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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
2-Acetamido-2-deoxy-D-glucose
aldehydo-N-acetyl-D-glucosamine
D-GlcNAc
N-Acetyl-D-glucosamine
N-Acetylchitosamine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AflexaNot Available
GS-500Not Available
Maxi GSNot Available
Natures Blend GlucosamineNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIV956696549
CAS number7512-17-6
WeightAverage: 221.2078
Monoisotopic: 221.089937217
Chemical FormulaC8H15NO6
InChI KeyInChIKey=MBLBDJOUHNCFQT-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)[[email protected]](NC(C)=O)[C@@H](O)[[email protected]](O)[[email protected]](O)CO
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 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.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct ParentAmino sugars
Alternative Parents
Substituents
  • Mannosamine
  • Beta-hydroxy aldehyde
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Carboxamide group
  • 1,2-diol
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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).
Related Articles
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
Sialuria or French Type SialuriaDiseaseSMP00217
Amino Sugar MetabolismMetabolicSMP00045
Tay-Sachs DiseaseDiseaseSMP00390
Sialuria or French Type SialuriaDiseaseSMP00216
G(M2)-Gangliosidosis: Variant B, Tay-sachs diseaseDiseaseSMP00534
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7511
Blood Brain Barrier+0.7394
Caco-2 permeable-0.8423
P-glycoprotein substrateNon-substrate0.7321
P-glycoprotein inhibitor INon-inhibitor0.8669
P-glycoprotein inhibitor IINon-inhibitor0.8873
Renal organic cation transporterNon-inhibitor0.971
CYP450 2C9 substrateNon-substrate0.7733
CYP450 2D6 substrateNon-substrate0.8286
CYP450 3A4 substrateNon-substrate0.6654
CYP450 1A2 substrateNon-inhibitor0.9215
CYP450 2C9 inhibitorNon-inhibitor0.9064
CYP450 2D6 inhibitorNon-inhibitor0.9409
CYP450 2C19 inhibitorNon-inhibitor0.944
CYP450 3A4 inhibitorNon-inhibitor0.9473
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9766
Ames testNon AMES toxic0.7108
CarcinogenicityNon-carcinogens0.9044
BiodegradationReady biodegradable0.9048
Rat acute toxicity1.5975 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.995
hERG inhibition (predictor II)Non-inhibitor0.9616
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Acetyl-d-glucosamine powder3.75USD g
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 Solubility148.0 mg/mLALOGPS
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 Area127.09 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity48.45 m3·mol-1ChemAxon
Polarizability20.49 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-0pvi-1931000000-fa145dffe949e1d8fc54View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-0lmr-2972000000-0672da151d0105b7b011View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-1000-2941000000-6e4ded528b518089efcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (73.5 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
activator
General Function:
Alpha-n-acetylglucosaminidase activity
Specific Function:
Involved in the degradation of heparan sulfate.
Gene Name:
NAGLU
Uniprot ID:
P54802
Molecular Weight:
82264.92 Da
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:15112051 ]
  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):890-5. [PubMed:16349528 ]
  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:15932346 ]
  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:17414423 ]
  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:17576230 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
N-acylglucosamine 2-epimerase activity
Specific Function:
Catalyzes the interconversion of N-acetylglucosamine to N-acetylmannosamine. Binds to renin forming a protein complex called high molecular weight (HMW) renin and inhibits renin activity. Involved in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway: although human is not able to catalyze formation of Neu5Gc due to the inactive CMAHP enzyme, Neu5Gc is present in food and must be degraded.
Gene Name:
RENBP
Uniprot ID:
P51606
Molecular Weight:
48830.6 Da
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:17292397 ]
  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:17349707 ]
  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:16011304 ]
  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:17565386 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Udp-galactosyltransferase activity
Specific Function:
The Golgi complex form catalyzes the production of lactose in the lactating mammary gland and could also be responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.The cell surface form functions as a recognition molecule during a variety of cell to cell and cell to matrix interactions, as those occurring ...
Gene Name:
B4GALT1
Uniprot ID:
P15291
Molecular Weight:
43919.895 Da
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:15736931 ]
  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:16157350 ]
  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:17370997 ]
  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:17203585 ]
  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:15449940 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
N-acetyllactosamine synthase activity
Specific Function:
Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.
Gene Name:
B4GALT3
Uniprot ID:
O60512
Molecular Weight:
43927.63 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:
N-acetyllactosamine synthase activity
Specific Function:
Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.
Gene Name:
B4GALT4
Uniprot ID:
O60513
Molecular Weight:
40040.865 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. 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:11948877 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
N-acetyllactosamine synthase activity
Specific Function:
Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids. Can produce lactose.
Gene Name:
B4GALT2
Uniprot ID:
O60909
Molecular Weight:
41971.815 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:
N-acylmannosamine kinase activity
Specific Function:
Converts endogenous N-acetylglucosamine (GlcNAc), a major component of complex carbohydrates, from lysosomal degradation or nutritional sources into GlcNAc 6-phosphate. Involved in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway: although human is not able to catalyze formation of Neu5Gc due to the inactive CMAHP enzyme, Neu5Gc is present in food and must be degraded. Also has ManNAc...
Gene Name:
NAGK
Uniprot ID:
Q9UJ70
Molecular Weight:
37375.305 Da
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:17010375 ]
  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:15489439 ]
  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:16674097 ]
  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:16857666 ]
  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:17229727 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
N-acetylglucosamine-1-phosphodiester alpha-n-acetylglucosaminidase activity
Specific Function:
Catalyzes the second step in the formation of the mannose 6-phosphate targeting signal on lysosomal enzyme oligosaccharides by removing GlcNAc residues from GlcNAc-alpha-P-mannose moieties, which are formed in the first step. Also hydrolyzes UDP-GlcNAc, a sugar donor for Golgi N-acetylglucosaminyltransferases.
Gene Name:
NAGPA
Uniprot ID:
Q9UK23
Molecular Weight:
56072.49 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. 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:8294420 ]
  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 Nov 6;46(44):12604-17. Epub 2007 Oct 10. [PubMed:17927214 ]
  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:9722550 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23