UDP-acetyl-glucosamine

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  • Name: UDP-acetyl-glucosamine
  • Description: 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 nucleocytoplasm... ic 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). This compound is found in lower levels in older healthy people, among others, due to its involvment in physical activities. (HMDB:HMDB0000902, PNAS April 19, 2016 113 (16) 4252-4259).
Overview of age-variations
Age group comparisons
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
27036001 Age 29 ± 4, Gender ⚥ 0.58 (CV (CV=SD of metabolite abundance (peak areas from LC-MS) divided by the mean)) LC-MS blood
27036001 Age 81 ± 7, Gender ⚥ 0.54 (CV (CV=SD of metabolite abundance (peak areas from LC-MS) divided by the mean)) LC-MS blood
Linear regression
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
log2 ratio/log2(FC)
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
Summary
  • Synonym:
    UDP-N-acetyl-D-glucosamine; UDP-N-acetylglucosamine; UDP-glcNac;uridine diphosphate-N-acetylglucosamine; UDP-N-acetyl-alpha-D-glucosamine
  • Chemical Formula:
    C17H27N3O17P2
  • Systematic name:
    [(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate; [({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
  • SMILES:
    CC(=O)NC1C(C(C(OC1OP(=O)(O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)CO)O)O
  • InChI:
    InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1
  • InChI Key:
    LFTYTUAZOPRMMI-CFRASDGPSA-N
  • CAS number:
    91183-98-1
Related resources
Pathway info P = product of S = substrate of
Metabolite sources and localization
  • Metabolite location:
    Human organism, Body part, Human body biofluids, Biofluid tissues, Blood, Saliva, Organ, Liver, Muscle, Tissue, Adipose tissue, Cellular (general class), Subcellular, Golgi apparatus
  • Metabolite source:
    Homo sapiens, endogenous metabolite
Age-variations
Age group comparisons
Method: LC-MS
Sample: blood
PubMed PMID: 27036001
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