N-Acetyl-D-mannosamine (BioDeep_00000260986)

Main id: BioDeep_00000014399

Secondary id: BioDeep_00000014849, BioDeep_00000405416, BioDeep_00000599033, BioDeep_00000840367, BioDeep_00001868525

natural product PANOMIX_OTCML-2023


代谢物信息卡片


2-acetamido-2-deoxy-D-mannose

化学式: C8H15NO6 (221.089933)
中文名称: N-乙酰-D-甘露糖胺, 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 Homo sapiens(urine) 0.1%

分子结构信息

SMILES: C=C(O)NC1C(O)OC(CO)C(O)C1O
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-/m0/s1

描述信息

An N-acetylmannosamine having D-configuration.
COVID info from COVID-19 Disease Map
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
CONFIDENCE standard compound; INTERNAL_ID 145
Cyclic N-Acetyl-D-mannosamine (Cyclic ManNAc) is an endogenous metabolite.

同义名列表

4 个代谢物同义名

2-acetamido-2-deoxy-D-mannose; N-Acetyl-D-mannosamine; Cyclic ManNAc; Cyclic N-Acetyl-D-mannosamine



数据库引用编号

28 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)

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]
  • Udayanath Aich, M Adam Meledeo, Srinivasa-Gopalan Sampathkumar, Jie Fu, Mark B Jones, Christopher A Weier, Sung Yun Chung, Benjamin C Tang, Ming Yang, Justin Hanes, Kevin J Yarema. Development of delivery methods for carbohydrate-based drugs: controlled release of biologically-active short chain fatty acid-hexosamine analogs. Glycoconjugate journal. 2010 May; 27(4):445-59. doi: 10.1007/s10719-010-9292-3. [PMID: 20458533]
  • 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]
  • Fabrizio Grosjean. [Proteinuria: many actors but one protagonist?]. Giornale italiano di nefrologia : organo ufficiale della Societa italiana di nefrologia. 2008 Jan; 25(1):9. doi: NULL. [PMID: 18264910]
  • 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]
  • Belinda Galeano, Riko Klootwijk, Irini Manoli, MaoSen Sun, Carla Ciccone, Daniel Darvish, Matthew F Starost, Patricia M Zerfas, Victoria J Hoffmann, Shelley Hoogstraten-Miller, Donna M Krasnewich, William A Gahl, Marjan Huizing. Mutation in the key enzyme of sialic acid biosynthesis causes severe glomerular proteinuria and is rescued by N-acetylmannosamine. The Journal of clinical investigation. 2007 Jun; 117(6):1585-94. doi: 10.1172/jci30954. [PMID: 17549255]
  • 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]
  • J P Yan, D D Ilsley, C Frohlick, R Steet, E T Hall, R D Kuchta, P Melançon. 3'-Azidothymidine (zidovudine) inhibits glycosylation and dramatically alters glycosphingolipid synthesis in whole cells at clinically relevant concentrations. The Journal of biological chemistry. 1995 Sep; 270(39):22836-41. doi: 10.1074/jbc.270.39.22836. [PMID: 7559416]
  • P Ghosh, C Okoh, Q H Liu, M R Lakshman. Effects of chronic ethanol on enzymes regulating sialylation and desialylation of transferrin in rats. Alcoholism, clinical and experimental research. 1993 Jun; 17(3):576-9. doi: 10.1111/j.1530-0277.1993.tb00802.x. [PMID: 8333587]
  • F S Ekwunife, J Singh, K G Taylor, R J Doyle. Isolation and purification of cell wall polysaccharide of Bacillus anthracis (delta Sterne). FEMS microbiology letters. 1991 Aug; 66(3):257-62. doi: 10.1016/0378-1097(91)90270-k. [PMID: 1769521]
  • N M Ng Ying Kin, D Chung. In vivo incorporation of N-acetyl-D-[U-14C]mannosamine into brain gangliosides of rats with quinolinic acid-induced lesions of the forebrain nucleus basalis magnocellularis. Molecular and chemical neuropathology. 1990 Dec; 13(3):233-41. doi: 10.1007/bf03159926. [PMID: 2151595]
  • P Weiss, F Tietze, W A Gahl, R Seppala, G Ashwell. Identification of the metabolic defect in sialuria. The Journal of biological chemistry. 1989 Oct; 264(30):17635-6. doi: . [PMID: 2808337]
  • R Durrie, A Rosenberg. Anabolic sialosylation of gangliosides in situ in rat brain cortical slices. Journal of lipid research. 1989 Aug; 30(8):1259-66. doi: . [PMID: 2769077]
  • T Kawaguchi, T Takaoka, E Yoshida, M Iwamori, K Takatsuki, Y Nagai. A new approach to the modification of cell membrane glycosphingolipids: ganglioside composition of JTC-12 P3 cells altered by feeding with galactose as a sole carbohydrate source in protein- and lipid-free synthetic medium. Experimental cell research. 1988 Dec; 179(2):507-16. doi: 10.1016/0014-4827(88)90288-1. [PMID: 3142784]
  • W Kreisel, C Hanski, T A Tran-Thi, N Katz, K Decker, W Reutter, W Gerok. Remodeling of a rat hepatocyte plasma membrane glycoprotein. De- and reglycosylation of dipeptidyl peptidase IV. The Journal of biological chemistry. 1988 Aug; 263(24):11736-42. doi: 10.1016/s0021-9258(18)37845-1. [PMID: 2900246]
  • S Usuki, S C Lyu, C C Sweeley. Sialidase activities of cultured human fibroblasts and the metabolism of GM3 ganglioside. The Journal of biological chemistry. 1988 May; 263(14):6847-53. doi: NULL. [PMID: 3129431]
  • Y Ohsumi, C A Hoppe, T Ogawa, Y C Lee. Enhancement of macromolecular ligand binding by rabbit alveolar macrophages by mannose oligosaccharides and related compounds. Archives of biochemistry and biophysics. 1988 Jan; 260(1):241-9. doi: 10.1016/0003-9861(88)90446-8. [PMID: 3341742]
  • S Ivanov, E Gavazova, M Antonova, H Chelibonova-Lorer. Effect of fluororotic acid on the sialylation of the chicken liver, hepatoma MC-29 and serum glycoconjugates. Neoplasma. 1988; 35(2):145-51. doi: NULL. [PMID: 3374705]
  • M E Taylor, J A Summerfield. Carbohydrate-binding proteins of human serum: isolation of two mannose/fucose-specific lectins. Biochimica et biophysica acta. 1987 Sep; 915(1):60-7. doi: 10.1016/0167-4838(87)90125-7. [PMID: 3620482]
  • A Siegbahn, R C Garcia, K Kishi, K Nilsson, P Venge. Specific binding of B-CLL cell-derived chemokinetic inhibitory factor (CIF) to human polymorphonuclear leukocytes. European journal of haematology. 1987 Aug; 39(2):172-9. doi: 10.1111/j.1600-0609.1987.tb00749.x. [PMID: 3666104]
  • A P Corfield, J R Clamp, S A Wagner. The metabolism of sialic acids in isolated rat colonic mucosal cells. The Biochemical journal. 1985 Feb; 226(1):163-74. doi: 10.1042/bj2260163. [PMID: 3977862]
  • M E Mailliard, M F Sorrell, G D Volentine, D J Tuma. Impaired plasma membrane glycoprotein assembly in the liver following acute ethanol administration. Biochemical and biophysical research communications. 1984 Sep; 123(3):951-8. doi: 10.1016/s0006-291x(84)80226-0. [PMID: 6487336]
  • K Kakehi, K Maeda, M Teramae, S Honda, T Takai. Analysis of sialic acids by gas chromatography of the mannosamine derivatives released by the action of N-acetylneuraminate lyase. Journal of chromatography. 1983 Jan; 272(1):1-8. doi: 10.1016/s0378-4347(00)86097-1. [PMID: 6841529]
  • S C Fu, T F Cruz, J W Gurd. Development of synaptic glycoproteins: effect of postnatal age on the synthesis and concentration of synaptic membrane and synaptic junctional fucosyl and sialyl glycoproteins. Journal of neurochemistry. 1981 Apr; 36(4):1338-51. doi: 10.1111/j.1471-4159.1981.tb00571.x. [PMID: 7264630]
  • G Bennett, F W Kan, D O'Shaughnessy. The site of incorporation of sialic acid residues into glycoproteins and the subsequent fates of these molecules in various rat and mouse cell types as shown by radioautography after injection of [3H]N-acetylmannosamine. II. Observations in tissues other than liver. The Journal of cell biology. 1981 Jan; 88(1):16-28. doi: 10.1083/jcb.88.1.16. [PMID: 7204485]
  • G Bennett, D O'Shaughnessy. The site of incorporation of sialic acid residues into glycoproteins and the subsequent fates of these molecules in various rat and mouse cell types as shown by radioautography after injection of [3H]N-acetylmannosamine. I. Observations in hepatocytes. The Journal of cell biology. 1981 Jan; 88(1):1-15. doi: 10.1083/jcb.88.1.1. [PMID: 7204482]
  • M B Allen, D G Walker. Kinetic characterization of N-acetyl-D-glucosamine kinase from rat liver and kidney. The Biochemical journal. 1980 Mar; 185(3):577-82. doi: 10.1042/bj1850577. [PMID: 6248026]