Coprostanone (BioDeep_00000398232)

Main id: BioDeep_00000003861

Secondary id: BioDeep_00000014384

PANOMIX_OTCML-2023 natural product Volatile Flavor Compounds


代谢物信息卡片


(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one

化学式: C27H46O (386.3548466)
中文名称: 5Alpha-胆甾烷-3-酮, 5-α-胆甾烷-3-酮
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 2.55%

分子结构信息

SMILES: C(C)(C1)(C(C(C)CCCC(C)C)4)C(CC4)C(C2)C(C(C)(C3)C([H])(CC(C3)=O)C2)C1
InChI: InChI=1S/C27H46O/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/h18-20,22-25H,6-17H2,1-5H3/t19-,20+,22+,23-,24+,25+,26+,27-/m1/s1

描述信息

A 3-oxo-5alpha- steroid that is 5alpha-cholestane substituted by an oxo group at position 3.
Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong.
5α-Cholestan-3-one is an endogenous metabolite.

同义名列表

21 个代谢物同义名

Coprostanone; 3-Oxocholestane; 5alpha-cholestan-3-one; 5alpha-cholestanone; ST 27:1;O; (5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one; (5a,17b)-17-Octylandrostan-3-one; (5α)-Cholestan-3-one; 5α-Cholestane-3-one; 5α-Cholestan-3-one; (5α)-Cholestanone; 5α-Coprostanone; 5α-Cholestanone; 5a(H)-Cholestan-3-one; 5a-Cholestan-3-one; 5a-Cholestanone; Cholestan-3-one; 5α-Cholestanone; 5α-Cholestan-3-one; 5beta-Cholestan-3-one; 5alpha-Cholestan-3-one



数据库引用编号

41 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)

17 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

  • M R Kasimov, G F Zakyrjanova, A R Giniatullin, A L Zefirov, A M Petrov. Similar oxysterols may lead to opposite effects on synaptic transmission: Olesoxime versus 5α-cholestan-3-one at the frog neuromuscular junction. Biochimica et biophysica acta. 2016 Jul; 1861(7):606-16. doi: 10.1016/j.bbalip.2016.04.010. [PMID: 27102612]
  • Matthew G K Benesch, Ruthven N A H Lewis, David A Mannock, Ronald N McElhaney. A DSC and FTIR spectroscopic study of the effects of the epimeric coprostan-3-ols and coprostan-3-one on the thermotropic phase behaviour and organization of dipalmitoylphosphatidylcholine bilayer membranes: Comparison with their 5-cholesten analogues. Chemistry and physics of lipids. 2015 May; 188(?):10-26. doi: 10.1016/j.chemphyslip.2015.03.002. [PMID: 25804450]
  • M R Kasimov, A R Giniatullin, A L Zefirov, A M Petrov. Effects of 5α-cholestan-3-one on the synaptic vesicle cycle at the mouse neuromuscular junction. Biochimica et biophysica acta. 2015 May; 1851(5):674-85. doi: 10.1016/j.bbalip.2015.02.012. [PMID: 25725358]
  • H Gylling, M Hallikainen, P Simonen, H E Miettinen, M J Nissinen, T A Miettinen. Serum and lipoprotein sitostanol and non-cholesterol sterols after an acute dose of plant stanol ester on its long-term consumption. European journal of nutrition. 2012 Aug; 51(5):615-22. doi: 10.1007/s00394-011-0249-5. [PMID: 21947207]
  • Charles Desmarchelier, Christoph Dahlhoff, Sylvia Keller, Manuela Sailer, Gerhard Jahreis, Hannelore Daniel. C57Bl/6 N mice on a western diet display reduced intestinal and hepatic cholesterol levels despite a plasma hypercholesterolemia. BMC genomics. 2012 Mar; 13(?):84. doi: 10.1186/1471-2164-13-84. [PMID: 22394543]
  • Alison Colyer, Matthew S Gilham, Beate Kamlage, Dietrich Rein, David Allaway. Identification of intra- and inter-individual metabolite variation in plasma metabolite profiles of cats and dogs. The British journal of nutrition. 2011 Oct; 106 Suppl 1(?):S146-9. doi: 10.1017/s000711451100081x. [PMID: 22005413]
  • Piia Simonen, Anna Kotronen, Maarit Hallikainen, Ksenia Sevastianova, Janne Makkonen, Antti Hakkarainen, Nina Lundbom, Tatu A Miettinen, Helena Gylling, Hannele Yki-Järvinen. Cholesterol synthesis is increased and absorption decreased in non-alcoholic fatty liver disease independent of obesity. Journal of hepatology. 2011 Jan; 54(1):153-9. doi: 10.1016/j.jhep.2010.05.037. [PMID: 20947198]
  • Yuguang Lin, Mario A Vermeer, Elke A Trautwein. Triterpenic Acids Present in Hawthorn Lower Plasma Cholesterol by Inhibiting Intestinal ACAT Activity in Hamsters. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):801272. doi: 10.1093/ecam/nep007. [PMID: 19228775]
  • Mikko P Pakarinen, Annika Kurvinen, Helena Gylling, Tatu A Miettinen, Maria Pesonen, Markku Kallio, Antti I Koivusalo, Markku J Nissinen. Cholesterol metabolism in pediatric short bowel syndrome after weaning off parenteral nutrition. Digestive and liver disease : official journal of the Italian Society of Gastroenterology and the Italian Association for the Study of the Liver. 2010 Aug; 42(8):554-9. doi: 10.1016/j.dld.2010.01.003. [PMID: 20538532]
  • M J Nissinen, T E Miettinen, H Gylling, T A Miettinen. Applicability of non-cholesterol sterols in predicting response in cholesterol metabolism to simvastatin and fluvastatin treatment among hypercholesterolemic men. Nutrition, metabolism, and cardiovascular diseases : NMCD. 2010 Jun; 20(5):308-16. doi: 10.1016/j.numecd.2009.04.014. [PMID: 19695854]
  • Jussi Pihlajamäki, Sari Grönlund, Marko Simonen, Pirjo Käkelä, Leena Moilanen, Matti Pääkkönen, Elina Pirinen, Marjukka Kolehmainen, Vesa Kärjä, Sakari Kainulainen, Matti Uusitupa, Esko Alhava, Tatu A Miettinen, Helena Gylling. Cholesterol absorption decreases after Roux-en-Y gastric bypass but not after gastric banding. Metabolism: clinical and experimental. 2010 Jun; 59(6):866-72. doi: 10.1016/j.metabol.2009.10.004. [PMID: 20015521]
  • T A Miettinen, M Hallikainen, O T Raitakari, J Viikari, H Gylling. Twenty-one year tracking of serum non-cholesterol sterols. The Cardiovascular Risk in Young Finns study. Nutrition, metabolism, and cardiovascular diseases : NMCD. 2009 Oct; 19(8):525-31. doi: 10.1016/j.numecd.2008.10.009. [PMID: 19185477]
  • Bianka Ditscheid, Sylvia Keller, Gerhard Jahreis. Faecal steroid excretion in humans is affected by calcium supplementation and shows gender-specific differences. European journal of nutrition. 2009 Feb; 48(1):22-30. doi: 10.1007/s00394-008-0755-2. [PMID: 19009227]
  • H K Berthold, R Laaksonen, T Lehtimäki, H Gylling, W Krone, I Gouni-Berthold. SREBP-1c gene polymorphism is associated with increased inhibition of cholesterol-absorption in response to ezetimibe treatment. Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association. 2008 May; 116(5):262-7. doi: 10.1055/s-2007-993144. [PMID: 18072016]
  • Thomas A Wilson, Robert J Nicolosi, Benjamin Woolfrey, David Kritchevsky. Rice bran oil and oryzanol reduce plasma lipid and lipoprotein cholesterol concentrations and aortic cholesterol ester accumulation to a greater extent than ferulic acid in hypercholesterolemic hamsters. The Journal of nutritional biochemistry. 2007 Feb; 18(2):105-12. doi: 10.1016/j.jnutbio.2006.03.006. [PMID: 16713234]
  • Heng-Ling Liou, Sayali S Dixit, Sujuan Xu, G Stephen Tint, Ann M Stock, Peter Lobel. NPC2, the protein deficient in Niemann-Pick C2 disease, consists of multiple glycoforms that bind a variety of sterols. The Journal of biological chemistry. 2006 Dec; 281(48):36710-23. doi: 10.1074/jbc.m608743200. [PMID: 17018531]
  • J W Readman, G Fillmann, I Tolosa, J Bartocci, L D Mee. The use of steroid markers to assess sewage contamination of the Black Sea. Marine pollution bulletin. 2005 Mar; 50(3):310-8. doi: 10.1016/j.marpolbul.2004.11.002. [PMID: 15757694]
  • Sylvia Keller, Gerhard Jahreis. Determination of underivatised sterols and bile acid trimethyl silyl ether methyl esters by gas chromatography-mass spectrometry-single ion monitoring in faeces. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Dec; 813(1-2):199-207. doi: 10.1016/j.jchromb.2004.09.046. [PMID: 15556534]
  • Mikko P Pakarinen, Jouni Lauronen, Paula Pirinen, Pekka Kuusanmäki, Peter Raivio, Jorma Halttunen. Octreotide in the treatment of small intestinal dysfunction after a model of jejunoileal autotransplantation in the pig. Pediatric surgery international. 2004 Oct; 20(10):791-6. doi: 10.1007/s00383-004-1167-x. [PMID: 15322839]
  • Helena Gylling, Maarit Hallikainen, Jussi Pihlajamäki, Jyrki Agren, Markku Laakso, Radhakrishnan A Rajaratnam, Rainer Rauramaa, Tatu A Miettinen. Polymorphisms in the ABCG5 and ABCG8 genes associate with cholesterol absorption and insulin sensitivity. Journal of lipid research. 2004 Sep; 45(9):1660-5. doi: 10.1194/jlr.m300522-jlr200. [PMID: 15175352]
  • Huanling Yu, Ruiyue Yang, Junbo Wang, Weixing Yan, Yong Li. [Fundamental study on the cholesterol-lowering effect of whole turtle egg powder in SD rats]. Wei sheng yan jiu = Journal of hygiene research. 2004 Sep; 33(5):581-3. doi: . [PMID: 15612486]
  • Gerhard Dongowski, Angelika Lorenz. Intestinal steroids in rats are influenced by the structural parameters of pectin. The Journal of nutritional biochemistry. 2004 Apr; 15(4):196-205. doi: 10.1016/s0955-2863(03)00080-9. [PMID: 15068812]
  • Tatu A Miettinen, Helena Gylling, Juha Tuominen, Piia Simonen, Veikko Koivisto. Low synthesis and high absorption of cholesterol characterize type 1 diabetes. Diabetes care. 2004 Jan; 27(1):53-8. doi: 10.2337/diacare.27.1.53. [PMID: 14693966]
  • R Chaler, B R Simoneit, J O Grimalt. Bile acids and sterols in urban sewage treatment plants. Journal of chromatography. A. 2001 Aug; 927(1-2):155-60. doi: 10.1016/s0021-9673(01)01086-x. [PMID: 11572384]
  • E Kim, S M Jeon, M S Choi. Effects of gamma-irradiated fats on plasma lipid concentrations and hepatic cholesterol metabolism in rats. Annals of nutrition & metabolism. 2001; 45(4):152-8. doi: 10.1159/000046723. [PMID: 11463998]
  • K Suzuki, T Shimizu, T Nakata. The cholesterol metabolite cholest-4-en-3-one and its 3-oxo derivatives suppress body weight gain, body fat accumulation and serum lipid concentration in mice. Bioorganic & medicinal chemistry letters. 1998 Aug; 8(16):2133-8. doi: 10.1016/s0960-894x(98)00362-x. [PMID: 9873500]
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  • A Sziegoleit, D Linder. Studies on the sterol-binding capacity of human pancreatic elastase 1. Gastroenterology. 1991 Mar; 100(3):768-74. doi: 10.1016/0016-5085(91)80024-4. [PMID: 1993499]
  • A K Bhattacharyya, D A Eggen, P Correa, J P Strong. Differences in fecal excretion of cholesterol and bacterial degradation products in high- and low-responding rhesus monkeys: implications in colon cancer. Nutrition and cancer. 1989; 12(1):69-73. doi: 10.1080/01635588909514003. [PMID: 2496397]
  • G V Vahouny, R Khalafi, S Satchithanandam, D W Watkins, J A Story, M M Cassidy, D Kritchevsky. Dietary fiber supplementation and fecal bile acids, neutral steroids and divalent cations in rats. The Journal of nutrition. 1987 Dec; 117(12):2009-15. doi: 10.1093/jn/117.12.2009. [PMID: 2826726]
  • H K Kaul, D B Couch, J D Gingerich, W R Bruce, J A Heddle. Genotoxicity of two fecal steroids in murine colonic epithelium assessed by the sister chromatid exchange technique. Mutagenesis. 1987 Nov; 2(6):441-4. doi: 10.1093/mutage/2.6.441. [PMID: 3328036]
  • P P Nair, N Turjman, G T Goodman, C Guidry, B M Calkins. Diet, nutrition intake, and metabolism in populations at high and low risk for colon cancer. Metabolism of neutral sterols. The American journal of clinical nutrition. 1984 10; 40(4 Suppl):931-6. doi: 10.1093/ajcn/40.4.931. [PMID: 6435444]
  • G E Mott, E M Jackson. Loss of tritium from coprostanone derived from [1,2(n)-3H]cholesterol or [7(n)-3H]cholesterol. Journal of lipid research. 1980 May; 21(4):480-4. doi: . [PMID: 6770018]