N-acetyl-beta-D-glucosamine (CHEBI:28009)

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

ChEBI ID	CHEBI:28009
ChEBI Name	N-acetyl-β-D-glucosamine
Stars
ASCII Name	N-acetyl-beta-D-glucosamine
Definition	An N-acetyl-D-glucosamine having β-configuration at the anomeric centre.
Secondary ChEBI IDs	CHEBI:7140, CHEBI:7169, CHEBI:21579, CHEBI:44166
Last Modified	29 March 2024
Downloads	Molfile

Formula	C8H15NO6
Net Charge	0
Average Mass	221.209
Monoisotopic Mass	221.08994
SMILES	CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O
WURCS	WURCS=2.0/1,1,0/[a2122h-1b_1-5_2*NCC/3=O]/1/
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

Roles Classification

Biological Roles:

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.

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.

ChEBI Ontology

Outgoing Relation(s)
	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 Relation(s)
	N,N'-diacetylchitobiono-1,5-lactone (CHEBI:143145) has functional parent N-acetyl-β-D-glucosamine (CHEBI:28009)
	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)-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→2−)α-D-Galp (CHEBI:152962) 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→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→4)-D-Manp (CHEBI:147602) 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→6)-D-Galp (CHEBI:147045) 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-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)
	[6)-β-D-GlcpNAc-(1→] residue (CHEBI:140449) is substituent group from N-acetyl-β-D-glucosamine (CHEBI:28009)

IUPAC Names
2-acetamido-2-deoxyhexopyranose
2-acetamido-2-deoxy-β-D-glucopyranose

Synonyms	Source
2-Acetamido-2-deoxy-D-glucose	ChemIDplus
2-Acetylamino-2-deoxy-D-glucose	ChemIDplus
2-(acetylamino)-2-deoxy-β-D-glucopyranose	ChEBI
Acetylglucosamine	ChemIDplus
GlcNAc-β	ChEBI
N-Acetyl-beta-D-glucosamine	KEGG COMPOUND

UniProt Name	Source
N-acetyl-β-D-glucosamine	UniProt

Manual Xrefs	Databases
2FIK	PDB
2Q86	PDB
4615	DrugCentral
C03878	KEGG COMPOUND
G49108TO	GlyTouCan
G49108TO	GlyGen
HMDB0000803	HMDB
NAG	PDBeChem

Registry Numbers	Sources
Reaxys:1247660	Reaxys
Gmelin:721281	Gmelin
CAS:7512-17-6	ChemIDplus

Citations