CHEBI:16264 - UDP-N-acetyl-α-D-glucosamine

ChEBI IDCHEBI:16264
ChEBI NameUDP-N-acetyl-α-D-glucosamine
Stars
ASCII NameUDP-N-acetyl-alpha-D-glucosamine
DefinitionA UDP-amino sugar having N-acetyl-α-D-glucosamine as the amino sugar component.
Secondary ChEBI IDsCHEBI:9823, CHEBI:13456, CHEBI:13473, CHEBI:13475, CHEBI:13476, CHEBI:22115, CHEBI:46243, CHEBI:46287
Last Modified27 January 2016
DownloadsMolfile
FormulaC17H27N3O17P2
Net Charge0
Average Mass607.355
Monoisotopic Mass607.08157
SMILESCC(=O)N[C@H]1[C@@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)nc3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O
InChIInChI=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
InChIKeyLFTYTUAZOPRMMI-CFRASDGPSA-N
Species of MetaboliteComponentSourceComments
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Biological Roles:
Escherichia coli metabolite  Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
ChEBI Ontology
Outgoing Relation(s)
UDP-N-acetyl-α-D-glucosamine (CHEBI:16264) has functional parent UDP-D-glucosamine (CHEBI:22102)
UDP-N-acetyl-α-D-glucosamine (CHEBI:16264) has role Escherichia coli metabolite (CHEBI:76971)
UDP-N-acetyl-α-D-glucosamine (CHEBI:16264) has role mouse metabolite (CHEBI:75771)
UDP-N-acetyl-α-D-glucosamine (CHEBI:16264) is a UDP-amino sugar (CHEBI:35262)
UDP-N-acetyl-α-D-glucosamine (CHEBI:16264) is conjugate acid of UDP-N-acetyl-α-D-glucosamine(2−) (CHEBI:57705)
Incoming Relation(s)
UDP-N-acetyl-α-D-glucosamine(2−) (CHEBI:57705) is conjugate base of UDP-N-acetyl-α-D-glucosamine (CHEBI:16264)
IUPAC Name 
uridine 5'-[3-(2-acetamido-2-deoxy-α-D-glucopyranosyl) dihydrogen diphosphate]
Synonyms  Source
(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)PDBeChem
UDP-GlcNAcKEGG GLYCAN
UDP-N-acetyl-D-glucosamineKEGG COMPOUND
UDP-N-acetylglucosamineKEGG COMPOUND
URIDINE-DIPHOSPHATE-N-ACETYLGLUCOSAMINEPDBeChem
Manual XrefsDatabases
C00019358KNApSAcK
C00043KEGG COMPOUND
G10610KEGG GLYCAN
HMDB0000290HMDB
UD1PDBeChem
Registry NumbersSources
Reaxys:78982Reaxys
CAS:528-04-1KEGG COMPOUND
CAS:528-04-1ChemIDplus
Citations