CHEBI:44278 - N-acetyl-α-D-glucosamine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name N-acetyl-α-D-glucosamine
ChEBI ID CHEBI:44278
ChEBI ASCII Name N-acetyl-alpha-D-glucosamine
Definition An N-acetyl-D-glucosamine that has α-configuration at the anomeric centre.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C8H15NO6
Net Charge 0
Average Mass 221.20780
Monoisotopic Mass 221.08994
InChI InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8+/m1/s1
InChIKey OVRNDRQMDRJTHS-PVFLNQBWSA-N
SMILES CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O
Roles Classification
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
(via N-acetyl-D-glucosamine )
EC 2.7.1.1 (hexokinase) inhibitor
An EC 2.7.1.* (phosphotransferases with an alcohol group as acceptor) inhibitor that interferes with the action of hexokinase, EC 2.7.1.1, an enzyme that phosphorylates hexoses forming hexose phosphate.
(via N-acetylglucosamine )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing N-acetyl-α-D-glucosamine (CHEBI:44278) is a N-acetyl-D-glucosamine (CHEBI:506227)
Incoming Δ4-β-D-GlcpA-(1→4)-α-D-GlcpNAc (CHEBI:150237) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
Δ4-β-D-GlcpA2S-(1→3)-α-D-GlcpNAc (CHEBI:148337) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
α-D-Galp-(1→3)-α-D-GlcpNAc (CHEBI:145589) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
α-D-GlcpNAc-(1→1)-α-D-Glcp (CHEBI:152022) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
α-D-GlcpNAc-(1→2)-β-D-Glcp (CHEBI:149311) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
α-D-GlcpNAc-(1→3)-D-Glcp (CHEBI:150150) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
α-D-GlcpNAc-(1→4)-β-D-GlcpA (CHEBI:150151) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
α-D-GlcpNAc-(1→4)-β-D-Manp (CHEBI:152193) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
α-D-GlcpNAc-(1→4)-D-GlcpNAc (CHEBI:154293) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
α-D-Manp-(1→3)-α-D-GlcpNAc (CHEBI:145596) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
α-D-Manp-(1→4)-α-D-GlcpNAc (CHEBI:152096) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
α-L-Fucp-(1→3)-α-D-GlcpNAc (CHEBI:155347) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
α-L-Fucp-(1→4)-α-D-GlcpNAc (CHEBI:154344) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
α-L-Fucp-(1→6)-α-D-GlcpNAc (CHEBI:154755) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
β-D-Galp-(1→3)-α-D-GlcpNAc (CHEBI:145593) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
β-D-Galp-(1→6)-α-D-GlcpNAc (CHEBI:150486) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
β-D-GlcpNAc-(1→3)-α-D-GlcpNAc (CHEBI:153445) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
β-L-Fucp-(1→6)-α-D-GlcNAc (CHEBI:146502) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
N-acetyl-α-D-glucosaminyl-L-threonyl residue (CHEBI:156086) has functional parent N-acetyl-α-D-glucosamine (CHEBI:44278)
IUPAC Name
2-acetamido-2-deoxy-α-D-glucopyranose
Synonyms Sources
2-(acetylamino)-2-deoxy-α-D-glucopyranose ChEBI
α-D-GlcNAc ChEBI
α-GlcNAc ChEBI
N-acetyl-α-D-glucosamine UniProt
WURCS=2.0/1,1,0/[a2122h-1a_1-5_2*NCC/3=O]/1/ GlyTouCan
Manual Xrefs Databases
C20328 KEGG COMPOUND
CPD-12541 MetaCyc
G68544GH GlyGen
G68544GH GlyTouCan
NDG PDBeChem
View more database links
Registry Numbers Types Sources
10036-64-3 CAS Registry Number KEGG COMPOUND
10036-64-3 CAS Registry Number ChemIDplus
1429039 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11673851 PubMed citation Europe PMC
18412409 PubMed citation Europe PMC
6013453 PubMed citation Europe PMC
Last Modified
07 April 2021