22-Hydroxycholesterol (BioDeep_00000269112)
Main id: BioDeep_00000636693
代谢物信息卡片
22-alpha-Hydroxy Cholesterol
化学式: C27H46O2 (402.3498)
中文名称: 22(R)-羟基胆固醇
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C12=CCC3C([C@]1(CC[C@@H](C2)O)C)CC[C@]1(C3CCC1[C@@H]([C@@H](CCC(C)C)O)C)C
InChI: InChI=1S/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25?,26-,27+/m0/s1
数据库引用编号
14 个数据库交叉引用编号
- ChEBI: CHEBI:166802
- PubChem: 107724
- Metlin: METLIN41648
- ChEMBL: CHEMBL3218924
- KNApSAcK: C00051948
- CAS: 17711-16-9
- CAS: 17954-98-2
- LipidMAPS: LMST01010054
- PDB-CCD: HC9
- KEGG: C22446
- RefMet: 22-Hydroxycholesterol
- KEGG: C05502
- PubChem: 7855
- KNApSAcK: 67237
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。
| 亚细胞结构定位 | 关联基因列表 |
|---|
文献列表
- Chen Zhou, Yuhui Yang, Jingyi Tian, Yihan Wu, Faliang An, Changfu Li, Yansheng Zhang. 22R- but not 22S-hydroxycholesterol is recruited for diosgenin biosynthesis.
The Plant journal : for cell and molecular biology.
2022 02; 109(4):940-951. doi:
10.1111/tpj.15604. [PMID: 34816537] - Yaoyao Xiao, Lijia Zhao, Weidong Li, Xiaoyu Wang, Tiantian Ma, Luda Yang, Lei Gao, Cuimei Li, Manhui Zhang, Dan Yang, Jing Zhang, Haizhen Jiang, Hongcong Zhao, Yiqun Wang, Hsu-Wen Chao, Aihua Wang, Yaping Jin, Huatao Chen. Circadian clock gene BMAL1 controls testosterone production by regulating steroidogenesis-related gene transcription in goat Leydig cells.
Journal of cellular physiology.
2021 09; 236(9):6706-6725. doi:
10.1002/jcp.30334. [PMID: 33598947] - Syed Kashif Zaidi, Wen-Jun Shen, Yuan Cortez, Stefanie Bittner, Alex Bittner, Sara Arshad, Ting-Ting Huang, Fredric B Kraemer, Salman Azhar. SOD2 deficiency-induced oxidative stress attenuates steroidogenesis in mouse ovarian granulosa cells.
Molecular and cellular endocrinology.
2021 01; 519(?):110888. doi:
10.1016/j.mce.2020.110888. [PMID: 32717420] - K Yoshida, Y Ohta, N Kawate, M Takahashi, T Inaba, S Hatoya, H Morii, K Takahashi, M Ito, H Tamada. Long-term feeding of hydroalcoholic extract powder of Lepidium meyenii (maca) enhances the steroidogenic ability of Leydig cells to alleviate its decline with ageing in male rats.
Andrologia.
2018 Feb; 50(1):. doi:
10.1111/and.12803. [PMID: 28295471] - Teerasak Wongwan, Suticha Kittayaruksakul, Nithi Asavapanumas, Varanuj Chatsudthipong, Sunhapas Soodvilai. Activation of liver X receptor inhibits OCT2-mediated organic cation transport in renal proximal tubular cells.
Pflugers Archiv : European journal of physiology.
2017 11; 469(11):1471-1481. doi:
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Toxicology and applied pharmacology.
2017 09; 330(?):100-106. doi:
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The Journal of biological chemistry.
2016 Dec; 291(50):26109-26125. doi:
10.1074/jbc.m116.740928. [PMID: 27815506] - Tae-Young Na, Young-Hyun Han, Na-Lee Ka, Han-Su Park, Yun Pyo Kang, Sung Won Kwon, Byung-Hoon Lee, Mi-Ock Lee. 22-S-Hydroxycholesterol protects against ethanol-induced liver injury by blocking the auto/paracrine activation of MCP-1 mediated by LXRα.
The Journal of pathology.
2015 Apr; 235(5):710-20. doi:
10.1002/path.4494. [PMID: 25557254] - Jing-Min Wang, Dong Wang, Yu-Yan Tan, Gang Zhao, Zhen-Ling Ji. 22(R)-hydroxycholesterol and pioglitazone synergistically decrease cholesterol ester via the PPARγ-LXRα-ABCA1 pathway in cholesterosis of the gallbladder.
Biochemical and biophysical research communications.
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American journal of physiology. Renal physiology.
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Circulation.
2012 Nov; 126(22):2612-24. doi:
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Lipids.
2012 May; 47(5):483-93. doi:
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Journal of experimental botany.
2012 Mar; 63(5):1823-33. doi:
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American journal of physiology. Renal physiology.
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The Journal of steroid biochemistry and molecular biology.
2012 Feb; 128(3-5):154-64. doi:
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PloS one.
2012; 7(3):e26751. doi:
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Journal of lipids.
2012; 2012(?):139875. doi:
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Evidence-based complementary and alternative medicine : eCAM.
2012; 2012(?):190107. doi:
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Indian journal of endocrinology and metabolism.
2011 Oct; 15 Suppl 4(?):S298-312. doi:
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Comparative biochemistry and physiology. Part A, Molecular & integrative physiology.
2011 Oct; 160(2):125-36. doi:
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Lipids in health and disease.
2011 Sep; 10(?):172. doi:
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Molecular endocrinology (Baltimore, Md.).
2011 Jul; 25(7):1211-22. doi:
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2011 Mar; 52(3):531-9. doi:
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Placenta.
2011 Feb; 32(2):183-91. doi:
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Molecular pharmacology.
2010 Dec; 78(6):1046-58. doi:
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Reproduction in domestic animals = Zuchthygiene.
2010 Dec; 45(6):e434-9. doi:
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Endocrinology.
2010 Nov; 151(11):5519-27. doi:
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Journal of natural products.
2010 Aug; 73(8):1332-6. doi:
10.1021/np100120c. [PMID: 20695472] - WenChieh Chen, Shaw-Jenq Tsai, Hamm-Ming Sheu, Jih-Chien Tsai, Christos C Zouboulis. Testosterone synthesized in cultured human SZ95 sebocytes derives mainly from dehydroepiandrosterone.
Experimental dermatology.
2010 May; 19(5):470-2. doi:
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The Journal of biological chemistry.
2010 Apr; 285(16):11974-82. doi:
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2010 Apr; 82(4-6):211-8. doi:
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Respiratory research.
2010 Feb; 11(?):19. doi:
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Reproductive biology and endocrinology : RB&E.
2010 Feb; 8(?):13. doi:
10.1186/1477-7827-8-13. [PMID: 20144211] - Marina Cardellini, Rossella Menghini, Eugenio Martelli, Viviana Casagrande, Arianna Marino, Stefano Rizza, Ottavia Porzio, Alessandro Mauriello, Anna Solini, Arnaldo Ippoliti, Renato Lauro, Franco Folli, Massimo Federici. TIMP3 is reduced in atherosclerotic plaques from subjects with type 2 diabetes and increased by SirT1.
Diabetes.
2009 Oct; 58(10):2396-401. doi:
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Journal of neuroscience research.
2009 Aug; 87(11):2498-508. doi:
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Journal of lipid research.
2009 Jul; 50(7):1305-15. doi:
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Experimental dermatology.
2009 Jul; 18(7):643-9. doi:
10.1111/j.1600-0625.2009.00841.x. [PMID: 19236478] - Marina S Figueiroa, Juliany S B César Vieira, Disleide S Leite, Ruben C O Andrade Filho, Fabiano Ferreira, Patrícia S Gouveia, Daniel P Udrisar, Maria I Wanderley. Green tea polyphenols inhibit testosterone production in rat Leydig cells.
Asian journal of andrology.
2009 May; 11(3):362-70. doi:
10.1038/aja.2009.2. [PMID: 19330017] - Akira Honda, Kouwa Yamashita, Takashi Hara, Tadashi Ikegami, Teruo Miyazaki, Mutsumi Shirai, Guorong Xu, Mitsuteru Numazawa, Yasushi Matsuzaki. Highly sensitive quantification of key regulatory oxysterols in biological samples by LC-ESI-MS/MS.
Journal of lipid research.
2009 Feb; 50(2):350-7. doi:
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PPAR research.
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Journal of clinical biochemistry and nutrition.
2008 Nov; 43(3):131-8. doi:
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International journal of cardiology.
2008 Aug; 128(1):42-7. doi:
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Arteriosclerosis, thrombosis, and vascular biology.
2008 Jun; 28(6):1144-50. doi:
10.1161/atvbaha.107.157115. [PMID: 18369155] - Il Hong, Min-Ho Lee, Tae-Young Na, Christos C Zouboulis, Mi-Ock Lee. LXRalpha enhances lipid synthesis in SZ95 sebocytes.
The Journal of investigative dermatology.
2008 May; 128(5):1266-72. doi:
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Indian journal of pharmaceutical sciences.
2008 Mar; 70(2):135-44. doi:
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American journal of respiratory cell and molecular biology.
2008 Mar; 38(3):283-92. doi:
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Acta biochimica Polonica.
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American journal of physiology. Gastrointestinal and liver physiology.
2007 Dec; 293(6):G1178-89. doi:
10.1152/ajpgi.00295.2007. [PMID: 17916647] - Chiara Buono, Yifu Li, Stephen W Waldo, Howard S Kruth. Liver X receptors inhibit human monocyte-derived macrophage foam cell formation by inhibiting fluid-phase pinocytosis of LDL.
Journal of lipid research.
2007 Nov; 48(11):2411-8. doi:
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Diabetologia.
2007 Oct; 50(10):2171-80. doi:
10.1007/s00125-007-0760-7. [PMID: 17661008] - Guosong Qiu, John S Hill. Atorvastatin decreases lipoprotein lipase and endothelial lipase expression in human THP-1 macrophages.
Journal of lipid research.
2007 Oct; 48(10):2112-22. doi:
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Zhong nan da xue xue bao. Yi xue ban = Journal of Central South University. Medical sciences.
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Arteriosclerosis, thrombosis, and vascular biology.
2007 Jul; 27(7):1618-24. doi:
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Lipids.
2007 Jul; 42(7):671-8. doi:
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Endocrine.
2006 Dec; 30(3):313-23. doi:
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Biochimica et biophysica acta.
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Reproductive toxicology (Elmsford, N.Y.).
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Shock (Augusta, Ga.).
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The Journal of endocrinology.
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The Canadian journal of cardiology.
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The Journal of steroid biochemistry and molecular biology.
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Circulation research.
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Placenta.
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International journal of molecular medicine.
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