N-Acetyl-D-glucosamine (BioDeep_00000002137)

 

Secondary id: BioDeep_00000014849, BioDeep_00000271219, BioDeep_00000400251, BioDeep_00000405919

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


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

化学式: C8H15NO6 (221.0899)
中文名称: N-乙酰-D-氨基葡萄糖, N-乙酰基-D-葡糖胺, N-乙酰-D-葡糖胺
谱图信息: 最多检出来源 Viridiplantae(plant) 17.97%

分子结构信息

SMILES: CC(=O)NC1C(C(C(OC1O)CO)O)O
InChI: InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8?/m1/s1

描述信息

N-Acetyl-D-Glucosamine (N-acetlyglucosamine) is a monosaccharide derivative of glucose. Chemically it is an amide between glucosamine and acetic acid. A single N-acetlyglucosamine moiety linked to serine or threonine residues on nuclear and cytoplasmic proteins -O-GlcNAc, is an ubiquitous post-translational protein modification. O-GlcNAc modified proteins are involved in sensing the nutrient status of the surrounding cellular environment and adjusting the activity of cellular proteins accordingly. O-GlcNAc regulates cellular responses to hormones such as insulin, initiates a protective response to stress, modulates a cells capacity to grow and divide, and regulates gene transcription. In humans, it exists in skin, cartilage and blood vessel as a component of hyaluronic acid, and bone tissue, cornea and aorta as a component of keratan sulfate. (PMID 16237703).
Monomer of Chitinand is also in the exopolysaccharide from blue-green alga Cyanospira capsulata (CCD)
N-Acetyl-D-Glucosamine (N-Acetyl-2-amino-2-deoxy-D-glucose) is a monosaccharide derivative of glucose.

同义名列表

20 个代谢物同义名

N-[(3R,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide; 2-Acetamido-2-deoxy-D-glucopyranose; 2-Acetylamino-2-deoxy-D-glucose; 2-Acetamido-2-deoxy-D-glucose; 2-(Acetylamino)-2-deoxyhexose; 2 Acetamido 2 deoxy D glucose; 2 Acetamido 2 deoxyglucose; 2-Acetamido-2-deoxyglucose; N-acetyl-α-D-glucosamine; N-Acetyl-D-glucosamine; N Acetyl D glucosamine; 2-Acetamido-D-glucose; N-Acetylchitosamine; N-Acetylglucosamine; Acetylglucosamine; GlcNAc; N-Acetyl-D-glucosamine; N-Acetyl-2-amino-2-deoxy-D-glucose; N-Acetyl-D-glucosamine; N-Acetyl-D-Glucosamine



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(5)

PlantCyc(0)

代谢反应

83 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(22)

WikiPathways(2)

Plant Reactome(0)

INOH(2)

PlantCyc(31)

COVID-19 Disease Map(0)

PathBank(26)

PharmGKB(0)

9 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。

亚细胞结构定位 关联基因列表
Cytoplasm 2 GNPTG, SP1
Endoplasmic reticulum membrane 2 CD4, HSP90B1
Nucleus 2 HSP90B1, SP1
cytosol 4 ENGASE, GFPT1, HSP90B1, NAGK
nucleoplasm 1 SP1
Cell membrane 4 CD4, ITGAM, SELE, TNF
Golgi apparatus membrane 4 GBGT1, GCNT7, MGAT1, MGAT5
cell surface 2 ITGAM, TNF
Golgi apparatus 5 FUT8, GBGT1, GNPTG, MGAT1, MGAT5
Golgi membrane 8 FUT8, GBGT1, GCNT7, GNPTG, INS, MGAT1, MGAT3, MGAT5
lysosomal membrane 1 EGF
neuronal cell body 1 TNF
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 1 ENGASE
plasma membrane 5 CD4, EGF, ITGAM, SELE, TNF
Membrane 9 EGF, EOGT, FUT8, GBGT1, HSP90B1, ITGAM, MGAT1, MGAT3, MGAT5
caveola 1 SELE
extracellular exosome 10 EGF, FUT8, GFPT1, GNPTG, HSP90B1, ITGAM, LYZ, MGAT1, MGAT5, NAGK
endoplasmic reticulum 1 HSP90B1
extracellular space 7 EGF, INS, ITGAM, LYZ, SELE, SP1, TNF
perinuclear region of cytoplasm 3 HSP90B1, MGAT1, SELE
protein-containing complex 1 HSP90B1
intracellular membrane-bounded organelle 1 GNPTG
Single-pass type I membrane protein 3 CD4, ITGAM, SELE
Secreted 4 GNPTG, INS, MGAT5, SP1
extracellular region 7 EGF, HSP90B1, INS, LYZ, MGAT5, SP1, TNF
external side of plasma membrane 4 CD4, ITGAM, SELE, TNF
Extracellular vesicle 1 MGAT1
midbody 1 HSP90B1
Early endosome 1 CD4
clathrin-coated pit 1 SELE
recycling endosome 1 TNF
Single-pass type II membrane protein 7 FUT8, GBGT1, GCNT7, MGAT1, MGAT3, MGAT5, TNF
vesicle 1 GBGT1
Cytoplasm, perinuclear region 1 MGAT1
Membrane raft 4 CD4, ITGAM, SELE, TNF
focal adhesion 1 HSP90B1
collagen-containing extracellular matrix 1 HSP90B1
chromatin 1 SP1
phagocytic cup 1 TNF
Endomembrane system 1 GNPTG
endosome lumen 1 INS
specific granule membrane 1 ITGAM
tertiary granule membrane 1 ITGAM
Melanosome 1 HSP90B1
Golgi cisterna membrane 1 FUT8
euchromatin 1 SP1
sperm plasma membrane 1 HSP90B1
plasma membrane raft 1 ITGAM
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 4 CD4, EOGT, HSP90B1, INS
transcription repressor complex 1 SP1
platelet alpha granule lumen 1 EGF
specific granule lumen 1 LYZ
tertiary granule lumen 1 LYZ
transport vesicle 1 INS
azurophil granule lumen 1 LYZ
Golgi apparatus, Golgi stack membrane 1 FUT8
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 INS, MGAT1
clathrin-coated endocytic vesicle membrane 2 CD4, EGF
Sarcoplasmic reticulum lumen 1 HSP90B1
protein-DNA complex 1 SP1
integrin complex 1 ITGAM
endocytic vesicle lumen 1 HSP90B1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
T cell receptor complex 1 CD4
cortical cytoskeleton 1 SELE
integrin alphaM-beta2 complex 1 ITGAM
endoplasmic reticulum chaperone complex 1 HSP90B1
[Secreted alpha-1,6-mannosylglycoprotein 6-beta-N-acetylglucosaminyltransferase A]: Secreted 1 MGAT5
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
UDP-N-acetylglucosamine-lysosomal-enzyme N-acetylglucosaminephosphotransferase complex 1 GNPTG


文献列表

  • Meng Zhang, Wanhui Zhou, Yu Cao, Lele Kou, Chunwei Liu, Xiaoshuang Li, Boxi Zhang, Wenjin Guo, Bin Xu, Shize Li. O-GlcNAcylation regulates long-chain fatty acid metabolism by inhibiting ACOX1 ubiquitination-dependent degradation. International journal of biological macromolecules. 2024 May; 266(Pt 2):131151. doi: 10.1016/j.ijbiomac.2024.131151. [PMID: 38547945]
  • Lulu Chen, Mengxue Hu, Luojun Chen, Yihan Peng, Cai Zhang, Xin Wang, Xiangpan Li, Yi Yao, Qibin Song, Jing Li, Huadong Pei. Targeting O-GlcNAcylation in cancer therapeutic resistance: The sugar Saga continues. Cancer letters. 2024 Apr; 588(?):216742. doi: 10.1016/j.canlet.2024.216742. [PMID: 38401884]
  • Ruben Shrestha, Sumudu Karunadasa, TaraBryn S Grismer, Andres V Reyes, Shou-Ling Xu. SECRET AGENT O-GlcNAcylates Hundreds of Proteins Involved in Diverse Cellular Processes in Arabidopsis. Molecular & cellular proteomics : MCP. 2024 Apr; 23(4):100732. doi: 10.1016/j.mcpro.2024.100732. [PMID: 38336175]
  • Sang-Mo Kang, Arjun Adhikari, Eun-Hae Kwon, Ho-Jun Gam, Jin Ryeol Jeon, Ji-In Woo, In-Jung Lee. Influence of N-Acetylglucosamine and Melatonin Interaction in Modeling the Photosynthetic Component and Metabolomics of Cucumber under Salinity Stress. International journal of molecular sciences. 2024 Feb; 25(5):. doi: 10.3390/ijms25052844. [PMID: 38474090]
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  • Jia-Xuan Zhang, Xiao-le Liu, Li Wang, Zhen Fang. Two-stage process production of microbial lipid by co-fermentation of glucose and N-acetylglucosamine from food wastes with Cryptococcus curvatus. Bioresource technology. 2023 Nov; 387(?):129685. doi: 10.1016/j.biortech.2023.129685. [PMID: 37595808]
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  • Zeqi Li, Bo Fu, Aili Wei, Yanchen Wu, Ming Huang, Enhao Zhang, Bo Cui, Bo Wang, Hui Peng. d-Glucosamine induces circadian phase delay by promoting BMAL1 degradation through AMPK/mTOR pathway. Life sciences. 2023 Jul; 325(?):121765. doi: 10.1016/j.lfs.2023.121765. [PMID: 37169147]
  • Maria J Gonzalez-Rellan, Tamara Parracho, Violeta Heras, Amaia Rodriguez, Marcos F Fondevila, Eva Novoa, Natalia Lima, Marta Varela-Rey, Ana Senra, Maria Dp Chantada-Vazquez, Cristina Ameneiro, Ganeko Bernardo, David Fernandez-Ramos, Fernando Lopitz-Otsoa, Jon Bilbao, Diana Guallar, Miguel Fidalgo, Susana Bravo, Carlos Dieguez, Maria L Martinez-Chantar, Oscar Millet, Jose M Mato, Markus Schwaninger, Vincent Prevot, Javier Crespo, Gema Frühbeck, Paula Iruzubieta, Ruben Nogueiras. Hepatocyte-specific O-GlcNAc transferase downregulation ameliorates nonalcoholic steatohepatitis by improving mitochondrial function. Molecular metabolism. 2023 Jul; ?(?):101776. doi: 10.1016/j.molmet.2023.101776. [PMID: 37453647]
  • Chao Wen, He-Chun Wu, Wen-Hong Ouyang, Jia-Xing Nie, Yi-Ping Guo, Feng Wang, Li-Li Hu, Jin-Hua Yang, Li-Juan Zheng, Jia-Lu Wang, Wei Huang, Guang-Ping Liang, Ren-Wang Jiang. Exploring the Catalytic Flexibility and Reversibility of Plant Glycosyltransferase HtUGT72AS1 for Glycodiversification of Phenolic Compounds. Journal of agricultural and food chemistry. 2023 Jun; ?(?):. doi: 10.1021/acs.jafc.3c01459. [PMID: 37260384]
  • Akiko Nakamoto, Natsuko Ohashi, Lucia Sugawara, Katsutaro Morino, Shogo Ida, Rachel J Perry, Ikki Sakuma, Tsuyoshi Yanagimachi, Yukihiro Fujita, Satoshi Ugi, Shinji Kume, Gerald I Shulman, Hiroshi Maegawa. O-GlcNAc modification is essential for physiological adipose expansion induced by high-fat feeding. American journal of physiology. Endocrinology and metabolism. 2023 May; ?(?):. doi: 10.1152/ajpendo.00263.2022. [PMID: 37224467]
  • Peibo Liang, Jingmin Li, Wei Chen, Jianyang Li, Qing Yang, Jianjun Zhang. Application of Natural Bioresources to Sustainable Agriculture: A C-Glycoside Insecticide Based on N-Acetyl-glucosamine for Regulating Insect Molting of Ostrinia furnacalis. Journal of agricultural and food chemistry. 2023 Apr; ?(?):. doi: 10.1021/acs.jafc.2c08760. [PMID: 37013678]
  • Keyan Zhang, Danqing Yao, Yue Chen, Haifan Wen, Jian Pan, Tingting Xiao, Duo Lv, Huanle He, Junsong Pan, Run Cai, Gang Wang. Mapping and identification of CsSF4, a gene encoding a UDP-N-acetyl glucosamine-peptide N-acetylglucosaminyltransferase required for fruit elongation in cucumber (Cucumis sativus L.). TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik. 2023 Mar; 136(3):54. doi: 10.1007/s00122-023-04246-9. [PMID: 36912991]
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  • Rodolfo Zentella, Yan Wang, Emily Zahn, Jianhong Hu, Liang Jiang, Jeffrey Shabanowitz, Donald F Hunt, Tai-Ping Sun. SPINDLY O-fucosylates nuclear and cytoplasmic proteins involved in diverse cellular processes in plants. Plant physiology. 2023 Feb; ?(?):. doi: 10.1093/plphys/kiad011. [PMID: 36740243]
  • Maxence Noel, Daniel I Chasman, Samia Mora, James D Otvos, Christopher D Palmer, Patrick J Parsons, Jordan W Smoller, Richard D Cummings, Robert G Mealer. The Inflammation Biomarker GlycA Reflects Plasma N-Glycan Branching. Clinical chemistry. 2023 01; 69(1):80-87. doi: 10.1093/clinchem/hvac160. [PMID: 36254612]
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  • Riccardo Zanni, Jesús Martínez-Cruz, María Gálvez-Llompart, Dolores Fernández-Ortuño, Diego Romero, Ramón García-Domènech, Alejandro Pérez-García, Jorge Gálvez. Rational Design of Chitin Deacetylase Inhibitors for Sustainable Agricultural Use Based on Molecular Topology. Journal of agricultural and food chemistry. 2022 Oct; 70(41):13118-13131. doi: 10.1021/acs.jafc.2c02377. [PMID: 36194443]
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  • Jiqiang Chen, Xu Zou, Weixing Zhu, Yanwei Duan, Hans Merzendorfer, Zhangwu Zhao, Qing Yang. Fatty acid binding protein is required for chitin biosynthesis in the wing of Drosophila melanogaster. Insect biochemistry and molecular biology. 2022 10; 149(?):103845. doi: 10.1016/j.ibmb.2022.103845. [PMID: 36165873]
  • Makoto Ogata, Mao Sakamoto, Noriko Yamauchi, Masato Nakazawa, Ami Koizumi, Remi Anazawa, Kenichi Kurumada, Kazuya I P J Hidari, Hiroyuki Kono. Optimization of the conditions for the immobilization of glycopolypeptides on hydrophobic silica particulates and simple purification of lectin using glycopolypeptide-immobilized particulates. Carbohydrate research. 2022 Sep; 519(?):108624. doi: 10.1016/j.carres.2022.108624. [PMID: 35749901]
  • Qiushi Chen, Yuanliang Zhang, Keren Zhang, Jie Liu, Huozhen Pan, Xinran Wang, Siqi Li, Dandan Hu, Zhilong Lin, Yun Zhao, Guixue Hou, Feng Guan, Hong Li, Siqi Liu, Yan Ren. Profiling the Bisecting N-acetylglucosamine Modification in Amniotic Membrane via Mass Spectrometry. Genomics, proteomics & bioinformatics. 2022 Aug; 20(4):648-656. doi: 10.1016/j.gpb.2021.09.010. [PMID: 35123071]
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  • Jiuyun Sun, Shuhua Li, Chunyang Fan, Kangjia Cui, Hongxiao Tan, Liping Qiao, Laifeng Lu. N-Acetylglucosamine Promotes Tomato Plant Growth by Shaping the Community Structure and Metabolism of the Rhizosphere Microbiome. Microbiology spectrum. 2022 06; 10(3):e0035822. doi: 10.1128/spectrum.00358-22. [PMID: 35665438]
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  • Zhi-Kui Hao, Jian-Song Li, Dan-Hua Wang, Fei He, Jing-Shi Xue, Liang-Hong Yin, Hua-Bao Zheng. Efficient production of GlcNAc in an aqueous-organic system with a Chitinolyticbacter meiyuanensis SYBC-H1 mutant. Biotechnology letters. 2022 Apr; 44(4):623-633. doi: 10.1007/s10529-022-03248-9. [PMID: 35384608]
  • Peipei Han, Yingying Wei, Shu Jiang, Yi Chen, Feng Xu, Hongfei Wang, Xingfeng Shao. N-Acetyl-d-glucosamine Inhibition of Hexokinase Results in Downregulation of the Phenylpropanoid Metabolic Pathway and Decreased Resistance to Brown Rot in Peach Fruit. Journal of agricultural and food chemistry. 2022 Mar; 70(12):3917-3928. doi: 10.1021/acs.jafc.1c06573. [PMID: 35298175]
  • Victoria Jiménez-Castillo, Daniela Illescas-Barbosa, Edgar Zenteno, Beatriz Xóchitl Ávila-Curiel, Maria Cristina Castañeda-Patlán, Martha Robles-Flores, Daniel Montante-Montes De Oca, Eduardo Pérez-Campos, Anayetzin Torres-Rivera, Abdelouhab Bouaboud, Patrick Pagesy, Carlos Josué Solórzano-Mata, Tarik Issad. Increased O-GlcNAcylation promotes IGF-1 receptor/PhosphatidyI Inositol-3 kinase/Akt pathway in cervical cancer cells. Scientific reports. 2022 03; 12(1):4464. doi: 10.1038/s41598-022-08445-0. [PMID: 35296731]
  • Ankur Tripathi, Vipin Hallan, Rajan Katoch. Cloning, Characterization, Expression Analysis, and Agglutination Studies of Novel Gene Encoding β-D-Galactose, N-Acetyl-D-Glucosamine and Lactose-Binding Lectin from Rice Bean (Vigna umbellata). Molecular biotechnology. 2022 Mar; 64(3):293-310. doi: 10.1007/s12033-021-00410-y. [PMID: 34611825]
  • Aqib Rehman Magray, Joan Martorell Ribera, Lisa Isernhagen, Sebastian P Galuska, Juliane Günther, Marieke Verleih, Torsten Viergutz, Ronald M Brunner, Bashir Ahmad Ganai, Fayaz Ahmad, Kristina Zlatina, Alexander Rebl. Evaluation of blood cell viability rate, gene expression, and O-GlcNAcylation profiles as indicative signatures for fungal stimulation of salmonid cell models. Molecular immunology. 2022 02; 142(?):120-129. doi: 10.1016/j.molimm.2021.12.019. [PMID: 34979452]
  • Daria V Grigorieva, Irina V Gorudko, Natalia A Grudinina, Oleg M Panasenko, Igor V Semak, Alexey V Sokolov, Alexander V Timoshenko. Lactoferrin modified by hypohalous acids: Partial loss in activation of human neutrophils. International journal of biological macromolecules. 2022 Jan; 195(?):30-40. doi: 10.1016/j.ijbiomac.2021.11.165. [PMID: 34863835]
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  • Zengdi Zhang, Oscar C Salgado, Bing Liu, Zahra Moazzami, Kristin A Hogquist, Michael A Farrar, Hai-Bin Ruan. An OGT-STAT5 Axis in Regulatory T Cells Controls Energy and Iron Metabolism. Frontiers in immunology. 2022; 13(?):874863. doi: 10.3389/fimmu.2022.874863. [PMID: 35874700]
  • Jing-Jing Shi, Hao-Fei Liu, Tian Hu, Xin Gao, Yong-Bin Zhang, Wei-Rong Li, Qi Wang, Shi-Jie Zhang, Dan Tang, Yun-Bo Chen. Danggui-Shaoyao-San improves cognitive impairment through inhibiting O-GlcNAc-modification of estrogen α receptor in female db/db mice. Journal of ethnopharmacology. 2021 Dec; 281(?):114562. doi: 10.1016/j.jep.2021.114562. [PMID: 34438027]
  • Susanne K Kahn, Colette Cywes-Bentley, Glenn P Blodgett, Nathan M Canaday, Carly E Turner-Garcia, Patricia Flores-Ahlschwede, Laurie L Metcalfe, Mark Nevill, Mariana Vinacur, Patrick J Sutter, Sarah C Meyer, Angela I Bordin, Gerald B Pier, Noah D Cohen. Randomized, controlled trial comparing Rhodococcus equi and poly-N-acetyl glucosamine hyperimmune plasma to prevent R equi pneumonia in foals. Journal of veterinary internal medicine. 2021 Nov; 35(6):2912-2919. doi: 10.1111/jvim.16294. [PMID: 34738651]
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