PMID: 29045302]
  • Wadha Abushareeda, Emmanouil Lyris, Suhail Kraiem, Aisha Al Wahaibi, Sameera Alyazidi, Najib Dbes, Arjen Lommen, Michel Nielen, Peter L Horvatovich, Mohammed Alsayrafi, Costas Georgakopoulos. Gas chromatographic quadrupole time-of-flight full scan high resolution mass spectrometric screening of human urine in antidoping analysis. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Sep; 1063(?):74-83. doi: 10.1016/j.jchromb.2017.08.019. [PMID: 28850889]
  • Christopher M Jones, Ashwini Mallappa, Nicole Reisch, Nikolaos Nikolaou, Nils Krone, Beverly A Hughes, Donna M O'Neil, Martin J Whitaker, Jeremy W Tomlinson, Karl-Heinz Storbeck, Deborah P Merke, Richard J Ross, Wiebke Arlt. Modified-Release and Conventional Glucocorticoids and Diurnal Androgen Excretion in Congenital Adrenal Hyperplasia. The Journal of clinical endocrinology and metabolism. 2017 06; 102(6):1797-1806. doi: 10.1210/jc.2016-2855. [PMID: 27845856]
  • Jelle Vehof, Pirro G Hysi, Christopher J Hammond. A Metabolome-Wide Study of Dry Eye Disease Reveals Serum Androgens as Biomarkers. Ophthalmology. 2017 04; 124(4):505-511. doi: 10.1016/j.ophtha.2016.12.011. [PMID: 28139245]
  • Maureen D'Souza-Anjo, Bruce W Christensen, Kristin Brabender, Waltraut Zimmermann, Philip H Kass, Franz Schwarzenberger. A comparison of fecal steroid metabolite concentrations between harem and bachelor stallions in a free-Ranging population of przewalski's horses (Equus ferus przewalskii). Zoo biology. 2017 Mar; 36(2):127-131. doi: 10.1002/zoo.21348. [PMID: 28114737]
  • Yuyong Ke, Renaud Gonthier, Fernand Labrie. A sensitive and accurate LC-MS/MS assay with the derivatization of 1-Amino-4-methylpiperazine applied to serum allopregnanolone, pregnenolone and androsterone in pre- and postmenopausal women. Steroids. 2017 02; 118(?):25-31. doi: 10.1016/j.steroids.2016.11.007. [PMID: 27913096]
  • Cristina C Jacob, Gaud Dervilly-Pinel, Yoann Deceuninck, Audrey Gicquiau, Patrick Chevillon, Michel Bonneau, Bruno Le Bizec. Urinary signature of pig carcasses with boar taint by liquid chromatography-high-resolution mass spectrometry. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2017 Feb; 34(2):218-227. doi: 10.1080/19440049.2016.1265152. [PMID: 27885948]
  • Sara Corral, Carmela Belloch, José Javier López-Díez, Ana Salvador, Mónica Flores. Yeast inoculation as a strategy to improve the physico-chemical and sensory properties of reduced salt fermented sausages produced with entire male fat. Meat science. 2017 Jan; 123(?):1-7. doi: 10.1016/j.meatsci.2016.08.007. [PMID: 27579788]
  • Clemens Kamrath, Lisa Wettstaedt, Claudia Boettcher, Michaela F Hartmann, Stefan A Wudy. The urinary steroidome of treated children with classic 21-hydroxylase deficiency. The Journal of steroid biochemistry and molecular biology. 2017 01; 165(Pt B):396-406. doi: 10.1016/j.jsbmb.2016.08.006. [PMID: 27544322]
  • Aristotelis Kotronoulas, Alex Gomez-Gomez, Jordi Segura, Rosa Ventura, Jesús Joglar, Oscar J Pozo. Evaluation of two glucuronides resistant to enzymatic hydrolysis as markers of testosterone oral administration. The Journal of steroid biochemistry and molecular biology. 2017 01; 165(Pt B):212-218. doi: 10.1016/j.jsbmb.2016.06.006. [PMID: 27328448]
  • Nasser A Dhayat, Bernhard Dick, Brigitte M Frey, Claudia H d'Uscio, Bruno Vogt, Christa E Flück. Androgen biosynthesis during minipuberty favors the backdoor pathway over the classic pathway: Insights into enzyme activities and steroid fluxes in healthy infants during the first year of life from the urinary steroid metabolome. The Journal of steroid biochemistry and molecular biology. 2017 01; 165(Pt B):312-322. doi: 10.1016/j.jsbmb.2016.07.009. [PMID: 27471148]
  • Alessandro Casilli, Thomas Piper, Fábio Azamor de Oliveira, Monica Costa Padilha, Henrique Marcelo Pereira, Mario Thevis, Francisco Radler de Aquino Neto. Optimization of an online heart-cutting multidimensional gas chromatography clean-up step for isotopic ratio mass spectrometry and simultaneous quadrupole mass spectrometry measurements of endogenous anabolic steroid in urine. Drug testing and analysis. 2016 Nov; 8(11-12):1204-1211. doi: 10.1002/dta.2119. [PMID: 27739243]
  • Geoffrey D Miller, Vinod Nair, M Scott Morrison, Maggie Summers, Stuart E Willick, Daniel Eichner. Intranasal delivery of Natesto® testosterone gel and its effects on doping markers. Drug testing and analysis. 2016 Nov; 8(11-12):1197-1203. doi: 10.1002/dta.2106. [PMID: 27714988]
  • Brian R Stolze, Verena Gounden, Jianghong Gu, Elizabeth A Elliott, Likhona S Masika, Brent S Abel, Deborah P Merke, Monica C Skarulis, Steven J Soldin. An improved micro-method for the measurement of steroid profiles by APPI-LC-MS/MS and its use in assessing diurnal effects on steroid concentrations and optimizing the diagnosis and treatment of adrenal insufficiency and CAH. The Journal of steroid biochemistry and molecular biology. 2016 09; 162(?):110-6. doi: 10.1016/j.jsbmb.2015.12.024. [PMID: 26721696]
  • Susanne Pribbenow, Bettina Wachter, Carsten Ludwig, Annika Weigold, Martin Dehnhard. Validation of an enzyme-immunoassay for the non-invasive monitoring of faecal testosterone metabolites in male cheetahs (Acinonyx jubatus). General and comparative endocrinology. 2016 Mar; 228(?):40-47. doi: 10.1016/j.ygcen.2016.01.015. [PMID: 26828820]
  • Pedro E Martinez, David R Rubinow, Lynnette K Nieman, Deloris E Koziol, A Leslie Morrow, Crystal E Schiller, Dahima Cintron, Karla D Thompson, Khursheed K Khine, Peter J Schmidt. 5α-Reductase Inhibition Prevents the Luteal Phase Increase in Plasma Allopregnanolone Levels and Mitigates Symptoms in Women with Premenstrual Dysphoric Disorder. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2016 Mar; 41(4):1093-102. doi: 10.1038/npp.2015.246. [PMID: 26272051]
  • Ines Braga Goncalves, Michael Heistermann, Peter Santema, Ben Dantzer, Jelena Mausbach, Andre Ganswindt, Marta B Manser. Validation of a Fecal Glucocorticoid Assay to Assess Adrenocortical Activity in Meerkats Using Physiological and Biological Stimuli. PloS one. 2016; 11(4):e0153161. doi: 10.1371/journal.pone.0153161. [PMID: 27077741]
  • 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]
  • Juha P Ahtiainen, Kai Nyman, Ilpo Huhtaniemi, Tapani Parviainen, Mika Helste, Antti Rannikko, William J Kraemer, Keijo Häkkinen. Effects of resistance training on testosterone metabolism in younger and older men. Experimental gerontology. 2015 Sep; 69(?):148-58. doi: 10.1016/j.exger.2015.06.010. [PMID: 26079649]
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  • Alain Y Dury, Yuyong Ke, Renaud Gonthier, Maxim Isabelle, Jean-Nicolas Simard, Fernand Labrie. Validated LC-MS/MS simultaneous assay of five sex steroid/neurosteroid-related sulfates in human serum. The Journal of steroid biochemistry and molecular biology. 2015 May; 149(?):1-10. doi: 10.1016/j.jsbmb.2015.01.006. [PMID: 25595042]
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  • Aristotelis Kotronoulas, Andreu Fabregat, Ignacio Alfonso, Teodor Parella, Jordi Segura, Rosa Ventura, Jesús Joglar, Oscar J Pozo. Synthesis and characterization of 6β-hydroxyandrosterone and 6β-hydroxyetiocholanolone conjugated with glucuronic acid. Drug testing and analysis. 2015 Mar; 7(3):247-52. doi: 10.1002/dta.1738. [PMID: 25363899]
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