Cytidine 5'-monophosphate-N-acetylneuraminic acid (BioDeep_00000004384)

 

Secondary id: BioDeep_00001868999

human metabolite Endogenous


代谢物信息卡片


(2R,4S,5R,6R)-2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

化学式: C20H31N4O16P (614.1472616)
中文名称:
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 5.26%

分子结构信息

SMILES: CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=NC3=O)N)O)O)O
InChI: InChI=1S/C20H31N4O16P/c1-7(26)22-12-8(27)4-20(18(32)33,39-16(12)13(29)9(28)5-25)40-41(35,36)37-6-10-14(30)15(31)17(38-10)24-3-2-11(21)23-19(24)34/h2-3,8-10,12-17,25,27-31H,4-6H2,1H3,(H,22,26)(H,32,33)(H,35,36)(H2,21,23,34)/t8-,9+,10+,12+,13+,14+,15+,16+,17+,20+/m0/s1

描述信息

Cytidine 5-monophosphate-N-acetylneuraminic acid (CMP-Neu5Ac), also known as CMP-N-acetyl-β-neuraminic acid, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. CMP-Neu5Ac is an extremely weak basic (essentially neutral) compound (based on its pKa). CMP-Neu5Ac donates N-acetylneuraminic acid to the terminal sugar of a ganglioside or glycoprotein.
A nucleoside monophosphate sugar which donates N-acetylneuraminic acid to the terminal sugar of a ganglioside or glycoprotein. [HMDB]
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同义名列表

50 个代谢物同义名

(2R,4S,5R,6R)-2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid; 5-acetylamino-2-[[5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid; CYTIDINE-5-monophosphoric acid-5-N-acetylneuraminic acid; Cytidine 5-monophosphoric acid-N-acetylneuraminic acid; Cytidine 5’-monophosphic acid-N-acetylneuraminic acid; Cytidine 5-monophosphic acid-N-acetylneuraminic acid; Cytidine monophosphoric acid N-acetylneuraminic acid; Cytidine monophosphic acid N-acetylneuraminic acid; CYTIDINE-5-monophosphATE-5-N-acetylneuraminIC ACID; Cytidine 5’-monophosphate-N-acetylneuraminic acid; Cytidine 5-monophosphate N-acetylneuraminic acid; Cytidine 5-monophosphate-N-acetylneuraminic acid; Cytidine-5-monophosphono-N-acetylneuraminic acid; Cytidine 5’-monophospho-N-acetylneuraminic acid; Cytidine monophosphate N acetylneuraminic acid; Cytidine-5-monophospho-N-acetylneuraminic acid; Cytidine monophosphate N-acetylneuraminic acid; Cytidine 5-monophospho-N-acetylneuraminic acid; CYTIDINE-5-monophosphate-5-N-acetylneuraminate; Cytidine 5’-monophosphate-N-acetylneuraminate; Cytidine-5-monophosphono-N-acetylneuraminate; Cytidine 5-monophosphate-N-acetylneuraminate; Cytidine 5’-monophospho-N-acetylneuraminate; Cytidine 5-monophospho-N-acetylneuraminate; Cytidine-5-monophospho-N-acetylneuraminate; Cytidine monophosphate N-acetylneuraminate; CMP-N-Acetyl-beta-neuraminic acid; CMP-N-Acetyl-β-neuraminic acid; CMP-N-Acetyl-b-neuraminic acid; CMP-N-Acetyl-beta-neuraminate; CMP-N-Acetylneuraminic acid; Acetylneuraminic acid, CMP; CMP-N-Acetyl-β-neuraminate; CMP-N-Acetyl-b-neuraminate; Acid, CMP acetylneuraminic; CMP Acetylneuraminic acid; CMP-N-Acetylneuraminate; CMP-N-Acylneuraminate; CMP Acetylneuraminate; Acid, CMP-sialic; CMP Sialic acid; CMP-Sialic acid; CMP-beta-Neu5ac; CMP-Β-neu5ac; CMP-b-Neu5ac; CMP-Sialate; CMP-Neu5ac; CMP-NeuNAc; CMP-NeuAc; Cmp-nana



数据库引用编号

20 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

32 个相关的代谢反应过程信息。

Reactome(14)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(17)

PharmGKB(0)

5 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

  • Emmanuel Nji, Ashutosh Gulati, Abdul Aziz Qureshi, Mathieu Coincon, David Drew. Structural basis for the delivery of activated sialic acid into Golgi for sialyation. Nature structural & molecular biology. 2019 06; 26(6):415-423. doi: 10.1038/s41594-019-0225-y. [PMID: 31133698]
  • J Alfredo Blakeley-Ruiz, Alison R Erickson, Brandi L Cantarel, Weili Xiong, Rachel Adams, Janet K Jansson, Claire M Fraser, Robert L Hettich. Metaproteomics reveals persistent and phylum-redundant metabolic functional stability in adult human gut microbiomes of Crohn's remission patients despite temporal variations in microbial taxa, genomes, and proteomes. Microbiome. 2019 02; 7(1):18. doi: 10.1186/s40168-019-0631-8. [PMID: 30744677]
  • Sunita Gulati, Ian C Schoenhofen, Dennis M Whitfield, Andrew D Cox, Jianjun Li, Frank St Michael, Evgeny V Vinogradov, Jacek Stupak, Bo Zheng, Makoto Ohnishi, Magnus Unemo, Lisa A Lewis, Rachel E Taylor, Corinna S Landig, Sandra Diaz, George W Reed, Ajit Varki, Peter A Rice, Sanjay Ram. Utilizing CMP-Sialic Acid Analogs to Unravel Neisseria gonorrhoeae Lipooligosaccharide-Mediated Complement Resistance and Design Novel Therapeutics. PLoS pathogens. 2015 Dec; 11(12):e1005290. doi: 10.1371/journal.ppat.1005290. [PMID: 26630657]
  • Paola Rota, Federica Cirillo, Marco Piccoli, Antonio Gregorio, Guido Tettamanti, Pietro Allevi, Luigi Anastasia. Synthesis and biological evaluation of several dephosphonated analogues of CMP-Neu5Ac as inhibitors of GM3-synthase. Chemistry (Weinheim an der Bergstrasse, Germany). 2015 Oct; 21(41):14614-29. doi: 10.1002/chem.201501770. [PMID: 26397189]
  • Christopher Burlak, Marshall Bern, Alejandro E Brito, Dragan Isailovic, Zheng-Yu Wang, Jose L Estrada, Ping Li, A Joseph Tector. N-linked glycan profiling of GGTA1/CMAH knockout pigs identifies new potential carbohydrate xenoantigens. Xenotransplantation. 2013 Sep; 20(5):277-91. doi: 10.1111/xen.12047. [PMID: 24033743]
  • Thomas J Inzana, Rajiv Balyan, Michael D Howard. Decoration of Histophilus somni lipooligosaccharide with N-acetyl-5-neuraminic acid enhances bacterial binding of complement factor H and resistance to killing by serum and polymorphonuclear leukocytes. Veterinary microbiology. 2012 Dec; 161(1-2):113-21. doi: 10.1016/j.vetmic.2012.07.008. [PMID: 22868182]
  • Birgit Weinhold, Melanie Sellmeier, Wiebke Schaper, Linda Blume, Brigitte Philippens, Elina Kats, Ulrike Bernard, Sebastian P Galuska, Hildegard Geyer, Rudolf Geyer, Kirstin Worthmann, Mario Schiffer, Stephanie Groos, Rita Gerardy-Schahn, Anja K Münster-Kühnel. Deficits in sialylation impair podocyte maturation. Journal of the American Society of Nephrology : JASN. 2012 Aug; 23(8):1319-28. doi: 10.1681/asn.2011090947. [PMID: 22745475]
  • Leo Y-C Lin, Bojana Rakic, Cecilia P C Chiu, Emilie Lameignere, Warren W Wakarchuk, Stephen G Withers, Natalie C J Strynadka. Structure and mechanism of the lipooligosaccharide sialyltransferase from Neisseria meningitidis. The Journal of biological chemistry. 2011 Oct; 286(43):37237-48. doi: 10.1074/jbc.m111.249920. [PMID: 21880735]
  • M Eugenia Giorgi, Rosa M de Lederkremer. Trans-sialidase and mucins of Trypanosoma cruzi: an important interplay for the parasite. Carbohydrate research. 2011 Sep; 346(12):1389-93. doi: 10.1016/j.carres.2011.04.006. [PMID: 21645882]
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  • Yohei Hayashi, Techuan Chan, Masaki Warashina, Masakazu Fukuda, Takashi Ariizumi, Koji Okabayashi, Naoya Takayama, Makoto Otsu, Koji Eto, Miho Kusuda Furue, Tatsuo Michiue, Kiyoshi Ohnuma, Hiromitsu Nakauchi, Makoto Asashima. Reduction of N-glycolylneuraminic acid in human induced pluripotent stem cells generated or cultured under feeder- and serum-free defined conditions. PloS one. 2010 Nov; 5(11):e14099. doi: 10.1371/journal.pone.0014099. [PMID: 21124894]
  • Nabin B Basnet, Kentaro Ide, Hiroyuki Tahara, Yuka Tanaka, Hideki Ohdan. Deficiency of N-glycolylneuraminic acid and Galα1-3Galβ1-4GlcNAc epitopes in xenogeneic cells attenuates cytotoxicity of human natural antibodies. Xenotransplantation. 2010 Nov; 17(6):440-8. doi: 10.1111/j.1399-3089.2010.00610.x. [PMID: 21158945]
  • Karin Ilg, Elif Yavuz, Carola Maffioli, Bernard Priem, Markus Aebi. Glycomimicry: display of the GM3 sugar epitope on Escherichia coli and Salmonella enterica sv Typhimurium. Glycobiology. 2010 Oct; 20(10):1289-97. doi: 10.1093/glycob/cwq091. [PMID: 20574043]
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  • Alexandra Castilho, Richard Strasser, Johannes Stadlmann, Josephine Grass, Jakub Jez, Pia Gattinger, Renate Kunert, Heribert Quendler, Martin Pabst, Renaud Leonard, Friedrich Altmann, Herta Steinkellner. In planta protein sialylation through overexpression of the respective mammalian pathway. The Journal of biological chemistry. 2010 May; 285(21):15923-30. doi: 10.1074/jbc.m109.088401. [PMID: 20305285]
  • Chawaree Chaipan, Imke Steffen, Theodros Solomon Tsegaye, Stephanie Bertram, Ilona Glowacka, Yukinari Kato, Jan Schmökel, Jan Münch, Graham Simmons, Rita Gerardy-Schahn, Stefan Pöhlmann. Incorporation of podoplanin into HIV released from HEK-293T cells, but not PBMC, is required for efficient binding to the attachment factor CLEC-2. Retrovirology. 2010 May; 7(?):47. doi: 10.1186/1742-4690-7-47. [PMID: 20482880]
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  • Mariano R Gabri, Laura L Otero, Daniel E Gomez, Daniel F Alonso. Exogenous incorporation of neugc-rich mucin augments n-glycolyl sialic acid content and promotes malignant phenotype in mouse tumor cell lines. Journal of experimental & clinical cancer research : CR. 2009 Dec; 28(?):146. doi: 10.1186/1756-9966-28-146. [PMID: 19951433]
  • Shou Takashima, Junichi Seino, Takeshi Nakano, Kazuhito Fujiyama, Masafumi Tsujimoto, Nobuhiro Ishida, Yasuhiro Hashimoto. Analysis of CMP-sialic acid transporter-like proteins in plants. Phytochemistry. 2009 Dec; 70(17-18):1973-81. doi: 10.1016/j.phytochem.2009.09.017. [PMID: 19822337]
  • Thierry Hennet. From glycosylation disorders back to glycosylation: what have we learned?. Biochimica et biophysica acta. 2009 Sep; 1792(9):921-4. doi: 10.1016/j.bbadis.2008.10.006. [PMID: 19007883]
  • Hans Bakker, Françoise Routier, Angel Ashikov, Detlef Neumann, Dirk Bosch, Rita Gerardy-Schahn. A CMP-sialic acid transporter cloned from Arabidopsis thaliana. Carbohydrate research. 2008 Aug; 343(12):2148-52. doi: 10.1016/j.carres.2008.01.010. [PMID: 18258224]
  • Alexandra Castilho, Martin Pabst, Renaud Leonard, Christiane Veit, Friedrich Altmann, Lukas Mach, Josef Glössl, Richard Strasser, Herta Steinkellner. Construction of a functional CMP-sialic acid biosynthesis pathway in Arabidopsis. Plant physiology. 2008 May; 147(1):331-9. doi: 10.1104/pp.108.117572. [PMID: 18326787]
  • Daniel R Hill, Jared J Aumiller, Xianzong Shi, Donald L Jarvis. Isolation and analysis of a baculovirus vector that supports recombinant glycoprotein sialylation by SfSWT-1 cells cultured in serum-free medium. Biotechnology and bioengineering. 2006 Sep; 95(1):37-47. doi: 10.1002/bit.20945. [PMID: 16607656]
  • Ryo Misaki, Kazuhito Fujiyama, Tatsuji Seki. Expression of human CMP-N-acetylneuraminic acid synthetase and CMP-sialic acid transporter in tobacco suspension-cultured cell. Biochemical and biophysical research communications. 2006 Jan; 339(4):1184-9. doi: 10.1016/j.bbrc.2005.11.130. [PMID: 16343442]
  • Mariusz Olczak, Eduardo Guillen. Characterization of a mutation and an alternative splicing of UDP-galactose transporter in MDCK-RCAr cell line. Biochimica et biophysica acta. 2006 Jan; 1763(1):82-92. doi: 10.1016/j.bbamcr.2005.12.006. [PMID: 16434112]
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