3β,5α,6β-Trihydroxycholestane (BioDeep_00001868339)

Main id: BioDeep_00000005816

 


代谢物信息卡片


3beta,5alpha,6beta-Trihydroxycholestane

化学式: C27H48O3 (420.36032579999994)
中文名称: 3β,5α,6β-三羟基胆甾烷
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC(C4(C3(CCC(C4)O)C)O)O)C
InChI: InChI=1S/C27H48O3/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24(29)27(30)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28-30H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27+/m1/s1

描述信息

D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents
D009676 - Noxae > D000963 - Antimetabolites

同义名列表

2 个代谢物同义名

3beta,5alpha,6beta-Trihydroxycholestane; 3β,5α,6β-Trihydroxycholestane



数据库引用编号

8 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)

3 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

  • Uğur Ünlütürk, Merve Savaş, Seda Hanife Oğuz, Afshin Samadi, Büşra Fırlatan, Deniz Yüce, İncilay Lay, Alper Gürlek. Oxysterol species generated by auto-oxidation in subclinical hypothyroidism. Clinical biochemistry. 2021 Jul; 93(?):73-79. doi: 10.1016/j.clinbiochem.2021.04.007. [PMID: 33861988]
  • William J Griffiths, Eylan Yutuc, Jonas Abdel-Khalik, Peter J Crick, Thomas Hearn, Alison Dickson, Brian W Bigger, Teresa Hoi-Yee Wu, Anu Goenka, Arunabha Ghosh, Simon A Jones, Douglas F Covey, Daniel S Ory, Yuqin Wang. Metabolism of Non-Enzymatically Derived Oxysterols: Clues from sterol metabolic disorders. Free radical biology & medicine. 2019 11; 144(?):124-133. doi: 10.1016/j.freeradbiomed.2019.04.020. [PMID: 31009661]
  • Ahmet Yalcinkaya, Afshin Samadi, Incilay Lay, Selma Unal, Suna Sabuncuoglu, Yesim Oztas. Oxysterol concentrations are associated with cholesterol concentrations and anemia in pediatric patients with sickle cell disease. Scandinavian journal of clinical and laboratory investigation. 2019 Oct; 79(6):381-387. doi: 10.1080/00365513.2019.1627578. [PMID: 31187639]
  • Lipeng Tang, Min Yan, Tiandong Leng, Wei Yin, Song Cai, Songwei Duan, Wenbo Zhu, Suizhen Lin, Jiayu Huang, Guangmei Yan, Guangjuan Zheng, Yupin Chen. Cholestane-3β, 5α, 6β-triol suppresses neuronal hyperexcitability via binding to voltage-gated sodium channels. Biochemical and biophysical research communications. 2018 01; 496(1):95-100. doi: 10.1016/j.bbrc.2018.01.004. [PMID: 29307820]
  • Frank Kannenberg, Jerzy-Roch Nofer, Erhard Schulte, Janine Reunert, Thorsten Marquardt, Manfred Fobker. Determination of serum cholestane-3β,5α,6β-triol by gas chromatography-mass spectrometry for identification of Niemann-Pick type C (NPC) disease. The Journal of steroid biochemistry and molecular biology. 2017 05; 169(?):54-60. doi: 10.1016/j.jsbmb.2016.02.030. [PMID: 26940355]
  • Sara Boenzi, Federica Deodato, Roberta Taurisano, Bianca Maria Goffredo, Cristiano Rizzo, Carlo Dionisi-Vici. Evaluation of plasma cholestane-3β,5α,6β-triol and 7-ketocholesterol in inherited disorders related to cholesterol metabolism. Journal of lipid research. 2016 Mar; 57(3):361-7. doi: 10.1194/jlr.m061978. [PMID: 26733147]
  • Janine Reunert, Manfred Fobker, Frank Kannenberg, Ingrid Du Chesne, Maria Plate, Judith Wellhausen, Stephan Rust, Thorsten Marquardt. Rapid Diagnosis of 83 Patients with Niemann Pick Type C Disease and Related Cholesterol Transport Disorders by Cholestantriol Screening. EBioMedicine. 2016 Feb; 4(?):170-5. doi: 10.1016/j.ebiom.2015.12.018. [PMID: 26981555]
  • Sonia Pajares, Angela Arias, Judit García-Villoria, Judit Macías-Vidal, Emilio Ros, Javier de las Heras, Marisa Girós, Maria J Coll, Antonia Ribes. Cholestane-3β,5α,6β-triol: high levels in Niemann-Pick type C, cerebrotendinous xanthomatosis, and lysosomal acid lipase deficiency. Journal of lipid research. 2015 Oct; 56(10):1926-35. doi: 10.1194/jlr.m060343. [PMID: 26239048]
  • Sara Boenzi, Federica Deodato, Roberta Taurisano, Diego Martinelli, Daniela Verrigni, Rosalba Carrozzo, Enrico Bertini, Anna Pastore, Carlo Dionisi-Vici, David W Johnson. A new simple and rapid LC-ESI-MS/MS method for quantification of plasma oxysterols as dimethylaminobutyrate esters. Its successful use for the diagnosis of Niemann-Pick type C disease. Clinica chimica acta; international journal of clinical chemistry. 2014 Nov; 437(?):93-100. doi: 10.1016/j.cca.2014.07.010. [PMID: 25038260]
  • Xuntian Jiang, Rohini Sidhu, Forbes D Porter, Nicole M Yanjanin, Anneliese O Speak, Danielle Taylor te Vruchte, Frances M Platt, Hideji Fujiwara, David E Scherrer, Jessie Zhang, Dennis J Dietzen, Jean E Schaffer, Daniel S Ory. A sensitive and specific LC-MS/MS method for rapid diagnosis of Niemann-Pick C1 disease from human plasma. Journal of lipid research. 2011 07; 52(7):1435-45. doi: 10.1194/jlr.d015735. [PMID: 21518695]
  • Hongmei Liu, Tiebing Wang, Kaixun Huang. Cholestane-3beta,5alpha,6beta-triol-induced reactive oxygen species production promotes mitochondrial dysfunction in isolated mice liver mitochondria. Chemico-biological interactions. 2009 May; 179(2-3):81-7. doi: 10.1016/j.cbi.2008.12.003. [PMID: 19121293]
  • 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]
  • Qingzhi Wu, Kaixun Huang. Protective effect of ebselen on cytotoxicity induced by cholestane-3 beta, 5 alpha, 6 beta-triol in ECV-304 cells. Biochimica et biophysica acta. 2006 Mar; 1761(3):350-9. doi: 10.1016/j.bbalip.2006.02.017. [PMID: 16581291]
  • Rong Tang, Hongmei Liu, Tiebing Wang, Kaixun Huang. Mechanisms of selenium inhibition of cell apoptosis induced by oxysterols in rat vascular smooth muscle cells. Archives of biochemistry and biophysics. 2005 Sep; 441(1):16-24. doi: 10.1016/j.abb.2005.06.006. [PMID: 16039982]
  • Kaixun Huang, Hongmei Liu, Zexian Chen, Huibi Xu. Role of selenium in cytoprotection against cholesterol oxide-induced vascular damage in rats. Atherosclerosis. 2002 May; 162(1):137-44. doi: 10.1016/s0021-9150(01)00707-9. [PMID: 11947907]
  • H Cantwell, R Devery. The response of the antioxidant defense system in rat hepatocytes challenged with oxysterols is modified by Covi-ox. Cell biology and toxicology. 1998 Dec; 14(6):401-9. doi: 10.1023/a:1007595527176. [PMID: 9879932]
  • B Zipser, J J Bradford, R I Hollingsworth. Cholesterol and its derivatives, are the principal steroids isolated from the leech species Hirudo medicinalis. Comparative biochemistry and physiology. Part C, Pharmacology, toxicology & endocrinology. 1998 Aug; 120(2):269-82. doi: 10.1016/s0742-8413(98)10005-1. [PMID: 9827041]
  • 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]
  • M M Mahfouz, F A Kummerow. Oxysterols and TBARS are among the LDL oxidation products which enhance thromboxane A2 synthesis by platelets. Prostaglandins & other lipid mediators. 1998 Jul; 56(4):197-217. doi: 10.1016/s0090-6980(98)00056-2. [PMID: 9777653]
  • A M Wilson, R M Sisk, N M O'Brien. Modulation of cholestane-3 beta,5 alpha,6 beta-triol toxicity by butylated hydroxytoluene, alpha-tocopherol and beta-carotene in newborn rat kidney cells in vitro. The British journal of nutrition. 1997 Sep; 78(3):479-92. doi: 10.1079/bjn19970165. [PMID: 9306888]
  • K Ohtani, T Terada, M Kamei, I Matsui-Yuasa. Cytotoxicity of cholestane 3 beta,5 alpha,6 beta-triol on cultured intestinal epithelial crypt cells (IEC-6). Bioscience, biotechnology, and biochemistry. 1997 Apr; 61(4):573-6. doi: 10.1271/bbb.61.573. [PMID: 9145512]
  • O Breuer, S Dzeletovic, E Lund, U Diczfalusy. The oxysterols cholest-5-ene-3 beta,4 alpha-diol, cholest-5-ene-3 beta,4 beta-diol and cholestane-3 beta,5 alpha,6 alpha-triol are formed during in vitro oxidation of low density lipoprotein, and are present in human atherosclerotic plaques. Biochimica et biophysica acta. 1996 Jul; 1302(2):145-52. doi: 10.1016/0005-2760(96)00052-5. [PMID: 8695664]
  • M M Mahfouz, T L Smith, Q Zhou, F A Kummerow. Cholestane-3 beta, 5 alpha, 6 beta-triol stimulates phospholipid synthesis and CTP-phosphocholine cytidyltransferase in cultured LLC-PK cells. The international journal of biochemistry & cell biology. 1996 Jul; 28(7):739-50. doi: 10.1016/1357-2725(96)00025-8. [PMID: 8925405]
  • D Matthias, C H Becker, R Riezler, P H Kindling. Homocysteine induced arteriosclerosis-like alterations of the aorta in normotensive and hypertensive rats following application of high doses of methionine. Atherosclerosis. 1996 May; 122(2):201-16. doi: 10.1016/0021-9150(95)05740-4. [PMID: 8769683]
  • S Ramasamy, D W Lipke, G A Boissonneault, H Guo, B Hennig. Oxidized lipid-mediated alterations in proteoglycan metabolism in cultured pulmonary endothelial cells. Atherosclerosis. 1996 Feb; 120(1-2):199-208. doi: 10.1016/0021-9150(95)05702-1. [PMID: 8645361]
  • M Mahfouz, T Smith, F A Kummerow. Changes in linoleic acid metabolism and membrane fatty acids of LLC-PK cells in culture induced by 5 alpha-cholestane-3 beta,5,6 beta-triol. Lipids. 1995 Nov; 30(11):977-85. doi: 10.1007/bf02536281. [PMID: 8569437]
  • B A Cunningham, L Midmore, O Kucuk, L J Lis, M P Westerman, W Bras, D H Wolfe, P J Quinn, S B Qadri. Sterols stabilize the ripple phase structure in dihexadecylphosphatidylcholine. Biochimica et biophysica acta. 1995 Jan; 1233(1):75-83. doi: 10.1016/0005-2736(94)00240-p. [PMID: 7833353]
  • M Toborek, B Hennig. Vitamin E attenuates induction of elastase-like activity by tumor necrosis factor-alpha, cholestan-3 beta,5 alpha,6 beta-triol and linoleic acid in cultured endothelial cells. Clinica chimica acta; international journal of clinical chemistry. 1993 Jun; 215(2):201-11. doi: 10.1016/0009-8981(93)90126-o. [PMID: 8403435]
  • 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]
  • C Seillan. Oxysterol mediated changes in fatty acid distribution and lipid synthesis in cultured bovine aortic smooth muscle cells. Lipids. 1990 Mar; 25(3):172-6. doi: 10.1007/bf02544334. [PMID: 2110280]
  • R J Morin, S K Peng. Effects of cholesterol oxidation derivatives on cholesterol esterifying and cholesteryl ester hydrolytic enzyme activity of cultured rabbit aortic smooth muscle cells. Lipids. 1989 Mar; 24(3):217-20. doi: 10.1007/bf02535237. [PMID: 2761354]
  • 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]
  • B Hennig, G A Boissonneault. Cholestan-3 beta,5 alpha,6 beta-triol decreases barrier function of cultured endothelial cell monolayers. Atherosclerosis. 1987 Dec; 68(3):255-61. doi: 10.1016/0021-9150(87)90205-x. [PMID: 3426658]
  • D Matthias, C H Becker, W Gödicke, R Schmidt, K Ponsold. Action of cholestane-3 beta,5 alpha,6 beta-triol on rats with particular reference to the aorta. Atherosclerosis. 1987 Feb; 63(2-3):115-24. doi: 10.1016/0021-9150(87)90111-0. [PMID: 3827976]
  • B H Cho, P O Egwim, G C Fahey. Effects of pure and auto-oxidized forms of cholesterol on plasma, liver lipids and hepatic lipogenesis in chicks. Comparative biochemistry and physiology. B, Comparative biochemistry. 1986; 83(4):767-70. doi: 10.1016/0305-0491(86)90143-4. [PMID: 3709111]
  • M S Jacobson, M G Price, A E Shamoo, F P Heald. Atherogenesis in white carneau pigeons. Effects of low-level cholestane-triol feeding. Atherosclerosis. 1985 Nov; 57(2-3):209-17. doi: 10.1016/0021-9150(85)90034-6. [PMID: 4084355]
  • S K Peng, J C Hill, R J Morin, C B Taylor. Influence of cholesterol oxidation derivatives on membrane bound enzymes in cultured aortic smooth muscle cells. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 1985 Oct; 180(1):126-32. doi: 10.3181/00379727-180-42153. [PMID: 2994076]
  • N A Higley, S L Taylor. The steatotic and cytotoxic effects of cholesterol oxides in cultured L cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1984 Dec; 22(12):983-92. doi: 10.1016/0278-6915(84)90148-0. [PMID: 6542547]
  • 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]
  • 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]
  • 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]