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
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).
DBLinks
- CAS Registry Number: 528-04-1
- PubChem CID: 445675
- ChEBI: 16264
- HMDB: HMDB0000290
- LipidMaps: LMSL01010002
- KEGG: C00043
- BioCyc:
- NCBI MeSH: Uridine Diphosphate N-Acetylglucosamine
- Wikipedia: Uridine_diphosphate_N-acetylglucosamine
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
- WishartLab ClassyFire: [Pyrimidine nucleotide sugars] Pyrimidine nucleotide sugars
- RefMet: [Pyrimidine rNDP] Pyrimidine rNDP
- LipidMaps: [Monoacylaminosugars [SL0101]] Monoacylaminosugars [SL0101]
- ChEBI: [CHEBI:16264] UDP-N-acetyl-alpha-D-glucosamine
- Coconut NaturalProduct: [Aminosugars] Aminosugars
| 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 |
Taxonomy Source
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 |