Details of Metabolite

General Information of MET (ID: META00237)
Name UDP-N-acetylglucosamine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2R,3R,4R,5S,6R)-3-(Acetylamino)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphate (non-preferred name); (2R,3R,4R,5S,6R)-3-(Acetylamino)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphoric acid (non-preferred name); Acetylglucosamine, UDP; Diphosphate N-acetylglucosamine, uridine; Diphospho-N-acetylglucosamine, uridine; N-Acetylglucosamine, uridine diphosphate; N-[2-[[[5-[(2,4-Dioxo-1H-pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy-phosphinoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide; Pyrophosphoacetylglucosamine, uridine; UDP Acetylglucosamine; UDP-Acetyl-D-glucosamine; UDP-Acetyl-delta-glucosamine; UDP-Acetylglucosamine; UDP-GlcNAc; UDP-N-Acetyl-D-glucosamine; UDP-N-Acetyl-delta-glucosamine; UDP-N-Acetyl-glucosamine; UDP-N-Acetylglucosamine; UDP-a-D-N-Acetylglucosamine; UDP-alpha-D-N-Acetylglucosamine; UDP-alpha-delta-N-Acetylglucosamine; UDPGNAc; UPPAG', Uridine 5'-diphospho-N-acetlyglucosamine, Uridine 5'-diphospho-N-acetylglucosamine, 'Uridine diphosphate N-acetyl-D-glucosamine; URIDINE-diphosphATE-N-acetylglucosamine; URIDINE-diphosphoric acid-N-acetylglucosamine; Uridine diphosphate N acetylglucosamine; Uridine diphosphate N-acetyl-delta-glucosamine; Uridine diphosphate N-acetylglucosamine; Uridine diphospho N acetylglucosamine; Uridine diphospho-2-acetamido-2-deoxy-D-glucose; Uridine diphospho-2-acetamido-2-deoxy-delta-glucose; Uridine diphospho-N-acetyl-D-glucosamine; Uridine diphospho-N-acetyl-delta-glucosamine; Uridine diphospho-N-acetylglucosamine; Uridine diphosphoacetylglucosamine; Uridine diphosphoric acid-N-acetylglucosamine; Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-glucopyranosyl ester; Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-glucopyranosyl ester; Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl ester; Uridine pyrophosphoacetylglucosamine; [[3-Acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinate; [[3-Acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinic acid
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food
Structure Type   Pyrimidine nucleotide sugars  (Click to Show/Hide the Complete Structure Type Hierarchy)
Nucleosides, nucleotides, and analogues
Pyrimidine nucleotides
Pyrimidine nucleotide sugars
PubChem CID
445675
HMDB ID
HMDB0000290
Formula
C17H27N3O17P2
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00043
DrugBank ID
DB03397
ChEBI ID
16264
FooDB ID
FDB021930
ChemSpider ID
393240
METLIN ID
5281
Physicochemical Properties Molecular Weight 607.4 Topological Polar Surface Area 300
XlogP -6.6 Complexity 1080
Heavy Atom Count 39 Rotatable Bond Count 10
Hydrogen Bond Donor Count 9 Hydrogen Bond Acceptor Count 17
Function
Uridine diphosphate-N-acetylglucosamine (uridine 5'-diphosphate-GlcNAc, or UDP-Glc-NAc) is an acetylated aminosugar nucleotide. UDP-GlcNAc is the donor substrate for modification of nucleocytoplasmic proteins at serine and threonine residues with N-acetylglucosamine (O-GlcNAc). Nutrient sensing in mammals is done through the hexosamine biosynthetic pathway (HSP), which produces uridine 5'-diphospho-N-acetylglucosamine (UDP-Glc-NAc) as its end product. Mammals respond to nutrient excess by activating O-GlcNAcylation (addition of O-linked N-acetylglucosamine). O-GlcNAc addition (and removal) is key to histone remodeling, transcription, proliferation, apoptosis, and proteasomal degradation. This nutrient-responsive signaling pathway also modulates important cellular pathways, including the insulin signaling cascade in. Alterations in O-GlcNAc metabolism are associated with various human diseases including diabetes mellitus and neurodegeneration. Due to the chemical makeup of UDP-GlcNAc, it is well positioned to serve as a glucose sensor in that it is a high-energy compound that requires and/or responds to glucose, amino acid, fatty acid and nucleotide metabolism for synthesis. Elevated levels of O-GlcNAc have an effect on insulin-stimulated glucose uptake.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      GPCR rhodopsin (GPCR-1)
            P2Y purinoceptor 14 (P2RY14) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation UDP-N-acetylglucosamine addition (2 hours)
                      Induced Change P2RY14 protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that UDP-N-acetylglucosamine addition causes the increase of P2RY14 protein activity compared with control group.
Full List of Protein(s) Regulating This Metabolite
      Lyases (EC 4)
            Cystathionine gamma-lyase (CTH) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockout of Cth
                      Induced Change UDP-N-acetylglucosamine concentration: increase (FC = 2.17)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Organic acid disorderss [ICD-11: 5C50]
                      Details It is reported that knockout of Cth leads to the increase of UDP-N-acetylglucosamine levels compared with control group.
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Knockout of TP53
                      Induced Change UDP-N-acetylglucosamine concentration: increase (Log2 FC=1.05)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the increase of UDP-N-acetylglucosamine levels compared with control group.
      Transferases (EC 2)
            Pyridoxal kinase (PDXK) Click to Show/Hide the Full List of Regulating Pair(s):   2 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [4]
                      Introduced Variation Knockout (CRISPR/Cas9 sgRNA) of Pdxk
                      Induced Change UDP-N-acetylglucosamine concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Acute myeloid leukaemia [ICD-11: 2A60]
                      Details It is reported that knockout of Pdxk leads to the decrease of UDP-N-acetylglucosamine levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [4]
                      Introduced Variation Knockout (CRISPR/Cas9 sgRNA) of PDXK
                      Induced Change UDP-N-acetylglucosamine concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Acute myeloid leukaemia [ICD-11: 2A60]
                      Details It is reported that knockout of PDXK leads to the decrease of UDP-N-acetylglucosamine levels compared with control group.
            SNF-related serine/threonine-protein kinase (SNRK) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [5]
                      Introduced Variation Knockdown (shRNA) of SNRK
                      Induced Change UDP-N-acetylglucosamine concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockdown of SNRK leads to the decrease of UDP-N-acetylglucosamine levels compared with control group.
References
1 Gi-dependent cell signaling responses of the human P2Y14 receptor in model cell systems. J Pharmacol Exp Ther. 2009 Jul;330(1):162-8.
2 Hydrogen Sulfide Is a Regulator of Hemoglobin Oxygen-Carrying Capacity via Controlling 2,3-BPG Production in Erythrocytes. Oxid Med Cell Longev. 2021 Feb 13;2021:8877691.
3 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.
4 Vitamin B6 Addiction in Acute Myeloid Leukemia. Cancer Cell. 2020 Jan 13;37(1):71-84.e7.
5 Sucrose Nonfermenting-Related Kinase Enzyme-Mediated Rho-Associated Kinase Signaling is Responsible for Cardiac Function. Circ Cardiovasc Genet. 2016 Dec;9(6):474-486.

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