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ChEBI
> Main
CHEBI:506227 -
N
-acetyl-
D
-glucosamine
Main
ChEBI Ontology
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ChEBI Name
N
-acetyl-
D
-glucosamine
ChEBI ID
CHEBI:506227
ChEBI ASCII Name
N-acetyl-D-glucosamine
Definition
The
D
isomer of
N
-acetylglucosamine.
Stars
This entity has been manually annotated by the ChEBI Team.
Supplier Information
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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-RTRLPJTCSA-N
SMILES
CC(=O)N[C@H]1C(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.
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-
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
α-
D
-Gal
p
NAc-(1→3)-
D
-Glc
p
NAc (
CHEBI:148388
)
has functional parent
N
-acetyl-
D
-glucosamine (
CHEBI:506227
)
α-
D
-Glc
p
-(1→4)-
D
-Glc
p
NAc (
CHEBI:152766
)
has functional parent
N
-acetyl-
D
-glucosamine (
CHEBI:506227
)
α-
D
-Glc
p
-(1→6)-
D
-Glc
p
NAc (
CHEBI:151906
)
has functional parent
N
-acetyl-
D
-glucosamine (
CHEBI:506227
)
α-
D
-Glc
p
NAc-(1→4)-
D
-Glc
p
NAc (
CHEBI:154293
)
has functional parent
N
-acetyl-
D
-glucosamine (
CHEBI:506227
)
α-
D
-Man
p
-(1→6)-
D
-Glc
p
NAc (
CHEBI:152042
)
has functional parent
N
-acetyl-
D
-glucosamine (
CHEBI:506227
)
α-
L
-Fuc
p
-(1→4)-
D
-Glc
p
NAc (
CHEBI:151318
)
has functional parent
N
-acetyl-
D
-glucosamine (
CHEBI:506227
)
β-
D
-Gal
f
-(1→4)-
D
-Glc
p
NAc (
CHEBI:148184
)
has functional parent
N
-acetyl-
D
-glucosamine (
CHEBI:506227
)
β-
D
-Gal
p
3S-(1→4)-
D
-Glc
p
NAc (
CHEBI:147626
)
has functional parent
N
-acetyl-
D
-glucosamine (
CHEBI:506227
)
β-
D
-Gal
p
NAc4S-(1→4)-
D
-GlcNAc (
CHEBI:147909
)
has functional parent
N
-acetyl-
D
-glucosamine (
CHEBI:506227
)
β-
D
-Glc
p
-(1→3)-
D
-Glc
p
NAc (
CHEBI:152894
)
has functional parent
N
-acetyl-
D
-glucosamine (
CHEBI:506227
)
β-
D
-Glc
p
-(1→6)-
D
-Glc
p
NAc (
CHEBI:146757
)
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
)
N
-acetyl-1-seleno-β-
D
-glucosamine(1−) (
CHEBI:195547
)
has functional parent
N
-acetyl-
D
-glucosamine (
CHEBI:506227
)
N
-acetyl-
D
-glucosamine 4-sulfate (
CHEBI:28406
)
has functional parent
N
-acetyl-
D
-glucosamine (
CHEBI:506227
)
D
-Gal
p
-(1→4)-
D
-Glc
p
NAc (
CHEBI:147906
)
has functional parent
N
-acetyl-
D
-glucosamine (
CHEBI:506227
)
α-
D
-Man
p
-(1→3)-
D
-Glc
p
NAc (
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
Sources
2-Acetamido-2-deoxy-D-glucose
DrugBank
2-Acetamido-2-deoxy-D-glucose
KEGG COMPOUND
GlcNAc
DrugBank
GlcNAc
KEGG COMPOUND
N-Acetyl-D-glucosamine
KEGG COMPOUND
N
-acetyl-
D
-glucosamine
UniProt
N-Acetylchitosamine
DrugBank
N-Acetylchitosamine
KEGG COMPOUND
WURCS=2.0/1,1,0/[a2122h-1x_1-5_2*NCC/3=O]/1/
GlyTouCan
Manual Xrefs
Databases
C00140
KEGG COMPOUND
DB00141
DrugBank
G64581RP
GlyGen
G64581RP
GlyTouCan
NAG
PDBeChem
View more database links
Registry Numbers
Types
Sources
1913592
Beilstein Registry Number
Beilstein
7512-17-6
CAS Registry Number
KEGG COMPOUND
Citations
Types
Sources
11549596
PubMed citation
Europe PMC
11787731
PubMed citation
Europe PMC
11950472
PubMed citation
Europe PMC
1366057
PubMed citation
Europe PMC
14608143
PubMed citation
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16237703
PubMed citation
Europe PMC
19212411
PubMed citation
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2026685
PubMed citation
Europe PMC
21487204
PubMed citation
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22308371
PubMed citation
Europe PMC
22411374
PubMed citation
Europe PMC
2619923
PubMed citation
Europe PMC
3757018
PubMed citation
Europe PMC
405259
PubMed citation
Europe PMC
6174502
PubMed citation
Europe PMC
6226355
PubMed citation
Europe PMC
7583460
PubMed citation
Europe PMC
7688662
PubMed citation
Europe PMC
8056619
PubMed citation
Europe PMC
Last Modified
20 April 2021