N-Acetylmannosamine (BioDeep_00000014399)

 

Secondary id: BioDeep_00000260986

natural product human metabolite PANOMIX_OTCML-2023 Endogenous BioNovoGene_Lab2019 Volatile Flavor Compounds


代谢物信息卡片


N-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

化学式: C8H15NO6 (221.089933)
中文名称: N-乙酰-D-甘露糖胺一水合物, N-乙酰-D-甘露糖胺
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.91%

分子结构信息

SMILES: CC(=O)NC1C(C(C(OC1O)CO)O)O
InChI: InChI=1S/C8H15NO6/c1-4(12)9-5(2-10)7(14)8(15)6(13)3-11/h2,5-8,11,13-15H,3H2,1H3,(H,9,12)/t5-,6-,7-,8-/m1/s1

描述信息

N-Acetylmannosamine, also known as beta-ManNAcc or β-ManNAc, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. Within humans, N-acetylmannosamine participates in a number of enzymatic reactions. In particular, N-acetylmannosamine can be biosynthesized from N-acetyl-D-glucosamine, which is catalyzed by the enzyme N-acylglucosamine 2-epimerase. In addition, N-acetylmannosamine and uridine 5-diphosphate can be biosynthesized from uridine diphosphate-N-acetylglucosamine; which is mediated by the enzyme bifunctional UDP-N-acetyl glucosamine 2-epimerase / N-acetylmannosamine kinase. In humans, N-acetylmannosamine is involved in the metabolic disorder called the salla disease/infantile sialic acid storage disease pathway. In the rate-limiting step of the pathway, UDP-GlcNAc is converted into ManNAc by UDP-GlcNAc 2-epimerase, encoded by the epimerase domain of GNE. Improved sialylation after the addition of ManNAc and other supporting ingredients to the culture medium not only increases manufacturing yield, but also improves therapeutic efficacy by increasing solubility, increasing half-life and reducing immunogenicity by reducing the formation of antibodies to the therapeutic glycoprotein When the GNE epimerase kinase does not function correctly in the human body thereby reducing the available ManNAc, it is reasonable to assume that treatment with ManNAc could assist with improving health benefits. There is no available therapy to treat GNE myopathy. ManNAc is the first committed biological precursor of N-acetylneuraminic acid (Neu5Ac, sialic acid).
N-Acetylmannosamine is a monosaccharide involved in a range of metabolic processes. It is an amino sugar/amino acid that consists of neuraminic acids, glycolipids and glycoproteins, and is used for the synthesis of sialic acid. [Wikipedia]
COVID info from COVID-19 Disease Map
Corona-virus
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COVID-19
SARS-CoV
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SARS
Cyclic N-Acetyl-D-mannosamine (Cyclic ManNAc) is an endogenous metabolite.

同义名列表

19 个代谢物同义名

N-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide; 2-Acetamido-2-deoxy-D-mannopyranose; N-Acetylmannosamine, (L)-isomer; N-Acetylmannosamine, (D)-isomer; 2-acetamido-2-deoxy-D-mannose; beta-D-N-Acetylmannosamine; N-Acetyl-beta-mannosamine; N-Acetyl-b-mannosamine; N-Acetyl-D-mannosamine; N-Acetyl-β-mannosamine; N-Acetylmannosamine; beta-ManNAc; b-ManNAc; Β-mannac; ManNAc; N-Acetylmannosamine; Cyclic ManNAc; Cyclic N-Acetyl-D-mannosamine; N-Acetyl-D-mannosamine



数据库引用编号

29 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

29 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(8)

WikiPathways(0)

Plant Reactome(0)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(1)

PathBank(18)

PharmGKB(0)

2 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

  • Yanmin Gao, Yanli Ma, Di Xie, Hua Jiang. ManNAc protects against podocyte pyroptosis via inhibiting mitochondrial damage and ROS/NLRP3 signaling pathway in diabetic kidney injury model. International immunopharmacology. 2022 Jun; 107(?):108711. doi: 10.1016/j.intimp.2022.108711. [PMID: 35338958]
  • Nuria Carrillo, May C Malicdan, Petcharat Leoyklang, Joseph A Shrader, Galen Joe, Christina Slota, John Perreault, John D Heiss, Bradley Class, Chia-Ying Liu, Kennan Bradley, Colleen Jodarski, Carla Ciccone, Claire Driscoll, Rebecca Parks, Scott Van Wart, Levent Bayman, Christopher S Coffey, Melanie Quintana, Scott M Berry, Marjan Huizing, William A Gahl. Safety and efficacy of N-acetylmannosamine (ManNAc) in patients with GNE myopathy: an open-label phase 2 study. Genetics in medicine : official journal of the American College of Medical Genetics. 2021 11; 23(11):2067-2075. doi: 10.1038/s41436-021-01259-x. [PMID: 34257421]
  • Laura Morelli, Luigi Lay, Darielys Santana-Mederos, Yury Valdes-Balbin, Vicente Verez Bencomo, Angela van Diepen, Cornelis H Hokke, Fabrizio Chiodo, Federica Compostella. Glycan Array Evaluation of Synthetic Epitopes between the Capsular Polysaccharides from Streptococcus pneumoniae 19F and 19A. ACS chemical biology. 2021 09; 16(9):1671-1679. doi: 10.1021/acschembio.1c00347. [PMID: 34469105]
  • Scott Van Wart, Donald E Mager, Cindy J Bednasz, Marjan Huizing, Nuria Carrillo. Population Pharmacokinetic Model of N-acetylmannosamine (ManNAc) and N-acetylneuraminic acid (Neu5Ac) in Subjects with GNE Myopathy. Drugs in R&D. 2021 Jun; 21(2):189-202. doi: 10.1007/s40268-021-00343-6. [PMID: 33893973]
  • Petra Kranaster, Christiaan Karreman, Jeremias E G A Dold, Alice Krebs, Melina Funke, Anna-Katharina Holzer, Stefanie Klima, Johanna Nyffeler, Stefan Helfrich, Valentin Wittmann, Marcel Leist. Time and space-resolved quantification of plasma membrane sialylation for measurements of cell function and neurotoxicity. Archives of toxicology. 2020 02; 94(2):449-467. doi: 10.1007/s00204-019-02642-z. [PMID: 31828357]
  • Xin Xu, Amy Q Wang, Lea L Latham, Frank Celeste, Carla Ciccone, May Christine Malicdan, Barry Goldspiel, Pramod Terse, James Cradock, Nora Yang, Selwyn Yorke, John C McKew, William A Gahl, Marjan Huizing, Nuria Carrillo. Safety, pharmacokinetics and sialic acid production after oral administration of N-acetylmannosamine (ManNAc) to subjects with GNE myopathy. Molecular genetics and metabolism. 2017 09; 122(1-2):126-134. doi: 10.1016/j.ymgme.2017.04.010. [PMID: 28641925]
  • Clara D M van Karnebeek, Luisa Bonafé, Xiao-Yan Wen, Maja Tarailo-Graovac, Sara Balzano, Beryl Royer-Bertrand, Angel Ashikov, Livia Garavelli, Isabella Mammi, Licia Turolla, Catherine Breen, Dian Donnai, Valérie Cormier-Daire, Delphine Heron, Gen Nishimura, Shinichi Uchikawa, Belinda Campos-Xavier, Antonio Rossi, Thierry Hennet, Koroboshka Brand-Arzamendi, Jacob Rozmus, Keith Harshman, Brian J Stevenson, Enrico Girardi, Giulio Superti-Furga, Tammie Dewan, Alissa Collingridge, Jessie Halparin, Colin J Ross, Margot I Van Allen, Andrea Rossi, Udo F Engelke, Leo A J Kluijtmans, Ed van der Heeft, Herma Renkema, Arjan de Brouwer, Karin Huijben, Fokje Zijlstra, Torben Heise, Thomas Boltje, Wyeth W Wasserman, Carlo Rivolta, Sheila Unger, Dirk J Lefeber, Ron A Wevers, Andrea Superti-Furga. NANS-mediated synthesis of sialic acid is required for brain and skeletal development. Nature genetics. 2016 07; 48(7):777-84. doi: 10.1038/ng.3578. [PMID: 27213289]
  • Yifan Shi, Xin Xu, Meng Fang, Michael Zhang, Yinghe Li, Brad Gillespie, Selwyn Yorke, Nora Yang, John C McKew, William A Gahl, Marjan Huizing, Nuria Carrillo-Carrasco, Amy Qiu Wang. Quantitative hydrophilic interaction chromatography-mass spectrometry analysis of N-acetylneuraminic acid and N-acetylmannosamine in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Sep; 1000(?):105-11. doi: 10.1016/j.jchromb.2015.07.018. [PMID: 26218770]
  • Katherine A Patzel, Tal Yardeni, Erell Le Poëc-Celic, Petcharat Leoyklang, Heidi Dorward, Dominic S Alonzi, Nikolay V Kukushkin, Bixue Xu, Yongmin Zhang, Matthieu Sollogoub, Yves Blériot, William A Gahl, Marjan Huizing, Terry D Butters. Non-specific accumulation of glycosphingolipids in GNE myopathy. Journal of inherited metabolic disease. 2014 Mar; 37(2):297-308. doi: 10.1007/s10545-013-9655-6. [PMID: 24136589]
  • Qi Gao, Cristina Zaccaria, Marta Tontini, Laura Poletti, Paolo Costantino, Luigi Lay. Synthesis and preliminary biological evaluation of carba analogues from Neisseria meningitidis A capsular polysaccharide. Organic & biomolecular chemistry. 2012 Sep; 10(33):6673-81. doi: 10.1039/c2ob25222h. [PMID: 22850927]
  • Sravan Kakani, Tal Yardeni, Justin Poling, Carla Ciccone, Terren Niethamer, Enriko D Klootwijk, Irini Manoli, Daniel Darvish, Shelley Hoogstraten-Miller, Patricia Zerfas, E Tian, Kelly G Ten Hagen, Jeffrey B Kopp, William A Gahl, Marjan Huizing. The Gne M712T mouse as a model for human glomerulopathy. The American journal of pathology. 2012 Apr; 180(4):1431-40. doi: 10.1016/j.ajpath.2011.12.023. [PMID: 22322304]
  • Satoru Noguchi, May Christine V Malicdan, Ichizo Nishino. [Animal model of distal myopathy with rimmed vacuoles/hereditary inclusion body myopathy and preclinical trial with sugar compounds]. Brain and nerve = Shinkei kenkyu no shinpo. 2010 Jun; 62(6):601-7. doi: . [PMID: 20548120]
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  • Shiyuan Hu, Jun Chen, Zhongyi Yang, Lijun Shao, Hua Bai, Jiali Luo, Weihong Jiang, Yunliu Yang. Coupled bioconversion for preparation of N-acetyl-D: -neuraminic acid using immobilized N-acetyl-D: -glucosamine-2-epimerase and N-acetyl-D: -neuraminic acid lyase. Applied microbiology and biotechnology. 2010 Feb; 85(5):1383-91. doi: 10.1007/s00253-009-2163-9. [PMID: 19707758]
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  • Susan E Quaggin. Sizing up sialic acid in glomerular disease. The Journal of clinical investigation. 2007 Jun; 117(6):1480-3. doi: 10.1172/jci32482. [PMID: 17549251]
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  • Karthik Viswanathan, Shawn Lawrence, Stephan Hinderlich, Kevin J Yarema, Yuan C Lee, Michael J Betenbaugh. Engineering sialic acid synthetic ability into insect cells: identifying metabolic bottlenecks and devising strategies to overcome them. Biochemistry. 2003 Dec; 42(51):15215-25. doi: 10.1021/bi034994s. [PMID: 14690432]
  • Yeongjin Hong, Pamela Stanley. Lec3 Chinese hamster ovary mutants lack UDP-N-acetylglucosamine 2-epimerase activity because of mutations in the epimerase domain of the Gne gene. The Journal of biological chemistry. 2003 Dec; 278(52):53045-54. doi: 10.1074/jbc.m309967200. [PMID: 14561743]
  • H L Byers, K A Homer, E Tarelli, D Beighton. N-acetylneuraminic acid transport by Streptococcus oralis strain AR3. Journal of medical microbiology. 1999 Apr; 48(4):375-381. doi: 10.1099/00222615-48-4-375. [PMID: 10509480]
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