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Showing Compound N-Acetylglucosamine (FDB008032)

Record Information
Version1.0
Creation date2010-04-08 22:07:53 UTC
Update date2019-11-26 03:01:56 UTC
Primary IDFDB008032
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-Acetylglucosamine
DescriptionMonomer of Chitinand is also in the exopolysaccharide from blue-green alga Cyanospira capsulata (CCD) N-Acetylglucosamine (N-acetyl-D-glucosamine, or GlcNAc, or NAG) is a monosaccharide derivative of glucose. It is part of a biopolymer in the bacterial cell wall, built from alternating units of GlcNAc and N-acetylmuramic acid (MurNAc), cross-linked with oligopeptides at the lactic acid residue of MurNAc. GlcNAc is the monomeric unit of the polymer chitin, which forms the outer coverings of insects and crustaceans. N-Acetylglucosamine is found in peach.
CAS Number7512-17-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-Acetamido-2-deoxy-D-glucoseChEBI
GlcNAcChEBI
N-AcetylchitosamineChEBI
2-(Acetylamino)-2-deoxyhexoseHMDB
2-Acetamido-2-deoxy-D-glucopyranoseHMDB
2-Acetamido-2-deoxyglucoseHMDB
2-Acetamido-D-glucoseHMDB
2-Acetylamino-2-deoxy-D-glucoseHMDB
AcetylglucosamineHMDB
N-AcetylglucosamineHMDB
N-[(3R,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamideHMDB
2 Acetamido 2 deoxyglucoseHMDB
N Acetyl D glucosamineHMDB
2 Acetamido 2 deoxy D glucoseHMDB
2-(Acetylamino)-2-deoxyglucose, 9CImanual
2-(acetylamino)-2-DeoxyhexoseHMDB
2-acetamido-2-Deoxy-D-glucopyranoseHMDB
2-acetamido-2-Deoxy-D-glucoseChEBI
2-acetamido-2-DeoxyglucoseHMDB
2-acetamido-D-GlucoseHMDB
2-acetylamino-2-Deoxy-D-glucoseHMDB
N-Acetyl-D-glucosaminemanual
Predicted Properties
PropertyValueSource
Water Solubility254 g/LALOGPS
logP-2.6ALOGPS
logP-3.2ChemAxon
logS0.06ALOGPS
pKa (Strongest Acidic)11.6ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area119.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability20.56 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H15NO6
IUPAC nameN-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
InChI IdentifierInChI=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
InChI KeyOVRNDRQMDRJTHS-RTRLPJTCSA-N
Isomeric SMILESCC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
Average Molecular Weight221.2078
Monoisotopic Molecular Weight221.089937217
Classification
Description Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Hexose monosaccharide
  • Monosaccharide
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 43.44%; H 6.83%; N 6.33%; O 43.40%CCD
Melting PointMp 205°CCD
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a] 18D +64CCD
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSN-Acetylglucosamine, non-derivatized, GC-MS Spectrumsplash10-0ktb-1931000000-1c4cb4ec9b01c3571b7dSpectrum
GC-MSN-Acetylglucosamine, non-derivatized, GC-MS Spectrumsplash10-0ktb-0931000000-943fefe13d3449a92db7Spectrum
GC-MSN-Acetylglucosamine, non-derivatized, GC-MS Spectrumsplash10-0f9j-1930000000-388fd70c48f209a58653Spectrum
GC-MSN-Acetylglucosamine, non-derivatized, GC-MS Spectrumsplash10-00di-9620000000-1fd16b8e8608db3ef657Spectrum
GC-MSN-Acetylglucosamine, non-derivatized, GC-MS Spectrumsplash10-00di-9620000000-ceed8b621b338130ce76Spectrum
GC-MSN-Acetylglucosamine, non-derivatized, GC-MS Spectrumsplash10-00di-9620000000-8a3ade37d256b2bd4585Spectrum
GC-MSN-Acetylglucosamine, non-derivatized, GC-MS Spectrumsplash10-0ktb-1931000000-1c4cb4ec9b01c3571b7dSpectrum
GC-MSN-Acetylglucosamine, non-derivatized, GC-MS Spectrumsplash10-0ktb-0931000000-943fefe13d3449a92db7Spectrum
GC-MSN-Acetylglucosamine, non-derivatized, GC-MS Spectrumsplash10-0f9j-1930000000-388fd70c48f209a58653Spectrum
GC-MSN-Acetylglucosamine, non-derivatized, GC-MS Spectrumsplash10-00di-9620000000-1fd16b8e8608db3ef657Spectrum
GC-MSN-Acetylglucosamine, non-derivatized, GC-MS Spectrumsplash10-00di-9620000000-ceed8b621b338130ce76Spectrum
GC-MSN-Acetylglucosamine, non-derivatized, GC-MS Spectrumsplash10-00di-9620000000-8a3ade37d256b2bd4585Spectrum
Predicted GC-MSN-Acetylglucosamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ue9-6920000000-c07df80c6fb758af9cd2Spectrum
Predicted GC-MSN-Acetylglucosamine, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0007-3332900000-ee533266929b5b95ee4dSpectrum
Predicted GC-MSN-Acetylglucosamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetylglucosamine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetylglucosamine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetylglucosamine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetylglucosamine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetylglucosamine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetylglucosamine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetylglucosamine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetylglucosamine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetylglucosamine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetylglucosamine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-9800000000-d2628c9d8baf55923bf52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0pb9-9500000000-76ab0b7c683cc252741d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0pb9-9400000000-5b6f61c6f220e75c67362021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0pb9-9500000000-17fd92d5a45dc38915af2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-ccb575a1c77c8addd5fe2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0pb9-9500000000-bf8c7a4f84891bcf3eb22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-9000000000-f38ecd220da0924d093c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-9400000000-eaa89be4aad99c7a45032021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-3900000000-819a6ad0f73785d9287c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-1910000000-723db02c59f390b489a72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0537-9000000000-735f54db3223e736c3372021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-003e-9600000000-197c8bc76e52b96b98712021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1490000000-40dfe33adabe6ad7a7a82015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0il0-2940000000-880c7b1fb58ed63f0ee22015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9400000000-e1f07558d7921e9f24e12015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05g0-8920000000-d504941e0508d1593f332015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9820000000-753556be259b7e745ba72015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-bad102d081eb3bbc006b2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9500000000-2c2b09cb6bfb290390852021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abc-9540000000-a1f7d557237a521d306a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-18eabe9e3d36578883602021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0390000000-3820a7eec5a8c72f49d92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h90-9740000000-db880363194a3979c6372021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-9200000000-cdcf015aa799dc7d6d8b2021-09-24View Spectrum
NMRNot Available
ChemSpider ID388319
ChEMBL IDCHEMBL240524
KEGG Compound IDC00140
Pubchem Compound ID439174
Pubchem Substance IDNot Available
ChEBI ID506227
Phenol-Explorer IDNot Available
DrugBank IDDB00141
HMDB IDHMDB00215
CRC / DFC (Dictionary of Food Compounds) IDBXT68-E:BXT68-E
EAFUS IDNot Available
Dr. Duke IDN-ACETYL-GLUCOSAMINE
BIGG ID34006
KNApSAcK IDNot Available
HET IDNGZ
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDN-Acetylglucosamine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Lysozyme CLYZP61626
Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinaseGNEQ9Y223
N-acylglucosamine 2-epimeraseRENBPP51606
Beta-hexosaminidase subunit betaHEXBP07686
Beta-hexosaminidase subunit alphaHEXAP06865
N-acetyl-D-glucosamine kinaseNAGKQ9UJ70
Acidic mammalian chitinaseCHIAQ9BZP6
N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidaseNAGPAQ9UK23
Chitotriosidase-1CHIT1Q13231
Alpha-N-acetylglucosaminidaseNAGLUP54802
Lysozyme-like protein 1LYZL1Q6UWQ5
Lysozyme-like protein 2LYZL2Q7Z4W2
Sperm acrosome-associated protein 5SPACA5Q96QH8
Lysozyme-like protein 6LYZL6O75951
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045 map00520
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).