Cholesterol beta-epoxide (BioDeep_00000005814)

   


代谢物信息卡片


(3-beta,5-beta,6-beta)-5,6-Epoxycholestan-3-ol

化学式: C27H46O2 (402.3498)
中文名称: 5β,6β-epoxy Cholestanol
谱图信息: 最多检出来源 Homo sapiens(otcml) 12.84%

分子结构信息

SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC4C5(C3(CCC(C5)O)C)O4)C
InChI: InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24-27(29-24)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1



数据库引用编号

10 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。

亚细胞结构定位 关联基因列表
Cytoplasm 6 BCL2, CASP2, CASP3, CASP8, CNBP, DMPK
Peripheral membrane protein 1 CYP27A1
Endoplasmic reticulum membrane 5 BCL2, CYP19A1, DMPK, HMGCR, RAC2
Mitochondrion membrane 1 CYP27A1
Nucleus 7 BCL2, CASP2, CASP3, CASP8, CNBP, FASLG, ZNF77
cytosol 7 BCL2, CASP2, CASP3, CASP8, CNBP, DMPK, RAC2
nucleoplasm 2 CASP3, CASP8
Cell membrane 4 DMPK, FASLG, NPC1L1, TNF
Cytoplasmic side 1 DMPK
lamellipodium 2 CASP8, RAC2
Multi-pass membrane protein 3 CYP19A1, HMGCR, NPC1L1
cell surface 2 SDC1, TNF
glutamatergic synapse 1 CASP3
Golgi membrane 1 INS
mitochondrial inner membrane 1 CYP27A1
neuronal cell body 2 CASP3, TNF
Cytoplasm, cytosol 1 DMPK
plasma membrane 6 DMPK, FASLG, NPC1L1, RAC2, SDC1, TNF
Membrane 7 BCL2, CYP19A1, FASLG, HMGCR, LCAT, NPC1L1, SDC1
apical plasma membrane 1 NPC1L1
caveola 1 FASLG
extracellular exosome 4 FASLG, LCAT, RAC2, SDC1
endoplasmic reticulum 4 BCL2, CNBP, CYP19A1, HMGCR
extracellular space 7 CXCL10, CXCL8, CXCL9, FASLG, INS, LCAT, TNF
lysosomal lumen 2 FASLG, SDC1
perinuclear region of cytoplasm 1 FASLG
mitochondrion 3 BCL2, CASP8, CYP27A1
protein-containing complex 3 BCL2, CASP8, SDC1
Microsome membrane 1 CYP19A1
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 SDC1
Secreted 6 CXCL10, CXCL8, FASLG, INS, LCAT, SDC1
extracellular region 7 CXCL10, CXCL8, CXCL9, FASLG, INS, LCAT, TNF
Mitochondrion outer membrane 2 BCL2, DMPK
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 4 BCL2, CASP8, DMPK, RAC2
mitochondrial matrix 1 CYP27A1
Cytoplasmic vesicle lumen 1 FASLG
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 BCL2, DMPK
external side of plasma membrane 5 CXCL10, CXCL9, FASLG, SDC1, TNF
high-density lipoprotein particle 1 LCAT
nucleolus 1 CASP2
recycling endosome 1 TNF
Single-pass type II membrane protein 2 FASLG, TNF
Apical cell membrane 1 NPC1L1
Cell projection, lamellipodium 1 CASP8
Mitochondrion inner membrane 1 CYP27A1
Membrane raft 1 TNF
pore complex 1 BCL2
focal adhesion 1 RAC2
peroxisomal membrane 1 HMGCR
Nucleus outer membrane 1 DMPK
nuclear outer membrane 1 DMPK
phagocytic cup 1 TNF
phagocytic vesicle membrane 1 RAC2
cytoskeleton 1 CASP8
[Isoform 5]: Cytoplasm 1 CNBP
brush border membrane 1 NPC1L1
nuclear envelope 1 RAC2
Endomembrane system 1 NPC1L1
endosome lumen 1 INS
Cytoplasmic vesicle membrane 1 NPC1L1
cell body 1 CASP8
myelin sheath 1 BCL2
Peroxisome membrane 1 HMGCR
[Isoform 1]: Cytoplasm 1 CNBP
[Isoform 4]: Cytoplasm 1 CNBP
secretory granule lumen 1 INS
Golgi lumen 2 INS, SDC1
endoplasmic reticulum lumen 1 INS
transport vesicle 1 INS
Secreted, extracellular exosome 1 SDC1
Lysosome lumen 1 FASLG
Sarcoplasmic reticulum membrane 1 DMPK
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
Single-pass type IV membrane protein 1 DMPK
[Isoform 2]: Cytoplasm 1 CNBP
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 2 CASP3, CASP8
ripoptosome 1 CASP8
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
NADPH oxidase complex 1 RAC2
BAD-BCL-2 complex 1 BCL2
[Isoform 6]: Cytoplasm 1 CNBP
endopeptidase complex 1 CASP2
[Tumor necrosis factor ligand superfamily member 6, soluble form]: Secreted 1 FASLG
[FasL intracellular domain]: Nucleus 1 FASLG
[Isoform 8]: Cytoplasm 1 CNBP
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Tomasz Wielkoszyński, Jolanta Zalejska-Fiolka, Joanna K Strzelczyk, Aleksander J Owczarek, Armand Cholewka, Katarzyna Kokoszczyk, Agata Stanek. 5α,6α-Epoxyphytosterols and 5α,6α-Epoxycholesterol Increase Nitrosative Stress and Inflammatory Cytokine Production in Rats on Low-Cholesterol Diet. Oxidative medicine and cellular longevity. 2020; 2020(?):4751803. doi: 10.1155/2020/4751803. [PMID: 32587660]
  • Tomasz Wielkoszyński, Jolanta Zalejska-Fiolka, Joanna K Strzelczyk, Aleksander J Owczarek, Armand Cholewka, Aneta Krawczyk, Agata Stanek. 5α,6α-Epoxyphytosterols and 5α,6α-Epoxycholesterol Increase Oxidative Stress in Rats on Low-Cholesterol Diet. Oxidative medicine and cellular longevity. 2019; 2019(?):1983975. doi: 10.1155/2019/1983975. [PMID: 31827670]
  • Da-Lin Lu, Disorn Sookthai, Charlotte Le Cornet, Verena A Katzke, Theron S Johnson, Rudolf Kaaks, Renée T Fortner. Reproducibility of serum oxysterols and lanosterol among postmenopausal women: Results from EPIC-Heidelberg. Clinical biochemistry. 2018 Feb; 52(?):117-122. doi: 10.1016/j.clinbiochem.2017.11.001. [PMID: 29108727]
  • 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]
  • Florence Dalenc, Luiggi Iuliano, Thomas Filleron, Chiara Zerbinati, Maud Voisin, Cécile Arellano, Etienne Chatelut, Pierre Marquet, Mohammad Samadi, Henri Roché, Marc Poirot, Sandrine Silvente-Poirot. Circulating oxysterol metabolites as potential new surrogate markers in patients with hormone receptor-positive breast cancer: Results of the OXYTAM study. The Journal of steroid biochemistry and molecular biology. 2017 05; 169(?):210-218. doi: 10.1016/j.jsbmb.2016.06.010. [PMID: 27343991]
  • Dana-Marie Telesford, Dominique Verreault, Victoria Reick-Mitrisin, Heather C Allen. Reduced Condensing and Ordering Effects by 7-Ketocholesterol and 5β,6β-Epoxycholesterol on DPPC Monolayers. Langmuir : the ACS journal of surfaces and colloids. 2015 Sep; 31(36):9859-69. doi: 10.1021/acs.langmuir.5b02539. [PMID: 26322794]
  • 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]
  • C Helmschrodt, S Becker, J Thiery, U Ceglarek. Preanalytical standardization for reactive oxygen species derived oxysterol analysis in human plasma by liquid chromatography-tandem mass spectrometry. Biochemical and biophysical research communications. 2014 Apr; 446(3):726-30. doi: 10.1016/j.bbrc.2013.12.087. [PMID: 24370823]
  • Christin Helmschrodt, Susen Becker, Jenny Schröter, Max Hecht, Gabriela Aust, Joachim Thiery, Uta Ceglarek. Fast LC-MS/MS analysis of free oxysterols derived from reactive oxygen species in human plasma and carotid plaque. Clinica chimica acta; international journal of clinical chemistry. 2013 Oct; 425(?):3-8. doi: 10.1016/j.cca.2013.06.022. [PMID: 23827692]
  • Michael R Paillasse, Nathalie Saffon, Heinz Gornitzka, Sandrine Silvente-Poirot, Marc Poirot, Philippe de Medina. Surprising unreactivity of cholesterol-5,6-epoxides towards nucleophiles. Journal of lipid research. 2012 Apr; 53(4):718-25. doi: 10.1194/jlr.m023689. [PMID: 22285872]
  • Thomas J Berrodin, Qi Shen, Elaine M Quinet, Matthew R Yudt, Leonard P Freedman, Sunil Nagpal. Identification of 5α, 6α-epoxycholesterol as a novel modulator of liver X receptor activity. Molecular pharmacology. 2010 Dec; 78(6):1046-58. doi: 10.1124/mol.110.065193. [PMID: 20837678]
  • Beata Kosmider, Joan E Loader, Robert C Murphy, Robert J Mason. Apoptosis induced by ozone and oxysterols in human alveolar epithelial cells. Free radical biology & medicine. 2010 Jun; 48(11):1513-24. doi: 10.1016/j.freeradbiomed.2010.02.032. [PMID: 20219673]