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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H15NO6
Molecular Weight 221.2078
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of N-ACETYL-.ALPHA.-D-GLUCOSAMINE

SMILES

CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O

InChI

InChIKey=OVRNDRQMDRJTHS-PVFLNQBWSA-N
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

HIDE SMILES / InChI

Molecular Formula C8H15NO6
Molecular Weight 221.2078
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23430107 | https://www.ncbi.nlm.nih.gov/pubmed/19006331 | https://www.ncbi.nlm.nih.gov/pubmed/7305946 | https://www.ncbi.nlm.nih.gov/pubmed/7759502

N-Acetyl-α-D-glucosamine (alpha-GlcNAc) is a major component of complex carbohydrates, that has been found in N- and O-glycans and glycolipids. Glycosaminoglycans and the glycosylphosphatidylinositol anchor of membrane-bound glycoproteins also contain GlcNAc moieties. GlcNAc is derived from the degradation of glycoconjugates by glycosidases and from nutritional sources. GlcNAc is converted into GlcNAc-6-phosphate by the N-acetylglucosamine kinase. GlcNAc-6-phosphate can enter a catabolic pathway that ultimately leads to the formation of fructose-6-phosphate, or it can enter an anabolic pathway leading to the formation of UDP-GlcNAc.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9UJ70
Gene ID: 55577.0
Gene Symbol: NAGK
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Addition of α-O-GlcNAc to threonine residues define the post-translational modification of mucin-like molecules in Trypanosoma cruzi.
2013-10
Patents

Patents

Sample Use Guides

During the 12- weeks treatment phase of the study, the daily dose of 100mg*3 (3 tablets) will be taken 30 minutes after breakfast, lunch and supper.
Route of Administration: Oral
The effect of N-acetylglucosamine (NAG) on in vitro synthesis of glycosaminoglycans by human peritoneal mesothelial cells and fibroblasts was studied. In contrast to isosmotic concentrations of glucose, NAG increases the synthesis of hyaluronan by mesothelial cells and fibroblasts in a dose-dependent manner. Glucose inhibits synthesis of sulphated glycosaminoglycans by peritoneal mesothelial cells and fibroblasts, whereas NAG stimulates their production. It was demonstrated that NAG was an effective stimulator of the in vitro glycosaminoglycans synthesis by human peritoneal mesothelial cells and fibroblasts.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:27:09 GMT 2025
Edited
by admin
on Mon Mar 31 18:27:09 GMT 2025
Record UNII
T13TI5GH3D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
.ALPHA.-D-GLUCOPYRANOSE, 2-(ACETYLAMINO)-2-DEOXY-
Preferred Name English
N-ACETYL-.ALPHA.-D-GLUCOSAMINE
Common Name English
GLUCOPYRANOSE, 2-ACETAMIDO-2-DEOXY-, .ALPHA.-D
Systematic Name English
2-ACETAMIDO-2-DEOXY-.ALPHA.-D-GLUCOPYRANOSE
Systematic Name English
2-DEOXY-2-ACETAMIDO-.ALPHA.-D-GLUCOPYRANOSE
Systematic Name English
2-ACETAMIDO-2-DEOXY-.ALPHA.-D-GLUCOSE
Systematic Name English
Code System Code Type Description
PUBCHEM
82313
Created by admin on Mon Mar 31 18:27:09 GMT 2025 , Edited by admin on Mon Mar 31 18:27:09 GMT 2025
PRIMARY
RXCUI
2280292
Created by admin on Mon Mar 31 18:27:09 GMT 2025 , Edited by admin on Mon Mar 31 18:27:09 GMT 2025
PRIMARY
DAILYMED
T13TI5GH3D
Created by admin on Mon Mar 31 18:27:09 GMT 2025 , Edited by admin on Mon Mar 31 18:27:09 GMT 2025
PRIMARY
DRUG BANK
DB03740
Created by admin on Mon Mar 31 18:27:09 GMT 2025 , Edited by admin on Mon Mar 31 18:27:09 GMT 2025
PRIMARY
FDA UNII
T13TI5GH3D
Created by admin on Mon Mar 31 18:27:09 GMT 2025 , Edited by admin on Mon Mar 31 18:27:09 GMT 2025
PRIMARY
NCI_THESAURUS
C77375
Created by admin on Mon Mar 31 18:27:09 GMT 2025 , Edited by admin on Mon Mar 31 18:27:09 GMT 2025
PRIMARY
ECHA (EC/EINECS)
233-115-1
Created by admin on Mon Mar 31 18:27:09 GMT 2025 , Edited by admin on Mon Mar 31 18:27:09 GMT 2025
PRIMARY
EPA CompTox
DTXSID20905442
Created by admin on Mon Mar 31 18:27:09 GMT 2025 , Edited by admin on Mon Mar 31 18:27:09 GMT 2025
PRIMARY
CAS
10036-64-3
Created by admin on Mon Mar 31 18:27:09 GMT 2025 , Edited by admin on Mon Mar 31 18:27:09 GMT 2025
PRIMARY