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 (466.2567)
中文名称: 雄酮葡萄糖醛酸
谱图信息: 最多检出来源 Homo sapiens(lipidsearch) 34.81%

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 2024-12-22) (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

23 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; Androsterone glucuronide



数据库引用编号

16 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。

亚细胞结构定位 关联基因列表
Cytoplasm 3 AR, NT5C2, PGR
Peripheral membrane protein 1 CYP1B1
Endosome membrane 1 ITM2B
Endoplasmic reticulum membrane 4 CYP19A1, CYP1B1, UGT2B15, UGT2B17
Mitochondrion membrane 1 ABCG2
Nucleus 3 AR, KLK3, PGR
cytosol 3 AR, NT5C2, PGR
mitochondrial membrane 1 ABCG2
nucleoplasm 3 ABCG2, AR, PGR
Cell membrane 5 ABCG2, ITM2B, SLCO1B1, SLCO1B3, SLCO2B1
Multi-pass membrane protein 7 ABCC3, ABCG2, CYP19A1, SLC22A24, SLCO1B1, SLCO1B3, SLCO2B1
Golgi apparatus membrane 1 ITM2B
Golgi apparatus 1 ITM2B
Golgi membrane 2 INS, ITM2B
lysosomal membrane 1 EGF
Cytoplasm, cytosol 1 NT5C2
plasma membrane 11 ABCC3, ABCG2, AR, EGF, ITM2B, KLK3, PGR, SLC22A24, SLCO1B1, SLCO1B3, SLCO2B1
Membrane 12 ABCC3, ABCG2, AR, CYP19A1, CYP1B1, EGF, ITM2B, SLCO1B1, SLCO1B3, SLCO2B1, UGT2B15, UGT2B17
apical plasma membrane 2 ABCG2, SLCO2B1
basolateral plasma membrane 4 ABCC3, SLCO1B1, SLCO1B3, SLCO2B1
extracellular exosome 4 EGF, ITM2B, KLK3, SHBG
endoplasmic reticulum 1 CYP19A1
extracellular space 6 AMH, EGF, GNRH1, INS, ITM2B, KLK3
mitochondrion 1 CYP1B1
protein-containing complex 2 AR, KLK3
intracellular membrane-bounded organelle 2 CYP1B1, ITM2B
Microsome membrane 2 CYP19A1, CYP1B1
Secreted 3 AMH, INS, SHBG
extracellular region 7 AMH, EGF, GNRH1, INS, ITM2B, KLK3, SHBG
Single-pass membrane protein 2 UGT2B15, UGT2B17
mitochondrial outer membrane 1 PGR
Single-pass type II membrane protein 1 ITM2B
Apical cell membrane 2 ABCG2, SLCO2B1
Membrane raft 1 ABCG2
secretory granule 1 KLK3
nuclear speck 1 AR
chromatin 2 AR, PGR
brush border membrane 1 ABCG2
Basolateral cell membrane 4 ABCC3, SLCO1B1, SLCO1B3, SLCO2B1
organelle membrane 1 ITM2B
endosome lumen 1 INS
Golgi-associated vesicle membrane 1 ITM2B
basal plasma membrane 4 ABCC3, SLCO1B1, SLCO1B3, SLCO2B1
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 1 INS
platelet alpha granule lumen 1 EGF
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
clathrin-coated endocytic vesicle membrane 1 EGF
Basal cell membrane 4 ABCC3, SLCO1B1, SLCO1B3, SLCO2B1
external side of apical plasma membrane 1 ABCG2
[Isoform 4]: Mitochondrion outer membrane 1 PGR
[Integral membrane protein 2B]: Golgi apparatus membrane 1 ITM2B
[BRI2, membrane form]: Cell membrane 1 ITM2B
[Bri23 peptide]: Secreted 1 ITM2B
[BRI2C, soluble form]: Secreted 1 ITM2B


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]
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  • 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]
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  • 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]
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  • 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]
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