5-acetamido-2-[2-[4,5-dihydroxy-2-(hydroxymethyl)-6-[(E)-3-hydroxy-2-(octadecanoylamino)octadec-4-enoxy]oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid (BioDeep_00000912299)

   


代谢物信息卡片


5-acetamido-2-[2-[4,5-dihydroxy-2-(hydroxymethyl)-6-[(E)-3-hydroxy-2-(octadecanoylamino)octadec-4-enoxy]oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

化学式: C59H108N2O21 (1180.7444198)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)O)OC3(CC(C(C(O3)C(C(CO)O)O)NC(=O)C)O)C(=O)O)O)O)O)C(C=CCCCCCCCCCCCCC)O
InChI: InChI=1S/C59H108N2O21/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-46(69)61-40(41(66)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)38-77-56-51(73)50(72)53(45(37-64)79-56)80-57-52(74)55(49(71)44(36-63)78-57)82-59(58(75)76)34-42(67)47(60-39(3)65)54(81-59)48(70)43(68)35-62/h30,32,40-45,47-57,62-64,66-68,70-74H,4-29,31,33-38H2,1-3H3,(H,60,65)(H,61,69)(H,75,76)/b32-30+



数据库引用编号

2 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

  • Juntao Wang, Dan Lu, Ran Sun, Shuwen Lei, Shuhua Luo, Xin Dang, Yang Zhang, Chang Yuan, Yong Zhang, Jinhong Wu, Guangyu Yang, Lei Fu, Faqin Jiang. One-Pot Enzymatic Synthesis and Biological Evaluation of Ganglioside GM3 Derivatives as Potential Cancer Immunotherapeutics. Journal of medicinal chemistry. 2022 02; 65(3):1883-1897. doi: 10.1021/acs.jmedchem.1c01301. [PMID: 35073068]
  • James C Dodge, Thomas J Tamsett, Christopher M Treleaven, Tatyana V Taksir, Peter Piepenhagen, S Pablo Sardi, Seng H Cheng, Lamya S Shihabuddin. Glucosylceramide synthase inhibition reduces ganglioside GM3 accumulation, alleviates amyloid neuropathology, and stabilizes remote contextual memory in a mouse model of Alzheimer's disease. Alzheimer's research & therapy. 2022 02; 14(1):19. doi: 10.1186/s13195-022-00966-0. [PMID: 35105352]
  • Hirotaka Kanoh. [Homeostatic and Pathophysiological Regulation of Toll-like Receptor 4 Signaling by GM3 Ganglioside Molecular Species]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2022; 142(3):195-203. doi: 10.1248/yakushi.21-00193. [PMID: 35228371]
  • Mikito Nakano, Shinya Hanashima, Toshiaki Hara, Kazuya Kabayama, Yuya Asahina, Hironobu Hojo, Naoko Komura, Hiromune Ando, Thomas K M Nyholm, J Peter Slotte, Michio Murata. FRET detects lateral interaction between transmembrane domain of EGF receptor and ganglioside GM3 in lipid bilayers. Biochimica et biophysica acta. Biomembranes. 2021 08; 1863(8):183623. doi: 10.1016/j.bbamem.2021.183623. [PMID: 33933428]
  • Shiomi Koudatsu, Tatsunori Masatani, Rikako Konishi, Masahito Asada, Hassan Hakimi, Yuna Kurokawa, Kanna Tomioku, Osamu Kaneko, Akikazu Fujita. Glycosphingolipid GM3 is localized in both exoplasmic and cytoplasmic leaflets of Plasmodium falciparum malaria parasite plasma membrane. Scientific reports. 2021 07; 11(1):14890. doi: 10.1038/s41598-021-94037-3. [PMID: 34290278]
  • Rhona McGonigal, Jennifer A Barrie, Denggao Yao, Lauren E Black, Mark McLaughlin, Hugh J Willison. Neuronally expressed a-series gangliosides are sufficient to prevent the lethal age-dependent phenotype in GM3-only expressing mice. Journal of neurochemistry. 2021 07; 158(2):217-232. doi: 10.1111/jnc.15365. [PMID: 33864399]
  • Takuto Shimizu, Masaki Nagane, Mira Suzuki, Akinori Yamauchi, Kazuhiro Kato, Nagako Kawashima, Yuki Nemoto, Takuya Maruo, Yasushi Kawakami, Tadashi Yamashita. Tumor hypoxia regulates ganglioside GM3 synthase, which contributes to oxidative stress resistance in malignant melanoma. Biochimica et biophysica acta. General subjects. 2020 12; 1864(12):129723. doi: 10.1016/j.bbagen.2020.129723. [PMID: 32861756]
  • Jin-Wen Song, Sin Man Lam, Xing Fan, Wen-Jing Cao, Si-Yu Wang, He Tian, Gek Huey Chua, Chao Zhang, Fan-Ping Meng, Zhe Xu, Jun-Liang Fu, Lei Huang, Peng Xia, Tao Yang, Shaohua Zhang, Bowen Li, Tian-Jun Jiang, Raoxu Wang, Zehua Wang, Ming Shi, Ji-Yuan Zhang, Fu-Sheng Wang, Guanghou Shui. Omics-Driven Systems Interrogation of Metabolic Dysregulation in COVID-19 Pathogenesis. Cell metabolism. 2020 08; 32(2):188-202.e5. doi: 10.1016/j.cmet.2020.06.016. [PMID: 32610096]
  • Hirotaka Kanoh, Takahiro Nitta, Shinji Go, Kei-Ichiro Inamori, Lucas Veillon, Wataru Nihei, Mayu Fujii, Kazuya Kabayama, Atsushi Shimoyama, Koichi Fukase, Umeharu Ohto, Toshiyuki Shimizu, Taku Watanabe, Hiroki Shindo, Sorama Aoki, Kenichi Sato, Mika Nagasaki, Yutaka Yatomi, Naoko Komura, Hiromune Ando, Hideharu Ishida, Makoto Kiso, Yoshihiro Natori, Yuichi Yoshimura, Asia Zonca, Anna Cattaneo, Marilena Letizia, Maria Ciampa, Laura Mauri, Alessandro Prinetti, Sandro Sonnino, Akemi Suzuki, Jin-Ichi Inokuchi. Homeostatic and pathogenic roles of GM3 ganglioside molecular species in TLR4 signaling in obesity. The EMBO journal. 2020 06; 39(12):e101732. doi: 10.15252/embj.2019101732. [PMID: 32378734]
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  • Tamara K Nowling, Jessalyn Rodgers, Thirumagal Thiyagarajan, Bethany Wolf, Evelyn Bruner, Kamala Sundararaj, Ivan Molano, Gary Gilkeson. Targeting glycosphingolipid metabolism as a potential therapeutic approach for treating disease in female MRL/lpr lupus mice. PloS one. 2020; 15(3):e0230499. doi: 10.1371/journal.pone.0230499. [PMID: 32187230]
  • Yosuke Takeuchi, Yuichiro Inatomi, Makoto Nakajima, Toshiro Yonehara. [Guillain-Barré syndrome with refractory optic neuropathy]. Rinsho shinkeigaku = Clinical neurology. 2019 Oct; 59(10):652-658. doi: 10.5692/clinicalneurol.cn-001329. [PMID: 31564705]
  • Qinying Li, Mei Sun, Mingsheng Yu, Qianyun Fu, Hao Jiang, Guangli Yu, Guoyun Li. Gangliosides profiling in serum of breast cancer patient: GM3 as a potential diagnostic biomarker. Glycoconjugate journal. 2019 10; 36(5):419-428. doi: 10.1007/s10719-019-09885-z. [PMID: 31297734]
  • Masako Nishikawa, Makoto Kurano, Takahiro Nitta, Hirotaka Kanoh, Jin-Ichi Inokuchi, Yutaka Yatomi. Serum GM3(d18:1-16:0) and GM3(d18:1-24:1) levels may be associated with lymphoma: An exploratory study with haematological diseases. Scientific reports. 2019 04; 9(1):6308. doi: 10.1038/s41598-019-42817-3. [PMID: 31004109]
  • Pieter Vrijens, Sam Noppen, Talitha Boogaerts, Els Vanstreels, Roberto Ronca, Paola Chiodelli, Manon Laporte, Evelien Vanderlinden, Sandra Liekens, Annelies Stevaert, Lieve Naesens. Influenza virus entry via the GM3 ganglioside-mediated platelet-derived growth factor receptor β signalling pathway. The Journal of general virology. 2019 04; 100(4):583-601. doi: 10.1099/jgv.0.001235. [PMID: 30762518]
  • Kaare Bjerregaard-Andersen, Hedda Johannesen, Noha Abdel-Rahman, Julie Elisabeth Heggelund, Helene Mykland Hoås, Fana Abraha, Paula A Bousquet, Lene Støkken Høydahl, Daniel Burschowsky, Gertrudis Rojas, Stefan Oscarson, Geir Åge Løset, Ute Krengel. Crystal structure of an L chain optimised 14F7 anti-ganglioside Fv suggests a unique tumour-specificity through an unusual H-chain CDR3 architecture. Scientific reports. 2018 Jul; 8(1):10836. doi: 10.1038/s41598-018-28918-5. [PMID: 30022069]
  • Josko Bozic, Anita Markotic, Vedrana Cikes-Culic, Anela Novak, Josip A Borovac, Hrvoje Vucemilovic, Gorana Trgo, Tina Ticinovic Kurir. Ganglioside GM3 content in skeletal muscles is increased in type 2 but decreased in type 1 diabetes rat models: Implications of glycosphingolipid metabolism in pathophysiology of diabetes. Journal of diabetes. 2018 Feb; 10(2):130-139. doi: 10.1111/1753-0407.12569. [PMID: 28544772]
  • Mayrel Labrada, Denise Dorvignit, Giselle Hevia, Nely Rodríguez-Zhurbenko, Ana M Hernández, Ana M Vázquez, Luis E Fernández. GM3(Neu5Gc) ganglioside: an evolution fixed neoantigen for cancer immunotherapy. Seminars in oncology. 2018 01; 45(1-2):41-51. doi: 10.1053/j.seminoncol.2018.04.003. [PMID: 30318083]
  • Kenichi G N Suzuki, Hiromune Ando, Naoko Komura, Miku Konishi, Akihiro Imamura, Hideharu Ishida, Makoto Kiso, Takahiro K Fujiwara, Akihiro Kusumi. Revealing the Raft Domain Organization in the Plasma Membrane by Single-Molecule Imaging of Fluorescent Ganglioside Analogs. Methods in enzymology. 2018; 598(?):267-282. doi: 10.1016/bs.mie.2017.06.038. [PMID: 29306438]
  • Fumi Shishido, Satoshi Uemura, Takahiro Nitta, Jin-Ichi Inokuchi. Identification of a new liver-specific c-type mRNA transcriptional variant for mouse ST3GAL5 (GM3/GM4 synthase). Glycoconjugate journal. 2017 10; 34(5):651-659. doi: 10.1007/s10719-017-9788-1. [PMID: 28808804]
  • Kenichi G N Suzuki, Hiromune Ando, Naoko Komura, Takahiro K Fujiwara, Makoto Kiso, Akihiro Kusumi. Development of new ganglioside probes and unraveling of raft domain structure by single-molecule imaging. Biochimica et biophysica acta. General subjects. 2017 Oct; 1861(10):2494-2506. doi: 10.1016/j.bbagen.2017.07.012. [PMID: 28734966]
  • Hyo-Jin Park, Sung-Kyu Chae, Jin-Woo Kim, Seul-Gi Yang, Jae-Min Jung, Min-Ji Kim, Gabbine Wee, Dong-Seok Lee, Sun-Uk Kim, Deog-Bon Koo. Ganglioside GM3 induces cumulus cell apoptosis through inhibition of epidermal growth factor receptor-mediated PI3K/AKT signaling pathways during in vitro maturation of pig oocytes. Molecular reproduction and development. 2017 Aug; 84(8):702-711. doi: 10.1002/mrd.22848. [PMID: 28585705]
  • Hyunju Choi, Un-Ho Jin, Sung-Koo Kang, Fukushi Abekura, Jun-Young Park, Kyung-Min Kwon, Seok-Jong Suh, Seung-Hak Cho, Ki-Tae Ha, Young-Coon Lee, Tae-Wook Chung, Cheorl-Ho Kim. Monosialyl Ganglioside GM3 Decreases Apolipoprotein B-100 Secretion in Liver Cells. Journal of cellular biochemistry. 2017 08; 118(8):2168-2181. doi: 10.1002/jcb.25860. [PMID: 28019668]
  • Shinji Go, Shiori Go, Lucas Veillon, Maria Grazia Ciampa, Laura Mauri, Chihiro Sato, Ken Kitajima, Alessandro Prinetti, Sandro Sonnino, Jin-Ichi Inokuchi. Altered expression of ganglioside GM3 molecular species and a potential regulatory role during myoblast differentiation. The Journal of biological chemistry. 2017 04; 292(17):7040-7051. doi: 10.1074/jbc.m116.771253. [PMID: 28275055]
  • Naoko Komura, Kenichi G N Suzuki, Hiromune Ando, Miku Konishi, Akihiro Imamura, Hideharu Ishida, Akihiro Kusumi, Makoto Kiso. Syntheses of Fluorescent Gangliosides for the Studies of Raft Domains. Methods in enzymology. 2017; 597(?):239-263. doi: 10.1016/bs.mie.2017.06.004. [PMID: 28935104]
  • Robin B Chan, Adler J Perotte, Bowen Zhou, Christopher Liong, Evan J Shorr, Karen S Marder, Un J Kang, Cheryl H Waters, Oren A Levy, Yimeng Xu, Hong Bin Shim, Itsik Pe'er, Gilbert Di Paolo, Roy N Alcalay. Elevated GM3 plasma concentration in idiopathic Parkinson's disease: A lipidomic analysis. PloS one. 2017; 12(2):e0172348. doi: 10.1371/journal.pone.0172348. [PMID: 28212433]
  • M Virginia Gentilini, M Eugenia Pérez, Pablo Mariano Fernández, Leonardo Fainboim, Eloísa Arana. The tumor antigen N-glycolyl-GM3 is a human CD1d ligand capable of mediating B cell and natural killer T cell interaction. Cancer immunology, immunotherapy : CII. 2016 May; 65(5):551-62. doi: 10.1007/s00262-016-1812-y. [PMID: 26969612]
  • J M Wentworth, G Naselli, K Ngui, G K Smyth, R Liu, P E O'Brien, C Bruce, J Weir, M Cinel, P J Meikle, L C Harrison. GM3 ganglioside and phosphatidylethanolamine-containing lipids are adipose tissue markers of insulin resistance in obese women. International journal of obesity (2005). 2016 Apr; 40(4):706-13. doi: 10.1038/ijo.2015.223. [PMID: 26499445]
  • Yo Sugawara, Masao Iwamori, Takuhiro Matsumura, Masahiro Yutani, Sho Amatsu, Yukako Fujinaga. Clostridium botulinum type C hemagglutinin affects the morphology and viability of cultured mammalian cells via binding to the ganglioside GM3. The FEBS journal. 2015 Sep; 282(17):3334-47. doi: 10.1111/febs.13346. [PMID: 26077172]
  • Alessandra Mozzi, Matilde Forcella, Alice Riva, Carlotta Difrancesco, Francesca Molinari, Vittoria Martin, Nadia Papini, Barbara Bernasconi, Simona Nonnis, Gabriella Tedeschi, Luca Mazzucchelli, Eugenio Monti, Paola Fusi, Milo Frattini. NEU3 activity enhances EGFR activation without affecting EGFR expression and acts on its sialylation levels. Glycobiology. 2015 Aug; 25(8):855-68. doi: 10.1093/glycob/cwv026. [PMID: 25922362]
  • Tetsuya Kaneko, Yoshiharu Tsubakihara, Hiroaki Fushimi, Seiji Yamaguchi, Yoshitsugu Takabatake, Hiromi Rakugi, Hayato Kawakami, Yoshitaka Isaka. Histochemical and immunoelectron microscopic analysis of ganglioside GM3 in human kidney. Clinical and experimental nephrology. 2015 Jun; 19(3):403-10. doi: 10.1007/s10157-014-1003-0. [PMID: 24985965]
  • Misato Yoshikawa, Shinji Go, Shun-ichi Suzuki, Akemi Suzuki, Yukio Katori, Thierry Morlet, Steven M Gottlieb, Michihiro Fujiwara, Katsunori Iwasaki, Kevin A Strauss, Jin-ichi Inokuchi. Ganglioside GM3 is essential for the structural integrity and function of cochlear hair cells. Human molecular genetics. 2015 May; 24(10):2796-807. doi: 10.1093/hmg/ddv041. [PMID: 25652401]
  • Sen-Itiroh Hakomori, Kazuko Handa. GM3 and cancer. Glycoconjugate journal. 2015 Feb; 32(1-2):1-8. doi: 10.1007/s10719-014-9572-4. [PMID: 25613425]
  • Nadia Martinez-Martin, Abel Viejo-Borbolla, Rocío Martín, Soledad Blanco, Jeffrey L Benovic, Marcus Thelen, Antonio Alcamí. Herpes simplex virus enhances chemokine function through modulation of receptor trafficking and oligomerization. Nature communications. 2015 Jan; 6(?):6163. doi: 10.1038/ncomms7163. [PMID: 25625471]
  • Lucas Veillon, Shinji Go, Wakana Matsuyama, Akemi Suzuki, Mika Nagasaki, Yutaka Yatomi, Jin-Ichi Inokuchi. Identification of Ganglioside GM3 Molecular Species in Human Serum Associated with Risk Factors of Metabolic Syndrome. PloS one. 2015; 10(6):e0129645. doi: 10.1371/journal.pone.0129645. [PMID: 26102277]
  • Igor Vukovic, Josko Bozic, Anita Markotic, Srecko Ljubicic, Tina Ticinovic Kurir. The missing link - likely pathogenetic role of GM3 and other gangliosides in the development of diabetic nephropathy. Kidney & blood pressure research. 2015; 40(3):306-14. doi: 10.1159/000368506. [PMID: 26043887]
  • Elena Lukina, Nora Watman, Marta Dragosky, Gregory M Pastores, Elsa Avila Arreguin, Hanna Rosenbaum, Ari Zimran, Jennifer Angell, Leorah Ross, Ana Cristina Puga, Judith M Peterschmitt. Eliglustat, an investigational oral therapy for Gaucher disease type 1: Phase 2 trial results after 4 years of treatment. Blood cells, molecules & diseases. 2014 Dec; 53(4):274-6. doi: 10.1016/j.bcmd.2014.04.002. [PMID: 24835462]
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  • Alison E Willing, Svitlana N Garbuzova-Davis, Olga Zayko, Hiranya M Derasari, Ashley E Rawls, Chris R James, Ron F Mervis, Cyndy D Sanberg, Nicole Kuzmin-Nichols, Paul R Sanberg. Repeated administrations of human umbilical cord blood cells improve disease outcomes in a mouse model of Sanfilippo syndrome type III B. Cell transplantation. 2014; 23(12):1613-30. doi: 10.3727/096368914x676916. [PMID: 25565636]
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