5beta-Coprostanol (BioDeep_00000018885)

 

Secondary id: BioDeep_00000003825, BioDeep_00000398245, BioDeep_00000858812

human metabolite Endogenous Volatile Flavor Compounds


代谢物信息卡片


(1S,2S,5S,7R,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

化学式: C27H48O (388.37049579999996)
中文名称: 粪甾烷-3-醇
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 34.96%

分子结构信息

SMILES: C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCCC(C)C)CC[C@@]4([H])[C@]3([H])CC[C@@]2([H])C[C@H](O)C1
InChI: InChI=1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3

描述信息

Coprosterol or coprostanol is a cholesterol derivative found in human feces, gallstones, eggs, and other biological matter. Coprosterol is the odorous principle of feces. It is formed from the biohydrogenation of cholesterol (cholest-5en-3β-ol) in the gut of most higher animals and birds. This compound has frequently been used as a biomarker for the presence of human faecal matter in the environment. American physician Austin Flint named it stercorin (Wikipedia). The transformation of cholesterol into coprosterol in its passage through the body involves a reduction of the C5:C6 double bond, and a transition from the allocholanic- to the cholanic-ring system. Although it is established that the bacterial flora of the intestine is concerned in the reduction process, the mechanism by which the stereochemical change is brought about is unknown. Current data suggests that cholestenone and coprostanone, and not cholesterol itself, are the immediate precursors of coprosterol which is formed from them in the intestine by bacterial reduction. Coprosterol is also a microbial metabolite, it can be produced by Lactobacillus (PMID: 20338415).
Coprosterol or coprostanol is a cholesterol derivative found in human feces, gallstones, eggs, and other biological matter. Coprosterol is the odorous principle of feces. It is formed from the biohydrogenation of cholesterol (cholest-5en-3β-ol) in the gut of most higher animals and birds. This compound has frequently been used as a biomarker for the presence of human faecal matter in the environment. American physician Austin Flint named it stercorin . The transformation of cholesterol into coprosterol in its passage through the body involves a reduction of the C5:C6 double bond, and a transition from the allocholanic- to the cholanic-ring system. Although it is established that the bacterial flora of the intestine is concerned in the reduction process, the mechanism by which the stereochemical change is brought about is unknown. Current data suggests that cholestenone and coprostanone, and not cholesterol itself, are the immediate precursors of coprosterol which is formed from them in the intestine by bacterial reduction. [HMDB]
Same as: D01527

同义名列表

40 个代谢物同义名

(1S,2S,5S,7R,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol; Cholestanol, (3alpha, 5beta)-isomer; 5 alpha-Cholestan-3 alpha-ol; 5 alpha Cholestan 3 alpha ol; (3beta,5beta)-Cholestan-3-ol; 5 beta-Cholestan-3 alpha-ol; beta-Cholestan-3 beta-ol, 5; 5 alpha-Cholestan-3 beta-ol; 5 alpha Cholestan 3 beta ol; beta-Ol, 5 beta-cholestan-3; 5alpha-cholestan-3alpha-ol; Cholestan-3-ol, (3.beta.)-; 5 beta Cholestan 3 beta ol; 5 beta-Cholestan-3 beta-ol; 3b-Hydroxy-5b-cholestanol; 5beta-cholestan-3beta-ol; (3b,5b)-Cholestan-3-ol; (3Β,5β)-cholestan-3-ol; Epidihydrocholesterin; Dihydrocholesterol; 5b-Cholestan-3b-ol; 5Β-cholestan-3β-ol; 5beta-Coprostanol; 5beta Coprostanol; beta-Cholestanol; beta Cholestanol; Epi-cholestanol; 5b-Coprostanol; 5Β-coprostanol; Epicholestanol; 5b Coprostanol; 5Β coprostanol; Cholestan-3-ol; Cholestan 3 ol; Cholestanol; coprosterol; Coprostanol; ST 27:0;O; Stercorin; Epidihydrocholesterin



数据库引用编号

23 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

0 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(0)

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

  • Yun-Yuan Tian, Lin-Lin Bi, Wen-Wen Chen, Shu-Xian Zheng, Yu Cao, Yan-Hua Xie, Hai-Feng Tang, Yun-Yang Lu, Si-Wang Wang. Two previously undescribed cholestanol saponins from the rhizomes of Paris fargesii var. petiolata. Fitoterapia. 2024 Jun; 175(?):105881. doi: 10.1016/j.fitote.2024.105881. [PMID: 38438054]
  • Adrián Cortés-Martín, Carlos E Iglesias-Aguirre, Alicia Marín, María Romo-Vaquero, Fernando Vallejo, Juan Carlos Espín, María Victoria Selma. Urolithin A production drives the effects of pomegranate on the gut microbial metabolism of bile acids and cholesterol in mild dyslipidaemic overweight and obese individuals. Food & function. 2024 Mar; 15(5):2422-2432. doi: 10.1039/d3fo05014a. [PMID: 38329279]
  • Muhammed Köroğlu, Mustafa Karakaplan, Enes Gündüz, Betül Kesriklioğlu, Emre Ergen, Okan Aslantürk, Zeynep Maraş Özdemir. Cerebrotendinous Xanthomatosis patients with late diagnosed in single orthopedic clinic: two novel variants in the CYP27A1 gene. Orphanet journal of rare diseases. 2024 Feb; 19(1):53. doi: 10.1186/s13023-024-03082-4. [PMID: 38336741]
  • Yan Li, Yuanjue Wu, Yanyan Ge, Shanshan Huang, Yang Yang, Zhen Zhang, Ningning Cui, Junan Yan, Yonggang Li, Ping Luo, Liping Hao, Guoping Xiong, Xuefeng Yang. Pregnancy Cholesterol Metabolism Markers and the Risk of Gestational Diabetes Mellitus: A Nested Case-Control Study. Nutrients. 2023 Aug; 15(17):. doi: 10.3390/nu15173809. [PMID: 37686841]
  • Laura Stanasila, Pedro Marques-Vidal. Serum Phytosterols Are Not Associated with Inflammatory Markers in Two Cross-Sectional, Swiss Population-Based Studies (The CoLaus PsyCoLaus Study). Nutrients. 2022 Jun; 14(12):. doi: 10.3390/nu14122500. [PMID: 35745232]
  • María José Contreras, María Elena Arias, Mauricio Silva, Paulina Cabrera, Ricardo Felmer. Effect of cholestanol and cholesterol-loaded cyclodextrin on stallion sperm function and capacitation post-cryopreservation. Theriogenology. 2022 Jun; 189(?):1-10. doi: 10.1016/j.theriogenology.2022.06.005. [PMID: 35714521]
  • Christos Stenos, Konstantinos Kalafatakis, Pantelis Constantoulakis, Katerina Zekiou, Anna Margoni, Panagiota Kardara, Aspasia Terentiou, Georgios Stouraitis, Georgios Nikolaou. A case of cerebrotendinous xanthomatosis with brain and spinal involvement without tendon xanthomas: Identification of a novel mutation of the CYP27A1 gene. Journal of clinical lipidology. 2022 May; 16(3):281-285. doi: 10.1016/j.jacl.2022.03.011. [PMID: 35428606]
  • Sultan Mashnafi, Jogchum Plat, Ronald P Mensink, Peter J Joris, Yvo H A M Kusters, Alfons J H M Houben, Coen D A Stehouwer, Casper G Schalkwijk, Sabine Baumgartner. Effects of Diet-Induced Weight Loss on Plasma Markers for Cholesterol Absorption and Synthesis: Secondary Analysis of a Randomized Trial in Abdominally Obese Men. Nutrients. 2022 Apr; 14(8):. doi: 10.3390/nu14081546. [PMID: 35458107]
  • Yoshiaki Zaizen, Masaki Tominaga, Shuji Nagata, Tomoaki Hoshino. Cerebrotendinous xanthomatosis with radiological abnormalities of the chest. BMJ case reports. 2021 Sep; 14(9):. doi: 10.1136/bcr-2021-243715. [PMID: 34479889]
  • Bianca M L Stelten, Maria Teresa Dotti, Aad Verrips, Bülent Elibol, Tzipora C Falik-Zaccai, Kate Hanman, Andrea Mignarri, Belina Sithole, Robert D Steiner, Surabhi Verma, Gilad Yahalom, Tanyel Zubarioglu, Fanny Mochel, Antonio Federico. Expert opinion on diagnosing, treating and managing patients with cerebrotendinous xanthomatosis (CTX): a modified Delphi study. Orphanet journal of rare diseases. 2021 08; 16(1):353. doi: 10.1186/s13023-021-01980-5. [PMID: 34362411]
  • Pelin Teke Kısa, Gonca Kilic Yildirim, Burcu Ozturk Hismi, Sevil Dorum, Ozge Yilmaz Kusbeci, Ali Topak, Figen Baydan, Fatma Nazlı Durmaz Celik, Orhan Gorukmez, Zumrut Arslan Gulten, Arzu Ekici, Serhat Ozkan, Aylin Yaman, Nur Arslan. Patients with cerebrotendinous xanthomatosis diagnosed with diverse multisystem involvement. Metabolic brain disease. 2021 08; 36(6):1201-1211. doi: 10.1007/s11011-021-00714-7. [PMID: 33704661]
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  • Ken Takasone, Teruya Morizumi, Katsuya Nakamura, Yusuke Mochizuki, Tsuneaki Yoshinaga, Shingo Koyama, Yoshiki Sekijima. A Late-onset and Relatively Rapidly Progressive Case of Pure Spinal Form Cerebrotendinous Xanthomatosis with a Novel Mutation in the CYP27A1 Gene. Internal medicine (Tokyo, Japan). 2020 Oct; 59(20):2587-2591. doi: 10.2169/internalmedicine.5037-20. [PMID: 32581172]
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  • Michel Rubens Dos Reis Souza, Ewerton Santos, Jaiane Santos Suzarte, Laiane Oliveira do Carmo, Laiane Santos Soares, Lukas Gomes Gadelha Vieira Santos, Antônio Rodrigues Vilela Júnior, Laiza Canielas Krause, Morgana Frena, Flaviana Cardoso Damasceno, Yongsong Huang, Marcelo da Rosa Alexandre. The impact of anthropogenic activity at the tropical Sergipe-Poxim estuarine system, Northeast Brazil: Fecal indicators. Marine pollution bulletin. 2020 May; 154(?):111067. doi: 10.1016/j.marpolbul.2020.111067. [PMID: 32319900]
  • Lin Yan, Bret M Rust, Matthew J Picklo. Plasma Metabolomic Changes in Mice With Time-restricted Feeding-attenuated Spontaneous Metastasis of Lewis Lung Carcinoma. Anticancer research. 2020 Apr; 40(4):1833-1841. doi: 10.21873/anticanres.14137. [PMID: 32234871]
  • Aad Verrips, Maria Teresa Dotti, Andrea Mignarri, Bianca M L Stelten, Sue Verma, Antonio Federico. The safety and effectiveness of chenodeoxycholic acid treatment in patients with cerebrotendinous xanthomatosis: two retrospective cohort studies. Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology. 2020 Apr; 41(4):943-949. doi: 10.1007/s10072-019-04169-8. [PMID: 31863326]
  • Cécile Vors, Laurie Joumard-Cubizolles, Manon Lecomte, Emmanuel Combe, Lemlih Ouchchane, Jocelyne Drai, Ketsia Raynal, Florent Joffre, Laure Meiller, Mélanie Le Barz, Patrice Gaborit, Aurélie Caille, Monique Sothier, Carla Domingues-Faria, Adeline Blot, Aurélie Wauquier, Emilie Blond, Valérie Sauvinet, Geneviève Gésan-Guiziou, Jean-Pierre Bodin, Philippe Moulin, David Cheillan, Hubert Vidal, Béatrice Morio, Eddy Cotte, Françoise Morel-Laporte, Martine Laville, Annick Bernalier-Donadille, Stéphanie Lambert-Porcheron, Corinne Malpuech-Brugère, Marie-Caroline Michalski. Milk polar lipids reduce lipid cardiovascular risk factors in overweight postmenopausal women: towards a gut sphingomyelin-cholesterol interplay. Gut. 2020 03; 69(3):487-501. doi: 10.1136/gutjnl-2018-318155. [PMID: 31189655]
  • Monica Gelzo, Maria Donata Di Taranto, Concetta Sica, Antonio Boscia, Francesco Papagni, Giuliana Fortunato, Gaetano Corso, Antonio Dello Russo. Age-related changes of cholestanol and lathosterol plasma concentrations: an explorative study. Lipids in health and disease. 2019 Dec; 18(1):235. doi: 10.1186/s12944-019-1176-3. [PMID: 31888647]
  • Benjamin L Stottrup, Juan TigreLazo, Vision B Bagonza, Joan C Kunz, Joseph A Zasadzinski. Comparison of Line Tension Measurement Methods for Lipid Monolayers at Liquid-Liquid Coexistence. Langmuir : the ACS journal of surfaces and colloids. 2019 12; 35(48):16053-16061. doi: 10.1021/acs.langmuir.9b01696. [PMID: 31343892]
  • Daniele Mandia, Annabelle Chaussenot, Gérard Besson, Foudil Lamari, Giovanni Castelnovo, Jonathan Curot, Fanny Duval, Philippe Giral, Jean-Michel Lecerf, Dominique Roland, Heloise Pierdet, Claire Douillard, Yann Nadjar. Cholic acid as a treatment for cerebrotendinous xanthomatosis in adults. Journal of neurology. 2019 Aug; 266(8):2043-2050. doi: 10.1007/s00415-019-09377-y. [PMID: 31115677]
  • Joon Hee Lee, Kyunghoon Lee, Sun Hee Jun, Sang Hoon Song, Choong Ho Shin, Junghan Song. A Multiplex Phytosterol Assay Utilizing Gas Chromatography-Mass Spectrometry for Diagnosis of Inherited Lipid Storage Disorders. Annals of laboratory medicine. 2019 Jul; 39(4):411-413. doi: 10.3343/alm.2019.39.4.411. [PMID: 30809990]
  • Maite M Schroor, Henriette P Sennels, Jan Fahrenkrug, Henrik L Jørgensen, Jogchum Plat, Ronald P Mensink. Diurnal Variation of Markers for Cholesterol Synthesis, Cholesterol Absorption, and Bile Acid Synthesis: A Systematic Review and the Bispebjerg Study of Diurnal Variations. Nutrients. 2019 Jun; 11(7):. doi: 10.3390/nu11071439. [PMID: 31247945]
  • Dieter Lütjohann, Ingemar Björkhem, Silvia Friedrichs, Anja Kerksiek, Anita Lövgren-Sandblom, Wolf-Jochen Geilenkeuser, Robert Ahrends, Isabel Andrade, Diana Ansorena, Iciar Astiasarán, Lucía Baila-Rueda, Bianca Barriuso, Susen Becker, Lionel Bretillon, Richard W Browne, Claudio Caccia, Uta Ceglarek, Ana Cenarro, Peter J Crick, Günter Fauler, Guadalupe Garcia-Llatas, Robert Gray, William J Griffiths, Helena Gylling, Scott Harding, Christin Helmschrodt, Luigi Iuliano, Hans-Gerd Janssen, Peter Jones, Leena Kaipiainen, Frank Kannenberg, María Jesús Lagarda, Valerio Leoni, Ana Maria Lottenberg, Dylan S MacKay, Silke Matysik, Jeff McDonald, Maria Menendez-Carreño, Semone B Myrie, Valéria Sutti Nunes, Richard E Ostlund, Eliana Polisecki, Fernando Ramos, Todd C Rideout, Ernst J Schaefer, Gerd Schmitz, Yuqin Wang, Chiara Zerbinati, Ulf Diczfalusy, Hans-Frieder Schött. First international descriptive and interventional survey for cholesterol and non-cholesterol sterol determination by gas- and liquid-chromatography-Urgent need for harmonisation of analytical methods. The Journal of steroid biochemistry and molecular biology. 2019 06; 190(?):115-125. doi: 10.1016/j.jsbmb.2019.03.025. [PMID: 30940596]
  • Ernst J Schaefer, Andrew S Geller, Gregory Endress. The biochemical and genetic diagnosis of lipid disorders. Current opinion in lipidology. 2019 04; 30(2):56-62. doi: 10.1097/mol.0000000000000590. [PMID: 30720493]
  • Morgana Frena, Ana Paula Stein Santos, Michel R R Souza, Shalana Santos Carvalho, Luiz A S Madureira, Marcelo R Alexandre. Sterol biomarkers and fecal coliforms in a tropical estuary: Seasonal distribution and sources. Marine pollution bulletin. 2019 Feb; 139(?):111-116. doi: 10.1016/j.marpolbul.2018.12.007. [PMID: 30686407]
  • Moacir Guimarães de Melo, Brina Aguiar da Silva, Gilcllys de Souza Costa, João Cândido André da Silva Neto, Patrícia Kaori Soares, Adalberto Luis Val, Jamal da Silva Chaar, Hector Henrique Ferreira Koolen, Giovana Anceski Bataglion. Sewage contamination of Amazon streams crossing Manaus (Brazil) by sterol biomarkers. Environmental pollution (Barking, Essex : 1987). 2019 Jan; 244(?):818-826. doi: 10.1016/j.envpol.2018.10.055. [PMID: 30390455]
  • Stefano Fiorucci, Eleonora Distrutti. Chenodeoxycholic Acid: An Update on Its Therapeutic Applications. Handbook of experimental pharmacology. 2019; 256(?):265-282. doi: 10.1007/164_2019_226. [PMID: 31267167]
  • Helena Gylling, Matilda Korhonen, Annika Mutanen, Markku J Nissinen, Mikko Pakarinen, Piia Simonen. Serum non-cholesterol sterols and cholesterol metabolism in childhood and adolescence. Atherosclerosis. 2018 11; 278(?):91-96. doi: 10.1016/j.atherosclerosis.2018.09.017. [PMID: 30261473]
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  • Susel Castellanos-Iglesias, Ana Caroline Cabral, César C Martins, Maikon Di Domenico, R M Rocha, Maria Angélica Haddad. Organic contamination as a driver of structural changes of hydroid's assemblages of the coral reefs near to Havana Harbour, Cuba. Marine pollution bulletin. 2018 Aug; 133(?):568-577. doi: 10.1016/j.marpolbul.2018.06.003. [PMID: 30041351]
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