Dehydroepiandrosterone (BioDeep_00000001231)

 

Secondary id: BioDeep_00000398237, BioDeep_00000422634

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one

化学式: C19H28O2 (288.2089188)
中文名称: 去氢表雄酮, 去氢表雄酮
谱图信息: 最多检出来源 Homo sapiens(blood) 0.02%

分子结构信息

SMILES: C1[C@]2(C)[C@@]3([H])CC[C@]4(C)C(=O)CC[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O)C1
InChI: InChI=1S/C19H28O2/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/h3,13-16,20H,4-11H2,1-2H3

描述信息

Dehydroepiandrosterone (DHEA) is a natural steroid hormone produced from cholesterol by the adrenal glands. DHEA is also produced in the gonads, adipose tissue and the brain. DHEA is structurally similar to, and is a precursor of, androstenedione, testosterone, estradiol, estrone and estrogen. It is the most abundant hormone in the human body. Most of DHEA is sulfated (dehydroepiandrosterone sulfate- DEHAS) before secretion. DHEAS is the sulfated version of DHEA; - this conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestines. In blood, most DHEA is found as DHEAS with levels that are about 300 times higher than free DHEA. Blood measurements of DHEAS/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have normal or mildly elevated levels of DHEAS. [HMDB]. Dehydroepiandrosterone is found in many foods, some of which are summer grape, quinoa, calabash, and chinese chives.
Dehydroepiandrosterone (DHEA) is a natural steroid hormone produced from cholesterol by the adrenal glands. DHEA is also produced in the gonads, adipose tissue, and the brain. DHEA is structurally similar to and is a precursor of, androstenedione, testosterone, estradiol, estrone, and estrogen. It is the most abundant hormone in the human body. Most of DHEA is sulfated (dehydroepiandrosterone sulfate or DHEA-S) before secretion. DHEA-S is the sulfated version of DHEA; this conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestines. In blood, most DHEA is found as DHEA-S with levels that are about 300 times higher than free DHEA. Blood measurements of DHEA-S/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have normal or mildly elevated levels of DHEA-S.
A - Alimentary tract and metabolism > A14 - Anabolic agents for systemic use > A14A - Anabolic steroids > A14AA - Androstan derivatives
G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3085
D007155 - Immunologic Factors

同义名列表

60 个代谢物同义名

(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one; (3beta,16alpha)-3,16-Dihydroxy-androst-5-en-17-one; (3-beta)-3-Hydroxyandrost-5-en-17-one; (3beta)-3-Hydroxy-androst-5-en-17-one; 3beta-Hydroxy-androst-5-en-17-one; 3-BETA-HYDROXY-5-androsten-17-one; 5-Androsten-3-beta-hydroxy-17-one; 3beta-Hydroxy-D5-androsten-17-one; 5 Androsten 3 beta hydroxy 17 one; 3-beta-Hydroxyandrost-5-en-17-one; 3beta-Hydroxy-5-androsten-17-one; 3beta-hydroxyandrost-5-en-17-one; 3-b-HYDROXY-5-androsten-17-one; 3-Β-hydroxy-5-androsten-17-one; 3b-Hydroxy-D5-androsten-17-one; 3b-Hydroxyandrost-5-en-17-one; 3Β-hydroxyandrost-5-en-17-one; Androst-5-ene-3beta-ol-17-one; Dehydroepiandrosterone (DHEA); 3-Hydroxyandrost-5-en-17-one; 5,6-Didehydroisoandrosterone; 5-Androsten-3-beta-ol-17-one; D5-Androsten-3beta-ol-17-one; 5-Androsten-3beta-ol-17-one; Prasterone, 3 alpha-isomer; Prasterone, 3 alpha isomer; Androst-5-ene-3b-ol-17-one; (+)-Dehydroisoandrosterone; 5,6-Dehydroisoandrosterone; Androsten-3beta-ol-17-one; D5-Androsten-3b-ol-17-one; EM-760Dehydroandrosterone; trans-Dehydroandrosterone; 5-Dehydro-epiandrosterone; 5-Androsten-3b-ol-17-one; 5-Dehydroepiandrosterone; Dehydro-epi-androsterone; 5 Androsten 3 ol 17 one; 5-Androsten-3-ol-17-one; Dehydroepiandrosterone; Dehydroisoandrosterone; Hydroxyandrostenone; Androstenolone; 17-Hormoforin; Psicosterone; 17-Chetovis; Andrestenol; Prasteronum; Prasterone; Prasterona; ST 19:2;O2; Diandrone; Intrarosa; Astenile; Deandros; Diandron; Prestara; Biolaif; DHEA; DHA



数据库引用编号

31 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(7)

BioCyc(1)

PlantCyc(0)

代谢反应

105 个相关的代谢反应过程信息。

Reactome(86)

BioCyc(3)

  • androgen biosynthesis: 17-α-hydroxypregnenolone + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ 3-β-hydroxyandrost-5-en-17-one + H+ + H2O + acetate + an oxidized [NADPH-hemoprotein reductase]
  • androgen biosynthesis: NADP+ + testosterone ⟶ H+ + NADPH + androst-4-ene-3,17-dione
  • androgen biosynthesis: NAD+ + dehydroepiandrosterone ⟶ 5-androstene-3,17-dione + H+ + NADH

WikiPathways(4)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(12)

PharmGKB(0)

5 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

  • Ying Liu, Feng Ni, Jing Huang, Yuqin Hu, Jing Wang, Xuemei Wang, Xin Du, Hong Jiang. PPAR-α inhibits DHEA-induced ferroptosis in granulosa cells through upregulation of FADS2. Biochemical and biophysical research communications. 2024 Jun; 715(?):150005. doi: 10.1016/j.bbrc.2024.150005. [PMID: 38678785]
  • Yuanyuan Chen, Zhaohua Liu, Hongmei Chen, Yi Wen, Lang Fan, Man Luo. Rhythm gene PER1 mediates ferroptosis and lipid metabolism through SREBF2/ALOX15 axis in polycystic ovary syndrome. Biochimica et biophysica acta. Molecular basis of disease. 2024 Jun; 1870(5):167182. doi: 10.1016/j.bbadis.2024.167182. [PMID: 38653359]
  • Shaojing He, Hui Li, Qianjie Zhang, Weimin Zhao, Wei Li, Chaohui Dai, Bixia Li, Jinhua Cheng, Shuang Wu, Zhongming Zhou, Jing Yang, Saijiao Li. Berberine alleviates inflammation in polycystic ovary syndrome by inhibiting hyaluronan synthase 2 expression. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 Jun; 128(?):155456. doi: 10.1016/j.phymed.2024.155456. [PMID: 38537446]
  • Peiwei Cong, Bing Shang, Lina Zhang, Zhaoli Wu, Yanan Wang, Jia Li, Lin Zhang. New insights into the treatment of polycystic ovary syndrome: HKDC1 promotes the growth of ovarian granulocyte cells by regulating mitochondrial function and glycolysis. Journal of molecular histology. 2024 Apr; 55(2):187-199. doi: 10.1007/s10735-024-10183-8. [PMID: 38478190]
  • Ruiyun Li, Rui Hu, Yi Huang, Dan Li, Xiaoling Ma, Yuan Yang. Astragalus polysaccharide alleviates polycystic ovary syndrome by reducing insulin resistance and oxidative stress and increasing the diversity of gut microbiota. Endocrine. 2024 Mar; 83(3):783-797. doi: 10.1007/s12020-023-03553-x. [PMID: 37824046]
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  • Tingting Zhang, Huimin Gao, Yali Fan, Shuya Chen, Yingying Li, Ruixia Liu, Tianhe Li, Chenghong Yin. Gut microbiota disorder induces liver dysfunction in polycystic ovary syndrome rats' model by regulating metabolite rosmarinic acid. Life sciences. 2023 Oct; 330(?):121912. doi: 10.1016/j.lfs.2023.121912. [PMID: 37423380]
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  • Jing Wang, Xinyao Pan, Jing Zhou, Xin Li, Yan Sun, Ling Wang. Advances in understanding the effect and mechanism of dehydroepiandrosterone on diminished ovarian reserve. Drug discoveries & therapeutics. 2023 May; 17(2):87-94. doi: 10.5582/ddt.2022.01109. [PMID: 37019659]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Ritu Rani, Havagiray R Chitme, Neha Kukreti, Pankaj Pant, Basel A Abdel-Wahab, Masood Medleri Khateeb, Mohammed Shafiuddin Habeeb, Marwa B Bakir. Regulation of Insulin Resistance, Lipid Profile and Glucose Metabolism Associated with Polycystic Ovary Syndrome by Tinospora cordifolia. Nutrients. 2023 May; 15(10):. doi: 10.3390/nu15102238. [PMID: 37242122]
  • Samuel D Offei, Hadi D Arman, Francis K Yoshimoto. Synthesis of menarandroside A from dehydroepiandrosterone. Organic & biomolecular chemistry. 2023 Mar; ?(?):. doi: 10.1039/d3ob00054k. [PMID: 36950968]
  • Yijie Jiang, Jianshu Yang, Ke Du, Kaiming Luo, Xin Yuan, Fei Hua. 1,25-Dihydroxyvitamin D3 alleviates hyperandrogen-induced ferroptosis in KGN cells. Hormones (Athens, Greece). 2023 Mar; ?(?):. doi: 10.1007/s42000-023-00439-5. [PMID: 36884209]
  • Fei Yu, Yanfeng Xue, Yunyan Zhao, Long Zhang, Xiao He, Zheng Liu. Isorhamnetin inhibits inflammatory response to alleviate DHEA-induced polycystic ovary syndrome in rats. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology. 2023 Feb; ?(?):2183045. doi: 10.1080/09513590.2023.2183045. [PMID: 36842967]
  • Neşe Başak Türkmen, Hande Yüce, Muhterem Aydın, Aslı Taşlıdere, Ayşegül Doğan, Dilan Aşkın Özek, Taha Bartu Hayal, Şeyma Yaşar, Osman Çiftçi, Songül Ünüvar. Nerolidol attenuates dehydroepiandrosterone-induced polycystic ovary syndrome in rats by regulating oxidative stress and decreasing apoptosis. Life sciences. 2023 Feb; 315(?):121380. doi: 10.1016/j.lfs.2023.121380. [PMID: 36640898]
  • Yao Yao, Ying Yang, Huihui Wang, Zhihao Jiang, Haitian Ma. Dehydroepiandrosterone alleviates oleic acid-induced lipid metabolism disorders through activation of AMPK-mTOR signal pathway in primary chicken hepatocytes. Poultry science. 2023 Feb; 102(2):102385. doi: 10.1016/j.psj.2022.102385. [PMID: 36565630]
  • Xiaowei Ji, Yao Ye, Lin Wang, Suying Liu, Xi Dong. PDE4 inhibitor Roflumilast modulates inflammation and lipid accumulation in PCOS mice to improve ovarian function and reduce DHEA-induced granulosa cell apoptosis in vitro. Drug development research. 2023 Jan; ?(?):. doi: 10.1002/ddr.22027. [PMID: 36621953]
  • S N Sankhwar, Pawan Kumar, Manashi Bagchi, Mehul Rungta, Debasis Bagchi. Safety and Efficacy of Furosap®, a Patented Trigonella foenum-graecum Seed Extract, in Boosting Testosterone Level, Reproductive Health and Mood Alleviation in Male Volunteers. Journal of the American Nutrition Association. 2023 Jan; 42(1):27-35. doi: 10.1080/07315724.2021.1978348. [PMID: 34694954]
  • Elliot D Mock, Berend Gagestein, Mario van der Stelt. Anandamide and other N-acylethanolamines: A class of signaling lipids with therapeutic opportunities. Progress in lipid research. 2023 01; 89(?):101194. doi: 10.1016/j.plipres.2022.101194. [PMID: 36150527]
  • Shanshan Chen, Shuo Li, Xinxin Zhang, Yuxin Fan, Ming Liu. Low serum dehydroepiandrosterone is associated with diabetic dyslipidemia risk in males with type 2 diabetes. Frontiers in endocrinology. 2023; 14(?):1272797. doi: 10.3389/fendo.2023.1272797. [PMID: 38075062]
  • Jing Cong, Yuehui Zhang, Xinming Yang, Yu Wang, Hui He, Mengying Wang. Anti-polycystic ovary syndrome effect of electroacupuncture: IMD inhibits ER stress-mediated apoptosis and autophagy in granulosa cells. Biochemical and biophysical research communications. 2022 12; 634(?):159-167. doi: 10.1016/j.bbrc.2022.10.030. [PMID: 36244114]
  • Fangxin Peng, Yichuan Hu, Shu Peng, Ni Zeng, Lei Shi. Apigenin exerts protective effect and restores ovarian function in dehydroepiandrosterone induced polycystic ovary syndrome rats: a biochemical and histological analysis. Annals of medicine. 2022 Dec; 54(1):578-587. doi: 10.1080/07853890.2022.2034933. [PMID: 35152800]
  • He Ding, Youyuan Wang, Zhiqiang Li, Qianqing Li, Hongyu Liu, Jing Zhao, Wenfa Lu, Jun Wang. Baogong decoction treats endometritis in mice by regulating uterine microbiota structure and metabolites. Microbial biotechnology. 2022 11; 15(11):2786-2799. doi: 10.1111/1751-7915.14127. [PMID: 35932174]
  • Ying-Li Cai, Feng Zhang, Xiu-Xiu Dou, Hua-Wu Zeng, Gao-Song Wu, Yan-Lin Liang, Xi-Ke Xu, Jing Zhao, Ji Ye, Wei-Dong Zhang. Integrated metabolomics and network pharmacology to reveal the therapeutic mechanism of Dingkun Pill on polycystic ovary syndrome. Journal of ethnopharmacology. 2022 Sep; 295(?):115442. doi: 10.1016/j.jep.2022.115442. [PMID: 35688255]
  • Ying Li, Yanqiu Zhou, Zongwei Cai, Ruizhen Li, Pei Leng, Hongxiu Liu, Juan Liu, Gaga Mahai, Yuanyuan Li, Shunqing Xu, Wei Xia. Associations of benzotriazoles and benzothiazoles with estrogens and androgens among pregnant women: A cohort study with repeated measurements. The Science of the total environment. 2022 Sep; 838(Pt 2):155998. doi: 10.1016/j.scitotenv.2022.155998. [PMID: 35588816]
  • Nazek Noureddine, Ivan Hartling, Paulina Wawrzyniak, Pakeerathan Srikanthan, Phing-How Lou, Eliana Lucchinetti, Stefanie D Krämer, Gerhard Rogler, Michael Zaugg, Martin Hersberger. Lipid emulsion rich in n-3 polyunsaturated fatty acids elicits a pro-resolution lipid mediator profile in mouse tissues and in human immune cells. The American journal of clinical nutrition. 2022 09; 116(3):786-797. doi: 10.1093/ajcn/nqac131. [PMID: 35849016]
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  • Georgina Gallucci, Ariana Díaz, Rocío Del Valle Fernandez, Bettina Bongiovanni, Matilde Imhoff, Estefanía Massa, Natalia Santucci, Diego Bértola, Susana Lioi, María Luisa Bay, Oscar Bottasso, Luciano D'Attilio. Differential expression of genes regulated by the glucocorticoid receptor pathway in patients with pulmonary tuberculosis. Life sciences. 2022 Jul; 301(?):120614. doi: 10.1016/j.lfs.2022.120614. [PMID: 35526591]
  • Soumita Mandal, Pradip Mukhopadhyay, Sujoy Ghosh. DHEA on Sexual Function in Sheehan Syndrome: A Randomized Double-Blind Placebo-Controlled Crossover Trial. The Journal of clinical endocrinology and metabolism. 2022 07; 107(8):e3395-e3402. doi: 10.1210/clinem/dgac260. [PMID: 35481572]
  • Neeharika Sriram, Priyanka Madaan, Prahbhjot Malhi, Naresh Sachdeva, Sandeep Negi, Jhumki Das, Rakesh Kumar, Jitendra Kumar Sahu, Pratibha Singhi. Evaluation of Hyperandrogenism in Children with Autism Spectrum Disorder. Indian journal of pediatrics. 2022 07; 89(7):717-719. doi: 10.1007/s12098-022-04080-9. [PMID: 35089488]
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  • Wei-Wei Yin, Chang-Chang Huang, Yi-Ru Chen, Dan-Qing Yu, Min Jin, Chun Feng. The effect of medication on serum anti-müllerian hormone (AMH) levels in women of reproductive age: a meta-analysis. BMC endocrine disorders. 2022 Jun; 22(1):158. doi: 10.1186/s12902-022-01065-9. [PMID: 35698127]
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