7-Hydroxycholesterol (BioDeep_00000175118)
human metabolite blood metabolite
代谢物信息卡片
2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
化学式: C27H46O2 (402.34976159999997)
中文名称:
谱图信息:
最多检出来源 () 0%
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
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)
2 个相关的物种来源信息
- 42017 - Gloiopeltis furcata: 10.1248/CPB.58.1236
- 9606 - Homo sapiens: -
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] - Hiroshi Takahashi, Tatsuya Hoshino. A comparative study of the effects of 7β-hydroxycholesterol, 25-hydroxycholesterol, and cholesterol on the structural and thermal phase behavior of multilamellar dipalmitoylphosphatidylcholine bilayer vesicles.
Chemistry and physics of lipids.
2020 03; 227(?):104872. doi:
10.1016/j.chemphyslip.2020.104872. [PMID: 31926857] - 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] - 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] - 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] - K Sassi, T Nury, A Zarrouk, R Sghaier, A Khalafi-Nezhad, A Vejux, M Samadi, F Ben Aissa-Fennira, G Lizard. Induction of a non-apoptotic mode of cell death associated with autophagic characteristics with steroidal maleic anhydrides and 7β-hydroxycholesterol on glioma cells.
The Journal of steroid biochemistry and molecular biology.
2019 07; 191(?):105371. doi:
10.1016/j.jsbmb.2019.04.020. [PMID: 31034873] - 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] - Amira Zarrouk, Mohammed Ali Smach, Jawhar Hafsa, Randa Sghaier, Hatem Majdoub, Mohammed Hammami, Bassem Charfeddine. Effects of Carpobrotus edulis Extract on Oxidative Stress and 158N Oligodendrocyte Death.
Biomedical and environmental sciences : BES.
2019 Apr; 32(4):291-299. doi:
10.3967/bes2019.039. [PMID: 31217065] - 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:
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Biochimica et biophysica acta. Molecular and cell biology of lipids.
2018 09; 1863(9):968-979. doi:
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Free radical biology & medicine.
2017 12; 113(?):539-550. doi:
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The Journal of steroid biochemistry and molecular biology.
2017 05; 169(?):111-122. doi:
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Nature communications.
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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] - 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] - Yoshiro Saito, Noriko Noguchi. 7-Hydroxycholestrol as a possible biomarker of cellular lipid peroxidation: difference between cellular and plasma lipid peroxidation.
Biochemical and biophysical research communications.
2014 Apr; 446(3):741-4. doi:
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Atherosclerosis.
2013 Sep; 230(1):48-51. doi:
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Biochemical pharmacology.
2013 Jul; 86(1):67-79. doi:
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Biochemical pharmacology.
2013 Jul; 86(1):161-7. doi:
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Ugeskrift for laeger.
2013 Jan; 175(5):285-6. doi:
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Digestive and liver disease : official journal of the Italian Society of Gastroenterology and the Italian Association for the Study of the Liver.
2012 Mar; 44(3):245-50. doi:
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Biochemical pharmacology.
2012 Jan; 83(1):37-46. doi:
10.1016/j.bcp.2011.09.022. [PMID: 21983033] - Wei Li, Moumita Ghosh, Sina Eftekhari, Xi-Ming Yuan. Lipid accumulation and lysosomal pathways contribute to dysfunction and apoptosis of human endothelial cells caused by 7-oxysterols.
Biochemical and biophysical research communications.
2011 Jun; 409(4):711-6. doi:
10.1016/j.bbrc.2011.05.071. [PMID: 21621514] - Yongsheng Wang, Lili Wang, Yan Hu, Lantong Zhang, Zhihan Wang. Isolation and identification of two steroid compounds from Oviductus Ranae.
Natural product research.
2010 Oct; 24(16):1518-22. doi:
10.1080/14786419.2010.484391. [PMID: 20835952] - Zhongmei Tang, F Peter Guengerich. Dansylation of unactivated alcohols for improved mass spectral sensitivity and application to analysis of cytochrome P450 oxidation products in tissue extracts.
Analytical chemistry.
2010 Sep; 82(18):7706-12. doi:
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Journal of lipid research.
2009 Feb; 50(2):350-7. doi:
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Atherosclerosis.
2008 Feb; 196(2):598-607. doi:
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Annals of nutrition & metabolism.
2008; 53(3-4):283-94. doi:
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Lipids.
2007 May; 42(5):439-49. doi:
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Free radical biology & medicine.
2007 Mar; 42(5):698-705. doi:
10.1016/j.freeradbiomed.2006.12.013. [PMID: 17291993] - Clett Erridge, David J Webb, Corinne M Spickett. 25-Hydroxycholesterol, 7beta-hydroxycholesterol and 7-ketocholesterol upregulate interleukin-8 expression independently of Toll-like receptor 1, 2, 4 or 6 signalling in human macrophages.
Free radical research.
2007 Mar; 41(3):260-6. doi:
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Analytica chimica acta.
2007 Feb; 585(1):86-93. doi:
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Diabetes/metabolism research and reviews.
2007 Jan; 23(1):35-42. doi:
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International journal of oncology.
2006 Dec; 29(6):1549-54. doi:
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The Journal of biological chemistry.
2006 May; 281(20):14440-5. doi:
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Archives of toxicology.
2006 Apr; 80(4):187-95. doi:
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Pathologie-biologie.
2006 Feb; 54(1):22-32. doi:
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Free radical biology & medicine.
2005 Oct; 39(7):864-75. doi:
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European journal of clinical investigation.
2005 Aug; 35(8):482-90. doi:
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European journal of nutrition.
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Cell death and differentiation.
2005 Feb; 12(2):128-35. doi:
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Annals of the New York Academy of Sciences.
2004 Dec; 1030(?):202-7. doi:
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Free radical research.
2004 Aug; 38(8):787-94. doi:
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Free radical research.
2004 Apr; 38(4):375-84. doi:
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Free radical research.
2003 Nov; 37(11):1235-44. doi:
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Arteriosclerosis, thrombosis, and vascular biology.
2003 May; 23(5):809-15. doi:
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Biochemical and biophysical research communications.
2003 Apr; 303(3):814-24. doi:
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Journal of agricultural and food chemistry.
2002 Oct; 50(21):5981-6. doi:
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Biochemical pharmacology.
2002 Aug; 64(3):527-41. doi:
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