N-acetyl-D-glucosamine (CHEBI:506227)

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CHEBI:506227 - N-acetyl-D-glucosamine

ChEBI ID	CHEBI:506227
ChEBI Name	N-acetyl-D-glucosamine
Stars
ASCII Name	N-acetyl-D-glucosamine
Definition	The D isomer of N-acetylglucosamine.
Last Modified	3 February 2025
Downloads	Molfile

Formula	C8H15NO6
Net Charge	0
Average Mass	221.209
Monoisotopic Mass	221.08994
SMILES	CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
WURCS	WURCS=2.0/1,1,0/[a2122h-1x_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-RTRLPJTCSA-N

Roles Classification

Biological Roles:

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-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 Relation(s)
	N-acetyl-D-glucosamine 4-sulfate (CHEBI:28406) 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-β-D-glucosamine 6-sulfate (CHEBI:28132) 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-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)
	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	Source
2-Acetamido-2-deoxy-D-glucose	KEGG COMPOUND
2-Acetamido-2-deoxy-D-glucose	DrugBank
GlcNAc	DrugBank
GlcNAc	KEGG COMPOUND
N-Acetylchitosamine	KEGG COMPOUND
N-Acetylchitosamine	DrugBank

UniProt Name	Source
N-acetyl-D-glucosamine	UniProt

Manual Xrefs	Databases
C00140	KEGG COMPOUND
DB00141	DrugBank
G64581RP	GlyTouCan
G64581RP	GlyGen
NAG	PDBeChem

Registry Numbers	Sources
Beilstein:1913592	Beilstein
CAS:7512-17-6	KEGG COMPOUND

Citations