N-acetyl-alpha-D-glucosamine (CHEBI:44278)

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

ChEBI ID	CHEBI:44278
ChEBI Name	N-acetyl-α-D-glucosamine
Stars
ASCII Name	N-acetyl-alpha-D-glucosamine
Definition	An N-acetyl-D-glucosamine that has α-configuration at the anomeric centre.
Last Modified	7 April 2021
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-1a_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-PVFLNQBWSA-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)
Outgoing Relation(s)	N-acetyl-α-D-glucosamine (CHEBI:44278) is a N-acetyl-D-glucosamine (CHEBI:506227)
Incoming Relation(s)
	N-acetyl-α-D-glucosaminyl-L-threonyl residue (CHEBI:156086) 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)-D-GlcpNAc (CHEBI:154293) 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-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)
	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)

IUPAC Name
2-acetamido-2-deoxy-α-D-glucopyranose

Synonyms	Source
2-(acetylamino)-2-deoxy-α-D-glucopyranose	ChEBI
α-GlcNAc	ChEBI
α-D-GlcNAc	ChEBI

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

Manual Xrefs	Databases
NDG	PDBeChem
C20328	KEGG COMPOUND
CPD-12541	MetaCyc
G68544GH	GlyTouCan
G68544GH	GlyGen

Registry Numbers	Sources
Reaxys:1429039	Reaxys
CAS:10036-64-3	ChemIDplus
CAS:10036-64-3	KEGG COMPOUND

Citations