3b-Allotetrahydrocortisol (BioDeep_00000002839)

 

Secondary id: BioDeep_00000027672, BioDeep_00000637531, BioDeep_00000873066

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


2-hydroxy-1-[(1S,2S,5S,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one

化学式: C21H34O5 (366.24061140000003)
中文名称: 5α-孕烷-3β,11β,17α,21-四醇-20-酮, 四氢皮质醇, 四氢皮质醇
谱图信息: 最多检出来源 Viridiplantae(plant) 1.01%

分子结构信息

SMILES: CC12CCC(CC1CCC3C2C(CC4(C3CCC4(C(=O)CO)O)C)O)O
InChI: InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3

描述信息

3b-Allotetrahydrocortisol is one of the tetrahydrometabolites of cortisol. The 11-beta-hydroxysteroid dehydrogenase (11beta-HSD) is responsible for the interconversion of both the hormonally inactive cortisone and the active cortisol, which has implications in the pathogenesis of numerous diseases, as reflected in the ratio of tetrahydrometabolites of cortisol. (PMID: 16310418). The daily excretion of allotetrahydrocortisol is above normal in hyperthyroid patients; In contrast, in hyperthyroidism the excretion is diminished below normal levels to approximately half that of normal subjects. (PMID 13906284). A decreased activity of the enzyme 11beta-HSD produces a pattern of urinary steroid metabolites with an abnormal elevation of tetrahydrocortisol and allo-tetrahydrocortisol compared to tetrahydrocortisone; this pattern of steroid excretion is essential for the diagnosis of the syndrome of apparent mineralocorticoid excess type 1. (PMID: 8834992).
3b-Allotetrahydrocortisol is one of the tetrahydrometabolites of cortisol. The 11-beta-hydroxysteroid dehydrogenase (11beta-HSD) is responsible for the interconversion of both the hormonally inactive cortisone and the active cortisol, which has implications in the pathogenesis of numerous diseases, as reflected in the ratio of tetrahydrometabolites of cortisol. (PMID: 16310418)
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
Tetrahydrocortisol is cortisol metabolite. The urinary Tetrahydrocortisol/Tetrahydrocortisone ratio decreases with increasing 11β-hydroxysteroid dehydrogenase (11β-HSD) activity[1][2].

同义名列表

16 个代谢物同义名

2-hydroxy-1-[(1S,2S,5S,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one; 3alpha,11beta,17alpha,21-dihydroxy-5beta-pregnane-20-one; 3alpha,11beta,17,21-tetrahydroxy-5beta-pregnan-20-one; Pregnan-20-one,3,11,17,21-tetrahydroxy-, (3a,5b,11b)-; Allopregnane-3beta,11beta,17alpha,21-tetrol-20-one; 3,11,17,21-Tetrahydroxypregnan-20-one; Allo-3-beta-tetrahydrocortisol; 3b-Allotetrahydrocortisol; 3b,5a-Tetrahydrocortisol; ReichsteinS substance V; ALLOTETRAHYDROCORTISOL; reichstein substance V; 5b-Tetrahydrocortisol; Tetrahydrocortisol; Urocortisol; Tetrahydrocortisol



数据库引用编号

21 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)

1 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

  • Susanna Bianzano, Matias Nordaby, Leona Plum-Mörschel, Barbara Peil, Tim Heise. Safety, tolerability, pharmacodynamics and pharmacokinetics following once-daily doses of BI 187004, an inhibitor of 11 beta-hydroxysteroid dehydrogenase-1, over 28 days in patients with type 2 diabetes mellitus and overweight or obesity. Diabetes, obesity & metabolism. 2023 Mar; 25(3):832-843. doi: 10.1111/dom.14932. [PMID: 36478142]
  • Thi Chi Mai Tran, Thi Ngoc Anh Tran, Hoang Bich Nga Le, Viet Hoa Nguyen, Minh Dien Tran, Chi Dung Vu, Ronda F Greaves. Validation of steroid ratios for random urine by mass spectrometry to detect 5α-reductase deficiency in Vietnamese children. Clinical chemistry and laboratory medicine. 2022 07; 60(8):1225-1233. doi: 10.1515/cclm-2022-0272. [PMID: 35607271]
  • Chaelin Lee, Seung Mi Lee, Dong Jun Byun, So Yeon Kim, Hugh I Kim, Do Yup Lee, Young Mi Jung, Chan-Wook Park, Joong Shin Park, Man Ho Choi. Maternal Signatures of Cortisol in First Trimester Small-for-Gestational Age. Reproductive sciences (Thousand Oaks, Calif.). 2022 05; 29(5):1498-1505. doi: 10.1007/s43032-021-00822-w. [PMID: 35001327]
  • Stéphanie Espiard, Johanna McQueen, Mark Sherlock, Oskar Ragnarsson, Ragnhildur Bergthorsdottir, Pia Burman, Per Dahlqvist, Bertil Ekman, Britt Edén Engström, Stanko Skrtic, Jeanette Wahlberg, Paul M Stewart, Gudmundur Johannsson. Improved Urinary Cortisol Metabolome in Addison Disease: A Prospective Trial of Dual-Release Hydrocortisone. The Journal of clinical endocrinology and metabolism. 2021 03; 106(3):814-825. doi: 10.1210/clinem/dgaa862. [PMID: 33236103]
  • Katarzyna Kosicka, Anna Siemiątkowska, Dąbrówka Pałka, Agata Szpera-Goździewicz, Grzegorz H Bręborowicz, Franciszek K Główka. Detailed analysis of cortisol, cortisone and their tetrahydro- and allo-tetrahydrometabolites in human urine by LC-MS/MS. Journal of pharmaceutical and biomedical analysis. 2017 Jun; 140(?):174-181. doi: 10.1016/j.jpba.2017.03.039. [PMID: 28359965]
  • Scott P Webster, Andrew McBride, Margaret Binnie, Karen Sooy, Jonathan R Seckl, Ruth Andrew, T David Pallin, Hazel J Hunt, Trevor R Perrior, Vincent S Ruffles, J William Ketelbey, Alan Boyd, Brian R Walker. Selection and early clinical evaluation of the brain-penetrant 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor UE2343 (Xanamem™). British journal of pharmacology. 2017 03; 174(5):396-408. doi: 10.1111/bph.13699. [PMID: 28012176]
  • Luca Chiesa, Sara Panseri, Radmila Pavlovic, Francesca Tiziana Cannizzo, Bartolomeo Biolatti, Sara Divari, Roberto Villa, Francesco Arioli. HPLC-ESI-MS/MS assessment of the tetrahydro-metabolites of cortisol and cortisone in bovine urine: promising markers of dexamethasone and prednisolone treatment. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2016 Jul; 33(7):1175-89. doi: 10.1080/19440049.2016.1202453. [PMID: 27310211]
  • Laura C Torchen, Jan Idkowiak, Naomi R Fogel, Donna M O'Neil, Cedric H L Shackleton, Wiebke Arlt, Andrea Dunaif. Evidence for Increased 5α-Reductase Activity During Early Childhood in Daughters of Women With Polycystic Ovary Syndrome. The Journal of clinical endocrinology and metabolism. 2016 05; 101(5):2069-75. doi: 10.1210/jc.2015-3926. [PMID: 26990942]
  • Judith Buehlmeier, Thomas Remer, Petra Frings-Meuthen, Christiane Maser-Gluth, Martina Heer. Glucocorticoid activity and metabolism with NaCl-induced low-grade metabolic acidosis and oral alkalization: results of two randomized controlled trials. Endocrine. 2016 Apr; 52(1):139-47. doi: 10.1007/s12020-015-0730-7. [PMID: 26349936]
  • Laura I Stirrat, James R O'Reilly, Sarah M Barr, Ruth Andrew, Simon C Riley, Alexander F Howie, Maria Bowman, Roger Smith, John G Lewis, Fiona C Denison, Shareen Forbes, Jonathan R Seckl, Brian R Walker, Jane E Norman, Rebecca M Reynolds. Decreased maternal hypothalamic-pituitary-adrenal axis activity in very severely obese pregnancy: Associations with birthweight and gestation at delivery. Psychoneuroendocrinology. 2016 Jan; 63(?):135-43. doi: 10.1016/j.psyneuen.2015.09.019. [PMID: 26444587]
  • Xuejia Zhai, Fen Chen, Chaoran Zhu, Yongning Lu. A simple LC-MS/MS method for the determination of cortisol, cortisone and tetrahydro-metabolites in human urine: assay development, validation and application in depression patients. Journal of pharmaceutical and biomedical analysis. 2015 Mar; 107(?):450-5. doi: 10.1016/j.jpba.2015.01.041. [PMID: 25668797]
  • Luigi Di Luigi, Francesco Botrè, Stefania Sabatini, Massimiliano Sansone, Monica Mazzarino, Laura Guidetti, Carlo Baldari, Andrea Lenzi, Daniela Caporossi, Francesco Romanelli, Paolo Sgrò. Acute effects of physical exercise and phosphodiesterase's type 5 inhibition on serum 11β-hydroxysteroid dehydrogenases related glucocorticoids metabolites: a pilot study. Endocrine. 2014 Dec; 47(3):952-8. doi: 10.1007/s12020-014-0185-2. [PMID: 24532078]
  • Xiaoya Hu, Yan Zhao, Beitao Chen, Yuan Liang, Luxi Li, Changming Xie, Yunhui Zhang, Zhenlang Lin, Ailan Xie, Shangqin Chen. [11beta-hydroxysteroid dehydrogenase type 2 enzyme activity effect after exposures phthalate esters in maternal]. Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine]. 2014 Sep; 48(9):800-4. doi: . [PMID: 25492292]
  • Weidong Dai, Peiyuan Yin, Ping Chen, Hongwei Kong, Ping Luo, Zhiliang Xu, Xin Lu, Guowang Xu. Study of urinary steroid hormone disorders: difference between hepatocellular carcinoma in early stage and cirrhosis. Analytical and bioanalytical chemistry. 2014 Jul; 406(18):4325-35. doi: 10.1007/s00216-014-7843-3. [PMID: 24817358]
  • Nils Eiel Steen, Paal Methlie, Steinar Lorentzen, Ingrid Dieset, Monica Aas, Mari Nerhus, Marit Haram, Ingrid Agartz, Ingrid Melle, Jens P Berg, Ole A Andreassen. Altered systemic cortisol metabolism in bipolar disorder and schizophrenia spectrum disorders. Journal of psychiatric research. 2014 May; 52(?):57-62. doi: 10.1016/j.jpsychires.2014.01.017. [PMID: 24534618]
  • Gregori Casals, Josep Marcos, Óscar J Pozo, Paula Aguilera, Carmen Herrero, Jordi To-Figueras. Gas chromatography-mass spectrometry profiling of steroids in urine of patients with acute intermittent porphyria. Clinical biochemistry. 2013 Jun; 46(9):819-24. doi: 10.1016/j.clinbiochem.2013.03.001. [PMID: 23499585]
  • E Rask, K Simonyte, L Lönn, M Axelson. Cortisol metabolism after weight loss: associations with 11 β-HSD type 1 and markers of obesity in women. Clinical endocrinology. 2013 May; 78(5):700-5. doi: 10.1111/j.1365-2265.2012.04333.x. [PMID: 22233384]
  • Radmila Pavlovic, Francesca Tiziana Cannizzo, Sara Panseri, Bartolomeo Biolatti, Natasa Trutic, Pier Antonio Biondi, Luca Chiesa. Tetrahydro-metabolites of cortisol and cortisone in bovine urine evaluated by HPLC-ESI-mass spectrometry. The Journal of steroid biochemistry and molecular biology. 2013 May; 135(?):30-5. doi: 10.1016/j.jsbmb.2012.12.015. [PMID: 23291109]
  • Jun Niu, Zifeng Pi, Hao Yue, Yang Wang, Qing Yu, Shuying Liu. Effect of ginseng polysaccharide on the urinary excretion of type 2 diabetic rats studied by liquid chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Oct; 907(?):7-12. doi: 10.1016/j.jchromb.2012.08.012. [PMID: 22998979]
  • Anil Mongia, Risa Vecker, Minu George, Anita Pandey, Hanan Tawadrous, Morris Schoeneman, Ozgul Muneyyirci-Delale, Vijaya Nacharaju, Svetlana Ten, Amrit Bhangoo. Role of 11βHSD type 2 enzyme activity in essential hypertension and children with chronic kidney disease (CKD). The Journal of clinical endocrinology and metabolism. 2012 Oct; 97(10):3622-9. doi: 10.1210/jc.2012-1411. [PMID: 22872687]
  • Carmen Campino, Hector Quinteros, Gareth I Owen, Cristian A Carvajal, Mauricio Morales, Oliviero Olivieri, Giancesare Guidi, Giovanni Faccini, Francesco Pasini, Rene Baudrand, Oslando Padilla, Carolina Valdivia, Juan Thichauer, Carlos F Lagos, Alexis M Kalergis, Carlos E Fardella. 11β-hydroxysteroid dehydrogenase type 2 polymorphisms and activity in a Chilean essential hypertensive and normotensive cohort. American journal of hypertension. 2012 May; 25(5):597-603. doi: 10.1038/ajh.2011.263. [PMID: 22278213]
  • Ildikó Bíró, Anita Bufa, Ferenc Wilhelm, Zoltán Mánfai, Ferenc Kilár, Péter Miklós Gocze. Urinary steroid profile in early pregnancy after in vitro fertilization. Acta obstetricia et gynecologica Scandinavica. 2012 May; 91(5):625-9. doi: 10.1111/j.1600-0412.2012.01387.x. [PMID: 22375705]
  • Wiebke Arlt, Michael Biehl, Angela E Taylor, Stefanie Hahner, Rossella Libé, Beverly A Hughes, Petra Schneider, David J Smith, Han Stiekema, Nils Krone, Emilio Porfiri, Giuseppe Opocher, Jerôme Bertherat, Franco Mantero, Bruno Allolio, Massimo Terzolo, Peter Nightingale, Cedric H L Shackleton, Xavier Bertagna, Martin Fassnacht, Paul M Stewart. Urine steroid metabolomics as a biomarker tool for detecting malignancy in adrenal tumors. The Journal of clinical endocrinology and metabolism. 2011 Dec; 96(12):3775-84. doi: 10.1210/jc.2011-1565. [PMID: 21917861]
  • Mark S Cooper, Hashir Kriel, Adrian Sayers, William D Fraser, Amanda M Williams, Paul M Stewart, Chris S Probert, Jonathan H Tobias. Can 11β-hydroxysteroid dehydrogenase activity predict the sensitivity of bone to therapeutic glucocorticoids in inflammatory bowel disease?. Calcified tissue international. 2011 Sep; 89(3):246-51. doi: 10.1007/s00223-011-9512-2. [PMID: 21695543]
  • Man Ho Choi, Ju-Yeon Moon, Sung-Hee Cho, Bong Chul Chung, Eun Jig Lee. Metabolic alteration of urinary steroids in pre- and post-menopausal women, and men with papillary thyroid carcinoma. BMC cancer. 2011 Aug; 11(?):342. doi: 10.1186/1471-2407-11-342. [PMID: 21824401]
  • Rong Liu, Faju Chen, Kun Zou, Tangbin Yang. One-step monoclonal antibody based enzyme-linked immunosorbent assay for direct determination of cortisol in serum. Hybridoma (2005). 2011 Jun; 30(3):279-86. doi: 10.1089/hyb.2010.0115. [PMID: 21707363]
  • Wassif S Wassif, Declan M McLoughlin, Royce P Vincent, Simon Conroy, Gerald F M Russell, Norman F Taylor. Steroid metabolism and excretion in severe anorexia nervosa: effects of refeeding. The American journal of clinical nutrition. 2011 May; 93(5):911-7. doi: 10.3945/ajcn.111.012666. [PMID: 21367953]
  • Alicja Kotłowska, Krzysztof Sworczak, Piotr Stepnowski. Urine metabolomics analysis for adrenal incidentaloma activity detection and biomarker discovery. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Feb; 879(5-6):359-63. doi: 10.1016/j.jchromb.2010.12.021. [PMID: 21247813]
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  • Andrea Dovio, Eliana Roveda, Chiara Sciolla, Angela Montaruli, Andrea Raffaelli, Alessandro Saba, Giovanna Calogiuri, Silvia De Francia, Paolo Borrione, Piero Salvadori, Franca Carandente, Alberto Angeli. Intense physical exercise increases systemic 11beta-hydroxysteroid dehydrogenase type 1 activity in healthy adult subjects. European journal of applied physiology. 2010 Mar; 108(4):681-7. doi: 10.1007/s00421-009-1265-5. [PMID: 19902242]
  • Carmen Campino, Cristian A Carvajal, Javiera Cornejo, Betty San Martín, Oliviero Olivieri, Giancesare Guidi, Giovanni Faccini, Francesco Pasini, Javiera Sateler, Rene Baudrand, Lorena Mosso, Gareth I Owen, Alexis M Kalergis, Oslando Padilla, Carlos E Fardella. 11β-Hydroxysteroid dehydrogenase type-2 and type-1 (11β-HSD2 and 11β-HSD1) and 5β-reductase activities in the pathogenia of essential hypertension. Endocrine. 2010 Feb; 37(1):106-14. doi: 10.1007/s12020-009-9269-9. [PMID: 19882252]
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  • Therése Andersson, Kotryna Simonyte, Ruth Andrew, Magnus Strand, Jonas Burén, Brian R Walker, Cecilia Mattsson, Tommy Olsson. Tissue-specific increases in 11beta-hydroxysteroid dehydrogenase type 1 in normal weight postmenopausal women. PloS one. 2009 Dec; 4(12):e8475. doi: 10.1371/journal.pone.0008475. [PMID: 20041117]
  • Shigeo Ikegawa, Maki Hasegawa, Rika Okihara, Chikara Shimidzu, Hitoshi Chiba, Takashi Iida, Kuniko Mitamura. Simultaneous determination of twelve tetrahydrocorticosteroid glucuronides in human urine by liquid chromatography/electrospray ionization-linear ion trap mass spectrometry. Analytical chemistry. 2009 Dec; 81(24):10124-35. doi: 10.1021/ac9018632. [PMID: 19874001]
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