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Record Information
Version1.0
Creation Date2016-07-13 19:42:22 UTC
Update Date2016-09-23 18:44:41 UTC
LmdbLMDB00100
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Acetyl-D-glucosamine
DescriptionN-Acetyl-D-glucosamine, also known as glcnac or N-acetylchitosamine, 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. O-N-Acetyl-D-glucosamine regulates cellular responses to hormones such as insulin, initiates a protective response to stress, modulates a cell's capacity to grow and divide, and regulates gene transcription. N-Acetyl-D-glucosamine is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-D-glucosamine exists in all living organisms, ranging from bacteria to humans. In humans, it exists in skin, cartilage and blood vessel as a component of hyaluronic acid, and bone tissue, cornea and aorta as a component of keratan sulfate. Within humans, N-acetyl-D-glucosamine participates in a number of enzymatic reactions. In particular, N-acetyl-D-glucosamine can be biosynthesized from chitobiose through the action of the enzyme Beta-hexosaminidase subunit alpha. In addition, N-acetyl-D-glucosamine can be biosynthesized from chitin through the action of the enzyme chitotriosidase-1. O-N-Acetyl-D-glucosamine modified proteins are involved in sensing the nutrient status of the surrounding cellular environment and adjusting the activity of cellular proteins accordingly. In humans, N-acetyl-D-glucosamine is involved in the metabolic disorder called the salla disease/infantile sialic acid storage disease pathway. Outside of the human body, N-Acetyl-D-glucosamine is found, on average, in the highest concentration within milk (cow). N-Acetyl-D-glucosamine has also been detected, but not quantified in, peachs. This could make N-acetyl-D-glucosamine a potential biomarker for the consumption of these foods. Chemically it is an amide between glucosamine and acetic acid. N-Acetyl-D-Glucosamine (N-acetlyglucosamine) is a monosaccharide derivative of glucose. A single N-acetlyglucosamine moiety linked to serine or threonine residues on nuclear and cytoplasmic proteins -O-GlcNAc, is an ubiquitous post-translational protein modification.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC8H15NO6
Average Molecular Weight221.2078
Monoisotopic Molecular Weight221.089937217
IUPAC NameN-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional NameGlcNAc
CAS Registry Number7512-17-6
SMILES
CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
InChI Identifier
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
InChI KeyOVRNDRQMDRJTHS-RTRLPJTCSA-N
Chemical Taxonomy
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
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ktb-1931000000-1c4cb4ec9b01c3571b7dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ktb-0931000000-943fefe13d3449a92db7Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f9j-1930000000-388fd70c48f209a58653Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-1fd16b8e8608db3ef657Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-ceed8b621b338130ce76Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-8a3ade37d256b2bd4585Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ktb-1931000000-1c4cb4ec9b01c3571b7dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ktb-0931000000-943fefe13d3449a92db7Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f9j-1930000000-388fd70c48f209a58653Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-1fd16b8e8608db3ef657Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-ceed8b621b338130ce76Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-8a3ade37d256b2bd4585Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-6920000000-c07df80c6fb758af9cd2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0007-3332900000-ee533266929b5b95ee4dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-9800000000-d2628c9d8baf55923bf5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0pb9-9500000000-76ab0b7c683cc252741dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0pb9-9400000000-5b6f61c6f220e75c6736Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0pb9-9500000000-17fd92d5a45dc38915afSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-ccb575a1c77c8addd5feSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0pb9-9500000000-bf8c7a4f84891bcf3eb2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-9000000000-f38ecd220da0924d093cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-9400000000-eaa89be4aad99c7a4503Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-3900000000-819a6ad0f73785d9287cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-1910000000-723db02c59f390b489a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0537-9000000000-735f54db3223e736c337Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-003e-9600000000-197c8bc76e52b96b9871Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1490000000-40dfe33adabe6ad7a7a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0il0-2940000000-880c7b1fb58ed63f0ee2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9400000000-e1f07558d7921e9f24e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05g0-8920000000-d504941e0508d1593f33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9820000000-753556be259b7e745ba7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-bad102d081eb3bbc006bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9500000000-2c2b09cb6bfb29039085Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abc-9540000000-a1f7d557237a521d306aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-18eabe9e3d3657888360Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0390000000-3820a7eec5a8c72f49d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h90-9740000000-db880363194a3979c637Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-9200000000-cdcf015aa799dc7d6d8bSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB0000215
FooDB IDFDB008032
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID34006
BioCyc IDNot Available
METLIN ID3356
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID388319
ChEBI ID506227
PubChem Compound ID439174
Kegg Compound IDC00140
YMDB IDNot Available
ECMDB IDECMDB21561
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Slawson C, Housley MP, Hart GW: O-GlcNAc cycling: how a single sugar post-translational modification is changing the way we think about signaling networks. J Cell Biochem. 2006 Jan 1;97(1):71-83. [16237703 ]