CHEBI:506227 - N-acetyl-D-glucosamine

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ChEBI Name N-acetyl-D-glucosamine
ChEBI ID CHEBI:506227
ChEBI ASCII Name N-acetyl-D-glucosamine
Definition The D isomer of N-acetylglucosamine.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB7198081, eMolecules:518529, ZINC000000388262
Download Molfile XML SDF
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-RTRLPJTCSA-N
SMILES CC(=O)N[C@H]1C(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.
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-D-glucosamine (CHEBI:506227) has role bacterial metabolite (CHEBI:76969)
N-acetyl-D-glucosamine (CHEBI:506227) is a N-acetyl-D-hexosamine (CHEBI:21601)
N-acetyl-D-glucosamine (CHEBI:506227) is a N-acetylglucosamine (CHEBI:59640)
Incoming α-D-GalpNAc-(1→3)-D-GlcpNAc (CHEBI:148388) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
α-D-Glcp-(1→4)-D-GlcpNAc (CHEBI:152766) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
α-D-Glcp-(1→6)-D-GlcpNAc (CHEBI:151906) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
α-D-GlcpNAc-(1→4)-D-GlcpNAc (CHEBI:154293) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
α-D-Manp-(1→6)-D-GlcpNAc (CHEBI:152042) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
α-L-Fucp-(1→4)-D-GlcpNAc (CHEBI:151318) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
β-D-Galf-(1→4)-D-GlcpNAc (CHEBI:148184) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
β-D-Galp3S-(1→4)-D-GlcpNAc (CHEBI:147626) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
β-D-GalpNAc4S-(1→4)-D-GlcNAc (CHEBI:147909) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
β-D-Glcp-(1→3)-D-GlcpNAc (CHEBI:152894) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
β-D-Glcp-(1→6)-D-GlcpNAc (CHEBI:146757) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
N-acetyl-β-D-glucosamine 6-sulfate (CHEBI:28132) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
N-acetyl-1-seleno-β-D-glucosamine(1−) (CHEBI:195547) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
N-acetyl-D-glucosamine 4-sulfate (CHEBI:28406) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
D-Galp-(1→4)-D-GlcpNAc (CHEBI:147906) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
PUGNAc (CHEBI:233425) has functional parent N-acetyl-D-glucosamine (CHEBI:506227)
α-D-Manp-(1→3)-D-GlcpNAc (CHEBI:152040) has parent hydride N-acetyl-D-glucosamine (CHEBI:506227)
N-acetyl-α-D-glucosamine (CHEBI:44278) is a N-acetyl-D-glucosamine (CHEBI:506227)
N-acetyl-β-D-glucosamine (CHEBI:28009) is a N-acetyl-D-glucosamine (CHEBI:506227)
N-acetyl-D-glucosaminyl group (CHEBI:73776) is substituent group from N-acetyl-D-glucosamine (CHEBI:506227)
IUPAC Name
2-acetamido-2-deoxy-D-glucopyranose
Synonyms Sources
2-Acetamido-2-deoxy-D-glucose DrugBank
2-Acetamido-2-deoxy-D-glucose KEGG COMPOUND
GlcNAc DrugBank
GlcNAc KEGG COMPOUND
N-Acetyl-D-glucosamine KEGG COMPOUND
N-acetyl-D-glucosamine UniProt
N-Acetylchitosamine DrugBank
N-Acetylchitosamine KEGG COMPOUND
WURCS=2.0/1,1,0/[a2122h-1x_1-5_2*NCC/3=O]/1/ GlyTouCan
Manual Xrefs Databases
C00140 KEGG COMPOUND
DB00141 DrugBank
G64581RP GlyGen
G64581RP GlyTouCan
NAG PDBeChem
View more database links
Registry Numbers Types Sources
1913592 Beilstein Registry Number Beilstein
7512-17-6 CAS Registry Number KEGG COMPOUND
Citations Types Sources
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Last Modified
03 February 2025