Androsterone glucuronide (BioDeep_00000001298)

 

Secondary id: BioDeep_00001875320

human metabolite Endogenous blood metabolite


代谢物信息卡片


(2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

化学式: C25H38O8 (466.2566548)
中文名称: 雄酮葡萄糖醛酸
谱图信息: 最多检出来源 Macaca mulatta(otcml) 4.34%

Reviewed

Last reviewed on 2024-07-16.

Cite this Page

Androsterone glucuronide. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/androsterone_glucuronide (retrieved 2024-11-09) (BioDeep RN: BioDeep_00000001298). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4=O)C)OC5C(C(C(C(O5)C(=O)O)O)O)O
InChI: InChI=1S/C25H38O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,13+,14-,15-,16-,18-,19-,20+,21-,23+,24-,25-/m0/s1

描述信息

Androsterone glucuronide (ADT-G) is one of the major circulating C19-steroid metabolites in humans. Human and monkey are unique in having high levels of circulating ADT-G. Furthermore, the plasma levels of these glucuronide derivatives reflect the peripheral tissue conversion of adrenal and gonadal precursor C19-steroids to active androgens in various pathophysiological conditions. Identification and characterization of human UDP-glucuronosyltransferase 2B (UGT2Bs) demonstrated the major role that these enzymes play in androgen conjugation, with UGT2B15 and UGT2B17 (EC 2.4.1.17) being the major androsterone-conjugating isoforms. Exaggerated androsterone metabolism, is observed in hyper-androgenic as well as in some normo-androgenic women with acne and androsterone glucuronide could be a marker in differentiating acne and hirsutism in hyperandrogenic women. Present data shows that the most practical and probably only valid means of assessing androgenic activity in women is to measure ADT-G, the metabolite that accounts for 93\\% of the total androgen glucuronide derivatives. (PMID: 12943709, 12445184, 16621522) [HMDB]
Androsterone glucuronide (ADT-G) is one of the major circulating C19-steroid metabolites in humans. Human and monkey are unique in having high levels of circulating ADT-G. Furthermore, the plasma levels of these glucuronide derivatives reflect the peripheral tissue conversion of adrenal and gonadal precursor C19-steroids to active androgens in various pathophysiological conditions. Identification and characterization of human UDP-glucuronosyltransferase 2B (UGT2Bs) demonstrated the major role that these enzymes play in androgen conjugation, with UGT2B15 and UGT2B17 (EC 2.4.1.17) being the major androsterone-conjugating isoforms. Exaggerated androsterone metabolism, is observed in hyper-androgenic as well as in some normo-androgenic women with acne and androsterone glucuronide could be a marker in differentiating acne and hirsutism in hyperandrogenic women. Present data shows that the most practical and probably only valid means of assessing androgenic activity in women is to measure ADT-G, the metabolite that accounts for 93\\% of the total androgen glucuronide derivatives. (PMID: 12943709, 12445184, 16621522).
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

同义名列表

22 个代谢物同义名

(2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid; 6-[(10,13-dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid; (3alpha,5alpha)-17-Oxoandrostan-3-yl beta-D-glucopyranosiduronic acid; Androsterone glucuronide, sodium salt, (3alpha,5alpha)-isomer; Androsterone glucuronide, sodium salt, (3alpha,5beta)-isomer; b-D-17-oxo-5a-Androstan-3a-yl glucopyranosiduronic acid; 3alpha-hydroxy-5alpha-androstan-17-one 3-D-glucuronide; 3alpha-Hydroxy-5alpha-androstan-17-one glucuronide; Androsterone glucuronide, (3beta,5alpha)-isomer; 3Α-hydroxy-5α-androstan-17-one glucuronide; 3a-Hydroxy-5a-androstan-17-one glucuronide; Androsterone glucuronide, (beta-D)-isomer; 5a-Androstan-3a-ol-17-one glucuronide; androsterone 3-glucosiduronic acid; Androsterone monoglucosiduronate; Androsterone glucosiduronic acid; Androsterone glucosiduronate; Etiocholanolone glucuronide; Androsterone 3-glucuronide; Androsterone glucuronoside; Androsterone glucuronide; ST 19:1;O2;GlcA



数据库引用编号

14 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

6 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(6)

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

  • 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]
  • 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]
  • 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]
  • 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]
  • Yuyong Ke, Renaud Gonthier, Maxim Isabelle, Jonathan Bertin, Jean-Nicolas Simard, Alain Y Dury, Fernand Labrie. A rapid and sensitive UPLC-MS/MS method for the simultaneous quantification of serum androsterone glucuronide, etiocholanolone glucuronide, and androstan-3α, 17β diol 17-glucuronide in postmenopausal women. The Journal of steroid biochemistry and molecular biology. 2015 May; 149(?):146-52. doi: 10.1016/j.jsbmb.2015.02.009. [PMID: 25701608]
  • Sarah Wåhlin-Jacobsen, Anette Tønnes Pedersen, Ellids Kristensen, Nanna Cassandra Laessøe, Marika Lundqvist, Arieh S Cohen, David M Hougaard, Annamaria Giraldi. Is there a correlation between androgens and sexual desire in women?. The journal of sexual medicine. 2015 Feb; 12(2):358-73. doi: 10.1111/jsm.12774. [PMID: 25475395]
  • Richard J Auchus, Elizabeth O Buschur, Alice Y Chang, Gary D Hammer, Carole Ramm, David Madrigal, George Wang, Martha Gonzalez, Xu Steven Xu, Johan W Smit, James Jiao, Margaret K Yu. Abiraterone acetate to lower androgens in women with classic 21-hydroxylase deficiency. The Journal of clinical endocrinology and metabolism. 2014 Aug; 99(8):2763-70. doi: 10.1210/jc.2014-1258. [PMID: 24780050]
  • 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]
  • 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]
  • Fernand Labrie, Leonello Cusan, Jose-Luis Gomez, Céline Martel, René Bérubé, Patrick Bélanger, Véronique Chaussade, Claire Deloche, Jacques Leclaire. Changes in serum DHEA and eleven of its metabolites during 12-month percutaneous administration of DHEA. The Journal of steroid biochemistry and molecular biology. 2008 May; 110(1-2):1-9. doi: 10.1016/j.jsbmb.2008.02.003. [PMID: 18359622]
  • Peter Gärtner, Clemens Novak, Christian Einzinger, Wolfgang Felzmann, Max Knollmüller, Günter Gmeiner, Wilhelm Schänzer. A facile and high yielding synthesis of 2,2,3,4,4-d5-androsterone-beta-D-glucuronide--an internal standard in dope. Steroids. 2003 Jan; 68(1):85-96. doi: 10.1016/s0039-128x(02)00119-8. [PMID: 12575693]
  • E Carmina, A J Godwin, F Z Stanczyk, J S Lippman, R A Lobo. The association of serum androsterone glucuronide with inflammatory lesions in women with adult acne. Journal of endocrinological investigation. 2002 Oct; 25(9):765-8. doi: 10.1007/bf03345509. [PMID: 12398233]
  • Olavi Ukkola, Tuomo Rankinen, Jacques Gagnon, Arthur S Leon, James S Skinner, Jack H Wilmore, D C Rao, Claude Bouchard. A genome-wide linkage scan for steroids and SHBG levels in black and white families: the HERITAGE Family Study. The Journal of clinical endocrinology and metabolism. 2002 Aug; 87(8):3708-20. doi: 10.1210/jcem.87.8.8725. [PMID: 12161500]
  • Y Hong, J Gagnon, T Rice, L Pérusse, A S Leon, J S Skinner, J H Wilmore, C Bouchard, D C Rao. Familial resemblance for free androgens and androgen glucuronides in sedentary black and white individuals: the HERITAGE Family Study. Health, Risk Factors, Exercise Training and Genetics. The Journal of endocrinology. 2001 Aug; 170(2):485-92. doi: 10.1677/joe.0.1700485. [PMID: 11479145]
  • A H Wu, A S Whittemore, L N Kolonel, F Z Stanczyk, E M John, R P Gallagher, D W West. Lifestyle determinants of 5alpha-reductase metabolites in older African-American, white, and Asian-American men. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2001 May; 10(5):533-8. doi: . [PMID: 11352865]
  • J Pritchard, J P Després, J Gagnon, A Tchernof, A Nadeau, A Tremblay, C Bouchard. Plasma adrenal, gonadal, and conjugated steroids following long-term exercise-induced negative energy balance in identical twins. Metabolism: clinical and experimental. 1999 Sep; 48(9):1120-7. doi: 10.1016/s0026-0495(99)90125-7. [PMID: 10484051]
  • J Pritchard, J P Després, J Gagnon, A Tchernof, A Nadeau, A Tremblay, C Bouchard. Plasma adrenal, gonadal, and conjugated steroids before and after long-term overfeeding in identical twins. The Journal of clinical endocrinology and metabolism. 1998 Sep; 83(9):3277-84. doi: 10.1210/jcem.83.9.5136. [PMID: 9745441]
  • J Young, B Couzinet, K Nahoul, S Brailly, P Chanson, E E Baulieu, G Schaison. Panhypopituitarism as a model to study the metabolism of dehydroepiandrosterone (DHEA) in humans. The Journal of clinical endocrinology and metabolism. 1997 Aug; 82(8):2578-85. doi: 10.1210/jcem.82.8.4157. [PMID: 9253337]
  • A Tchernof, F Labrie, A Bélanger, D Prud'homme, C Bouchard, A Tremblay, A Nadeau, J P Després. Androstane-3alpha,17beta-diol glucuronide as a steroid correlate of visceral obesity in men. The Journal of clinical endocrinology and metabolism. 1997 May; 82(5):1528-34. doi: 10.1210/jcem.82.5.3924. [PMID: 9141545]
  • H A Guess, G D Friedman, M C Sadler, F Z Stanczyk, J H Vogelman, J Imperato-McGinley, R A Lobo, N Orentreich. 5 alpha-reductase activity and prostate cancer: a case-control study using stored sera. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 1997 Jan; 6(1):21-4. doi: . [PMID: 8993793]
  • B Lavallée, P R Provost, Z Kahwash, J E Nestler, A Bélanger. Effect of insulin on serum levels of dehydroepiandrosterone metabolites in men. Clinical endocrinology. 1997 Jan; 46(1):93-100. doi: 10.1046/j.1365-2265.1997.d01-1736.x. [PMID: 9059564]
  • J Brind, N Borofsky, K Chervinsky, J H Vogelman, N Orentreich. A simple, differential extraction method for the simultaneous direct radioimmunoassay of androgens and androgen glucuronides in human serum. Steroids. 1996 Jul; 61(7):429-32. doi: 10.1016/0039-128x(96)00063-3. [PMID: 8837296]
  • P Boudou, C Naret, J Fiet, R Bonete, G Tritto, A Le Duc, J L Poignet, N K Man. Accumulation of 5 alpha-reduced androgen glucosiduronates associated with impaired removal in young male hemodialysis patients. The Journal of clinical endocrinology and metabolism. 1995 Dec; 80(12):3489-93. doi: 10.1210/jcem.80.12.8530588. [PMID: 8530588]
  • D M Duffy, R S Legro, L Chang, F Z Stanczyk, R A Lobo. Metabolism of dihydrotestosterone to 5 alpha-androstane-3 alpha, 17 beta-diol glucuronide is greater in the peripheral compartment than in the splanchnic compartment. Fertility and sterility. 1995 Oct; 64(4):736-9. doi: 10.1016/s0015-0282(16)57848-0. [PMID: 7672144]
  • E Carmina, F Z Stanczyk, E Gentzchein, R A Lobo. Time-dependent changes in serum 3 alpha-androstanediol glucuronide correlate with hirsutism scores after ovarian suppression. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology. 1995 Sep; 9(3):215-20. doi: 10.3109/09513599509160449. [PMID: 8540291]
  • 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]
  • V A Giagulli, J M Kaufman, A Vermeulen. Pathogenesis of the decreased androgen levels in obese men. The Journal of clinical endocrinology and metabolism. 1994 Oct; 79(4):997-1000. doi: 10.1210/jcem.79.4.7962311. [PMID: 7962311]
  • E Carmina, R A Lobo. Evidence for increased androsterone metabolism in some normoandrogenic women with acne. The Journal of clinical endocrinology and metabolism. 1993 May; 76(5):1111-4. doi: 10.1210/jcem.76.5.8496299. [PMID: 8496299]
  • V A Giagulli, R Giorgino, A Vermeulen. Origin and significance of plasma androsterone glucuronide levels: a parameter of adrenal androgen secretion and hepatic 5 alpha-reductase activity. The Journal of clinical endocrinology and metabolism. 1993 Apr; 76(4):918-23. doi: 10.1210/jcem.76.4.8473406. [PMID: 8473406]
  • R A Miles, D L Cassidenti, E Carmina, E Gentzschein, F Z Stanczyk, R A Lobo. Cutaneous application of an androstenedione gel as an in vivo test of 5 alpha-reductase activity in women. Fertility and sterility. 1992 Oct; 58(4):708-12. doi: 10.1016/s0015-0282(16)55316-3. [PMID: 1426314]
  • V A Giagulli, G De Pergola, F Giorgino, M Cignarelli, G Abbaticchio, A Vermeulen, R Giorgino. Increased free testosterone but normal 5 alpha-reduced testosterone metabolites in obese premenopausal women. Clinical endocrinology. 1992 Jun; 36(6):553-8. doi: 10.1111/j.1365-2265.1992.tb02264.x. [PMID: 1424180]
  • C B Whorwood, H Ueshiba, P del Blazo. Plasma levels of C19 steroid glucuronides in pre-menopausal women with non-classical congenital adrenal hyperplasia. The Journal of steroid biochemistry and molecular biology. 1992 Apr; 42(2):211-21. doi: 10.1016/0960-0760(92)90030-m. [PMID: 1314640]
  • E Carmina, R A Lobo. Peripheral androgen blockade versus glandular androgen suppression in the treatment of hirsutism. Obstetrics and gynecology. 1991 Nov; 78(5 Pt 1):845-9. doi: NULL. [PMID: 1833685]
  • D P Lookingbill, L M Demers, C Wang, A Leung, R S Rittmaster, R J Santen. Clinical and biochemical parameters of androgen action in normal healthy Caucasian versus Chinese subjects. The Journal of clinical endocrinology and metabolism. 1991 Jun; 72(6):1242-8. doi: 10.1210/jcem-72-6-1242. [PMID: 1827450]
  • D L Thompson, N Horton, R S Rittmaster. Androsterone glucuronide is a marker of adrenal hyperandrogenism in hirsute women. Clinical endocrinology. 1990 Mar; 32(3):283-92. doi: 10.1111/j.1365-2265.1990.tb00868.x. [PMID: 2160872]
  • D S Kiddy, P S Sharp, D M White, M F Scanlon, H D Mason, C S Bray, D W Polson, M J Reed, S Franks. Differences in clinical and endocrine features between obese and non-obese subjects with polycystic ovary syndrome: an analysis of 263 consecutive cases. Clinical endocrinology. 1990 Feb; 32(2):213-20. doi: 10.1111/j.1365-2265.1990.tb00857.x. [PMID: 2112067]
  • R S Rittmaster, E Stoner, D L Thompson, D Nance, K C Lasseter. Effect of MK-906, a specific 5 alpha-reductase inhibitor, on serum androgens and androgen conjugates in normal men. Journal of andrology. 1989 Jul; 10(4):259-62. doi: 10.1002/j.1939-4640.1989.tb00097.x. [PMID: 2550402]
  • A Bélanger, F Labrie, A Dupont, M Brochu, L Cusan. Endocrine effects of combined treatment with an LHRH agonist in association with flutamide in metastatic prostatic carcinoma. Clinical and investigative medicine. Medecine clinique et experimentale. 1988 Oct; 11(5):321-6. doi: . [PMID: 2972431]
  • M Brochu, A Bélanger, A Dupont, L Cusan, F Labrie. Effects of flutamide and aminoglutethimide on plasma 5 alpha-reduced steroid glucuronide concentrations in castrated patients with cancer of the prostate. Journal of steroid biochemistry. 1987 Dec; 28(6):619-22. doi: 10.1016/0022-4731(87)90388-8. [PMID: 2961945]
  • S H Andersson, T Cronholm, J Sjövall. Effects of ethanol on conjugated gonadal hormones in plasma of men. Alcohol and alcoholism (Oxford, Oxfordshire). Supplement. 1987; 1(?):529-31. doi: NULL. [PMID: 3426728]
  • J P Deslypere, G de Biscop, A Vermeulen. Seasonal variation of plasma dehydroepiandrosterone sulphate and urinary androgen excretion in post-menopausal women. Clinical endocrinology. 1983 Jan; 18(1):25-30. doi: 10.1111/j.1365-2265.1983.tb03182.x. [PMID: 6221834]
  • Y Shinohara, S Baba, Y Kasuya. Absorption, metabolism, and excretion of oral testosterone in humans by mass fragmentography. The Journal of clinical endocrinology and metabolism. 1980 Dec; 51(6):1459-62. doi: 10.1210/jcem-51-6-1459. [PMID: 7440707]
  • J ZANDER, J SCHMIDT-THOME. [Androsterone glucuronide excretion following injection of testosterone]. Klinische Wochenschrift. 1954 Jan; 32(1-2):24-7. doi: 10.1007/bf01470053. [PMID: 13143676]