5alpha-cholestan-6-oxo-3beta-ol (BioDeep_00001051907)
代谢物信息卡片
5alpha-cholestan-6-oxo-3beta-ol
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(CCC3C2CC(=O)C4C3(CCC(C4)O)C)C
InChI: InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-16-25(29)24-15-19(28)11-13-27(24,5)23(20)12-14-26(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20?,21-,22?,23?,24-,26-,27-/m1/s1
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。
文献列表
- Iliuza R Iaubasarova, Ljudmila S Khailova, Alexander M Firsov, Vera G Grivennikova, Roman S Kirsanov, Galina A Korshunova, Elena A Kotova, Yuri N Antonenko. The mitochondria-targeted derivative of the classical uncoupler of oxidative phosphorylation carbonyl cyanide m-chlorophenylhydrazone is an effective mitochondrial recoupler.
PloS one.
2020; 15(12):e0244499. doi:
10.1371/journal.pone.0244499. [PMID: 33378414] - Hujun Shen, Zhenhua Wu, Kun Zhao, Hengxiu Yang, Mingsen Deng, Shuiguo Wen. Effect of Cholesterol and 6-Ketocholestanol on Membrane Dipole Potential and Sterol Flip-Flop Motion in Bilayer Membranes.
Langmuir : the ACS journal of surfaces and colloids.
2019 08; 35(34):11232-11241. doi:
10.1021/acs.langmuir.9b01802. [PMID: 31373497] - Rebika Shrestha, Cari M Anderson, Alfredo E Cardenas, Ron Elber, Lauren J Webb. Direct Measurement of the Effect of Cholesterol and 6-Ketocholestanol on the Membrane Dipole Electric Field Using Vibrational Stark Effect Spectroscopy Coupled with Molecular Dynamics Simulations.
The journal of physical chemistry. B.
2017 04; 121(15):3424-3436. doi:
10.1021/acs.jpcb.6b09007. [PMID: 28071910] - Tamás Kovács, Gyula Batta, Tímea Hajdu, Ágnes Szabó, Tímea Váradi, Florina Zákány, István Csomós, János Szöllősi, Peter Nagy. The Dipole Potential Modifies the Clustering and Ligand Binding Affinity of ErbB Proteins and Their Signaling Efficiency.
Scientific reports.
2016 10; 6(?):35850. doi:
10.1038/srep35850. [PMID: 27775011] - Blanka Vrbková, Vendula Roblová, Edward S Yeung, Jan Preisler. Determination of sterols using liquid chromatography with off-line surface-assisted laser desorption/ionization mass spectrometry.
Journal of chromatography. A.
2014 Sep; 1358(?):102-9. doi:
10.1016/j.chroma.2014.06.077. [PMID: 25022478] - Yuta Hidaka, Koji Asami. Measurement of dipole potential in bilayer lipid membranes by dielectric spectroscopy.
The Journal of membrane biology.
2014 Aug; 247(8):721-7. doi:
10.1007/s00232-014-9697-1. [PMID: 24935731] - M Przybylo, J Procek, M Hof, M Langner. The alteration of lipid bilayer dynamics by phloretin and 6-ketocholestanol.
Chemistry and physics of lipids.
2014 Feb; 178(?):38-44. doi:
10.1016/j.chemphyslip.2013.11.005. [PMID: 24316311] - Olga S Ostroumova, Yuri A Kaulin, Philip A Gurnev, Ludmila V Schagina. Effect of agents modifying the membrane dipole potential on properties of syringomycin E channels.
Langmuir : the ACS journal of surfaces and colloids.
2007 Jun; 23(13):6889-92. doi:
10.1021/la7005452. [PMID: 17508767] - Mark F Vitha, Ronald J Clarke. Comparison of excitation and emission ratiometric fluorescence methods for quantifying the membrane dipole potential.
Biochimica et biophysica acta.
2007 Jan; 1768(1):107-14. doi:
10.1016/j.bbamem.2006.06.022. [PMID: 16904627] - Víctor Buzón, Josep Cladera. Effect of cholesterol on the interaction of the HIV GP41 fusion peptide with model membranes. Importance of the membrane dipole potential.
Biochemistry.
2006 Dec; 45(51):15768-75. doi:
10.1021/bi060622i. [PMID: 17176099] - Tudor Luchian, Loredana Mereuta. Phlorizin- and 6-ketocholestanol-mediated antagonistic modulation of alamethicin activity in phospholipid planar membranes.
Langmuir : the ACS journal of surfaces and colloids.
2006 Sep; 22(20):8452-7. doi:
10.1021/la0613777. [PMID: 16981762] - Noemí García, Cecilia Zazueta, Natalia Pavón, Edmundo Chávez. Agaric acid induces mitochondrial permeability transition through its interaction with the adenine nucleotide translocase. Its dependence on membrane fluidity.
Mitochondrion.
2005 Aug; 5(4):272-81. doi:
10.1016/j.mito.2005.05.002. [PMID: 16050990] - Vasyl V Shynkar, Andrey S Klymchenko, Guy Duportail, Alexander P Demchenko, Yves Mély. Two-color fluorescent probes for imaging the dipole potential of cell plasma membranes.
Biochimica et biophysica acta.
2005 Jun; 1712(2):128-36. doi:
10.1016/j.bbamem.2005.03.015. [PMID: 15921656] - Barbara G Auner, Michael A A O'Neill, Claudia Valenta, Jonathan Hadgraft. Interaction of phloretin and 6-ketocholestanol with DPPC-liposomes as phospholipid model membranes.
International journal of pharmaceutics.
2005 Apr; 294(1-2):149-55. doi:
10.1016/j.ijpharm.2005.01.031. [PMID: 15814239] - C Valenta, A Steininger, B G Auner. Phloretin and 6-ketocholestanol: membrane interactions studied by a phospholipid/polydiacetylene colorimetric assay and differential scanning calorimetry.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V.
2004 Mar; 57(2):329-36. doi:
10.1016/j.ejpb.2003.09.012. [PMID: 15018992] - Xin-Min Li, Maureen M Momsen, Howard L Brockman, Rhoderick E Brown. Sterol structure and sphingomyelin acyl chain length modulate lateral packing elasticity and detergent solubility in model membranes.
Biophysical journal.
2003 Dec; 85(6):3788-801. doi:
10.1016/s0006-3495(03)74794-8. [PMID: 14645069] - Josep Cladera, Paul O'Shea, Jonathan Hadgraft, Claudia Valenta. Influence of molecular dipoles on human skin permeability: Use of 6-ketocholestanol to enhance the transdermal delivery of bacitracin.
Journal of pharmaceutical sciences.
2003 May; 92(5):1018-27. doi:
10.1002/jps.10344. [PMID: 12712421] - T Asawakarn, J Cladera, P O'Shea. Effects of the membrane dipole potential on the interaction of saquinavir with phospholipid membranes and plasma membrane receptors of Caco-2 cells.
The Journal of biological chemistry.
2001 Oct; 276(42):38457-63. doi:
10.1074/jbc.m103269200. [PMID: 11500495] - A M Smondyrev, M L Berkowitz. Effects of oxygenated sterol on phospholipid bilayer properties: a molecular dynamics simulation.
Chemistry and physics of lipids.
2001 Jul; 112(1):31-9. doi:
10.1016/s0009-3084(01)00160-8. [PMID: 11518570] - C Valenta, M Nowak, J Hadgraft. Influence of phloretin and 6-ketocholestanol on the permeation of progesterone through porcine skin.
International journal of pharmaceutics.
2001 Apr; 217(1-2):79-86. doi:
10.1016/s0378-5173(01)00590-7. [PMID: 11292544] - S Bala, M H Kombrabail, B S Prabhananda. Effect of phloretin on ionophore mediated electroneutral transmembrane translocations of H(+), K(+) and Na(+) in phospholipid vesicles.
Biochimica et biophysica acta.
2001 Feb; 1510(1-2):258-69. doi:
10.1016/s0005-2736(00)00357-6. [PMID: 11342163] - J I Alakoskela, P K Kinnunen. Control of a redox reaction on lipid bilayer surfaces by membrane dipole potential.
Biophysical journal.
2001 Jan; 80(1):294-304. doi:
10.1016/s0006-3495(01)76014-6. [PMID: 11159402] - Y N Antonenko, T I Rokitskaya, E A Kotova. Effect of dipole modifiers on the kinetics of sensitized photoinactivation of gramicidin channels in bilayer lipid membranes.
Membrane & cell biology.
1999; 13(1):111-20. doi:
". [PMID: 10661474] - L Voglino, T J McIntosh, S A Simon. Modulation of the binding of signal peptides to lipid bilayers by dipoles near the hydrocarbon-water interface.
Biochemistry.
1998 Sep; 37(35):12241-52. doi:
10.1021/bi9805792. [PMID: 9724538] - J Cladera, P O'Shea. Intramembrane molecular dipoles affect the membrane insertion and folding of a model amphiphilic peptide.
Biophysical journal.
1998 May; 74(5):2434-42. doi:
10.1016/s0006-3495(98)77951-2. [PMID: 9591669] - T I Rokitskaya, Y N Antonenko, E A Kotova. Effect of the dipole potential of a bilayer lipid membrane on gramicidin channel dissociation kinetics.
Biophysical journal.
1997 Aug; 73(2):850-4. doi:
10.1016/s0006-3495(97)78117-7. [PMID: 9251801] - A Cuéllar, J Ramirez, V M Infante, E Chavez. Further studies on the recoupling effect of 6-ketocholestanol upon oxidative phosphorylation in uncoupled liver mitochondria.
FEBS letters.
1997 Jul; 411(2-3):365-8. doi:
10.1016/s0014-5793(97)00741-2. [PMID: 9271237] - R J Clarke, D J Kane. Optical detection of membrane dipole potential: avoidance of fluidity and dye-induced effects.
Biochimica et biophysica acta.
1997 Jan; 1323(2):223-39. doi:
10.1016/s0005-2736(96)00188-5. [PMID: 9042345] - B Fuks, F Homblé. Mechanism of proton permeation through chloroplast lipid membranes.
Plant physiology.
1996 Oct; 112(2):759-66. doi:
10.1104/pp.112.2.759. [PMID: 8883387] - F Macri, A Vianello, E Braidot, E Petrussa, E N Mokhova. Zearalenone-induced uncoupling in plant mitochondria is sensitive to 6-ketocholestanol.
Biochemistry and molecular biology international.
1996 Aug; 39(5):1001-6. doi:
10.1080/15216549600201152. [PMID: 8866017] - E Chávez, R Moreno-Sánchez, C Zazueta, A Cuéllar, J Ramirez, H Reyes-Vivas, C Bravo, S Rodríguez-Enríquez. On the mechanism by which 6-ketocholestanol protects mitochondria against uncoupling-induced Ca2+ efflux.
FEBS letters.
1996 Feb; 379(3):305-8. doi:
10.1016/0014-5793(95)01533-7. [PMID: 8603712] - A Vianello, F Macri, E Braidot, E N Mokhova. Effect of 6-ketocholestanol on FCCP- and DNP-induced uncoupling in plant mitochondria.
FEBS letters.
1995 May; 365(1):7-9. doi:
10.1016/0014-5793(95)00431-8. [PMID: 7774718] - O Küçük, J Stoner-Picking, S Yachnin, L I Gordon, R M Williams, L J Lis, M P Westerman. Inhibition of cytolytic T lymphocyte activity by oxysterols.
Lipids.
1994 Sep; 29(9):657-60. doi:
10.1007/bf02536101. [PMID: 7815901] - E Gross, R S Bedlack, L M Loew. Dual-wavelength ratiometric fluorescence measurement of the membrane dipole potential.
Biophysical journal.
1994 Jul; 67(1):208-16. doi:
10.1016/s0006-3495(94)80471-0. [PMID: 7918989] - J C Franklin, D S Cafiso. Internal electrostatic potentials in bilayers: measuring and controlling dipole potentials in lipid vesicles.
Biophysical journal.
1993 Jul; 65(1):289-99. doi:
10.1016/s0006-3495(93)81051-8. [PMID: 8396456] - S A Simon, T J McIntosh, A D Magid, D Needham. Modulation of the interbilayer hydration pressure by the addition of dipoles at the hydrocarbon/water interface.
Biophysical journal.
1992 Mar; 61(3):786-99. doi:
10.1016/s0006-3495(92)81883-0. [PMID: 1504249] - O Kucuk, J Stoner-Picking, S Yachnin, L I Gordon, R M Williams, L J Lis, M P Westerman. Inhibition of NK cell-mediated cytotoxicity by oxysterols.
Cellular immunology.
1992 Feb; 139(2):541-9. doi:
10.1016/0008-8749(92)90091-3. [PMID: 1733518] - M J Vasconcelles, S A Weitzman, S N Lee, S Prachard, L I Gordon. Inhibition of human polymorphonuclear leukocyte respiratory burst activity and aggregation by 6-ketocholestanol.
Free radical research communications.
1990; 8(3):185-93. doi:
10.3109/10715769009087992. [PMID: 2158478]