Cholesta-4,6-dien-3-one (BioDeep_00000018943)
human metabolite Endogenous
代谢物信息卡片
化学式: C27H42O (382.3235482)
中文名称: 4,6-胆固醇二烯-3-酮
谱图信息:
最多检出来源 Mentha canadensis(plant) 80%
分子结构信息
SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2C=CC4=CC(=O)CCC34C)C
InChI: InChI=1S/C27H42O/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/h9-10,17-19,22-25H,6-8,11-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1
描述信息
Cholesta-4,6-dien-3-one is a product of the oxidation of cholesteral. It may be metabolized to 4-cholesten-3-one and cholestanol by liver, adrenals and brain. An accumulation of cholesta-4,6-dien-3-one is found in serum of patients with cerebrotendinous xanthomatosis, and it is possible that accumulation of cholesterol in these patients is secondary to accumulation of cholesta-4,6-dien-3-one (PMID: 3557306; 16757819; 3676336) [HMDB]
Cholesta-4,6-dien-3-one is a product of the oxidation of cholesteral. It may be metabolized to 4-cholesten-3-one and cholestanol by liver, adrenals and brain. An accumulation of cholesta-4,6-dien-3-one is found in serum of patients with cerebrotendinous xanthomatosis, and it is possible that accumulation of cholesterol in these patients is secondary to accumulation of cholesta-4,6-dien-3-one (PMID: 3557306; 16757819; 3676336).
同义名列表
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:157665
- PubChem: 3034666
- PubChem: 273688
- HMDB: HMDB0002394
- ChEMBL: CHEMBL68121
- foodb: FDB022993
- chemspider: 2299095
- CAS: 566-93-8
- PMhub: MS000012823
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)
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
- Shishir Jaikishan, J Peter Slotte. Effect of hydrophobic mismatch and interdigitation on sterol/sphingomyelin interaction in ternary bilayer membranes.
Biochimica et biophysica acta.
2011 Jul; 1808(7):1940-5. doi:
10.1016/j.bbamem.2011.04.004. [PMID: 21515240] - Max Lönnfors, Jacques P F Doux, J Antoinette Killian, Thomas K M Nyholm, J Peter Slotte. Sterols have higher affinity for sphingomyelin than for phosphatidylcholine bilayers even at equal acyl-chain order.
Biophysical journal.
2011 Jun; 100(11):2633-41. doi:
10.1016/j.bpj.2011.03.066. [PMID: 21641308] - Christian Sergelius, Shou Yamaguchi, Tetsuya Yamamoto, J Peter Slotte, Shigeo Katsumura. N-cholesteryl sphingomyelin-A synthetic sphingolipid with unique membrane properties.
Biochimica et biophysica acta.
2011 Apr; 1808(4):1054-62. doi:
10.1016/j.bbamem.2010.12.021. [PMID: 21194522] - Anders Björkbom, Tomasz Róg, Pasi Kankaanpää, Daniel Lindroos, Karol Kaszuba, Mayuko Kurita, Shou Yamaguchi, Tetsuya Yamamoto, Shishir Jaikishan, Lassi Paavolainen, Joacim Päivärinne, Thomas K M Nyholm, Shigeo Katsumura, Ilpo Vattulainen, J Peter Slotte. N- and O-methylation of sphingomyelin markedly affects its membrane properties and interactions with cholesterol.
Biochimica et biophysica acta.
2011 Apr; 1808(4):1179-86. doi:
10.1016/j.bbamem.2011.01.009. [PMID: 21262197] - Oscar Ekholm, Shishir Jaikishan, Max Lönnfors, Thomas K M Nyholm, J Peter Slotte. Membrane bilayer properties of sphingomyelins with amide-linked 2- or 3-hydroxylated fatty acids.
Biochimica et biophysica acta.
2011 Mar; 1808(3):727-32. doi:
10.1016/j.bbamem.2010.12.006. [PMID: 21167130] - Shishir Jaikishan, Anders Björkbom, J Peter Slotte. Sphingomyelin analogs with branched N-acyl chains: the position of branching dramatically affects acyl chain order and sterol interactions in bilayer membranes.
Biochimica et biophysica acta.
2010 Oct; 1798(10):1987-94. doi:
10.1016/j.bbamem.2010.07.006. [PMID: 20637720] - Thomas K M Nyholm, Pia-Maria Grandell, Bodil Westerlund, J Peter Slotte. Sterol affinity for bilayer membranes is affected by their ceramide content and the ceramide chain length.
Biochimica et biophysica acta.
2010 May; 1798(5):1008-13. doi:
10.1016/j.bbamem.2009.12.025. [PMID: 20044977] - Luís M S Loura, Manuel Prieto, Fábio Fernandes. Quantification of protein-lipid selectivity using FRET.
European biophysics journal : EBJ.
2010 Mar; 39(4):565-78. doi:
10.1007/s00249-009-0532-z. [PMID: 20238256] - Y Jenny E Björkqvist, Jonathan Brewer, Luis A Bagatolli, J Peter Slotte, Bodil Westerlund. Thermotropic behavior and lateral distribution of very long chain sphingolipids.
Biochimica et biophysica acta.
2009 Jun; 1788(6):1310-20. doi:
10.1016/j.bbamem.2009.02.019. [PMID: 19272355] - Daniel Wüstner, Nils J Faergeman. Spatiotemporal analysis of endocytosis and membrane distribution of fluorescent sterols in living cells.
Histochemistry and cell biology.
2008 Nov; 130(5):891-908. doi:
10.1007/s00418-008-0488-6. [PMID: 18787836] - Anders Björkbom, Tetsuya Yamamoto, Satoshi Kaji, Shuji Harada, Shigeo Katsumura, J Peter Slotte. Importance of the phosphocholine linkage on sphingomyelin molecular properties and interactions with cholesterol; a study with phosphate oxygen modified sphingomyelin-analogues.
Biochimica et biophysica acta.
2008 Jun; 1778(6):1501-7. doi:
10.1016/j.bbamem.2008.03.005. [PMID: 18395514] - Y J E Björkqvist, S Nybond, T K M Nyholm, J P Slotte, B Ramstedt. N-palmitoyl-sulfatide participates in lateral domain formation in complex lipid bilayers.
Biochimica et biophysica acta.
2008 Apr; 1778(4):954-62. doi:
10.1016/j.bbamem.2007.12.016. [PMID: 18206111] - Anders Björkbom, Bodil Ramstedt, J Peter Slotte. Phosphatidylcholine and sphingomyelin containing an elaidoyl fatty acid can form cholesterol-rich lateral domains in bilayer membranes.
Biochimica et biophysica acta.
2007 Jul; 1768(7):1839-47. doi:
10.1016/j.bbamem.2007.04.009. [PMID: 17499576] - Stina Maunula, Y Jenny E Björkqvist, J Peter Slotte, Bodil Ramstedt. Differences in the domain forming properties of N-palmitoylated neutral glycosphingolipids in bilayer membranes.
Biochimica et biophysica acta.
2007 Feb; 1768(2):336-45. doi:
10.1016/j.bbamem.2006.09.003. [PMID: 17055448] - Bohdana Heczková, J Peter Slotte. Effect of anti-tumor ether lipids on ordered domains in model membranes.
FEBS letters.
2006 May; 580(10):2471-6. doi:
10.1016/j.febslet.2006.03.079. [PMID: 16638573] - Susanna Nybond, Y Jenny E Björkqvist, Bodil Ramstedt, J Peter Slotte. Acyl chain length affects ceramide action on sterol/sphingomyelin-rich domains.
Biochimica et biophysica acta.
2005 Dec; 1718(1-2):61-6. doi:
10.1016/j.bbamem.2005.10.009. [PMID: 16321609] - Sonja M K Alanko, Katrin K Halling, Stina Maunula, J Peter Slotte, Bodil Ramstedt. Displacement of sterols from sterol/sphingomyelin domains in fluid bilayer membranes by competing molecules.
Biochimica et biophysica acta.
2005 Sep; 1715(2):111-21. doi:
10.1016/j.bbamem.2005.08.002. [PMID: 16126159] - Y Jenny E Björkqvist, Thomas K M Nyholm, J Peter Slotte, Bodil Ramstedt. Domain formation and stability in complex lipid bilayers as reported by cholestatrienol.
Biophysical journal.
2005 Jun; 88(6):4054-63. doi:
10.1529/biophysj.104.054718. [PMID: 15792981] - Holger A Scheidt, Peter Muller, Andreas Herrmann, Daniel Huster. The potential of fluorescent and spin-labeled steroid analogs to mimic natural cholesterol.
The Journal of biological chemistry.
2003 Nov; 278(46):45563-9. doi:
10.1074/jbc.m303567200. [PMID: 12947110] - Tadashi Yoshida, Yasushi Matsuzaki, W Geoffrey Haigh, Sugano Fukushima, Kazuto Ikezawa, Naomi Tanaka, Sum P Lee. Origin of oxysterols in hepatic bile of patients with biliary infection.
The American journal of gastroenterology.
2003 Oct; 98(10):2275-80. doi:
10.1111/j.1572-0241.2003.07703.x. [PMID: 14572579] - W G Haigh, S P Lee. Identification of oxysterols in human bile and pigment gallstones.
Gastroenterology.
2001 Jul; 121(1):118-23. doi:
10.1053/gast.2001.25513. [PMID: 11438500] - 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] - M S Buchmann, I Björkhem, S Skrede. Metabolism of the cholestanol precursor cholesta-4,6-dien-3-one in different tissues.
Biochimica et biophysica acta.
1987 Nov; 922(2):111-7. doi:
10.1016/0005-2760(87)90144-5. [PMID: 3676336] - I Björkhem, S Skrede, M S Buchmann, C East, S Grundy. Accumulation of 7 alpha-hydroxy-4-cholesten-3-one and cholesta-4,6-dien-3-one in patients with cerebrotendinous xanthomatosis: effect of treatment with chenodeoxycholic acid.
Hepatology (Baltimore, Md.).
1987 Mar; 7(2):266-71. doi:
10.1002/hep.1840070210. [PMID: 3557306] - S A Wharton, S G De Martinez, C Green. Use of fluorescent probes in the study of phospholipid--sterol bilayers.
The Biochemical journal.
1980 Dec; 191(3):785-90. doi:
10.1042/bj1910785. [PMID: 7283973]