7alpha-Hydroxycholesterol (BioDeep_00000003251)

Main id: BioDeep_00000636693

Secondary id: BioDeep_00000419054

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Volatile Flavor Compounds


代谢物信息卡片


(1S,2R,5S,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol

化学式: C27H46O2 (402.34976159999997)
中文名称: 胆甾-5-烯-3,7二醇
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.08%

分子结构信息

SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2C(C=C4C3(CCC(C4)O)C)O)C
InChI: InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1

描述信息

7alpha-Hydroxycholesterol is an oxysterol and can serve as a biomarker for lipid peroxidation (PMID: 17386651). Products of cholesterol oxidation accumulate within atherosclerotic plaque and have been proposed to contribute to inflammatory signalling in the diseased artery (PMID: 17364953). 7alpha-Hydroxycholesterol is a cholesterol oxide that has been described as a biomarker of oxidative stress in subjects with impaired glucose tolerance and diabetes (PMID: 16634125). 7alpha-Hydroxycholesterol has been identified in the human placenta (PMID: 32033212).
7alpha-hydroxycholesterol is an oxysterol and can serve as a biomarker for lipid peroxidation. (PMID: 17386651) Products of cholesterol oxidation accumulate within atherosclerotic plaque and have been proposed to contribute to inflammatory signalling in the diseased artery. (PMID: 17364953)
7α-Hydroxycholesterol is a cholesterol oxide and is formed by both enzymatic and non-enzymatic oxidation. 7α-Hydroxycholesterol can be used as a biomarker for lipid peroxidation[1][2].

同义名列表

22 个代谢物同义名

(1S,2R,5S,9S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol; (3beta,7alpha)-Cholest-5-ene-3,7-diol; 7alpha-Hydroxycholest-5-en-3beta-ol; Cholest-5-en-3 beta,7 alpha-diol; Cholest-5-ene-3beta,7alpha-diol; cholest-5-en-3beta,7alpha-diol; (3Β,7α)-cholest-5-ene-3,7-diol; 7Α-hydroxycholest-5-en-3β-ol; 7α-hydroxy-cholesterol; 7alpha-hydroxy-cholesterol; 7-beta-Hydroxy-Cholesterol; 7 alpha-Hydroxycholesterol; 7alpha-Hydroxycholesterol; Cholest-5-ene-3β,7α-diol; Cholest-5-ene-3b,7a-diol; 7a-Hydroxy-cholesterol; 7Α-hydroxy-cholesterol; 7α-hydroxycholesterol; 7a-Hydroxycholesterol; 7AlphaOHChol; 7ΑOHChol; 7alpha-Hydroxycholesterol



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(10)

BioCyc(0)

PlantCyc(0)

代谢反应

102 个相关的代谢反应过程信息。

Reactome(96)

BioCyc(1)

WikiPathways(3)

Plant Reactome(0)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

5 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

  • Imen Ghzaiel, Amira Zarrouk, Vivien Pires, Jean-Paul Pais de Barros, Sonia Hammami, Mohamed Ksila, Mohamed Hammami, Taoufik Ghrairi, Pierre Jouanny, Anne Vejux, Gérard Lizard. 7β-Hydroxycholesterol and 7-ketocholesterol: New oxidative stress biomarkers of sarcopenia inducing cytotoxic effects on myoblasts and myotubes. The Journal of steroid biochemistry and molecular biology. 2023 Jun; 232(?):106345. doi: 10.1016/j.jsbmb.2023.106345. [PMID: 37286110]
  • Leila Rezig, Imen Ghzaiel, Mohamed Ksila, Aline Yammine, Thomas Nury, Amira Zarrouk, Mohammad Samadi, Moncef Chouaibi, Anne Vejux, Gérard Lizard. Cytoprotective activities of representative nutrients from the Mediterranean diet and of Mediterranean oils against 7-ketocholesterol- and 7β-hydroxycholesterol-induced cytotoxicity: Application to age-related diseases and civilization diseases. Steroids. 2022 11; 187(?):109093. doi: 10.1016/j.steroids.2022.109093. [PMID: 36029811]
  • Imen Ghzaiel, Amira Zarrouk, Soukaina Essadek, Lucy Martine, Souha Hammouda, Aline Yammine, Mohamed Ksila, Thomas Nury, Wiem Meddeb, Mounia Tahri Joutey, Wafa Mihoubi, Claudio Caccia, Valerio Leoni, Mohammad Samadi, Niyazi Acar, Pierre Andreoletti, Sonia Hammami, Taoufik Ghrairi, Anne Vejux, Mohamed Hammami, Gérard Lizard. Protective effects of milk thistle (Sylibum marianum) seed oil and α-tocopherol against 7β-hydroxycholesterol-induced peroxisomal alterations in murine C2C12 myoblasts: Nutritional insights associated with the concept of pexotherapy. Steroids. 2022 07; 183(?):109032. doi: 10.1016/j.steroids.2022.109032. [PMID: 35381271]
  • T Nury, A Yammine, I Ghzaiel, K Sassi, A Zarrouk, F Brahmi, M Samadi, S Rup-Jacques, D Vervandier-Fasseur, J P Pais de Barros, V Bergas, S Ghosh, M Majeed, A Pande, A Atanasov, S Hammami, M Hammami, J Mackrill, B Nasser, P Andreoletti, M Cherkaoui-Malki, A Vejux, G Lizard. Attenuation of 7-ketocholesterol- and 7β-hydroxycholesterol-induced oxiapoptophagy by nutrients, synthetic molecules and oils: Potential for the prevention of age-related diseases. Ageing research reviews. 2021 07; 68(?):101324. doi: 10.1016/j.arr.2021.101324. [PMID: 33774195]
  • Souha Hammouda, Imen Ghzaiel, Pol Picón-Pagès, Wiem Meddeb, Wided Khamlaoui, Sonia Hammami, Francisco J Muñoz, Mohamed Hammami, Amira Zarrouk. Nigella and Milk Thistle Seed Oils: Potential Cytoprotective Effects against 7β-Hydroxycholesterol-Induced Toxicity on SH-SY5Y Cells. Biomolecules. 2021 05; 11(6):. doi: 10.3390/biom11060797. [PMID: 34071950]
  • Mason McComb, Richard W Browne, Sonia Bhattacharya, Mary Lou Bodziak, Dejan Jakimovski, Bianca Weinstock-Guttman, Jens Kuhle, Robert Zivadinov, Murali Ramanathan. The cholesterol autoxidation products, 7-ketocholesterol and 7β-hydroxycholesterol are associated with serum neurofilaments in multiple sclerosis. Multiple sclerosis and related disorders. 2021 May; 50(?):102864. doi: 10.1016/j.msard.2021.102864. [PMID: 33677412]
  • Anne Vejux, Dehbia Abed-Vieillard, Khadija Hajji, Amira Zarrouk, John J Mackrill, Shubhrima Ghosh, Thomas Nury, Aline Yammine, Mohamed Zaibi, Wafa Mihoubi, Habiba Bouchab, Boubker Nasser, Yaël Grosjean, Gérard Lizard. 7-Ketocholesterol and 7β-hydroxycholesterol: In vitro and animal models used to characterize their activities and to identify molecules preventing their toxicity. Biochemical pharmacology. 2020 03; 173(?):113648. doi: 10.1016/j.bcp.2019.113648. [PMID: 31586589]
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  • Thomas Nury, Aline Yammine, Franck Menetrier, Amira Zarrouk, Anne Vejux, Gérard Lizard. 7-Ketocholesterol- and 7β-Hydroxycholesterol-Induced Peroxisomal Disorders in Glial, Microglial and Neuronal Cells: Potential Role in Neurodegeneration : 7-ketocholesterol and 7β-hydroxycholesterol-Induced Peroxisomal Disorders and Neurodegeneration. Advances in experimental medicine and biology. 2020; 1299(?):31-41. doi: 10.1007/978-3-030-60204-8_3. [PMID: 33417205]
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  • Randa Sghaier, Thomas Nury, Valerio Leoni, Claudio Caccia, Jean-Paul Pais De Barros, Ameur Cherif, Anne Vejux, Thibault Moreau, Khalifa Limem, Mohammad Samadi, John J Mackrill, Ahmed Slaheddine Masmoudi, Gérard Lizard, Amira Zarrouk. Dimethyl fumarate and monomethyl fumarate attenuate oxidative stress and mitochondrial alterations leading to oxiapoptophagy in 158N murine oligodendrocytes treated with 7β-hydroxycholesterol. The Journal of steroid biochemistry and molecular biology. 2019 11; 194(?):105432. doi: 10.1016/j.jsbmb.2019.105432. [PMID: 31344443]
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  • Randa Sghaier, Amira Zarrouk, Thomas Nury, Ilham Badreddine, Nora O'Brien, John J Mackrill, Anne Vejux, Mohammad Samadi, Boubker Nasser, Claudio Caccia, Valerio Leoni, Thibault Moreau, Mustapha Cherkaoui-Malki, Ahmed Salhedine Masmoudi, Gérard Lizard. Biotin attenuation of oxidative stress, mitochondrial dysfunction, lipid metabolism alteration and 7β-hydroxycholesterol-induced cell death in 158N murine oligodendrocytes. Free radical research. 2019 05; 53(5):535-561. doi: 10.1080/10715762.2019.1612891. [PMID: 31039616]
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  • Amira Zarrouk, Yosra Ben Salem, Jawhar Hafsa, Randa Sghaier, Bassem Charfeddine, Khalifa Limem, Mohamed Hammami, Hatem Majdoub. 7β-hydroxycholesterol-induced cell death, oxidative stress, and fatty acid metabolism dysfunctions attenuated with sea urchin egg oil. Biochimie. 2018 Oct; 153(?):210-219. doi: 10.1016/j.biochi.2018.06.027. [PMID: 30003930]
  • Yidan Sun, Susanne Kopp, Jasmin Strutz, Chaitanya Chakravarthi Gali, Martina Zandl-Lang, Elham Fanaee-Danesh, Andrijana Kirsch, Silvija Cvitic, Saša Frank, Richard Saffery, Ingemar Björkhem, Gernot Desoye, Christian Wadsack, Ute Panzenboeck. Gestational diabetes mellitus modulates cholesterol homeostasis in human fetoplacental endothelium. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2018 09; 1863(9):968-979. doi: 10.1016/j.bbalip.2018.05.005. [PMID: 29778664]
  • Monica Deiana, Simone Calfapietra, Alessandra Incani, Angela Atzeri, Daniela Rossin, Roberto Loi, Barbara Sottero, Noemi Iaia, Giuseppe Poli, Fiorella Biasi. Derangement of intestinal epithelial cell monolayer by dietary cholesterol oxidation products. Free radical biology & medicine. 2017 12; 113(?):539-550. doi: 10.1016/j.freeradbiomed.2017.10.390. [PMID: 29102636]
  • Frans Stellaard, Klaus von Bergmann, Thomas Sudhop, Dieter Lütjohann. The value of surrogate markers to monitor cholesterol absorption, synthesis and bioconversion to bile acids under lipid lowering therapies. The Journal of steroid biochemistry and molecular biology. 2017 05; 169(?):111-122. doi: 10.1016/j.jsbmb.2016.03.030. [PMID: 27060336]
  • Willem-Jan Keune, Jens Hausmann, Ruth Bolier, Dagmar Tolenaars, Andreas Kremer, Tatjana Heidebrecht, Robbie P Joosten, Manjula Sunkara, Andrew J Morris, Elisa Matas-Rico, Wouter H Moolenaar, Ronald P Oude Elferink, Anastassis Perrakis. Steroid binding to Autotaxin links bile salts and lysophosphatidic acid signalling. Nature communications. 2016 Apr; 7(?):11248. doi: 10.1038/ncomms11248. [PMID: 27075612]
  • Zoltán Pataj, Gerhard Liebisch, Gerd Schmitz, Silke Matysik. Quantification of oxysterols in human plasma and red blood cells by liquid chromatography high-resolution tandem mass spectrometry. Journal of chromatography. A. 2016 Mar; 1439(?):82-88. doi: 10.1016/j.chroma.2015.11.015. [PMID: 26607314]
  • Aliki A Rasmiena, Christopher K Barlow, Theodore W Ng, Dedreia Tull, Peter J Meikle. High density lipoprotein efficiently accepts surface but not internal oxidised lipids from oxidised low density lipoprotein. Biochimica et biophysica acta. 2016 Feb; 1861(2):69-77. doi: 10.1016/j.bbalip.2015.11.002. [PMID: 26569052]
  • Thomas Nury, Amira Zarrouk, John J Mackrill, Mohammad Samadi, Philippe Durand, Jean-Marc Riedinger, Margaux Doria, Anne Vejux, Emeric Limagne, Dominique Delmas, Michel Prost, Thibault Moreau, Mohamed Hammami, Régis Delage-Mourroux, Nora M O'Brien, Gérard Lizard. Induction of oxiapoptophagy on 158N murine oligodendrocytes treated by 7-ketocholesterol-, 7β-hydroxycholesterol-, or 24(S)-hydroxycholesterol: Protective effects of α-tocopherol and docosahexaenoic acid (DHA; C22:6 n-3). Steroids. 2015 Jul; 99(Pt B):194-203. doi: 10.1016/j.steroids.2015.02.003. [PMID: 25683890]
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  • Oliver Weingärtner, Constanze Husche, Hans F Schött, Timo Speer, Michael Böhm, Charlotte M Miller, Florence McCarthy, Jogchum Plat, Dieter Lütjohann, Ulrich Laufs. Vascular effects of oxysterols and oxyphytosterols in apoE -/- mice. Atherosclerosis. 2015 May; 240(1):73-9. doi: 10.1016/j.atherosclerosis.2015.02.032. [PMID: 25765595]
  • Yalong Wang, Han Jiang, Huizhi Huang, Yanqi Xie, Yunshi Zhao, Xiuhua You, Lipeng Tang, Youqiong Wang, Wei Yin, Pengxin Qiu, Guangmei Yan, Haiyan Hu. Determination of neuroprotective oxysterols in Calculus bovis, human gallstones, and traditional Chinese medicine preparations by liquid chromatography with mass spectrometry. Journal of separation science. 2015 Mar; 38(5):796-803. doi: 10.1002/jssc.201400850. [PMID: 25545614]
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  • Tadashi Ikegami, Akira Honda, Teruo Miyazaki, Motoyuki Kohjima, Makoto Nakamuta, Yasushi Matsuzaki. Increased serum oxysterol concentrations in patients with chronic hepatitis C virus infection. Biochemical and biophysical research communications. 2014 Apr; 446(3):736-40. doi: 10.1016/j.bbrc.2014.01.176. [PMID: 24525121]
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