3-deoxy-D-manno-octulosonate (BioDeep_00000004607)

 

Secondary id: BioDeep_00000172544, BioDeep_00001869711

human metabolite


代谢物信息卡片


(4R,5R,6R,7R)-4,5,6,7,8-pentahydroxy-2-oxooctanoic acid

化学式: C8H14O8 (238.0688644)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 2.39%

分子结构信息

SMILES: C(C(C(C(C(CO)O)O)O)O)C(=O)C(=O)O
InChI: InChI=1S/C8H14O8/c9-2-5(12)7(14)6(13)3(10)1-4(11)8(15)16/h3,5-7,9-10,12-14H,1-2H2,(H,15,16)/t3-,5-,6-,7-/m1/s1

描述信息

3-deoxy-d-manno-octulosonate, also known as kdo or 2-dehydro-3-deoxy-D-octonate, belongs to sugar acids and derivatives class of compounds. Those are compounds containing a saccharide unit which bears a carboxylic acid group. 3-deoxy-d-manno-octulosonate is soluble (in water) and a moderately acidic compound (based on its pKa). 3-deoxy-d-manno-octulosonate can be found in a number of food items such as peppermint, okra, horseradish tree, and hazelnut, which makes 3-deoxy-d-manno-octulosonate a potential biomarker for the consumption of these food products. 3-deoxy-d-manno-octulosonate may be a unique E.coli metabolite.

同义名列表

18 个代谢物同义名

(4R,5R,6R,7R)-4,5,6,7,8-pentahydroxy-2-oxooctanoic acid; oligo-alpha(2,8)-3-Deoxy-D-manno-2-octulosonic acid; 3-Deoxy-D-manno-oct-2-ulopyranosonic acid; 3-Deoxy-manno-oct-2-ulopyranosonic acid; 3-Deoxy-D-manno-2-octulosonic acid; Keto-3-deoxy-D-manno-octulosonate; 2-Dehydro-3-deoxy-D-octonic acid; 3-Deoxy-D-manno-octulosonic acid; 3-Deoxy-D-manno-2-octulosonate; 3-deoxy-D-manno-octulosonate; 2-Dehydro-3-deoxy-D-octonate; 3-deoxyoct-2-ulosonic acid; 3-Deoxyoctulosonic acid; Ketodeoxyoctonic acid; 3-Deoxyoctulosonate; Ketodeoxyoctonate; kdo Sugar acid; KDO



数据库引用编号

16 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

224 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(222)

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

  • Addison G DeBoer, Lei Lei, Chunfu Yang, Craig A Martens, Sarah L Anzick, Sophia Antonioli-Schmit, Robert J Suchland, Grant McClarty, Harlan D Caldwell, Daniel D Rockey. TargeTron Inactivation of Chlamydia trachomatis gseA Results in a Lipopolysaccharide 3-Deoxy-d-Manno-Oct-2-Ulosonic Acid-Deficient Strain That Is Cytotoxic for Cells. Infection and immunity. 2023 May; ?(?):e0009623. doi: 10.1128/iai.00096-23. [PMID: 37255490]
  • Gianluigi De Benedetto, Francesca Micoli, Silvia Londero, Laura Salvini, Luisa Sturiale, Domenico Garozzo, Neil Ravenscroft, Carlo Giannelli, Paola Cescutti. Characterization of the Salmonella Typhimurium core oligosaccharide and its reducing end 3-deoxy-d-manno-oct-2-ulosonic acid used for conjugate vaccine production. Carbohydrate research. 2019 Jul; 481(?):43-51. doi: 10.1016/j.carres.2019.05.014. [PMID: 31228656]
  • Wei Huang, Ying-Yu Zhou, Xing-Ling Pan, Xian-Yang Zhou, Jin-Cai Lei, Dong-Mei Liu, Yue Chu, Jin-Song Yang. Stereodirecting Effect of C5-Carboxylate Substituents on the Glycosylation Stereochemistry of 3-Deoxy-d- manno-oct-2-ulosonic Acid (Kdo) Thioglycoside Donors: Stereoselective Synthesis of α- and β-Kdo Glycosides. Journal of the American Chemical Society. 2018 03; 140(10):3574-3582. doi: 10.1021/jacs.7b09461. [PMID: 29481074]
  • Marina Harper, Amy Wright, Frank St Michael, Jianjun Li, Deanna Deveson Lucas, Mark Ford, Ben Adler, Andrew D Cox, John D Boyce. Characterization of Two Novel Lipopolysaccharide Phosphoethanolamine Transferases in Pasteurella multocida and Their Role in Resistance to Cathelicidin-2. Infection and immunity. 2017 11; 85(11):. doi: 10.1128/iai.00557-17. [PMID: 28874446]
  • Liuqing Wen, Yuan Zheng, Tiehai Li, Peng George Wang. Enzymatic synthesis of 3-deoxy-d-manno-octulosonic acid (KDO) and its application for LPS assembly. Bioorganic & medicinal chemistry letters. 2016 Jun; 26(12):2825-2828. doi: 10.1016/j.bmcl.2016.04.061. [PMID: 27173798]
  • Olga G Ovchinnikova, Evan Mallette, Akihiko Koizumi, Todd L Lowary, Matthew S Kimber, Chris Whitfield. Bacterial β-Kdo glycosyltransferases represent a new glycosyltransferase family (GT99). Proceedings of the National Academy of Sciences of the United States of America. 2016 May; 113(22):E3120-9. doi: 10.1073/pnas.1603146113. [PMID: 27199480]
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  • Tetsuto Nakagawa, Yoshimi Shimada, Nadejda V Pavlova, Su-Chen Li, Yu-Teh Li. Cloning and expression of 3-deoxy-d-manno-oct-2-ulosonic acid α-ketoside hydrolase from oyster hepatopancreas†. Glycobiology. 2015 Dec; 25(12):1431-40. doi: 10.1093/glycob/cwv074. [PMID: 26362869]
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  • Lisa M Willis, Chris Whitfield. KpsC and KpsS are retaining 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo) transferases involved in synthesis of bacterial capsules. Proceedings of the National Academy of Sciences of the United States of America. 2013 Dec; 110(51):20753-8. doi: 10.1073/pnas.1312637110. [PMID: 24302764]
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  • Simon Ittig, Buko Lindner, Marco Stenta, Pablo Manfredi, Evelina Zdorovenko, Yuriy A Knirel, Matteo dal Peraro, Guy R Cornelis, Ulrich Zähringer. The lipopolysaccharide from Capnocytophaga canimorsus reveals an unexpected role of the core-oligosaccharide in MD-2 binding. PLoS pathogens. 2012; 8(5):e1002667. doi: 10.1371/journal.ppat.1002667. [PMID: 22570611]
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  • Masaru Kobayashi, Nagisa Kouzu, Akina Inami, Kiminori Toyooka, Yuki Konishi, Ken Matsuoka, Toru Matoh. Characterization of Arabidopsis CTP:3-deoxy-D-manno-2-octulosonate cytidylyltransferase (CMP-KDO synthetase), the enzyme that activates KDO during rhamnogalacturonan II biosynthesis. Plant & cell physiology. 2011 Oct; 52(10):1832-43. doi: 10.1093/pcp/pcr120. [PMID: 21893514]
  • Yasunori Isshiki, Seiichi Kondo. Characterization of the carbohydrate backbone of Vibrio parahaemolyticus O6 lipopolysaccharides. Microbiology and immunology. 2011 Aug; 55(8):539-51. doi: 10.1111/j.1348-0421.2011.00355.x. [PMID: 21639862]
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  • Hak Suk Chung, Christian R H Raetz. Dioxygenases in Burkholderia ambifaria and Yersinia pestis that hydroxylate the outer Kdo unit of lipopolysaccharide. Proceedings of the National Academy of Sciences of the United States of America. 2011 Jan; 108(2):510-5. doi: 10.1073/pnas.1016462108. [PMID: 21178073]
  • Joanna Kubler-Kielb. Conjugation of LPS-derived oligosaccharides to proteins using oxime chemistry. Methods in molecular biology (Clifton, N.J.). 2011; 751(?):317-27. doi: 10.1007/978-1-61779-151-2_20. [PMID: 21674340]
  • L Cipolla, A Polissi, C Airoldi, L Gabrielli, S Merlo, F Nicotra. New targets for antibacterial design: Kdo biosynthesis and LPS machinery transport to the cell surface. Current medicinal chemistry. 2011; 18(6):830-52. doi: 10.2174/092986711794927676. [PMID: 21182480]
  • Christopher M Stead, Jinshi Zhao, Christian R H Raetz, M Stephen Trent. Removal of the outer Kdo from Helicobacter pylori lipopolysaccharide and its impact on the bacterial surface. Molecular microbiology. 2010 Nov; 78(4):837-52. doi: 10.1111/j.1365-2958.2010.07304.x. [PMID: 20659292]
  • Flavien Dardelle, Arnaud Lehner, Yasmina Ramdani, Muriel Bardor, Patrice Lerouge, Azeddine Driouich, Jean-Claude Mollet. Biochemical and immunocytological characterizations of Arabidopsis pollen tube cell wall. Plant physiology. 2010 Aug; 153(4):1563-76. doi: 10.1104/pp.110.158881. [PMID: 20547702]
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