UDP-N-acetyl-alpha-D-glucosamine (BioCAD00000019104)

saliva adipose tissue liver skeletal muscle microbial natural products

Metabolite Card

Formula: C17H27N3O17P2 (607.0816)
SMILES: CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O

Synonyms [en]

UDP-GlcNAc; UDP-N-acetylglucosamine; UDP-N-acetyl-alpha-D-glucosamine; UDP-N-acetyl-D-glucosamine; Uridine diphosphate-N-acetylglucosamine; URIDINE-DIPHOSPHATE-N-ACETYLGLUCOSAMINE

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

UDP-N-acetyl-alpha-D-glucosamine. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000019104). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

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. (PMID: 16317114) 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. (PMID: 12678487).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 528-04-1
  • CAS Registry Number: 91183-98-1
  • PubChem: 10705
  • PubChem: 445675
  • PubChem: 643981
  • ChEBI: ChEBI:16264
  • HMDB: HMDB0000290
  • HMDB: HMDB00290
  • HMDB: HMDB00304
  • LipidMaps: LMSL01010002
  • KEGG: C00043
  • NCBI MeSH: Uridine Diphosphate N-Acetylglucosamine
  • Wikipedia: Uridine_diphosphate_N-acetylglucosamine
  • DrugBank: DB03397
  • RefMet: RM0133219
  • MoNA: BAF_UVA_POS000963
  • MoNA: CCMSLIB00000578244
  • MoNA: CCMSLIB00005464491
  • MoNA: CCMSLIB00005720441
  • MoNA: CCMSLIB00005720741
  • MoNA: FiehnHILIC000838
  • MoNA: FiehnHILIC001563
  • MoNA: FiehnHILIC003040
  • MoNA: MoNA024055
  • MoNA: MoNA024070
  • MoNA: MoNA034124
  • MoNA: MoNA034125
  • MoNA: MoNA034127
  • MoNA: MoNA036097
  • MoNA: MoNA036098
  • MoNA: MoNA036099
  • MoNA: MoNA037900
  • MoNA: MoNA038579
  • MoNA: PR010241
  • MoNA: PR100620
  • MoNA: PR100621
  • MoNA: PS037001
  • MoNA: PS037002
  • MoNA: PS037003
  • MoNA: PS037004
  • MoNA: PS037006
  • MoNA: PS037007
  • MoNA: PS037008
  • MoNA: PS037009
  • MoNA: PS037010
  • Metlin: METLIN_41549
  • Coconut NaturalProduct: CNP0201907.1
  • Coconut NaturalProduct: CNP0201907.2
  • Coconut NaturalProduct: CNP0201907.6

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00414 3.2.1.183 UDP-N-acetyl-D-glucosamine 2-epimerase
KEGG:R00416 2.7.7.23 UTP:N-acetyl-alpha-D-glucosamine-1-phosphate uridylyltransferase
KEGG:R00417 2.4.1.94 UDP-N-acetyl-D-glucosamine:protein beta-N-acetyl-D-glucosaminyltransferase
KEGG:R00418 5.1.3.2 UDP-N-acetyl-D-glucosamine 4-epimerase
KEGG:R00420 5.1.3.14 UDP-N-acetyl-D-glucosamine 2-epimerase
KEGG:R00421 1.1.1.136 UDP-N-acetyl-D-glucosamine:NAD+ 6-oxidoreductase
KEGG:R00422 C00043<=>C05005
KEGG:R00423 C00043<=>C05114
KEGG:R00504 2.7.8.18 UDP-alpha-D-galactose:UDP-N-acetyl-alpha-D-glucosamine galactose phosphotransferase
KEGG:R00660 2.5.1.7 phosphoenolpyruvate:UDP-N-acetyl-D-glucosamine 1-carboxyvinyl-transferase
KEGG:R01007 2.7.8.15 UDP-N-acetyl-D-glucosamine:dolichyl-phosphate N-acetyl-D-glucosamine phosphotransferase
KEGG:R01008 2.4.1.153 UDP-N-acetyl-D-glucosamine:dolichyl-phosphate alpha-N-acetyl-D-glucosaminyltransferase
KEGG:R01996 2.4.1.56 UDP-N-acetyl-D-glucosamine:lipopolysaccharide N-acetylglucosaminyltransferase
KEGG:R02335 2.4.1.16 UDP-N-acetyl-D-glucosamine:chitin 4-beta-N-acetylglucosaminyl-transferase
KEGG:R02654 2.4.1.198 UDP-N-acetyl-D-glucosamine:phosphatidylinositol N-acetyl-D-glucosaminyltransferase
KEGG:R02717 2.4.1.70 UDP-N-acetyl-D-glucosamine:poly(ribitol-phosphate) N-acetyl-D-glucosaminyltransferase
KEGG:R02789 2.4.1.149 UDP-N-acetyl-alpha-D-glucosamine:beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-R beta-1,3-acetyl-D-glucosaminyltransferase
KEGG:R02790 2.4.1.150 UDP-N-acetyl-D-glucosamine:beta-D-galactosyl-1,4-N-acetyl-D-glucosaminide beta-1,6-N-acetyl-D-glucosaminyltransferase
KEGG:R03513 2.4.1.147 UDP-N-acetyl-D-glucosamine:O-glycosyl-glycoprotein (N-acetyl-D-glucosamine to N-acetyl-D-galactosaminyl-R) beta-1,3-N-acetyl-D-glucosaminyltransferase
KEGG:R03514 2.4.1.148 UDP-N-acetyl-D-glucosamine:O-oligosaccharide-glycoprotein (N-acetyl-D-glucosamine to N-acetyl-D-galactosamine of N-acetyl-beta-D-glucosaminyl-1,3-N-acetyl-D-galactosaminyl-R) beta-1,6-N-acetyl-D-glucosaminyltransferase
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Organism Source

Taxonomy Source

  1. Streptomyces tsukubaensis NRRL 18488 [ncbi taxid: ]
  2. Escherichia coli [ncbi taxid: 562]

Pathway Synthetic

pathway id name
BioCyc:LEISH_PWY3IU-20 glycophosphatidylinositol (GPI) anchor biosynthesis
BioCyc:LEISH_PWY3IU-1 glycoinositolphospholipid (GIPL) biosynthesis
BioCyc:TRYPANO_MANNOSYL-CHITO-DOLICHOL-BIOSYNTHESIS dolichyl-diphosphooligosaccharide biosynthesis
BioCyc:TRYPANO_PEP-LIPA-SYN-PWY peptidoglycan and lipid A precursor biosynthesis
BioCyc:TRYPANO_PWY1G-0 mycothiol biosynthesis
BioCyc:TRYPANO_PWY-6387 UDP-N-acetylmuramoyl-pentapeptide biosynthesis III (meso-DAP-containing)
BioCyc:LEISH_PWY3IU-555 lipophosphoglycan (LPG) biosynthesis
BioCyc:TRYPANO_PEPTIDOGLYCANSYN-PWY peptidoglycan biosynthesis I (meso-diaminopimelate containing)
BioCyc:TRYPANO_UDPNAGSYN-PWY UDP-N-acetyl-D-glucosamine biosynthesis I
BioCyc:LEISH_MANNOSYL-CHITO-DOLICHOL-BIOSYNTHESIS dolichyl-diphosphooligosaccharide biosynthesis
BioCyc:LEISH_PWY3IU-63 UDP-N-acetylglucosamine biosynthesis
BioCyc:TRYPANO_UDPNACETYLGALSYN-PWY UDP-N-acetyl-D-glucosamine biosynthesis II
WikiPathways:WP3641 SK UDPglcnac
PathBank:SMP0000851 Lipopolysaccharide Biosynthesis
PathBank:SMP0000905 Amino Sugar and Nucleotide Sugar Metabolism I
PathBank:SMP0000924 Peptidoglycan Biosynthesis I
PathBank:SMP0000975 Secondary Metabolites: Enterobacterial Common Antigen Biosynthesis
PathBank:SMP0001919 Lipopolysaccharide Biosynthesis II
PathBank:SMP0002059 Secondary Metabolites: Enterobacterial Common Antigen Biosynthesis 2
PathBank:SMP0002060 Secondary Metabolites: Enterobacterial Common Antigen Biosynthesis 3
View All Pathways