CHEBI:28009 - N-acetyl-β-D-glucosamine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name N-acetyl-β-D-glucosamine
ChEBI ID CHEBI:28009
ChEBI ASCII Name N-acetyl-beta-D-glucosamine
Definition An N-acetyl-D-glucosamine having β-configuration at the anomeric centre.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44166, CHEBI:7169, CHEBI:21579, CHEBI:7140
Supplier Information
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-FMDGEEDCSA-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): epitope
The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
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-β-D-glucosamine (CHEBI:28009) has role epitope (CHEBI:53000)
N-acetyl-β-D-glucosamine (CHEBI:28009) is a N-acetyl-D-glucosamine (CHEBI:506227)
Incoming α-D-Galf-(1→3)-β-D-GlcpNAc (CHEBI:148960) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
α-D-Galp-(1→3)-β-D-GlcpNAc (CHEBI:147845) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
α-D-Galp-(1→4)-β-D-GlcpNAc (CHEBI:61836) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
α-D-Galp-(1→6)-β-D-GlcpNAc (CHEBI:149016) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
α-D-Manp-(1→4)-β-D-GlcpNAc (CHEBI:150430) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
α-L-Fucp-(1→6)-β-D-GlcpNAc (CHEBI:154711) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GalpNAc4S-(1→4)-β-D-GlcpNAc (CHEBI:149323) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GclpNAc-(1→2)-[β-D-GlcpNAc-(1→3)]-D-Manp (CHEBI:146487) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-Glcp-(1→4)-β-D-GlcpNAc (CHEBI:150380) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→2−)α-D-Galp (CHEBI:152962) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→2)-β-D-Galp (CHEBI:149329) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→2)-β-D-Manp (CHEBI:150826) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→3)-α-D-Glcp (CHEBI:150053) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→3)-α-D-GlcpNAc (CHEBI:153445) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→3)-β-D-Galp-(1→4)-D-Glc-OH (CHEBI:147919) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→3)-β-D-GalpNAc (CHEBI:153935) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→3)-β-D-GlcpNAc (CHEBI:153675) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→3)-β-L-Fucp (CHEBI:146583) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→3)-D-Gal-OH (CHEBI:147553) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→3)-D-Galp (CHEBI:146464) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→3)-D-GalpNAc (CHEBI:154375) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→4)-β-D-Galp (CHEBI:146619) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→4)-β-D-GlcpA (CHEBI:150712) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→4)-D-Manp (CHEBI:147602) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→6)-α-D-GalpNAc3S (CHEBI:147940) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→6)-α-D-Manp (CHEBI:147740) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→6)-β-D-Galp (CHEBI:148094) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→6)-β-D-GlcpNAc (CHEBI:150453) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-D-GlcpNAc-(1→6)-D-Galp (CHEBI:147045) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-L-Fucp-(1→6)-β-D-GlcpNAc (CHEBI:152409) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
β-L-Galp-(1→3)-β-D-GlcpNAc (CHEBI:147144) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
N,N'-diacetylchitobiono-1,5-lactone (CHEBI:143145) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
[6)-β-D-GlcpNAc-(1→] residue (CHEBI:140449) is substituent group from N-acetyl-β-D-glucosamine (CHEBI:28009)
IUPAC Names
2-acetamido-2-deoxy-β-D-glucopyranose
2-acetamido-2-deoxyhexopyranose
Synonyms Sources
2-Acetamido-2-deoxy-D-glucose ChemIDplus
2-Acetylamino-2-deoxy-D-glucose ChemIDplus
Acetylglucosamine ChemIDplus
βGlcNAc ChEBI
GlcNAc-β ChEBI
N-Acetyl-beta-D-glucosamine KEGG COMPOUND
N-acetyl-β-D-glucosamine UniProt
N-Acetyl-D-glucosamine ChemIDplus
N-acetylglucosamine ChemIDplus
WURCS=2.0/1,1,0/[a2122h-1b_1-5_2*NCC/3=O]/1/ GlyTouCan
Manual Xrefs Databases
2FIK PDB
2Q86 PDB
4615 DrugCentral
C03878 KEGG COMPOUND
G49108TO GlyGen
G49108TO GlyTouCan
HMDB0000803 HMDB
NAG PDBeChem
View more database links
Registry Numbers Types Sources
1247660 Beilstein Registry Number Beilstein
1247660 Reaxys Registry Number Reaxys
721281 Gmelin Registry Number Gmelin
7512-17-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15692805 PubMed citation Europe PMC
16537470 PubMed citation Europe PMC
17991151 PubMed citation Europe PMC
18295796 PubMed citation Europe PMC
19443021 PubMed citation Europe PMC
25568069 PubMed citation Europe PMC
31537530 PubMed citation Europe PMC
32568414 PubMed citation Europe PMC
7521740 PubMed citation Europe PMC
Last Modified
17 January 2023