7a-Hydroxy-cholestene-3-one (BioDeep_00000005832)

Main id: BioDeep_00000010802

 

human metabolite Endogenous blood metabolite Volatile Flavor Compounds


代谢物信息卡片


(1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

化学式: C27H44O2 (400.3341124)
中文名称: 7α-羟基-4-胆固醇-3-酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2C(CC4=CC(=O)CCC34C)O)C
InChI: InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1

描述信息

7a-Hydroxy-cholestene-3-one is a metabolite in bile acid synthesis. It is derived from 7a-hydroxy-cholesterol and can be further metabolized to 7a,12a,-dihydroxy-cholest-4-en-3-one. Analysis of 7a-Hydroxycholestene-3-one (HCO) in serum may serve as a novel, simple, and sensitive method for the detection of bile acid malabsorption in patients with chronic diarrhea of unknown origin (PMID 9952217) [HMDB]
7a-Hydroxy-cholestene-3-one is a metabolite in bile acid synthesis. It is derived from 7a-hydroxy-cholesterol and can be further metabolized to 7a,12a,-dihydroxy-cholest-4-en-3-one. Analysis of 7a-Hydroxycholestene-3-one (HCO) in serum may serve as a novel, simple, and sensitive method for the detection of bile acid malabsorption in patients with chronic diarrhea of unknown origin (PMID 9952217).

同义名列表

23 个代谢物同义名

(1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one; 7a-Hydroxy-4-cholesten-3-one-12alpha; 7α-Hydroxycholest-4-en-3-one; 7 alpha-Hydroxy-4-cholesten-3-one; 7-alpha-Hydroxycholest-4-en-3-one; 7-alpha-Hydroxy-4-cholesten-3-one; 7alpha-Hydroxy-4-cholesten-3-one; 7alpha-Hydroxycholest-4-en-3-one; 7|A-Hydroxy-4-cholesten-3-one; 7-a-Hydroxycholest-4-en-3-one; Cholest-4-en-7 alpha-ol-3-one; 7-a-Hydroxy-4-cholesten-3-one; Cholest-4-en-7alpha-ol-3-one; 7a-Hydroxy-4-cholesten-3-one; 7α-Hydroxy-4-cholesten-3-one; 7-Hydroxycholest-4-en-3-one; 7-Hydroxy-4-cholesten-3-one; 7a-Hydroxy-cholestene-3-one; Cholest-4-en-7a-ol-3-one; Cholest-4-en-7α-ol-3-one; 7 alpha-3Ox-C; HCO; 7alpha-Hydroxycholest-4-en-3-one



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(11)

BioCyc(0)

PlantCyc(0)

代谢反应

169 个相关的代谢反应过程信息。

Reactome(144)

BioCyc(1)

WikiPathways(2)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(22)

PharmGKB(0)

4 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

  • Ivan Lyutakov, Valentin Lozanov, Paulina Sugareva, Hristo Valkov, Plamen Penchev. Serum 7-alfa-hydroxy-4-cholesten-3-one and fibroblast growth factor-19 as biomarkers diagnosing bile acid malabsorption in microscopic colitis and inflammatory bowel disease. European journal of gastroenterology & hepatology. 2021 03; 33(3):380-387. doi: 10.1097/meg.0000000000001925. [PMID: 33177381]
  • Ville Männistö, Dorota Kaminska, Pirjo Käkelä, Mikko Neuvonen, Mikko Niemi, Marcus Alvarez, Päivi Pajukanta, Stefano Romeo, Max Nieuwdorp, Albert K Groen, Jussi Pihlajamäki. Protein Phosphatase 1 Regulatory Subunit 3B Genotype at rs4240624 Has a Major Effect on Gallbladder Bile Composition. Hepatology communications. 2021 02; 5(2):244-257. doi: 10.1002/hep4.1630. [PMID: 33553972]
  • Lauren E Hughes, Clare Ford, Matthew J Brookes, Rousseau Gama. Bile acid diarrhoea: Current and potential methods of diagnosis. Annals of clinical biochemistry. 2021 01; 58(1):22-28. doi: 10.1177/0004563220966139. [PMID: 32998535]
  • Michael Camilleri, Priya Vijayvargiya. The Role of Bile Acids in Chronic Diarrhea. The American journal of gastroenterology. 2020 10; 115(10):1596-1603. doi: 10.14309/ajg.0000000000000696. [PMID: 32558690]
  • Philip N Newsome, Melissa Palmer, Bradley Freilich, Muhammad Y Sheikh, Aasim Sheikh, Harry Sarles, Robert Herring, Parvez Mantry, Zeid Kayali, Tarek Hassanein, Hak-Myung Lee, Guruprasad P Aithal. Volixibat in adults with non-alcoholic steatohepatitis: 24-week interim analysis from a randomized, phase II study. Journal of hepatology. 2020 08; 73(2):231-240. doi: 10.1016/j.jhep.2020.03.024. [PMID: 32234329]
  • Robert Battat, Marjolijn Duijvestein, Niels Vande Casteele, Siddharth Singh, Parambir S Dulai, Mark A Valasek, Larry Mimms, Judson McFarland, Kelly D Hester, Mark Renshaw, Anjali Jain, William J Sandborn, Brigid S Boland. Serum Concentrations of 7α-hydroxy-4-cholesten-3-one Are Associated With Bile Acid Diarrhea in Patients With Crohn's Disease. Clinical gastroenterology and hepatology : the official clinical practice journal of the American Gastroenterological Association. 2019 12; 17(13):2722-2730.e4. doi: 10.1016/j.cgh.2018.11.012. [PMID: 30448597]
  • Samer Al-Dury, Annika Wahlström, Katrin Panzitt, Anders Thorell, Marcus Ståhlman, Michael Trauner, Peter Fickert, Fredrik Bäckhed, Lars Fändriks, Martin Wagner, Hanns-Ulrich Marschall. Obeticholic acid may increase the risk of gallstone formation in susceptible patients. Journal of hepatology. 2019 11; 71(5):986-991. doi: 10.1016/j.jhep.2019.06.011. [PMID: 31254596]
  • Mary E Rinella, James F Trotter, Manal F Abdelmalek, Angelo H Paredes, Margery A Connelly, Mark J Jaros, Lei Ling, Stephen J Rossi, Alex M DePaoli, Stephen A Harrison. Rosuvastatin improves the FGF19 analogue NGM282-associated lipid changes in patients with non-alcoholic steatohepatitis. Journal of hepatology. 2019 04; 70(4):735-744. doi: 10.1016/j.jhep.2018.11.032. [PMID: 30529590]
  • Ivo P van de Peppel, Marcela Doktorova, Gitte Berkers, Hugo R de Jonge, Roderick H J Houwen, Henkjan J Verkade, Johan W Jonker, Frank A J A Bodewes. IVACAFTOR restores FGF19 regulated bile acid homeostasis in cystic fibrosis patients with an S1251N or a G551D gating mutation. Journal of cystic fibrosis : official journal of the European Cystic Fibrosis Society. 2019 03; 18(2):286-293. doi: 10.1016/j.jcf.2018.09.001. [PMID: 30279125]
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  • Dana Friedrich, Hanns-Ulrich Marschall, Frank Lammert. Response of fibroblast growth factor 19 and bile acid synthesis after a body weight-adjusted oral fat tolerance test in overweight and obese NAFLD patients: a non-randomized controlled pilot trial. BMC gastroenterology. 2018 Jun; 18(1):76. doi: 10.1186/s12876-018-0805-z. [PMID: 29866129]
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  • Leslie J Donato, Alan Lueke, Stacy M Kenyon, Jeffrey W Meeusen, Michael Camilleri. Description of analytical method and clinical utility of measuring serum 7-alpha-hydroxy-4-cholesten-3-one (7aC4) by mass spectrometry. Clinical biochemistry. 2018 Feb; 52(?):106-111. doi: 10.1016/j.clinbiochem.2017.10.008. [PMID: 29051033]
  • Renger G Tiessen, Ciara A Kennedy, Bradley T Keller, Nancy Levin, Lisette Acevedo, Bronislava Gedulin, Andre A van Vliet, Alejandro Dorenbaum, Melissa Palmer. Safety, tolerability and pharmacodynamics of apical sodium-dependent bile acid transporter inhibition with volixibat in healthy adults and patients with type 2 diabetes mellitus: a randomised placebo-controlled trial. BMC gastroenterology. 2018 Jan; 18(1):3. doi: 10.1186/s12876-017-0736-0. [PMID: 29304731]
  • Yanan Wang, Scott V Harding, Sijo J Thandapilly, Susan M Tosh, Peter J H Jones, Nancy P Ames. Barley β-glucan reduces blood cholesterol levels via interrupting bile acid metabolism. The British journal of nutrition. 2017 Nov; 118(10):822-829. doi: 10.1017/s0007114517002835. [PMID: 29115200]
  • Lijuan Kang, Thomas M Connolly, Naidong Weng, Wenying Jian. LC-MS/MS quantification of 7α-hydroxy-4-cholesten-3-one (C4) in rat and monkey plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Oct; 1064(?):49-55. doi: 10.1016/j.jchromb.2017.09.006. [PMID: 28915417]
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  • David N Assis, Osama Abdelghany, Shi-Ying Cai, Andrea A Gossard, John E Eaton, Jill C Keach, Yanhong Deng, Kenneth D R Setchell, Maria Ciarleglio, Keith D Lindor, James L Boyer. Combination Therapy of All-Trans Retinoic Acid With Ursodeoxycholic Acid in Patients With Primary Sclerosing Cholangitis: A Human Pilot Study. Journal of clinical gastroenterology. 2017 Feb; 51(2):e11-e16. doi: 10.1097/mcg.0000000000000591. [PMID: 27428727]
  • Serge J Zweers, Elisabeth M de Vries, Martin Lenicek, Dagmar Tolenaars, D Rudi de Waart, Kiran V K Koelfat, Albert K Groen, Steven W M Olde Damink, Ulrich Beuers, Cyriel Ponsioen, Peter L M Jansen, Frank G Schaap. Prolonged fibroblast growth factor 19 response in patients with primary sclerosing cholangitis after an oral chenodeoxycholic acid challenge. Hepatology international. 2017 Jan; 11(1):132-140. doi: 10.1007/s12072-016-9769-7. [PMID: 27696157]
  • T Blahová, L Peterková, M Leníček, M Vlachová, K Zemánková, V Adámková, L Vítek, J Kovář. The effect of colesevelam treatment on bile acid and lipid metabolism and glycemic control in healthy men. Physiological research. 2016 12; 65(6):995-1003. doi: 10.33549/physiolres.933276. [PMID: 27539104]
  • Long Yuan, Yi Luo, Hamza Kandoussi, Qin C Ji. A simple, fast, sensitive and robust LC-MS/MS bioanalytical assay for evaluating 7α-hydroxy-4-cholesten-3-one biomarker in a clinical program. Bioanalysis. 2016 Dec; 8(23):2445-2455. doi: 10.4155/bio-2016-0219. [PMID: 27855505]
  • Martin LeníĿek, Marek Vecka, Kateſina Žížalová, Libor Vítek. Comparison of simple extraction procedures in liquid chromatography-mass spectrometry based determination of serum 7α-hydroxy-4-cholesten-3-one, a surrogate marker of bile acid synthesis. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2016 Oct; 1033-1034(?):317-320. doi: 10.1016/j.jchromb.2016.08.046. [PMID: 27598558]
  • Alex Escalona, Rodrigo Muñoz, Veronica Irribarra, Sandra Solari, Fidel Allende, Juan Francisco Miquel. Bile acids synthesis decreases after laparoscopic sleeve gastrectomy. Surgery for obesity and related diseases : official journal of the American Society for Bariatric Surgery. 2016 May; 12(4):763-769. doi: 10.1016/j.soard.2015.11.015. [PMID: 26948941]
  • Miluše Vlachova, Tereza Blahova, Vera Lanska, Martin Leníček, Jan Pitha, Libor Vítek, Jan Kovar. Diurnal variation in cholesterol 7α-hydroxylase activity is determined by the -203A>C polymorphism of the CYP7A1 gene. Croatian medical journal. 2016 Apr; 57(2):111-7. doi: 10.3325/cmj.2016.57.111. [PMID: 27106353]
  • Andrea Mignarri, Alessandro Magni, Marina Del Puppo, Gian Nicola Gallus, Ingemar Björkhem, Antonio Federico, Maria Teresa Dotti. Evaluation of cholesterol metabolism in cerebrotendinous xanthomatosis. Journal of inherited metabolic disease. 2016 Jan; 39(1):75-83. doi: 10.1007/s10545-015-9873-1. [PMID: 26153518]
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  • Mats Rudling, Michael Camilleri, Hans Graffner, Jens Juul Holst, Leif Rikner. Specific inhibition of bile acid transport alters plasma lipids and GLP-1. BMC cardiovascular disorders. 2015 Jul; 15(?):75. doi: 10.1186/s12872-015-0070-9. [PMID: 26197999]
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  • Michael Camilleri, Irene Busciglio, Andres Acosta, Andrea Shin, Paula Carlson, Duane Burton, Michael Ryks, Deborah Rhoten, Jesse Lamsam, Alan Lueke, Leslie J Donato, Alan R Zinsmeister. Effect of increased bile acid synthesis or fecal excretion in irritable bowel syndrome-diarrhea. The American journal of gastroenterology. 2014 Oct; 109(10):1621-30. doi: 10.1038/ajg.2014.215. [PMID: 25070056]
  • F Gothe, F Beigel, C Rust, M Hajji, S Koletzko, F Freudenberg. Bile acid malabsorption assessed by 7 alpha-hydroxy-4-cholesten-3-one in pediatric inflammatory bowel disease: correlation to clinical and laboratory findings. Journal of Crohn's & colitis. 2014 Sep; 8(9):1072-8. doi: 10.1016/j.crohns.2014.02.027. [PMID: 24666974]
  • Michael Camilleri, Andrea Shin, Irene Busciglio, Paula Carlson, Andres Acosta, Adil E Bharucha, Duane Burton, Jesse Lamsam, Alan Lueke, Leslie J Donato, Alan R Zinsmeister. Genetic variation in GPBAR1 predisposes to quantitative changes in colonic transit and bile acid excretion. American journal of physiology. Gastrointestinal and liver physiology. 2014 Sep; 307(5):G508-16. doi: 10.1152/ajpgi.00178.2014. [PMID: 25012842]
  • Yuichiro Amano, Eiichiro Ishikawa, Emiko Shinozawa, Mitsuyuki Shimada, Shotaro Miura, Ryutaro Adachi, Ryuichi Tozawa. Combinational effects of farnesoid X receptor antagonist and statin on plasma lipid levels and low-density lipoprotein clearance in guinea pigs. Life sciences. 2014 Jul; 108(1):7-12. doi: 10.1016/j.lfs.2014.04.029. [PMID: 24805868]
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