17-beta-Estradiol-3-glucuronide (BioDeep_00000014555)

 

Secondary id: BioDeep_00000638200, BioDeep_00001868863

human metabolite Endogenous blood metabolite


代谢物信息卡片


(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-yl]oxy}oxane-2-carboxylic acid

化学式: C24H32O8 (448.20970719999997)
中文名称:
谱图信息: 最多检出来源 Macaca mulatta(otcml) 1.05%

分子结构信息

SMILES: CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4)OC5C(C(C(C(O5)C(=O)O)O)O)O
InChI: InChI=1S/C24H32O8/c1-24-9-8-14-13-5-3-12(10-11(13)2-4-15(14)16(24)6-7-17(24)25)31-23-20(28)18(26)19(27)21(32-23)22(29)30/h3,5,10,14-21,23,25-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,17+,18+,19+,20-,21+,23-,24+/m1/s1

描述信息

17beta-Estradiol 3-glucuronide belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton. 17beta-Estradiol 3-glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Estradiol glucuronide is believed to play an important role in the mechanism of 17beta-estradiol(E2)-mediated tumour formation. Conjugation with glucuronic acid lowers tissue levels by facilitating excretion. Heterotropic activation by daidzein appears to be specific for the glucuronidation of E2 because daidzein did not affect the glucuronidation of the 2- and 4-hydroxy metabolites of E2 (PMID: 16598814).
Estradiol glucuronide is believed to play important roles in the mechanism of 17beta-estradiol(E2)-mediated tumor formation. Conjugation with glucuronic acid lowers tissue levels by facilitating excretion.The heterotropic activation by daidzein appears to be specific for the glucuronidation of E2 because daidzein did not affect the glucuronidation of the 2- and 4-hydroxy metabolites of E2. (PMID: 16598814) [HMDB]
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

同义名列表

24 个代谢物同义名

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-yl]oxy}oxane-2-carboxylic acid; (17beta)-17-Hydroxyestra-1,3,5(10)-trien-3-yl beta-D-glucopyranosiduronic acid; (17Β)-17-hydroxyestra-1,3,5(10)-trien-3-yl β-D-glucopyranosiduronic acid; estra-1,3,5(10)-triene-3,17beta-diol 3-D-glucuronide; 17β-Estradiol 3-(β-D-glucuronide); Estradiol-17beta-3-(beta-D-glucuronide); 17beta-Estradiol 3-(beta-D-glucuronide); 17beta-Estradiol 3-glucosiduronate; 17b-Estradiol 3-(b-D-glucuronide); 17Β-estradiol 3-(β-D-glucuronide); Estradiol-17β-3-(β-D-glucuronide); 17Β-estradiol 3-glucosiduronate; 17-beta-Estradiol-3-glucuronide; Estradiol-17beta 3-glucuronide; 17beta-Estradiol 3-glucuronide; 17-b-Estradiol-3-glucuronide; 17-Β-estradiol-3-glucuronide; Estradiol 3-glucosiduronate; 17b-Estradiol 3-glucuronide; 17Β-estradiol 3-glucuronide; Estradiol-17b 3-glucuronide; Estradiol-17β 3-glucuronide; Estradiol 3-glucuronide; Estradiol-3-glucuronide



数据库引用编号

18 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

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(2)

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

  • Muren, Satoshi Kusuda, Osamu Doi, Hitomi Naito, Hisashi Hashikawa. Puberty, ovarian cycle, pregnancy, and postpartum ovulation in captive Sichuan golden monkeys (Rhinopithecus roxellana) based on changes in urinary and fecal gonadal steroid metabolites. Theriogenology. 2017 Jan; 87(?):179-186. doi: 10.1016/j.theriogenology.2016.08.020. [PMID: 27743688]
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  • Yuichiro Sato, Masanori Nagata, Akio Kawamura, Aiji Miyashita, Takashi Usui. Protein quantification of UDP-glucuronosyltransferases 1A1 and 2B7 in human liver microsomes by LC-MS/MS and correlation with glucuronidation activities. Xenobiotica; the fate of foreign compounds in biological systems. 2012 Sep; 42(9):823-9. doi: 10.3109/00498254.2012.665950. [PMID: 22435749]
  • Heidi Kidron, Gloria Wissel, Nenad Manevski, Marika Häkli, Raimo A Ketola, Moshe Finel, Marjo Yliperttula, Henri Xhaard, Arto Urtti. Impact of probe compound in MRP2 vesicular transport assays. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2012 May; 46(1-2):100-5. doi: 10.1016/j.ejps.2012.02.016. [PMID: 22406294]
  • Dirk R de Waart, Koen van de Wetering, Cindy Kunne, Suzanne Duijst, Coen C Paulusma, Ronald P J Oude Elferink. Oral availability of cefadroxil depends on ABCC3 and ABCC4. Drug metabolism and disposition: the biological fate of chemicals. 2012 Mar; 40(3):515-21. doi: 10.1124/dmd.111.041731. [PMID: 22166395]
  • Rick Greupink, Lieve Dillen, Mario Monshouwer, Maarten T Huisman, Frans G M Russel. Interaction of fluvastatin with the liver-specific Na+ -dependent taurocholate cotransporting polypeptide (NTCP). European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2011 Nov; 44(4):487-96. doi: 10.1016/j.ejps.2011.09.009. [PMID: 21945488]
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  • Chunshan Gui, Bruno Hagenbuch. Cloning/characterization of the canine organic anion transporting polypeptide 1b4 (Oatp1b4) and classification of the canine OATP/SLCO members. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2010 Apr; 151(3):393-9. doi: 10.1016/j.cbpc.2010.01.005. [PMID: 20079461]
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  • P Sharma, V E Holmes, R Elsby, C Lambert, D Surry. Validation of cell-based OATP1B1 assays to assess drug transport and the potential for drug-drug interaction to support regulatory submissions. Xenobiotica; the fate of foreign compounds in biological systems. 2010 Jan; 40(1):24-37. doi: 10.3109/00498250903351013. [PMID: 19919292]
  • Dirk R de Waart, Maria L H Vlaming, Cindy Kunne, Alfred H Schinkel, Ronald P J Oude Elferink. Complex pharmacokinetic behavior of ezetimibe depends on abcc2, abcc3, and abcg2. Drug metabolism and disposition: the biological fate of chemicals. 2009 Aug; 37(8):1698-702. doi: 10.1124/dmd.108.026146. [PMID: 19443695]
  • M-K Choi, H Kim, Y-H Han, I-S Song, C-K Shim. Involvement of Mrp2/MRP2 in the species different excretion route of benzylpenicillin between rat and human. Xenobiotica; the fate of foreign compounds in biological systems. 2009 Feb; 39(2):171-81. doi: 10.1080/00498250802642256. [PMID: 19255943]
  • Fernando A Crocenzi, Enrique J Sánchez Pozzi, María Laura Ruiz, Andrés E Zucchetti, Marcelo G Roma, Aldo D Mottino, Mary Vore. Ca(2+)-dependent protein kinase C isoforms are critical to estradiol 17beta-D-glucuronide-induced cholestasis in the rat. Hepatology (Baltimore, Md.). 2008 Dec; 48(6):1885-95. doi: 10.1002/hep.22532. [PMID: 18972403]
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  • Carina Ankarberg-Lindgren, Ensio Norjavaara. Twenty-four hours secretion pattern of serum estradiol in healthy prepubertal and pubertal boys as determined by a validated ultra-sensitive extraction RIA. BMC endocrine disorders. 2008 Sep; 8(?):10. doi: 10.1186/1472-6823-8-10. [PMID: 18817534]
  • Lauren Oleson, Michael H Court. Effect of the beta-glucuronidase inhibitor saccharolactone on glucuronidation by human tissue microsomes and recombinant UDP-glucuronosyltransferases. The Journal of pharmacy and pharmacology. 2008 Sep; 60(9):1175-82. doi: 10.1211/jpp.60.9.0009. [PMID: 18718121]
  • Chunshan Gui, Yi Miao, Lucas Thompson, Bret Wahlgren, Melissa Mock, Bruno Stieger, Bruno Hagenbuch. Effect of pregnane X receptor ligands on transport mediated by human OATP1B1 and OATP1B3. European journal of pharmacology. 2008 Apr; 584(1):57-65. doi: 10.1016/j.ejphar.2008.01.042. [PMID: 18321482]
  • Brigitte Chanteranne, Francesco Branca, A Kaardinal, K Wahala, Véronique Braesco, Philippe Ladroite, Fred Brouns, Véronique Coxam. Food matrix and isoflavones bioavailability in early post menopausal women: a European clinical study. Clinical interventions in aging. 2008; 3(4):711-8. doi: 10.2147/cia.s4085. [PMID: 19281063]
  • Jessica X Jia, Kishor M Wasan. Effects of monoglycerides on rhodamine 123 accumulation, estradiol 17 beta-D-glucuronide bidirectional transport and MRP2 protein expression within Caco-2 cells. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2008; 11(3):45-62. doi: 10.18433/j33s3z. [PMID: 18801307]
  • Alexander Treiber, Ralph Schneiter, Stephanie Häusler, Bruno Stieger. Bosentan is a substrate of human OATP1B1 and OATP1B3: inhibition of hepatic uptake as the common mechanism of its interactions with cyclosporin A, rifampicin, and sildenafil. Drug metabolism and disposition: the biological fate of chemicals. 2007 Aug; 35(8):1400-7. doi: 10.1124/dmd.106.013615. [PMID: 17496208]
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  • Markus Grube, Sebastian Reuther, Henriette Meyer Zu Schwabedissen, Kathleen Köck, Katrin Draber, Christoph A Ritter, Christoph Fusch, Gabriele Jedlitschky, Heyo K Kroemer. Organic anion transporting polypeptide 2B1 and breast cancer resistance protein interact in the transepithelial transport of steroid sulfates in human placenta. Drug metabolism and disposition: the biological fate of chemicals. 2007 Jan; 35(1):30-5. doi: 10.1124/dmd.106.011411. [PMID: 17020956]
  • Gail F Jurgella, Ashok Marwah, Jeffrey A Malison, Richard Peterson, Terence P Barry. Effects of xenobiotics and steroids on renal and hepatic estrogen metabolism in lake trout. General and comparative endocrinology. 2006 Sep; 148(2):273-81. doi: 10.1016/j.ygcen.2006.03.011. [PMID: 16677648]
  • Naoki Ishiguro, Kazuya Maeda, Wataru Kishimoto, Asami Saito, Akiko Harada, Thomas Ebner, Willy Roth, Takashi Igarashi, Yuichi Sugiyama. Predominant contribution of OATP1B3 to the hepatic uptake of telmisartan, an angiotensin II receptor antagonist, in humans. Drug metabolism and disposition: the biological fate of chemicals. 2006 Jul; 34(7):1109-15. doi: 10.1124/dmd.105.009175. [PMID: 16611857]
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