NAV

N-acetyl-alpha-D-glucosamine

Identification

Generic Name
N-acetyl-alpha-D-glucosamine
DrugBank Accession Number
DB03740
Background

The N-acetyl derivative of glucosamine.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 221.2078
Monoisotopic: 221.089937217
Chemical Formula
C8H15NO6
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
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAngiotensin-converting enzymeNot AvailableHumans
UAcetylcholinesteraseNot AvailableHumans
UGlucosylceramidaseNot AvailableHumans
UProbable polysaccharide deacetylase PdaANot AvailableBacillus subtilis (strain 168)
USialic acid-binding Ig-like lectin 7Not AvailableHumans
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 AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Aliphatic heteromonocyclic compound / Carboximidic acid / Carboximidic acid derivative / Hemiacetal / Hexose monosaccharide / Hydrocarbon derivative / Monosaccharide / N-acyl-alpha-hexosamine / Organic 1,3-dipolar compound
show 10 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
N-acetyl-D-glucosamine (CHEBI:44278)
Affected organisms
Not Available

Chemical Identifiers

UNII
T13TI5GH3D
CAS number
10036-64-3
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]acetamide
SMILES
CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O

References

General References
Not Available
PubChem Compound
82313
PubChem Substance
46508699
ChemSpider
74284
RxNav
2280292
ChEBI
44278
ChEMBL
CHEMBL1234669
ZINC
ZINC000003860151
PDBe Ligand
NDG
PDB Entries
1abr / 1aiv / 1atn / 1auk / 1ax2 / 1bcs / 1bqs / 1c1z / 1ciw / 1d0m …
show 445 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
logP-3.2Chemaxon
pKa (Strongest Acidic)11.6Chemaxon
pKa (Strongest Basic)-1.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area119.25 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity47.02 m3·mol-1Chemaxon
Polarizability20.42 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-MSsplash10-0kn9-9510000000-8257171f06e4c704d6c7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udr-0790000000-5b839d51e5242ec9b21d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pe9-3920000000-be171a0ee845c0660b4e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ue9-7920000000-752f5d479bfc9d473e21
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9710000000-f92b9a8a0b80e0acd787
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01qc-9400000000-3191ffa7a97335c517b0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9100000000-c03d87fd8e0f280763ce
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-147.7544534
predicted
DarkChem Lite v0.1.0
[M-H]-154.93822
predicted
DeepCCS 1.0 (2019)
[M+H]+148.2266534
predicted
DarkChem Lite v0.1.0
[M+H]+157.00285
predicted
DeepCCS 1.0 (2019)
[M+Na]+147.1240534
predicted
DarkChem Lite v0.1.0
[M+Na]+163.29001
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Angiotensin-converting enzyme
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
Details2. Acetylcholinesterase
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
Details3. Glucosylceramidase
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
Details4. Probable polysaccharide deacetylase PdaA
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. [Article]
  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. [Article]
Details5. Sialic acid-binding Ig-like lectin 7
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
Details6. Hemagglutinin-neuraminidase
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. [Article]
  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. [Article]
Details7. Fucose-binding lectin PA-IIL
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
Details8. Envelope glycoprotein gp160
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
Details9. Ig gamma-1 chain C region
Kind
Protein
Organism
Humans
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 at June 13, 2005 13:24 / Updated at June 12, 2020 16:52