UDP-N-acetyl-alpha-D-glucosamine(2-) (uacgam)

Human Metabolome Database (HMDB): 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).

Charged formula:

C17H25N3O17P2

Charge:

-2

InChIKey:

LFTYTUAZOPRMMI-CFRASDGPSA-L

SMILES:

[H]OC([H])([H])[C@@]1([H])O[C@]([H])(OP(=O)([O-])OP(=O)([O-])OC([H])([H])[C@@]2([H])O[C@@]([H])(n3c([H])c([H])c(=O)n([H])c3=O)[C@]([H])(O[H])[C@]2([H])O[H])[C@]([H])(N([H])C(=O)C([H])([H])[H])[C@@]([H])(O[H])[C@]1([H])O[H]

External links: hmdb.cakegg.jpebi.ac.ukpubchem.ncbi.nlm.nih.gov

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