Cholesterol hemisuccinate (BioDeep_00001028529)

   


代谢物信息卡片


4-[(3β)-Cholest-5-en-3-yloxy]-4-oxobutanoic acid

化学式: C31H50O4 (486.37089000000003)
中文名称: 胆固醇琥珀酸单酯
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)CCC(=O)O)C)C
InChI: InChI=1S/C31H50O4/c1-20(2)7-6-8-21(3)25-11-12-26-24-10-9-22-19-23(35-29(34)14-13-28(32)33)15-17-30(22,4)27(24)16-18-31(25,26)5/h9,20-21,23-27H,6-8,10-19H2,1-5H3,(H,32,33)/t21-,23+,24+,25-,26+,27+,30+,31-/m1/s1

描述信息

同义名列表

2 个代谢物同义名

4-[(3β)-Cholest-5-en-3-yloxy]-4-oxobutanoic acid; Cholesterol hemisuccinate



数据库引用编号

3 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)

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

  • Mohammad Mahmoudzadeh, Aniket Magarkar, Artturi Koivuniemi, Tomasz Róg, Alex Bunker. Mechanistic Insight into How PEGylation Reduces the Efficacy of pH-Sensitive Liposomes from Molecular Dynamics Simulations. Molecular pharmaceutics. 2021 07; 18(7):2612-2621. doi: 10.1021/acs.molpharmaceut.1c00122. [PMID: 34096310]
  • Rafael Maldonado-Hernández, Orestes Quesada, José O Colón-Sáez, José A Lasalde-Dominicci. Sequential purification and characterization of Torpedo californica nAChR-DC supplemented with CHS for high-resolution crystallization studies. Analytical biochemistry. 2020 12; 610(?):113887. doi: 10.1016/j.ab.2020.113887. [PMID: 32763308]
  • Bala M Xavier, Aiman A Zein, Angelica Venes, Junmei Wang, Jyh-Yeuan Lee. Transmembrane Polar Relay Drives the Allosteric Regulation for ABCG5/G8 Sterol Transporter. International journal of molecular sciences. 2020 Nov; 21(22):. doi: 10.3390/ijms21228747. [PMID: 33228147]
  • Bozena Augustyn, Piotr Stepien, Chetan Poojari, Edouard Mobarak, Agnieszka Polit, Anna Wisniewska-Becker, Tomasz Róg. Cholesteryl Hemisuccinate Is Not a Good Replacement for Cholesterol in Lipid Nanodiscs. The journal of physical chemistry. B. 2019 11; 123(46):9839-9845. doi: 10.1021/acs.jpcb.9b07853. [PMID: 31674185]
  • Lifeng Luo, Qiuyue Chen, Haoyu Gong, Lu Liu, Lingli Zhou, Haibing He, Yu Zhang, Tian Yin, Xing Tang. Capacity of cholesteryl hemisuccinate in ion pair/phospholipid complex to improve drug-loading, stability and antibacterial activity of clarithromycin intravenous lipid microsphere. Colloids and surfaces. B, Biointerfaces. 2018 Dec; 172(?):262-271. doi: 10.1016/j.colsurfb.2018.08.038. [PMID: 30173093]
  • Manju Kanamala, Brian D Palmer, Hamidreza Ghandehari, William R Wilson, Zimei Wu. PEG-Benzaldehyde-Hydrazone-Lipid Based PEG-Sheddable pH-Sensitive Liposomes: Abilities for Endosomal Escape and Long Circulation. Pharmaceutical research. 2018 May; 35(8):154. doi: 10.1007/s11095-018-2429-y. [PMID: 29855807]
  • Yunning Yang, Yuting Guo, Xinyi Tan, Haibing He, Yu Zhang, Tian Yin, Hui Xu, Xing Tang. Vincristine-loaded liposomes prepared by ion-paring techniques: Effect of lipid, pH and antioxidant on chemical stability. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2018 Jan; 111(?):104-112. doi: 10.1016/j.ejps.2017.09.045. [PMID: 28964951]
  • Deborah L Gater, Namareq Widatalla, Kinza Islam, Maryam AlRaeesi, Jeremy C M Teo, Yanthe E Pearson. Quantification of sterol-specific response in human macrophages using automated imaged-based analysis. Lipids in health and disease. 2017 Dec; 16(1):242. doi: 10.1186/s12944-017-0629-9. [PMID: 29237459]
  • Jing Zuo, Li Tong, Lina Du, Ming Yang, Yiguang Jin. Biomimetic nanoassemblies of 1-O-octodecyl-2-conjugated linoleoyl-sn-glycero-3-phosphatidyl gemcitabine with phospholipase A2-triggered degradation for the treatment of cancer. Colloids and surfaces. B, Biointerfaces. 2017 Apr; 152(?):467-474. doi: 10.1016/j.colsurfb.2017.02.001. [PMID: 28187380]
  • Neuza Domingues, Luís M B B Estronca, João Silva, Marisa R Encarnação, Rita Mateus, Diogo Silva, Inês B Santarino, Margarida Saraiva, Maria I L Soares, Teresa M V D Pinho E Melo, António Jacinto, Winchil L C Vaz, Otília V Vieira. Cholesteryl hemiesters alter lysosome structure and function and induce proinflammatory cytokine production in macrophages. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2017 Feb; 1862(2):210-220. doi: 10.1016/j.bbalip.2016.10.009. [PMID: 27793708]
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  • Xiaona Jing, Camilla Foged, Birte Martin-Bertelsen, Anan Yaghmur, Kolja M Knapp, Martin Malmsten, Henrik Franzyk, Hanne M Nielsen. Delivery of siRNA Complexed with Palmitoylated α-Peptide/β-Peptoid Cell-Penetrating Peptidomimetics: Membrane Interaction and Structural Characterization of a Lipid-Based Nanocarrier System. Molecular pharmaceutics. 2016 06; 13(6):1739-49. doi: 10.1021/acs.molpharmaceut.5b00309. [PMID: 26654841]
  • Yin Duan, Lihui Wei, Julia Petryk, Terrence D Ruddy. Formulation, characterization and tissue distribution of a novel pH-sensitive long-circulating liposome-based theranostic suitable for molecular imaging and drug delivery. International journal of nanomedicine. 2016 ; 11(?):5697-5708. doi: 10.2147/ijn.s111274. [PMID: 27843312]
  • Adam T Clay, Peihua Lu, Frances J Sharom. Interaction of the P-Glycoprotein Multidrug Transporter with Sterols. Biochemistry. 2015 Nov; 54(43):6586-97. doi: 10.1021/acs.biochem.5b00904. [PMID: 26484739]
  • Saeed Ghanbarzadeh, Arash Khorrami, Zhaleh Pourmoazzen, Sanam Arami. Plasma stable, pH-sensitive non-ionic surfactant vesicles simultaneously enhance antiproliferative effect and selectivity of Sirolimus. Pharmaceutical development and technology. 2015 May; 20(3):279-87. doi: 10.3109/10837450.2013.860553. [PMID: 24266760]
  • Waldemar Kulig, Piotr Jurkiewicz, Agnieszka Olżyńska, Joona Tynkkynen, Matti Javanainen, Moutusi Manna, Tomasz Rog, Martin Hof, Ilpo Vattulainen, Pavel Jungwirth. Experimental determination and computational interpretation of biophysical properties of lipid bilayers enriched by cholesteryl hemisuccinate. Biochimica et biophysica acta. 2015 Feb; 1848(2):422-32. doi: 10.1016/j.bbamem.2014.10.032. [PMID: 25450348]
  • H Q Nguyen, V V Chupin, D I Prokhorov, I E Chikunov, V Yu Kovtun, R A Tarumov, A N Grebenyuk, V I Shvets. Creation and study of triterpenoid nanoparticles and radioprotective substance genistein. Doklady. Biochemistry and biophysics. 2015; 464(?):338-40. doi: 10.1134/s160767291505018x. [PMID: 26518563]
  • Sávia C A Lopes, Marcus V M Novais, Diêgo S Ferreira, Fernão C Braga, Rogério Magalhães-Paniago, Ângelo Malachias, Mônica C Oliveira. Ursolic acid incorporation does not prevent the formation of a non-lamellar phase in pH-sensitive and long-circulating liposomes. Langmuir : the ACS journal of surfaces and colloids. 2014 Dec; 30(50):15083-90. doi: 10.1021/la502977j. [PMID: 25490253]
  • Waldemar Kulig, Joona Tynkkynen, Matti Javanainen, Moutusi Manna, Tomasz Rog, Ilpo Vattulainen, Pavel Jungwirth. How well does cholesteryl hemisuccinate mimic cholesterol in saturated phospholipid bilayers?. Journal of molecular modeling. 2014 Feb; 20(2):2121. doi: 10.1007/s00894-014-2121-z. [PMID: 24526383]
  • Joanne Oates, Belinda Faust, Helen Attrill, Peter Harding, Marcella Orwick, Anthony Watts. The role of cholesterol on the activity and stability of neurotensin receptor 1. Biochimica et biophysica acta. 2012 Sep; 1818(9):2228-33. doi: 10.1016/j.bbamem.2012.04.010. [PMID: 22551944]
  • Zeljka Vanić, Sabine Barnert, Regine Süss, Rolf Schubert. Fusogenic activity of PEGylated pH-sensitive liposomes. Journal of liposome research. 2012 Jun; 22(2):148-57. doi: 10.3109/08982104.2011.633267. [PMID: 22149717]
  • Tomohiro Kimura, Alexei A Yeliseev, Krishna Vukoti, Steven D Rhodes, Kejun Cheng, Kenner C Rice, Klaus Gawrisch. Recombinant cannabinoid type 2 receptor in liposome model activates g protein in response to anionic lipid constituents. The Journal of biological chemistry. 2012 Feb; 287(6):4076-87. doi: 10.1074/jbc.m111.268425. [PMID: 22134924]
  • Aaron A Thompson, Jeffrey J Liu, Eugene Chun, Daniel Wacker, Huixian Wu, Vadim Cherezov, Raymond C Stevens. GPCR stabilization using the bicelle-like architecture of mixed sterol-detergent micelles. Methods (San Diego, Calif.). 2011 Dec; 55(4):310-7. doi: 10.1016/j.ymeth.2011.10.011. [PMID: 22041719]
  • Michelle A O'Malley, Matthew E Helgeson, Norman J Wagner, Anne S Robinson. The morphology and composition of cholesterol-rich micellar nanostructures determine transmembrane protein (GPCR) activity. Biophysical journal. 2011 Jan; 100(2):L11-3. doi: 10.1016/j.bpj.2010.12.3698. [PMID: 21244820]
  • Nan Ding, Yao Lu, Robert J Lee, Chang Yang, Lei Huang, Jian Liu, Guangya Xiang. Folate receptor-targeted fluorescent paramagnetic bimodal liposomes for tumor imaging. International journal of nanomedicine. 2011; 6(?):2513-20. doi: 10.2147/ijn.s23934. [PMID: 22072885]
  • Benjamin Klasczyk, Steffen Panzner, Reinhard Lipowsky, Volker Knecht. Fusion-relevant changes in lipid shape of hydrated cholesterol hemisuccinate induced by pH and counterion species. The journal of physical chemistry. B. 2010 Nov; 114(46):14941-6. doi: 10.1021/jp1043943. [PMID: 20977247]
  • Jongwon Shim, Mi Jin Kim, Han-Kon Kim, Do-Hoon Kim, Seong Geun Oh, Seung Yong Ko, Ho Gyeom Jang, Jin-Woong Kim. Morphological effect of lipid carriers on permeation of lidocaine hydrochloride through lipid membranes. International journal of pharmaceutics. 2010 Mar; 388(1-2):251-6. doi: 10.1016/j.ijpharm.2009.12.049. [PMID: 20060459]
  • Hirofumi Fujita, Daisuke Shiva, Toshihiko Utsumi, Tetsuya Ogino, Tomohiro Ogawa, Koichi Abe, Tatsuji Yasuda, Kozo Utsumi, Junzo Sasaki. Alpha-tocopheryl succinate induces rapid and reversible phosphatidylserine externalization in histiocytic lymphoma through the caspase-independent pathway. Molecular and cellular biochemistry. 2010 Jan; 333(1-2):137-49. doi: 10.1007/s11010-009-0214-2. [PMID: 19633976]
  • Denitsa Momekova, Stanislav Rangelov, Nikolay Lambov. Long-circulating, pH-sensitive liposomes. Methods in molecular biology (Clifton, N.J.). 2010; 605(?):527-44. doi: 10.1007/978-1-60327-360-2_35. [PMID: 20072904]
  • Julia Lehtinen, Zanna Hyvönen, Astrid Subrizi, Heike Bunjes, Arto Urtti. Glycosaminoglycan-resistant and pH-sensitive lipid-coated DNA complexes produced by detergent removal method. Journal of controlled release : official journal of the Controlled Release Society. 2008 Oct; 131(2):145-9. doi: 10.1016/j.jconrel.2008.07.018. [PMID: 18691618]
  • Huan Xu, Yihui Deng, Dawei Chen, Weiwei Hong, Yi Lu, Xiaohui Dong. Esterase-catalyzed dePEGylation of pH-sensitive vesicles modified with cleavable PEG-lipid derivatives. Journal of controlled release : official journal of the Controlled Release Society. 2008 Sep; 130(3):238-45. doi: 10.1016/j.jconrel.2008.05.009. [PMID: 18657874]
  • Guangya Xiang, Jun Wu, Yanhui Lu, Zhilan Liu, Robert J Lee. Synthesis and evaluation of a novel ligand for folate-mediated targeting liposomes. International journal of pharmaceutics. 2008 May; 356(1-2):29-36. doi: 10.1016/j.ijpharm.2007.12.030. [PMID: 18258394]
  • Huan Xu, Yihui Deng, Dawei Chen, Jing Qin, Jianfang Liu, Li Shi, Yi Lu. Preparation and characterization of pH-sensitive vesicles made of cholesteryl hemisuccinate. Drug development and industrial pharmacy. 2008 Feb; 34(2):134-41. doi: 10.1080/03639040701410903. [PMID: 18302031]
  • Denitsa Momekova, Stanislav Rangelov, Stanislav Yanev, Elena Nikolova, Spiro Konstantinov, Birgit Romberg, Gert Storm, Nikolay Lambov. Long-circulating, pH-sensitive liposomes sterically stabilized by copolymers bearing short blocks of lipid-mimetic units. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2007 Dec; 32(4-5):308-17. doi: 10.1016/j.ejps.2007.08.009. [PMID: 17928206]
  • Chisato Ishimaru, Isoko Kuriyama, Noriko Shimazaki, Osamu Koiwai, Kengo Sakaguchi, Ikuo Kato, Hiromi Yoshida, Yoshiyuki Mizushina. Cholesterol hemisuccinate: a selective inhibitor of family X DNA polymerases. Biochemical and biophysical research communications. 2007 Mar; 354(2):619-25. doi: 10.1016/j.bbrc.2007.01.034. [PMID: 17241613]
  • Takuro Maeda, Keiji Fujimoto. A reduction-triggered delivery by a liposomal carrier possessing membrane-permeable ligands and a detachable coating. Colloids and surfaces. B, Biointerfaces. 2006 Apr; 49(1):15-21. doi: 10.1016/j.colsurfb.2006.02.006. [PMID: 16574385]
  • Wu-Xiao Ding, Xian-Rong Qi, Yu-Wu Chen, Ke-Ming Li, Ping Li. [Cholesteryl hemisuccinate as liposomal membrane stabilizer and its use in the preparation of saikosaponin-D liposomes]. Yao xue xue bao = Acta pharmaceutica Sinica. 2005 Jul; 40(7):623-7. doi: NULL. [PMID: 16196268]
  • Sandeep Akare, Jesse D Martinez. Bile acid induces hydrophobicity-dependent membrane alterations. Biochimica et biophysica acta. 2005 Jun; 1735(1):59-67. doi: 10.1016/j.bbalip.2005.04.006. [PMID: 15951237]
  • Kentaro Kogure, Rumiko Moriguchi, Kentaro Sasaki, Masaharu Ueno, Shiroh Futaki, Hideyoshi Harashima. Development of a non-viral multifunctional envelope-type nano device by a novel lipid film hydration method. Journal of controlled release : official journal of the Controlled Release Society. 2004 Aug; 98(2):317-23. doi: 10.1016/j.jconrel.2004.04.024. [PMID: 15262422]
  • Janny X Zhang, Samuel Zalipsky, Nasreen Mullah, Michal Pechar, Theresa M Allen. Pharmaco attributes of dioleoylphosphatidylethanolamine/cholesterylhemisuccinate liposomes containing different types of cleavable lipopolymers. Pharmacological research. 2004 Feb; 49(2):185-98. doi: 10.1016/j.phrs.2003.09.003. [PMID: 14643699]
  • Feng-Yi Wan, Yi-Nan Wang, Guo-Jiang Zhang. Influence of the physical states of membrane surface area and center area on lysosomal proton permeability. Archives of biochemistry and biophysics. 2002 Aug; 404(2):285-92. doi: 10.1016/s0003-9861(02)00280-1. [PMID: 12147267]
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