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> Main
CHEBI:44278 -
N
-acetyl-α-
D
-glucosamine
Main
ChEBI Ontology
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ChEBI Name
N
-acetyl-α-
D
-glucosamine
ChEBI ID
CHEBI:44278
ChEBI ASCII Name
N-acetyl-alpha-D-glucosamine
Definition
An
N
-acetyl-
D
-glucosamine that has α-configuration at the anomeric centre.
Stars
This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Molfile
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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-PVFLNQBWSA-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):
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-α-
D
-glucosamine (
CHEBI:44278
)
is a
N
-acetyl-
D
-glucosamine (
CHEBI:506227
)
Incoming
Δ
4
-β-
D
-Glc
p
A-(1→4)-α-
D
-Glc
p
NAc (
CHEBI:150237
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
Δ
4
-β-
D
-Glc
p
A2S-(1→3)-α-
D
-Glc
p
NAc (
CHEBI:148337
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
α-
D
-Gal
p
-(1→3)-α-
D
-Glc
p
NAc (
CHEBI:145589
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
α-
D
-Glc
p
NAc-(1→1)-α-
D
-Glc
p
(
CHEBI:152022
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
α-
D
-Glc
p
NAc-(1→2)-β-
D
-Glc
p
(
CHEBI:149311
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
α-
D
-Glc
p
NAc-(1→3)-
D
-Glc
p
(
CHEBI:150150
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
α-
D
-Glc
p
NAc-(1→4)-β-
D
-Glc
p
A (
CHEBI:150151
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
α-
D
-Glc
p
NAc-(1→4)-β-
D
-Man
p
(
CHEBI:152193
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
α-
D
-Glc
p
NAc-(1→4)-
D
-Glc
p
NAc (
CHEBI:154293
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
α-
D
-Man
p
-(1→3)-α-
D
-Glc
p
NAc (
CHEBI:145596
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
α-
D
-Man
p
-(1→4)-α-
D
-Glc
p
NAc (
CHEBI:152096
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
α-
L
-Fuc
p
-(1→3)-α-
D
-Glc
p
NAc (
CHEBI:155347
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
α-
L
-Fuc
p
-(1→4)-α-
D
-Glc
p
NAc (
CHEBI:154344
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
α-
L
-Fuc
p
-(1→6)-α-
D
-Glc
p
NAc (
CHEBI:154755
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
β-
D
-Gal
p
-(1→3)-α-
D
-Glc
p
NAc (
CHEBI:145593
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
β-
D
-Gal
p
-(1→6)-α-
D
-Glc
p
NAc (
CHEBI:150486
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
β-
D
-Glc
p
NAc-(1→3)-α-
D
-Glc
p
NAc (
CHEBI:153445
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
β-
L
-Fuc
p
-(1→6)-α-
D
-GlcNAc (
CHEBI:146502
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
N
-acetyl-α-
D
-glucosaminyl-
L
-threonyl residue (
CHEBI:156086
)
has functional parent
N
-acetyl-α-
D
-glucosamine (
CHEBI:44278
)
IUPAC Name
2-acetamido-2-deoxy-α-
D
-glucopyranose
Synonyms
Sources
2-(acetylamino)-2-deoxy-α-
D
-glucopyranose
ChEBI
α-
D
-GlcNAc
ChEBI
α-GlcNAc
ChEBI
N
-acetyl-α-
D
-glucosamine
UniProt
WURCS=2.0/1,1,0/[a2122h-1a_1-5_2*NCC/3=O]/1/
GlyTouCan
Manual Xrefs
Databases
C20328
KEGG COMPOUND
CPD-12541
MetaCyc
G68544GH
GlyGen
G68544GH
GlyTouCan
NDG
PDBeChem
View more database links
Registry Numbers
Types
Sources
10036-64-3
CAS Registry Number
KEGG COMPOUND
10036-64-3
CAS Registry Number
ChemIDplus
1429039
Reaxys Registry Number
Reaxys
Citations
Types
Sources
11673851
PubMed citation
Europe PMC
18412409
PubMed citation
Europe PMC
6013453
PubMed citation
Europe PMC
Last Modified
07 April 2021