N-Acetyl-9-O-acetylneuraminic acid (BioDeep_00000005377)

 

Secondary id: BioDeep_00001870528

human metabolite Endogenous


代谢物信息卡片


(2S,4S,5R,6R)-6-[(1R,2R)-3-(acetyloxy)-1,2-dihydroxypropyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid

化学式: C13H21NO10 (351.1165406)
中文名称:
谱图信息: 最多检出来源 Macaca mulatta(otcml) 8.7%

分子结构信息

SMILES: CC(=O)NC1C(CC(OC1C(C(COC(=O)C)O)O)(C(=O)O)O)O
InChI: InChI=1S/C13H21NO10/c1-5(15)14-9-7(17)3-13(22,12(20)21)24-11(9)10(19)8(18)4-23-6(2)16/h7-11,17-19,22H,3-4H2,1-2H3,(H,14,15)(H,20,21)/t7-,8+,9+,10+,11+,13-/m0/s1

描述信息

N-Acetyl-9-O-acetylneuraminic acid (alternatively 9-O-acetyl-N-acetylneuraminic acid) is an O acetylated sialic acid identified in human colon by using high-pressure liquid chromatography and gas-liquid chromatography/mass spectrometry (PMID 3623000). It also has been suggested that 9-O-acetyl-N-acetylneuraminic acid is an essential component of the cell surface receptor of influenza C virus (PMID 3700379).
9-O-acetyl-N-acetylneuraminic acid is an O acetylated sialic acid identified in human colon by using high-pressure liquid chromatography and gas-liquid chromatography/mass spectrometry. (PMID 3623000) It also has been suggested that 9-O-acetyl-N-acetylneuraminic acid is an essential component of the cell surface receptor of influenza C virus. (PMID 3700379) [HMDB]

同义名列表

13 个代谢物同义名

(2S,4S,5R,6R)-6-[(1R,2R)-3-(acetyloxy)-1,2-dihydroxypropyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid; N-Acetyl-9-O-acetylneuraminic acid; 9-O-Acetyl-N-acetylneuraminic acid; 9-O-Acetyl-N-acetylneuraminate; N-Acetyl-9-O-acetylneuraminate; N,9-O-Diacetylneuraminic acid; N,9-O-Diacetylneuraminate; 9-O-Acetylsialic acid; 9-O-Acetylsialate; SCHEMBL13190787; Neu5,9ac2; NeuAc9Ac; 9-Anana



数据库引用编号

18 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)

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

  • Jack Cheeseman, Concepcion Badia, Rebecca I Thomson, Gunter Kuhnle, Richard A Gardner, Daniel I R Spencer, Helen M I Osborn. Quantitative Standards of 4-O-Acetyl- and 9-O-Acetyl-N-Acetylneuraminic Acid for the Analysis of Plasma and Serum. Chembiochem : a European journal of chemical biology. 2022 03; 23(5):e202100662. doi: 10.1002/cbic.202100662. [PMID: 34874597]
  • Petar M Mitrasinovic. Prediction of Single Point Mutations in Human Coronavirus and Their Effects on Binding to 9-O-Acetylated Sialic Acid and Hidroxychloroquine. Acta chimica Slovenica. 2020 Sep; 67(3):949-956. doi: 10.17344/acsi.2020.6009. [PMID: 33533428]
  • Anna-Maria T Baumann, Mark J G Bakkers, Falk F R Buettner, Maike Hartmann, Melanie Grove, Martijn A Langereis, Raoul J de Groot, Martina Mühlenhoff. 9-O-Acetylation of sialic acids is catalysed by CASD1 via a covalent acetyl-enzyme intermediate. Nature communications. 2015 Jul; 6(?):7673. doi: 10.1038/ncomms8673. [PMID: 26169044]
  • Victor C Chu, Lisa J McElroy, Jed M Aronson, Trisha J Oura, Carole E Harbison, Beverley E Bauman, Gary R Whittaker. Feline aminopeptidase N is not a functional receptor for avian infectious bronchitis virus. Virology journal. 2007 Feb; 4(?):20. doi: 10.1186/1743-422x-4-20. [PMID: 17324273]
  • Suman Bandyopadhyay, Mitali Chatterjee, Shripad D Banavali, Santanu Pal, Chandrika N Nair, Suresh H Advani, Chitra Mandal. Antibodies against 9-O-acetylated sialic acids in childhood acute lymphoblastic leukemia: a two-year study with 186 samples following protocol MCP 943. Indian journal of biochemistry & biophysics. 2006 Feb; 43(1):7-14. doi: NULL. [PMID: 16955745]
  • Shyamasree Ghosh, Suman Bandyopadhyay, Dilip K Bhattacharya, Chitra Mandal. Altered erythrocyte membrane characteristics during anemia in childhood acute lymphoblastic leukemia. Annals of hematology. 2005 Feb; 84(2):76-84. doi: 10.1007/s00277-004-0933-0. [PMID: 15338196]
  • Walter Juergen Wurzer, Karola Obojes, Reinhard Vlasak. The sialate-4-O-acetylesterases of coronaviruses related to mouse hepatitis virus: a proposal to reorganize group 2 Coronaviridae. The Journal of general virology. 2002 Feb; 83(Pt 2):395-402. doi: 10.1099/0022-1317-83-2-395. [PMID: 11807232]
  • C Fahr, R Schauer. Detection of sialic acids and gangliosides with special reference to 9-O-acetylated species in basaliomas and normal human skin. The Journal of investigative dermatology. 2001 Feb; 116(2):254-60. doi: 10.1046/j.1523-1747.2001.01237.x. [PMID: 11180001]
  • U Hubl, H Ishida, M Kiso, A Hasegawa, R Schauer. Studies on the specificity and sensitivity of the influenza C virus binding assay for 9-O-acetylated sialic acids and its application to human melanomas. Journal of biochemistry. 2000 Jun; 127(6):1021-31. doi: 10.1093/oxfordjournals.jbchem.a022693. [PMID: 10833270]
  • M Krishna, A Varki. 9-O-Acetylation of sialomucins: a novel marker of murine CD4 T cells that is regulated during maturation and activation. The Journal of experimental medicine. 1997 Jun; 185(11):1997-2013. doi: 10.1084/jem.185.11.1997. [PMID: 9166429]
  • H C Siebert, C W von der Lieth, X Dong, G Reuter, R Schauer, H J Gabius, J F Vliegenthart. Molecular dynamics-derived conformation and intramolecular interaction analysis of the N-acetyl-9-O-acetylneuraminic acid-containing ganglioside GD1a and NMR-based analysis of its binding to a human polyclonal immunoglobulin G fraction with selectivity for O-acetylated sialic acids. Glycobiology. 1996 Sep; 6(6):561-72. doi: 10.1093/glycob/6.6.561-b. [PMID: 8922951]
  • G Zimmer, H D Klenk, G Herrler. Identification of a 40-kDa cell surface sialoglycoprotein with the characteristics of a major influenza C virus receptor in a Madin-Darby canine kidney cell line. The Journal of biological chemistry. 1995 Jul; 270(30):17815-22. doi: 10.1074/jbc.270.30.17815. [PMID: 7629082]
  • A P Corfield, S A Wagner, L J O'Donnell, P Durdey, R A Mountford, J R Clamp. The roles of enteric bacterial sialidase, sialate O-acetyl esterase and glycosulfatase in the degradation of human colonic mucin. Glycoconjugate journal. 1993 Feb; 10(1):72-81. doi: 10.1007/bf00731190. [PMID: 8358229]
  • I Muñoz-Barroso, A García-Sastre, E Villar, J C Manuguerra, C Hannoun, J A Cabezas. Increased influenza A virus sialidase activity with N-acetyl-9-O-acetylneuraminic acid-containing substrates resulting from influenza C virus O-acetylesterase action. Virus research. 1992 Sep; 25(1-2):145-53. doi: 10.1016/0168-1702(92)90106-j. [PMID: 1413991]
  • B Schultze, G Herrler. Bovine coronavirus uses N-acetyl-9-O-acetylneuraminic acid as a receptor determinant to initiate the infection of cultured cells. The Journal of general virology. 1992 Apr; 73 ( Pt 4)(?):901-6. doi: 10.1099/0022-1317-73-4-901. [PMID: 1321878]
  • G Zimmer, G Reuter, R Schauer. Use of influenza C virus for detection of 9-O-acetylated sialic acids on immobilized glycoconjugates by esterase activity. European journal of biochemistry. 1992 Feb; 204(1):209-15. doi: 10.1111/j.1432-1033.1992.tb16626.x. [PMID: 1740131]
  • H Stickl, W Huber, H Faillard, A Becker, R Holzhauser, H Graeff. [Change in acylneuraminic acid content of T-lymphocytes and in plasma in breast cancer]. Klinische Wochenschrift. 1991 Jan; 69(1):5-9. doi: 10.1007/bf01649046. [PMID: 2016848]