N-Retinylidene-N-retinylethanolamine (BioDeep_00000054072)

   

human metabolite Endogenous


代谢物信息卡片


2-[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]-1-(2-hydroxyethyl)-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl]pyridin-1-ium

化学式: C42H58NO+ (592.4518158)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC2=CC(=[N+](C=C2)CCO)C=C(C)C=CC=C(C)C=CC3=C(CCCC3(C)C)C)C
InChI: InChI=1S/C42H58NO/c1-32(20-22-39-35(4)17-12-25-41(39,6)7)14-10-16-34(3)30-38-31-37(24-27-43(38)28-29-44)19-11-15-33(2)21-23-40-36(5)18-13-26-42(40,8)9/h10-11,14-16,19-24,27,30-31,44H,12-13,17-18,25-26,28-29H2,1-9H3/q+1/b16-10+,19-11+,22-20+,23-21+,32-14+,33-15+,34-30+

描述信息

This compound belongs to the family of Sesquiterpenes. These are terpenes with three consecutive isoprene units.
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

同义名列表

4 个代谢物同义名

2-[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]-1-(2-hydroxyethyl)-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl]pyridin-1-ium; N-Retinylidene-N-retinylethanolamine; di-retinoid-pyridinium-ethanolamine; A2E



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(3)

BioCyc(0)

PlantCyc(0)

代谢反应

8 个相关的代谢反应过程信息。

Reactome(8)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 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

  • Alexander Dontsov, Marina Yakovleva, Natalia Trofimova, Natalia Sakina, Alexander Gulin, Arseny Aybush, Fedor Gostev, Alexander Vasin, Tatiana Feldman, Mikhail Ostrovsky. Water-Soluble Products of Photooxidative Destruction of the Bisretinoid A2E Cause Proteins Modification in the Dark. International journal of molecular sciences. 2022 Jan; 23(3):. doi: 10.3390/ijms23031534. [PMID: 35163454]
  • Dong Hee Kim, Yae Rim Choi, Jaewon Shim, Yun-Sang Choi, Yun Tai Kim, Mina K Kim, Min Jung Kim. Suppressive Effect of Arctium Lappa L. Leaves on Retinal Damage Against A2E-Induced ARPE-19 Cells and Mice. Molecules (Basel, Switzerland). 2020 Apr; 25(7):. doi: 10.3390/molecules25071737. [PMID: 32283798]
  • Peirong Huang, Junran Sun, Fenghua Wang, Xueting Luo, Hong Zhu, Qing Gu, Xiangjun Sun, Te Liu, Xiaodong Sun. DNMT1 and Sp1 competitively regulate the expression of BACE1 in A2E-mediated photo-oxidative damage in RPE cells. Neurochemistry international. 2018 12; 121(?):59-68. doi: 10.1016/j.neuint.2018.09.001. [PMID: 30273642]
  • Bom-Lee Lee, Jung-Hwan Kang, Hye-Mi Kim, Se-Hee Jeong, Dae-Sik Jang, Young-Pyo Jang, Se-Young Choung. Polyphenol-enriched Vaccinium uliginosum L. fractions reduce retinal damage induced by blue light in A2E-laden ARPE19 cell cultures and mice. Nutrition research (New York, N.Y.). 2016 Dec; 36(12):1402-1414. doi: 10.1016/j.nutres.2016.11.008. [PMID: 27993192]
  • Marina A Yakovleva, Alexander A Gulin, Tatiana B Feldman, Yuriy C Bel'skich, Patimat M Arbukhanova, Artem A Astaf'ev, Victor A Nadtochenko, Sergey A Borzenok, Mikhail A Ostrovsky. Time-of-flight secondary ion mass spectrometry to assess spatial distribution of A2E and its oxidized forms within lipofuscin granules isolated from human retinal pigment epithelium. Analytical and bioanalytical chemistry. 2016 Oct; 408(26):7521-8. doi: 10.1007/s00216-016-9854-8. [PMID: 27510279]
  • Valérie Fontaine, Elodie Monteiro, Elena Brazhnikova, Laëtitia Lesage, Christine Balducci, Louis Guibout, Laurence Feraille, Pierre-Paul Elena, José-Alain Sahel, Stanislas Veillet, René Lafont. Norbixin Protects Retinal Pigmented Epithelium Cells and Photoreceptors against A2E-Mediated Phototoxicity In Vitro and In Vivo. PloS one. 2016; 11(12):e0167793. doi: 10.1371/journal.pone.0167793. [PMID: 27992460]
  • Zhao Zhao, Tao Sun, Yun Jiang, Lijiang Wu, Xiangzhong Cai, Xiaodong Sun, Xiangjun Sun. Photooxidative damage in retinal pigment epithelial cells via GRP78 and the protective role of grape skin polyphenols. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2014 Dec; 74(?):216-24. doi: 10.1016/j.fct.2014.10.001. [PMID: 25447759]
  • Defen Shen, Xiaoguang Cao, Lian Zhao, Jingsheng Tuo, Wai T Wong, Chi-Chao Chan. Naloxone ameliorates retinal lesions in Ccl2/Cx3cr1 double-deficient mice via modulation of microglia. Investigative ophthalmology & visual science. 2011 May; 52(6):2897-904. doi: 10.1167/iovs.10-6114. [PMID: 21245403]
  • Xiaoguang Cao, Melissa Liu, Jingsheng Tuo, Defen Shen, Chi-Chao Chan. The effects of quercetin in cultured human RPE cells under oxidative stress and in Ccl2/Cx3cr1 double deficient mice. Experimental eye research. 2010 Jul; 91(1):15-25. doi: 10.1016/j.exer.2010.03.016. [PMID: 20361964]
  • Albert R Wielgus, Colin F Chignell, Patricia Ceger, Joan E Roberts. Comparison of A2E cytotoxicity and phototoxicity with all-trans-retinal in human retinal pigment epithelial cells. Photochemistry and photobiology. 2010 Jul; 86(4):781-91. doi: 10.1111/j.1751-1097.2010.00750.x. [PMID: 20497365]
  • L S Murdaugh, Z Wang, L V Del Priore, J Dillon, E R Gaillard. Age-related accumulation of 3-nitrotyrosine and nitro-A2E in human Bruch's membrane. Experimental eye research. 2010 May; 90(5):564-71. doi: 10.1016/j.exer.2010.01.014. [PMID: 20153746]
  • Yalin Wu, Emiko Yanase, Xidong Feng, Marshall M Siegel, Janet R Sparrow. Structural characterization of bisretinoid A2E photocleavage products and implications for age-related macular degeneration. Proceedings of the National Academy of Sciences of the United States of America. 2010 Apr; 107(16):7275-80. doi: 10.1073/pnas.0913112107. [PMID: 20368460]
  • Jilin Zhou, So Ra Kim, Barbro S Westlund, Janet R Sparrow. Complement activation by bisretinoid constituents of RPE lipofuscin. Investigative ophthalmology & visual science. 2009 Mar; 50(3):1392-9. doi: 10.1167/iovs.08-2868. [PMID: 19029031]
  • Cristofol Vives-Bauza, Monika Anand, Ashton K Shiraz, Arash K Shirazi, Jordi Magrane, Junping Gao, Heidi R Vollmer-Snarr, Giovanni Manfredi, Silvia C Finnemann. The age lipid A2E and mitochondrial dysfunction synergistically impair phagocytosis by retinal pigment epithelial cells. The Journal of biological chemistry. 2008 Sep; 283(36):24770-80. doi: 10.1074/jbc.m800706200. [PMID: 18621729]
  • Chandima Abeywickrama, Hiroko Matsuda, Steffen Jockusch, Jilin Zhou, Young P Jang, Bi-Xing Chen, Yasuhiro Itagaki, Bernard F Erlanger, Koji Nakanishi, Nicholas J Turro, Janet R Sparrow. Immunochemical recognition of A2E, a pigment in the lipofuscin of retinal pigment epithelial cells. Proceedings of the National Academy of Sciences of the United States of America. 2007 Sep; 104(37):14610-5. doi: 10.1073/pnas.0706806104. [PMID: 17804788]
  • Pranab K Mukherjee, Victor L Marcheselli, Sebastian Barreiro, Jane Hu, Dean Bok, Nicolas G Bazan. Neurotrophins enhance retinal pigment epithelial cell survival through neuroprotectin D1 signaling. Proceedings of the National Academy of Sciences of the United States of America. 2007 Aug; 104(32):13152-7. doi: 10.1073/pnas.0705949104. [PMID: 17670936]
  • Aparna Lakkaraju, Silvia C Finnemann, Enrique Rodriguez-Boulan. The lipofuscin fluorophore A2E perturbs cholesterol metabolism in retinal pigment epithelial cells. Proceedings of the National Academy of Sciences of the United States of America. 2007 Jun; 104(26):11026-31. doi: 10.1073/pnas.0702504104. [PMID: 17578916]
  • V S Sokolov, E A Sokolenko, A V Sokolov, A E Dontsov, Y A Chizmadzhev, M A Ostrovsky. Interaction of pyridinium bis-retinoid (A2E) with bilayer lipid membranes. Journal of photochemistry and photobiology. B, Biology. 2007 Feb; 86(2):177-85. doi: 10.1016/j.jphotobiol.2006.09.006. [PMID: 17070694]
  • Jilin Zhou, Young Pyo Jang, So Ra Kim, Janet R Sparrow. Complement activation by photooxidation products of A2E, a lipofuscin constituent of the retinal pigment epithelium. Proceedings of the National Academy of Sciences of the United States of America. 2006 Oct; 103(44):16182-7. doi: 10.1073/pnas.0604255103. [PMID: 17060630]
  • So Ra Kim, Koji Nakanishi, Yasuhiro Itagaki, Janet R Sparrow. Photooxidation of A2-PE, a photoreceptor outer segment fluorophore, and protection by lutein and zeaxanthin. Experimental eye research. 2006 May; 82(5):828-39. doi: 10.1016/j.exer.2005.10.004. [PMID: 16364293]
  • Roxana A Radu, Yun Han, Tam V Bui, Steven Nusinowitz, Dean Bok, Jay Lichter, Ken Widder, Gabriel H Travis, Nathan L Mata. Reductions in serum vitamin A arrest accumulation of toxic retinal fluorophores: a potential therapy for treatment of lipofuscin-based retinal diseases. Investigative ophthalmology & visual science. 2005 Dec; 46(12):4393-401. doi: 10.1167/iovs.05-0820. [PMID: 16303925]
  • A E Dontsov, N L Sakina, B Bilinska, L Krzyzanowski, T B Feldman, M A Ostrovsky. Comparison of photosensitizing effect of lipofuscin granules from retinal pigment epithelium of human donor eyes and their fluorophore A2E. Doklady. Biochemistry and biophysics. 2005 Nov; 405(?):458-60. doi: 10.1007/s10628-005-0139-y. [PMID: 16480152]
  • Young P Jang, Jilin Zhou, Koji Nakanishi, Janet R Sparrow. Anthocyanins protect against A2E photooxidation and membrane permeabilization in retinal pigment epithelial cells. Photochemistry and photobiology. 2005 May; 81(3):529-36. doi: 10.1562/2004-12-14-ra-402. [PMID: 15745429]
  • Jilin Zhou, Bolin Cai, Young P Jang, Sophia Pachydaki, Ann Marie Schmidt, Janet R Sparrow. Mechanisms for the induction of HNE- MDA- and AGE-adducts, RAGE and VEGF in retinal pigment epithelial cells. Experimental eye research. 2005 Apr; 80(4):567-80. doi: 10.1016/j.exer.2004.11.009. [PMID: 15781285]
  • Anna Pawlak, Marta Wrona, Malgorzata Rózanowska, Mariusz Zareba, Laura E Lamb, Joan E Roberts, John D Simon, Tadeusz Sarna. Comparison of the aerobic photoreactivity of A2E with its precursor retinal. Photochemistry and photobiology. 2003 Mar; 77(3):253-8. doi: 10.1562/0031-8655(2003)077<0253:cotapo>2.0.co;2. [PMID: 12685651]
  • Florian Schütt, Marion Bergmann, Frank G Holz, Jürgen Kopitz. Isolation of intact lysosomes from human RPE cells and effects of A2-E on the integrity of the lysosomal and other cellular membranes. Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie. 2002 Dec; 240(12):983-8. doi: 10.1007/s00417-002-0558-8. [PMID: 12483320]
  • F Schütt, M Bergmann, J Kopitz, F G Holz. [Detergent-like effects of the lipofuscin retinoid component A2-E in retinal pigment epithelial cells]. Der Ophthalmologe : Zeitschrift der Deutschen Ophthalmologischen Gesellschaft. 2002 Nov; 99(11):861-5. doi: 10.1007/s00347-002-0672-3. [PMID: 12430039]
  • Soma De, Thomas P Sakmar. Interaction of A2E with model membranes. Implications to the pathogenesis of age-related macular degeneration. The Journal of general physiology. 2002 Aug; 120(2):147-57. doi: 10.1085/jgp.20028566. [PMID: 12149277]
  • Silvia C Finnemann, Lawrence W Leung, Enrique Rodriguez-Boulan. The lipofuscin component A2E selectively inhibits phagolysosomal degradation of photoreceptor phospholipid by the retinal pigment epithelium. Proceedings of the National Academy of Sciences of the United States of America. 2002 Mar; 99(6):3842-7. doi: 10.1073/pnas.052025899. [PMID: 11904436]
  • Bo Gao, Andreas Wenzel, Christian Grimm, Stephan R Vavricka, Dietmar Benke, Peter J Meier, Charlotte E Remè. Localization of organic anion transport protein 2 in the apical region of rat retinal pigment epithelium. Investigative ophthalmology & visual science. 2002 Feb; 43(2):510-4. doi: NULL. [PMID: 11818398]
  • H Shaban, P Gazzotti, C Richter. Cytochrome c oxidase inhibition by N-retinyl-N-retinylidene ethanolamine, a compound suspected to cause age-related macula degeneration. Archives of biochemistry and biophysics. 2001 Oct; 394(1):111-6. doi: 10.1006/abbi.2001.2535. [PMID: 11566033]
  • J R Sparrow, C A Parish, M Hashimoto, K Nakanishi. A2E, a lipofuscin fluorophore, in human retinal pigmented epithelial cells in culture. Investigative ophthalmology & visual science. 1999 Nov; 40(12):2988-95. doi: NULL. [PMID: 10549662]