Androsterone sulfate (BioDeep_00000023754)

 

Secondary id: BioDeep_00000638226

human metabolite Endogenous blood metabolite


代谢物信息卡片


[(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxidanesulfonic acid

化学式: C19H30O5S (370.18138500000003)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(feces) 8.2%

分子结构信息

SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4=O)C)OS(=O)(=O)O
InChI: InChI=1S/C19H30O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h12-16H,3-11H2,1-2H3,(H,21,22,23)/t12-,13+,14-,15-,16-,18-,19-/m0/s1

描述信息

Androsterone sulfate (Andros-S) is the most abundant 5-alpha-reduced androgen metabolite in serum (PMID: 8380602). Androsterone sulfate is clinically recognized as one of the major androgen metabolites found in urine. It is a cognate substrate for human dehydroepiandrosterone sulfotransferase, which catalyzes the transfer of the sulfonate group from 3-phosphoadenosine-5-phosphosulfate to dehydroepiandrosterone (DHEA) (PMID: 14573603). Androsterone sulfate has been identified in the human placenta (PMID: 32033212).
Serum dehydroepiandrosterone-sulfate is a classic marker for adrenarche and, subsequently, for the individual hormonal milieu. (PMID 10599744) Dehydroepiandrosterone sulfate is an endogenously produced sex steroid that has been hypothesized to have anti aging effects. (PMID 16960027) It also has been inversely associated with development of atherosclerosis. (PMID 8956025) [HMDB]
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

同义名列表

45 个代谢物同义名

[(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxidanesulfonic acid; Androsterone sulfate, sodium salt, (3beta,5alpha)-isomer; Androsterone sulfate, sodium salt, (3alpha,5beta)-isomer; 3alpha-Hydroxy-5alpha-androstan-17-one 3-sulphuric acid; 3alpha-Hydroxy-5alpha-androstan-17-one 3-sulfuric acid; 3alpha-Hydroxy-5alpha-androstan-17-one 3-sulphate; 5alpha-Androstane-3alpha-ol-17-one sulphuric acid; 5alpha-Androstane-3alpha-ol-17-one sulfuric acid; 3alpha-hydroxy-5alpha-androstan-17-one 3-sulfate; 3a-Hydroxy-5a-androstan-17-one 3-sulphuric acid; 3Α-hydroxy-5α-androstan-17-one 3-sulphuric acid; 3Α-hydroxy-5α-androstan-17-one 3-sulfuric acid; 3a-Hydroxy-5a-androstan-17-one 3-sulfuric acid; Androsterone sulfate, (3alpha,5beta)-isomer; Androsterone sulfate, (3beta,5alpha)-isomer; 5alpha-Androstane-3alpha-ol-17-one sulphate; Androsterone sulfate, (3beta,5beta)-isomer; 5alpha-androstane-3alpha-ol-17-one sulfate; 5a-Androstane-3a-ol-17-one sulphuric acid; 3a-Hydroxy-5a-androstan-17-one 3-sulphate; 5Α-androstane-3α-ol-17-one sulphuric acid; 3Α-hydroxy-5α-androstan-17-one 3-sulphate; 5a-Androstane-3a-ol-17-one sulfuric acid; 5Α-androstane-3α-ol-17-one sulfuric acid; 3a-Hydroxy-5a-androstan-17-one 3-sulfate; 3Α-hydroxy-5α-androstan-17-one 3-sulfate; 3alpha-Sulfate-5alpha-androstan-17-one; 5a-Androstane-3a-ol-17-one sulphate; 5Α-androstane-3α-ol-17-one sulphate; 5a-Androstane-3a-ol-17-one sulfate; 5Α-androstane-3α-ol-17-one sulfate; Androsterone sulfate, sodium salt; Androsterone 3alpha-sulphate; 5alpha-Androsterone sulphate; Androsterone sulphuric acid; 5alpha-Androsterone sulfate; Androsterone 3alpha-sulfate; Androsterone sulfuric acid; Androsterone monosulphate; Androsterone monosulfate; Epiandrosterone sulfate; Androsterone sulphate; Androsterone sulfate; Andros-S; DHEAS



数据库引用编号

10 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

  • 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]
  • 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]
  • 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]
  • 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]
  • Elisabeth Altmaier, Rebecca T Emeny, Jan Krumsiek, Maria E Lacruz, Karoline Lukaschek, Sibylle Häfner, Gabi Kastenmüller, Werner Römisch-Margl, Cornelia Prehn, Robert P Mohney, Anne M Evans, Michael V Milburn, Thomas Illig, Jerzy Adamski, Fabian Theis, Karsten Suhre, Karl-Heinz Ladwig. Metabolomic profiles in individuals with negative affectivity and social inhibition: a population-based study of Type D personality. Psychoneuroendocrinology. 2013 Aug; 38(8):1299-309. doi: 10.1016/j.psyneuen.2012.11.014. [PMID: 23237813]
  • Kuniko Mitamura, Misako Setaka, Kazutake Shimada, Seijiro Honma, Mikio Namiki, Eitetsu Koh, Atsushi Mizokami. Determination of sulfates of androsterone and epiandrosterone in human serum using isotope diluted liquid chromatography-electrospray ionization-mass spectrometry. Biomedical chromatography : BMC. 2005 Dec; 19(10):796-801. doi: 10.1002/bmc.522. [PMID: 15954157]
  • Jennifer L Donovan, C Lindsay DeVane, John G Lewis, Jun-Sheng Wang, Ying Ruan, Kenneth D Chavin, John S Markowitz. Effects of St John's wort (Hypericum perforatum L.) extract on plasma androgen concentrations in healthy men and women: a pilot study. Phytotherapy research : PTR. 2005 Oct; 19(10):901-6. doi: 10.1002/ptr.1755. [PMID: 16261523]
  • J G Lewis, L M Bason, P A Elder. Production and characterization of monoclonal antibodies to dehydroepiandrosterone sulfate: application to direct enzyme-linked immunosorbent assays of dehydroepiandrosterone sulfate and androsterone/epiandrosterone sulfates in plasma. Steroids. 1996 Dec; 61(12):682-7. doi: 10.1016/s0039-128x(96)00189-4. [PMID: 8987136]
  • N Kanai, R Lu, Y Bao, A W Wolkoff, M Vore, V L Schuster. Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter. The American journal of physiology. 1996 Feb; 270(2 Pt 2):F326-31. doi: 10.1152/ajprenal.1996.270.2.f326. [PMID: 8779894]
  • E Carmina, E Gentzschein, F Z Stanczyk, R A Lobo. Substrate dependency of C19 conjugates in hirsute hyperandrogenic women and the influence of adrenal androgen. Human reproduction (Oxford, England). 1995 Feb; 10(2):299-303. doi: 10.1093/oxfordjournals.humrep.a135931. [PMID: 7769052]
  • H Zwicker, R S Rittmaster. Androsterone sulfate: physiology and clinical significance in hirsute women. The Journal of clinical endocrinology and metabolism. 1993 Jan; 76(1):112-6. doi: 10.1210/jcem.76.1.8380602. [PMID: 8380602]
  • K G Fehér, T Fehér. Plasma dehydroepiandrosterone, dehydroepiandrosterone sulphate and androsterone sulphate levels and their interaction with plasma proteins in rheumatoid arthritis. Experimental and clinical endocrinology. 1984 Oct; 84(2):197-202. doi: 10.1055/s-0029-1210387. [PMID: 6241153]
  • C E Bird, J Murphy, K Boroomand, W Finnis, D Dressel, A F Clark. Dehydroepiandrosterone: kinetics of metabolism in normal men and women. The Journal of clinical endocrinology and metabolism. 1978 Oct; 47(4):818-22. doi: 10.1210/jcem-47-4-818. [PMID: 162518]
  • J E PLAGER. THE BINDING OF ANDROSTERONE SULFATE, ETHIOCHOLANOLONE SULFATE, AND DEHYDROISOANDROSTERONE SULFATE BY HUMAN PLASMA PROTEIN. The Journal of clinical investigation. 1965 Jul; 44(?):1234-9. doi: 10.1172/jci105229. [PMID: 14328399]
  • J MCKENNA, A E RIPPON. THE EXTRACTION OF PLASMA 3-HYDROXY-17-OXO STEROID SULPHATES AND THE MEASUREMENT OF THE CONSTITUENT DEHYDROEPIANDROSTERONE SULPHATE AND ANDROSTERONE SULPHATE. The Biochemical journal. 1965 Apr; 95(?):107-17. doi: 10.1042/bj0950107. [PMID: 14333546]
  • S H CONRAD, M C LINDBERG, W L HERRMANN. SIGNIFICANCE OF PLASMA DEHYDROISOANDROSTERONE AND ANDROSTERONE SULFATES IN THE DIAGNOSIS OF VIRILIZING DISORDERS. American journal of obstetrics and gynecology. 1965 Feb; 91(?):449-56. doi: 10.1016/0002-9378(65)90117-1. [PMID: 14259133]
  • W STAIB, F SCHARF, F DJAVADIAN. [Steroid conjugates. VII. Excretion of dehydroisoandrosterone sulfate and androsterone sulfate in human urine]. Hoppe-Seyler's Zeitschrift fur physiologische Chemie. 1961 Sep; 325(?):177-82. doi: 10.1515/bchm2.1961.325.1.177. [PMID: 13916108]