N-acetyl-alpha-D-glucosamine

Identification

Name
N-acetyl-alpha-D-glucosamine
Accession Number
DB03740  (EXPT02319)
Type
Small Molecule
Groups
Experimental
Description

The N-acetyl derivative of glucosamine.

Structure
Thumb
Synonyms
  • 2-(acetylamino)-2-deoxy-A-D-glucopyranose
  • 2-(acetylamino)-2-deoxy-α-D-glucopyranose
  • N-acetyl-α-D-glucosamine
  • α-D-GlcNAc
  • α-GlcNAc
Categories
Not Available
UNII
T13TI5GH3D
CAS number
10036-64-3
Weight
Average: 221.2078
Monoisotopic: 221.089937217
Chemical Formula
C8H15NO6
InChI Key
OVRNDRQMDRJTHS-PVFLNQBWSA-N
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
IUPAC Name
N-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAngiotensin-converting enzymeNot AvailableHuman
UAcetylcholinesteraseNot AvailableHuman
UGlucosylceramidaseNot AvailableHuman
UProbable polysaccharide deacetylase PdaANot AvailableBacillus subtilis (strain 168)
USialic acid-binding Ig-like lectin 7Not AvailableHuman
UHemagglutinin-neuraminidaseNot AvailableNDV
UFucose-binding lectin PA-IILNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
UEnvelope glycoprotein gp160Not AvailableSIV-mac
UIg gamma-1 chain C regionNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
Not Available
External Links
ChemSpider
74284
ChEBI
44278
HET
NDG
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
1a14 / 1abr / 1aiv / 1atn / 1auk / 1ax2 / 1b41 / 1bcs / 1bqh / 1bqs
show 483 more
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility82.5 mg/mLALOGPS
logP-2.3ALOGPS
logP-2.4ChemAxon
logS-0.43ALOGPS
pKa (Strongest Acidic)7.38ChemAxon
pKa (Strongest Basic)1.46ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area122.74 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.55 m3·mol-1ChemAxon
Polarizability20.54 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
N-acyl-alpha-hexosamines
Alternative Parents
Hexoses / Oxanes / Secondary alcohols / Hemiacetals / Propargyl-type 1,3-dipolar organic compounds / Polyols / Oxacyclic compounds / Carboximidic acids / Primary alcohols / Organopnictogen compounds
show 2 more
Substituents
N-acyl-alpha-hexosamine / Hexose monosaccharide / Monosaccharide / Oxane / Hemiacetal / Secondary alcohol / Carboximidic acid / Carboximidic acid derivative / Oxacycle / Organoheterocyclic compound
show 10 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
N-acetyl-D-glucosamine (CHEBI:44278)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent...
Gene Name
ACE
Uniprot ID
P12821
Uniprot Name
Angiotensin-converting enzyme
Molecular Weight
149713.675 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serine hydrolase activity
Specific Function
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name
ACHE
Uniprot ID
P22303
Uniprot Name
Acetylcholinesterase
Molecular Weight
67795.525 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Receptor binding
Specific Function
Not Available
Gene Name
GBA
Uniprot ID
P04062
Uniprot Name
Glucosylceramidase
Molecular Weight
59715.745 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the deacetylation of N-acetylmuramic acid (MurNAc) residues in glycan strands of peptidoglycan, leading to the formation of muramic delta-lactam residues in spore cortex, after transpepti...
Gene Name
pdaA
Uniprot ID
O34928
Uniprot Name
Peptidoglycan-N-acetylmuramic acid deacetylase PdaA
Molecular Weight
30069.06 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Receptor activity
Specific Function
Putative adhesion molecule that mediates sialic-acid dependent binding to cells. Preferentially binds to alpha-2,3- and alpha-2,6-linked sialic acid. Also binds disialogangliosides (disialogalactos...
Gene Name
SIGLEC7
Uniprot ID
Q9Y286
Uniprot Name
Sialic acid-binding Ig-like lectin 7
Molecular Weight
51142.33 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
NDV
Pharmacological action
Unknown
General Function
Exo-alpha-(2->8)-sialidase activity
Specific Function
Attaches the virus to sialic acid-containing cell receptors and thereby initiating infection. Binding of HN protein to the receptor induces a conformational change that allows the F protein to trig...
Gene Name
HN
Uniprot ID
P32884
Uniprot Name
Hemagglutinin-neuraminidase
Molecular Weight
63141.66 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
lecB
Uniprot ID
Q9HYN5
Uniprot Name
Fucose-binding lectin PA-IIL
Molecular Weight
11862.99 Da
Kind
Protein
Organism
SIV-mac
Pharmacological action
Unknown
General Function
The surface protein gp120 (SU) attaches the virus to the host lymphoid cell by binding to the primary receptor CD4. This interaction induces a structural rearrangement creating a high affinity binding site for a chemokine coreceptor like CCR5. This peculiar 2 stage receptor-interaction strategy allows gp120 to maintain the highly conserved coreceptor-binding site in a cryptic conformation, protected from neutralizing antibodies. These changes are transmitted to the transmembrane protein gp41 and are thought to activate its fusogenic potential by unmasking its fusion peptide (By similarity).
Specific Function
Structural molecule activity
Gene Name
env
Uniprot ID
P05884
Uniprot Name
Envelope glycoprotein gp160
Molecular Weight
Not Available
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Immunoglobulin receptor binding
Specific Function
Not Available
Gene Name
IGHG1
Uniprot ID
P01857
Uniprot Name
Ig gamma-1 chain C region
Molecular Weight
36105.695 Da

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 05:26