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Identification
NameN-Acetyl-D-glucosamine
Accession NumberDB00141  (NUTR00040)
Typesmall molecule
Groupsapproved, nutraceutical
Description

The N-acetyl derivative of glucosamine. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
2-Acetamido-2-deoxy-D-glucoseNot AvailableNot Available
aldehydo-N-acetyl-D-glucosamineNot AvailableNot Available
D-GlcNAcNot AvailableNot Available
N-AcetylchitosamineNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
AflexaNot Available
GS-500Not Available
Maxi GSNot Available
Natures Blend GlucosamineNot Available
Brand mixturesNot Available
Categories
CAS number7512-17-6
WeightAverage: 221.2078
Monoisotopic: 221.089937217
Chemical FormulaC8H15NO6
InChI KeyMBLBDJOUHNCFQT-LXGUWJNJSA-N
InChI
InChI=1S/C8H15NO6/c1-4(12)9-5(2-10)7(14)8(15)6(13)3-11/h2,5-8,11,13-15H,3H2,1H3,(H,9,12)/t5-,6+,7+,8+/m0/s1
IUPAC Name
N-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide
SMILES
[H]C(=O)[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@H](O)CO
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassAmino Sugars
Direct parentAmino Sugars
Alternative parentsHexoses; Secondary Carboxylic Acid Amides; 1,2-Diols; Secondary Alcohols; Enolates; Polyamines; Primary Alcohols; Carboxylic Acids; Aldehydes
Substituentsmonosaccharide; polyol; carboxamide group; secondary alcohol; secondary carboxylic acid amide; 1,2-diol; carboxylic acid derivative; polyamine; carboxylic acid; enolate; primary alcohol; organonitrogen compound; amine; alcohol; aldehyde
Classification descriptionThis compound belongs to the amino sugars. These are sugars having one alcoholic hydroxy group replaced by an amino group; systematically known as x-amino-x-deoxymonosaccharides. These compounds do not include Glycosylamines.
Pharmacology
IndicationFor the treatment and prevention of osteoarthritis, by itself or in combination with chondroitin sulfate.
PharmacodynamicsNot Available
Mechanism of actionThe mechanism of action in relieving arthritic pain and in repair of cartilage is a matter of speculation. Biochemically, glucosamine is involved in glycoprotein metabolism. Glycoproteins, known as proteoglycans, form the ground substance in the extra-cellular matrix of connective tissue. Proteoglycans are polyanionic substances of high-molecular weight and contain many different types of heteropolysaccharide side-chains covalently linked to a polypeptide-chain backbone. These polysaccharides make up to 95% of the proteoglycan structure. In fact, chemically, proteoglycans resemble polysaccharides more than they do proteins. The polysaccharide groups in proteoglycans are called glycosaminoglycans (GAGs). GAGs include hyaluronic acid, chondroitin sulfate, dermatan sulfate, keratan sulfate, heparin and heparan sulfate. All of the GAGs contain derivatives of glucosamine or galactosamine. Glucosamine derivatives are found in hyaluronic acid, keratan sulfate and heparan sulfate. Chondroitin sulfate contains derivatives of galactosamine. The glucosamine-containing glycosaminoglycan hyaluronic acid is vital for the function of articular cartilage. GAG chains are fundamental components of aggrecan found in articular cartilage. Aggrecan confers upon articular cartilage shock-absorbing properties. It does this by providing cartilage with a swelling pressure that is restrained by the tensile forces of collagen fibers. This balance confers upon articular cartilage the deformable resilience vital to its function. In the early stages of degenerative joint disease, aggrecan biosynthesis is increased. However, in later stages, aggrecan synthesis is decreased, leading eventually to the loss of cartilage resiliency and to most of the symptoms that accompany osteoarthritis. During the progression of osteoarthritis, exogenous glucosamine may have a beneficial role. It is known that, in vitro, chondrocytes do synthesize more aggregan when the culture medium is supplemented with glucosamine. N-acetylglucosamine is found to be less effective in these in vitro studies. Glucosamine has also been found to have antioxidant activity and to be beneficial in animal models of experimental arthritis. The counter anion of the glucosamine salt (i.e. chloride or sulfate) is unlikely to play any role in the action or pharmacokinetics of glucosamine. Further, the sulfate in glucosamine sulfate supplements should not be confused with the glucosamine sulfate found in such GAGs as keratan sulfate and heparan sulfate. In the case of the supplement, sulfate is the anion of the salt. In the case of the above GAGs, sulfate is present as an ester. Also, there is no glucosamine sulfate in chondroitin sulfate (source: PDRhealth).
AbsorptionApproximately 90% of orally administered glucosamine (salt form) gets absorbed from the small intestine.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

A significant fraction of ingested glucosamine is catabolized by first-pass metabolism in the liver.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityMouse, intravenous LD50 is 4170 mg/kg. Side effects that have been reported are mainly mild gastrointestinal complaints such as heartburn, epigastric distress and diarrhea. No allergic reactions have been reported including sulfa-allergic reactions to glucosamine sulfate.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Salla Disease/Infantile Sialic Acid Storage DiseaseDiseaseSMP00240
Amino Sugar MetabolismMetabolicSMP00045
G(M2)-Gangliosidosis: Variant B, Tay-sachs diseaseDiseaseSMP00534
Tay-Sachs DiseaseDiseaseSMP00390
Sialuria or French Type SialuriaDiseaseSMP00216
Sjogren Larsson SyndromeDiseaseSMP00217
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.7511
Blood Brain Barrier + 0.7394
Caco-2 permeable - 0.8423
P-glycoprotein substrate Non-substrate 0.7321
P-glycoprotein inhibitor I Non-inhibitor 0.8669
P-glycoprotein inhibitor II Non-inhibitor 0.8873
Renal organic cation transporter Non-inhibitor 0.971
CYP450 2C9 substrate Non-substrate 0.7733
CYP450 2D6 substrate Non-substrate 0.8286
CYP450 3A4 substrate Non-substrate 0.6654
CYP450 1A2 substrate Non-inhibitor 0.9215
CYP450 2C9 substrate Non-inhibitor 0.9064
CYP450 2D6 substrate Non-inhibitor 0.9409
CYP450 2C19 substrate Non-inhibitor 0.944
CYP450 3A4 substrate Non-inhibitor 0.9473
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9766
Ames test Non AMES toxic 0.7108
Carcinogenicity Non-carcinogens 0.9044
Biodegradation Ready biodegradable 0.9048
Rat acute toxicity 1.5975 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.995
hERG inhibition (predictor II) Non-inhibitor 0.9616
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Acetyl-d-glucosamine powder3.75USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point205 °CNot Available
logP-2.1Not Available
Predicted Properties
PropertyValueSource
water solubility1.48e+02 g/lALOGPS
logP-2.1ALOGPS
logP-3.9ChemAxon
logS-0.18ALOGPS
pKa (strongest acidic)11.56ChemAxon
pKa (strongest basic)-1.2ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count6ChemAxon
hydrogen donor count5ChemAxon
polar surface area127.09ChemAxon
rotatable bond count6ChemAxon
refractivity48.45ChemAxon
polarizability20.49ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MS
References
Synthesis Reference

Naoko Yamano, Shizu Fujishima, Ryutarou Tanaka, “N-acetyl-D-glucosamine deacetylase and a process for preparing the same.” U.S. Patent USH00014532, issued October, 1993.

USH00014532
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC00140
BindingDB50223349
ChEBI17411
ChEMBLCHEMBL447878
Therapeutic Targets DatabaseDAP000872
PharmGKBPA164752287
HETNAG
PDRhealthhttp://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/glu_0122.shtml
ATC CodesM01AX05
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(73.5 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Beta-1,4-galactosyltransferase 3

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Beta-1,4-galactosyltransferase 3 O60512 Details

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
  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

2. Beta-1,4-galactosyltransferase 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Beta-1,4-galactosyltransferase 4 O60513 Details

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
  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
  3. Bulter T, Schumacher T, Namdjou DJ, Gutierrez Gallego R, Clausen H, Elling L: Chemoenzymatic synthesis of biotinylated nucleotide sugars as substrates for glycosyltransferases. Chembiochem. 2001 Dec 3;2(12):884-94. Pubmed

3. Beta-1,4-galactosyltransferase 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Beta-1,4-galactosyltransferase 2 O60909 Details

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
  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

4. N-acetyl-D-glucosamine kinase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
N-acetyl-D-glucosamine kinase Q9UJ70 Details

References:

  1. Weihofen WA, Berger M, Chen H, Saenger W, Hinderlich S: Structures of human N-Acetylglucosamine kinase in two complexes with N-Acetylglucosamine and with ADP/glucose: insights into substrate specificity and regulation. J Mol Biol. 2006 Dec 1;364(3):388-99. Epub 2006 Sep 3. Pubmed
  2. Uehara T, Park JT: The N-acetyl-D-glucosamine kinase of Escherichia coli and its role in murein recycling. J Bacteriol. 2004 Nov;186(21):7273-9. Pubmed
  3. An HJ, Kim DS, Park YK, Kim SK, Choi YP, Kang S, Ding B, Cho NH: Comparative proteomics of ovarian epithelial tumors. J Proteome Res. 2006 May;5(5):1082-90. Pubmed
  4. Yang C, Rodionov DA, Li X, Laikova ON, Gelfand MS, Zagnitko OP, Romine MF, Obraztsova AY, Nealson KH, Osterman AL: Comparative genomics and experimental characterization of N-acetylglucosamine utilization pathway of Shewanella oneidensis. J Biol Chem. 2006 Oct 6;281(40):29872-85. Epub 2006 Jul 20. Pubmed
  5. Nishimasu H, Fushinobu S, Shoun H, Wakagi T: Crystal structures of an ATP-dependent hexokinase with broad substrate specificity from the hyperthermophilic archaeon Sulfolobus tokodaii. J Biol Chem. 2007 Mar 30;282(13):9923-31. Epub 2007 Jan 17. Pubmed

5. N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase Q9UK23 Details

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
  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
  3. Mullis KG, Huynh M, Kornfeld RH: Purification and kinetic parameters of bovine liver N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase. J Biol Chem. 1994 Jan 21;269(3):1718-26. Pubmed
  4. Chavez CA, Bohnsack RN, Kudo M, Gotschall RR, Canfield WM, Dahms NM: Domain 5 of the Cation-Independent Mannose 6-Phosphate Receptor Preferentially Binds Phosphodiesters (Mannose 6-Phosphate N-Acetylglucosamine Ester). Biochemistry. 2007 Oct 10;. Pubmed
  5. Kornfeld R, Bao M, Brewer K, Noll C, Canfield WM: Purification and multimeric structure of bovine N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase. J Biol Chem. 1998 Sep 4;273(36):23203-10. Pubmed

6. Alpha-N-acetylglucosaminidase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: activator

Components

Name UniProt ID Details
Alpha-N-acetylglucosaminidase P54802 Details

References:

  1. Spiro RG: Role of N-linked polymannose oligosaccharides in targeting glycoproteins for endoplasmic reticulum-associated degradation. Cell Mol Life Sci. 2004 May;61(9):1025-41. Pubmed
  2. Nogawa M, Takahashi H, Kashiwagi A, Ohshima K, Okada H, Morikawa Y: Purification and Characterization of Exo-beta-d-Glucosaminidase from a Cellulolytic Fungus, Trichoderma reesei PC-3-7. Appl Environ Microbiol. 1998 Mar;64(3):890-895. Pubmed
  3. Vishu Kumar AB, Varadaraj MC, Gowda LR, Tharanathan RN: Characterization of chito-oligosaccharides prepared by chitosanolysis with the aid of papain and Pronase, and their bactericidal action against Bacillus cereus and Escherichia coli. Biochem J. 2005 Oct 15;391(Pt 2):167-75. Pubmed
  4. Zou L, Yang S, Hu S, Chaudry IH, Marchase RB, Chatham JC: The protective effects of PUGNAc on cardiac function after trauma-hemorrhage are mediated via increased protein O-GlcNAc levels. Shock. 2007 Apr;27(4):402-8. Pubmed
  5. Shirazi F, Kulkarni M, Deshpande MV: A rapid and sensitive method for screening of chitinase inhibitors using Ostazin Brilliant Red labelled chitin as a substrate for chitinase assay. Lett Appl Microbiol. 2007 Jun;44(6):660-5. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

7. N-acylglucosamine 2-epimerase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
N-acylglucosamine 2-epimerase P51606 Details

References:

  1. Lee YC, Wu HM, Chang YN, Wang WC, Hsu WH: The central cavity from the (alpha/alpha)6 barrel structure of Anabaena sp. CH1 N-acetyl-D-glucosamine 2-epimerase contains two key histidine residues for reversible conversion. J Mol Biol. 2007 Mar 30;367(3):895-908. Epub 2006 Nov 6. Pubmed
  2. Lee YC, Chien HC, Hsu WH: Production of N-acetyl-D-neuraminic acid by recombinant whole cells expressing Anabaena sp. CH1 N-acetyl-D-glucosamine 2-epimerase and Escherichia coli N-acetyl-D-neuraminic acid lyase. J Biotechnol. 2007 May 1;129(3):453-60. Epub 2007 Feb 9. Pubmed
  3. Takahashi S, Ogasawara H, Hiwatashi K, Hata K, Hori K, Koizumi Y, Sugiyama T: Amino acid residues conferring the nucleotide binding properties of N-acetyl-D-glucosamine 2-epimerase (renin binding protein). Biomed Res. 2005 Jun;26(3):117-21. Pubmed
  4. Ferrero MA, Martinez-Blanco H, Lopez-Velasco FF, Ezquerro-Saenz C, Navasa N, Lozano S, Rodriguez-Aparicio LB: Purification and characterization of GlcNAc-6-P 2-epimerase from Escherichia coli K92. Acta Biochim Pol. 2007;54(2):387-99. Epub 2007 Jun 14. Pubmed

8. Beta-1,4-galactosyltransferase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Beta-1,4-galactosyltransferase 1 P15291 Details

References:

  1. Ramakrishnan B, Boeggeman E, Qasba PK: Mutation of arginine 228 to lysine enhances the glucosyltransferase activity of bovine beta-1,4-galactosyltransferase I. Biochemistry. 2005 Mar 8;44(9):3202-10. Pubmed
  2. Ramasamy V, Ramakrishnan B, Boeggeman E, Ratner DM, Seeberger PH, Qasba PK: Oligosaccharide preferences of beta1,4-galactosyltransferase-I: crystal structures of Met340His mutant of human beta1,4-galactosyltransferase-I with a pentasaccharide and trisaccharides of the N-glycan moiety. J Mol Biol. 2005 Oct 14;353(1):53-67. Pubmed
  3. Boeggeman E, Ramakrishnan B, Kilgore C, Khidekel N, Hsieh-Wilson LC, Simpson JT, Qasba PK: Direct identification of nonreducing GlcNAc residues on N-glycans of glycoproteins using a novel chemoenzymatic method. Bioconjug Chem. 2007 May-Jun;18(3):806-14. Epub 2007 Mar 20. Pubmed
  4. Hidalgo A, Burgos V, Viola H, Medina J, Argibay P: Differential expression of glycans in the hippocampus of rats trained on an inhibitory learning paradigm. Neuropathology. 2006 Dec;26(6):501-7. Pubmed
  5. Ramakrishnan B, Boeggeman E, Qasba PK: Effect of the Met344His mutation on the conformational dynamics of bovine beta-1,4-galactosyltransferase: crystal structure of the Met344His mutant in complex with chitobiose. Biochemistry. 2004 Oct 5;43(39):12513-22. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 24, 2013 11:37