Epoxycholesterol (BioDeep_00000016647)

Main id: BioDeep_00000636693

 

Volatile Flavor Compounds


代谢物信息卡片


(1S,2R,5S,7R,9S,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-5-ol

化学式: C27H46O2 (402.34976159999997)
中文名称: 5α,6α-epoxy Cholestanol
谱图信息: 最多检出来源 Ailuropoda melanoleuca(viridiplantae) 50%

分子结构信息

SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC4C5(C3(CCC(C5)O)C)O4)C
InChI:

描述信息

5,6alpha-epoxy-5alpha-cholestan-3beta-ol is a 3beta-hydroxy steroid, an oxysterol and an epoxy steroid. It derives from a hydride of a 5alpha-cholestane.

同义名列表

6 个代谢物同义名

5,6alpha-Epoxy-5alpha-cholestan-3beta-ol; Cholesterol-5alpha,6alpha-epoxide; 5,6α-epoxy-5α-cholestan-3β-ol; epoxy-cholesterol; 5,6α Cholesterol-5alpha,6alpha-epoxide



数据库引用编号

9 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)

0 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

  • Katherine Windsor, Thiago C Genaro-Mattos, Sayuri Miyamoto, Donald F Stec, Hye-Young H Kim, Keri A Tallman, Ned A Porter. Assay of protein and peptide adducts of cholesterol ozonolysis products by hydrophobic and click enrichment methods. Chemical research in toxicology. 2014 Oct; 27(10):1757-68. doi: 10.1021/tx500229h. [PMID: 25185119]
  • Mariona Jové, José María Moreno-Navarrete, Reinald Pamplona, Wifredo Ricart, Manuel Portero-Otín, José Manuel Fernández-Real. Human omental and subcutaneous adipose tissue exhibit specific lipidomic signatures. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2014 Mar; 28(3):1071-81. doi: 10.1096/fj.13-234419. [PMID: 24265485]
  • Christophe Morisseau. Role of epoxide hydrolases in lipid metabolism. Biochimie. 2013 Jan; 95(1):91-5. doi: 10.1016/j.biochi.2012.06.011. [PMID: 22722082]
  • Michael R Paillasse, Nathalie Saffon, Heinz Gornitzka, Sandrine Silvente-Poirot, Marc Poirot, Philippe de Medina. Surprising unreactivity of cholesterol-5,6-epoxides towards nucleophiles. Journal of lipid research. 2012 Apr; 53(4):718-25. doi: 10.1194/jlr.m023689. [PMID: 22285872]
  • May-Thu Ma, Jing Zhang, Akhlaq A Farooqui, Peng Chen, Wei-Yi Ong. Effects of cholesterol oxidation products on exocytosis. Neuroscience letters. 2010 May; 476(1):36-41. doi: 10.1016/j.neulet.2010.03.078. [PMID: 20380872]
  • S Ferderbar, E C Pereira, E Apolinário, M C Bertolami, A Faludi, O Monte, L E Calliari, J E Sales, A R Gagliardi, H T Xavier, D S P Abdalla. Cholesterol oxides as biomarkers of oxidative stress in type 1 and type 2 diabetes mellitus. Diabetes/metabolism research and reviews. 2007 Jan; 23(1):35-42. doi: 10.1002/dmrr.645. [PMID: 16634125]
  • Melissa K Pulfer, Robert C Murphy. Formation of biologically active oxysterols during ozonolysis of cholesterol present in lung surfactant. The Journal of biological chemistry. 2004 Jun; 279(25):26331-8. doi: 10.1074/jbc.m403581200. [PMID: 15096493]
  • Ilona Staprans, Xian-Mang Pan, Joseph H Rapp, Kenneth R Feingold. Oxidized cholesterol in the diet is a source of oxidized lipoproteins in human serum. Journal of lipid research. 2003 Apr; 44(4):705-15. doi: 10.1194/jlr.m200266-jlr200. [PMID: 12562864]
  • Q Zhou, E Wasowicz, B Handler, L Fleischer, F A Kummerow. An excess concentration of oxysterols in the plasma is cytotoxic to cultured endothelial cells. Atherosclerosis. 2000 Mar; 149(1):191-7. doi: 10.1016/s0021-9150(99)00343-3. [PMID: 10704631]
  • D U Ahn, J I Lee, C Jo, J L Sell. Analysis of cholesterol oxides in egg yolk and turkey meat. Poultry science. 1999 Jul; 78(7):1060-4. doi: 10.1093/ps/78.7.1060. [PMID: 10404689]
  • D Caruso, B Berra, F Giavarini, N Cortesi, E Fedeli, G Galli. Effect of virgin olive oil phenolic compounds on in vitro oxidation of human low density lipoproteins. Nutrition, metabolism, and cardiovascular diseases : NMCD. 1999 Jun; 9(3):102-7. doi: ". [PMID: 10464782]
  • V Deckert, A Brunet, F Lantoine, G Lizard, E Millanvoye-van Brussel, S Monier, L Lagrost, M David-Dufilho, P Gambert, M A Devynck. Inhibition by cholesterol oxides of NO release from human vascular endothelial cells. Arteriosclerosis, thrombosis, and vascular biology. 1998 Jul; 18(7):1054-60. doi: 10.1161/01.atv.18.7.1054. [PMID: 9672065]
  • Y V Yuan, D D Kitts, D V Godin. Interactive effects of increased intake of saturated fat and cholesterol on atherosclerosis in the Japanese quail (Coturnix japonica). The British journal of nutrition. 1998 Jul; 80(1):89-100. doi: 10.1017/s0007114598001810. [PMID: 9797648]
  • J Y Chang, K D Phelan, L Z Liu. Establishment of two morphologically distinct PC12 cell lines resistant to 25-OH-cholesterol toxicity. Biochemical and biophysical research communications. 1997 Oct; 239(2):429-34. doi: 10.1006/bbrc.1997.7481. [PMID: 9344846]
  • J H Nielsen, C E Olsen, C Duedahl, L H Skibsted. Isolation and quantification of cholesterol oxides in dairy products by selected ion monitoring mass spectrometry. The Journal of dairy research. 1995 Feb; 62(1):101-13. doi: 10.1017/s0022029900033719. [PMID: 7738238]
  • Q T Li, N P Das. Comparison of the effects of cholesterol and oxysterols on phospholipid bilayer microheterogeneity: a study of fluorescence lifetime distributions. Archives of biochemistry and biophysics. 1994 Dec; 315(2):473-8. doi: 10.1006/abbi.1994.1527. [PMID: 7986094]
  • A Sevanian, R Seraglia, P Traldi, P Rossato, F Ursini, H Hodis. Analysis of plasma cholesterol oxidation products using gas- and high-performance liquid chromatography/mass spectrometry. Free radical biology & medicine. 1994 Nov; 17(5):397-409. doi: 10.1016/0891-5849(94)90166-x. [PMID: 7835746]
  • O Küçük, M Churley, M T Goodman, A Franke, L Custer, L R Wilkens, J St Pyrek. Increased plasma level of cholesterol-5 beta,6 beta-epoxide in endometrial cancer patients. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 1994 Oct; 3(7):571-4. doi: . [PMID: 7827587]
  • J J van den Berg, C C Winterbourn, F A Kuypers. Hypochlorous acid-mediated modification of cholesterol and phospholipid: analysis of reaction products by gas chromatography-mass spectrometry. Journal of lipid research. 1993 Nov; 34(11):2005-12. doi: 10.1016/s0022-2275(20)35117-8. [PMID: 8263423]
  • M A Arshad, S Bhadra, R M Cohen, M T Subbiah. Plasma lipoprotein peroxidation potential: a test to evaluate individual susceptibility to peroxidation. Clinical chemistry. 1991 Oct; 37(10 Pt 1):1756-8. doi: 10.1093/clinchem/37.10.1756. [PMID: 1914180]
  • G A Boissonneault, B Hennig, C M Ouyang. Oxysterols, cholesterol biosynthesis, and vascular endothelial cell monolayer barrier function. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 1991 Mar; 196(3):338-43. doi: 10.3181/00379727-196-43198. [PMID: 1998010]
  • A Sevanian, J Berliner, H Peterson. Uptake, metabolism, and cytotoxicity of isomeric cholesterol-5,6-epoxides in rabbit aortic endothelial cells. Journal of lipid research. 1991 Jan; 32(1):147-55. doi: 10.1016/s0022-2275(20)42253-9. [PMID: 2010686]
  • I Björkhem, O Breuer, B Angelin, S A Wikström. Assay of unesterified cholesterol-5,6-epoxide in human serum by isotope dilution mass spectrometry. Levels in the healthy state and in hyperlipoproteinemia. Journal of lipid research. 1988 Aug; 29(8):1031-8. doi: . [PMID: 3183516]
  • N L Petrakis, R E Lee, R Miike, M E Dupuy, M Morris. Coloration of breast fluid related to concentration of cholesterol, cholesterol epoxides, estrogen, and lipid peroxides. American journal of clinical pathology. 1988 Jan; 89(1):117-20. doi: 10.1093/ajcp/89.1.117. [PMID: 3337046]
  • L D Gruenke, M R Wrensch, N L Petrakis, R Miike, V L Ernster, J C Craig. Breast fluid cholesterol and cholesterol epoxides: relationship to breast cancer risk factors and other characteristics. Cancer research. 1987 Oct; 47(20):5483-7. doi: . [PMID: 3652048]
  • J Bascoul, N Domergue, J Mourot, G Debry, A Crastes de Paulet. Intestinal absorption and fecal excretion of 5,6 alpha-epoxy-5 alpha-cholesta-3 beta-ol by the male Wistar rat. Lipids. 1986 Dec; 21(12):744-7. doi: 10.1007/bf02535405. [PMID: 3821388]
  • T Watabe, A Tsubaki, M Isobe, N Ozawa, A Hiratsuka. A mechanism for epoxidation of cholesterol by hepatic microsomal lipid hydroperoxides. Biochimica et biophysica acta. 1984 Aug; 795(1):60-6. doi: 10.1016/0005-2760(84)90104-8. [PMID: 6466699]
  • T Watabe, M Isobe, A Tsubaki. Epoxidation of cholesterol by hepatic microsomal lipid hydroperoxides. Biochemical and biophysical research communications. 1982 Sep; 108(2):724-30. doi: 10.1016/0006-291x(82)90889-0. [PMID: 7150318]
  • A Baranowski, C W Adams, O B High, D B Bowyer. Connective tissue responses to oxysterols. Atherosclerosis. 1982 Feb; 41(2-3):255-66. doi: 10.1016/0021-9150(82)90190-3. [PMID: 7066074]
  • R F Raicht, B I Cohen. Sterol metabolism in the rat. Effect of cholesterol and cholesterol-alpha-epoxide on sterol metabolism in rats fed liquid diets. Biochimica et biophysica acta. 1981 Dec; 666(3):455-61. doi: 10.1016/0005-2760(81)90306-4. [PMID: 7326255]
  • N L Petrakis, L D Gruenke, J C Craig. Cholesterol and cholesterol epoxides in nipple aspirates of human breast fluid. Cancer research. 1981 Jun; 41(6):2563-5. doi: NULL. [PMID: 7237447]
  • T Watabe, M Isobe, M Kanai. Cholesterol diet increases plasma and liver concentrations of cholesterol epoxides and cholestanetriol. Journal of pharmacobio-dynamics. 1980 Oct; 3(10):553-6. doi: 10.1248/bpb1978.3.553. [PMID: 7205535]
  • A Sevanian, R A Stein, J F Mead. Lipid epoxide hydrolase in rat lung preparations. Biochimica et biophysica acta. 1980 Aug; 614(2):489-500. doi: 10.1016/0005-2744(80)90238-7. [PMID: 7407199]
  • K K Hwang, M I Kelsey. Evidence of epoxide hydrase activity in human intestinal microflora. Cancer biochemistry biophysics. 1978; 3(1):31-5. doi: . [PMID: 552896]