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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:48:59 UTC
HMDB IDHMDB0000215
Secondary Accession Numbers
  • HMDB0000533
  • HMDB0014288
  • HMDB00215
  • HMDB00533
  • HMDB14288
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
Data?1582752116
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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point210 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility167 mg/mLNot Available
LogP-2.1Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Astarita_neg142.730932474
[M+H]+MetCCS_test_pos147.2930932474
[M-H]-Not Available153.7http://allccs.zhulab.cn/database/detail?ID=AllCCS00002012
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+151.01631661259
DarkChem[M-H]-145.31931661259
AllCCS[M+H]+150.00732859911
AllCCS[M-H]-146.24432859911
DeepCCS[M+H]+149.28430932474
DeepCCS[M-H]-146.88830932474
DeepCCS[M-2H]-181.18630932474
DeepCCS[M+Na]+155.96430932474
AllCCS[M+H]+150.032859911
AllCCS[M+H-H2O]+146.332859911
AllCCS[M+NH4]+153.532859911
AllCCS[M+Na]+154.532859911
AllCCS[M-H]-146.232859911
AllCCS[M+Na-2H]-146.832859911
AllCCS[M+HCOO]-147.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Acetyl-D-glucosamineCC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O3681.1Standard polar33892256
N-Acetyl-D-glucosamineCC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O2002.4Standard non polar33892256
N-Acetyl-D-glucosamineCC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O2115.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetyl-D-glucosamine,1TMS,isomer #1CC(=O)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O1917.8Semi standard non polar33892256
N-Acetyl-D-glucosamine,1TMS,isomer #2CC(=O)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O1928.6Semi standard non polar33892256
N-Acetyl-D-glucosamine,1TMS,isomer #3CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O1918.6Semi standard non polar33892256
N-Acetyl-D-glucosamine,1TMS,isomer #4CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C1920.9Semi standard non polar33892256
N-Acetyl-D-glucosamine,1TMS,isomer #5CC(=O)N([C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C1860.6Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TMS,isomer #1CC(=O)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O1940.3Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TMS,isomer #10CC(=O)N([C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C1912.2Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TMS,isomer #2CC(=O)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O1941.2Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TMS,isomer #3CC(=O)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C1939.2Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TMS,isomer #4CC(=O)N([C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C1932.8Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TMS,isomer #5CC(=O)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O1963.6Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TMS,isomer #6CC(=O)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C1968.2Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TMS,isomer #7CC(=O)N([C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C1935.2Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TMS,isomer #8CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C1959.5Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TMS,isomer #9CC(=O)N([C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C1914.9Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TMS,isomer #1CC(=O)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O2002.1Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TMS,isomer #10CC(=O)N([C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C1974.7Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TMS,isomer #2CC(=O)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C2016.3Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TMS,isomer #3CC(=O)N([C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C1972.4Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TMS,isomer #4CC(=O)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2010.6Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TMS,isomer #5CC(=O)N([C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C1983.3Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TMS,isomer #6CC(=O)N([C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C1997.5Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TMS,isomer #7CC(=O)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2026.9Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TMS,isomer #8CC(=O)N([C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C1980.4Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TMS,isomer #9CC(=O)N([C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C1975.4Semi standard non polar33892256
N-Acetyl-D-glucosamine,4TMS,isomer #1CC(=O)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2037.2Semi standard non polar33892256
N-Acetyl-D-glucosamine,4TMS,isomer #2CC(=O)N([C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C2042.1Semi standard non polar33892256
N-Acetyl-D-glucosamine,4TMS,isomer #3CC(=O)N([C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C2048.3Semi standard non polar33892256
N-Acetyl-D-glucosamine,4TMS,isomer #4CC(=O)N([C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C2047.9Semi standard non polar33892256
N-Acetyl-D-glucosamine,4TMS,isomer #5CC(=O)N([C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C2040.3Semi standard non polar33892256
N-Acetyl-D-glucosamine,5TMS,isomer #1CC(=O)N([C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C2091.8Semi standard non polar33892256
N-Acetyl-D-glucosamine,5TMS,isomer #1CC(=O)N([C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C2155.6Standard non polar33892256
N-Acetyl-D-glucosamine,5TMS,isomer #1CC(=O)N([C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C2099.0Standard polar33892256
N-Acetyl-D-glucosamine,1TBDMS,isomer #1CC(=O)N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O2175.9Semi standard non polar33892256
N-Acetyl-D-glucosamine,1TBDMS,isomer #2CC(=O)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O2176.2Semi standard non polar33892256
N-Acetyl-D-glucosamine,1TBDMS,isomer #3CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2179.1Semi standard non polar33892256
N-Acetyl-D-glucosamine,1TBDMS,isomer #4CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2182.6Semi standard non polar33892256
N-Acetyl-D-glucosamine,1TBDMS,isomer #5CC(=O)N([C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C2137.2Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #1CC(=O)N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O2419.4Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #10CC(=O)N([C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2386.0Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #2CC(=O)N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2438.0Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #3CC(=O)N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2432.6Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #4CC(=O)N([C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C2396.2Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #5CC(=O)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2435.0Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #6CC(=O)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2452.0Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #7CC(=O)N([C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C2414.8Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #8CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2433.0Semi standard non polar33892256
N-Acetyl-D-glucosamine,2TBDMS,isomer #9CC(=O)N([C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C2398.4Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #1CC(=O)N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2686.1Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #10CC(=O)N([C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2631.3Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #2CC(=O)N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2672.0Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #3CC(=O)N([C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C2631.3Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #4CC(=O)N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2662.6Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #5CC(=O)N([C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C2643.3Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #6CC(=O)N([C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2634.5Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #7CC(=O)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2695.3Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #8CC(=O)N([C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C2657.1Semi standard non polar33892256
N-Acetyl-D-glucosamine,3TBDMS,isomer #9CC(=O)N([C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2648.6Semi standard non polar33892256
N-Acetyl-D-glucosamine,4TBDMS,isomer #1CC(=O)N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2889.4Semi standard non polar33892256
N-Acetyl-D-glucosamine,4TBDMS,isomer #2CC(=O)N([C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C2867.7Semi standard non polar33892256
N-Acetyl-D-glucosamine,4TBDMS,isomer #3CC(=O)N([C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2860.1Semi standard non polar33892256
N-Acetyl-D-glucosamine,4TBDMS,isomer #4CC(=O)N([C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2853.3Semi standard non polar33892256
N-Acetyl-D-glucosamine,4TBDMS,isomer #5CC(=O)N([C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2865.7Semi standard non polar33892256
N-Acetyl-D-glucosamine,5TBDMS,isomer #1CC(=O)N([C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3094.3Semi standard non polar33892256
N-Acetyl-D-glucosamine,5TBDMS,isomer #1CC(=O)N([C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3054.5Standard non polar33892256
N-Acetyl-D-glucosamine,5TBDMS,isomer #1CC(=O)N([C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2695.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)splash10-0ktb-1931000000-1c4cb4ec9b01c3571b7d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)splash10-0ktb-0931000000-943fefe13d3449a92db72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)splash10-0f9j-1930000000-388fd70c48f209a586532017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-1fd16b8e8608db3ef6572017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-ceed8b621b338130ce762017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-8a3ade37d256b2bd45852017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)splash10-0ktb-1931000000-1c4cb4ec9b01c3571b7d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)splash10-0ktb-0931000000-943fefe13d3449a92db72018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)splash10-0f9j-1930000000-388fd70c48f209a586532018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-1fd16b8e8608db3ef6572018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-ceed8b621b338130ce762018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetyl-D-glucosamine GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-8a3ade37d256b2bd45852018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-6920000000-c07df80c6fb758af9cd22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (4 TMS) - 70eV, Positivesplash10-0007-3332900000-ee533266929b5b95ee4d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-D-glucosamine GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-D-glucosamine 10V, Negative-QTOFsplash10-0pb9-9800000000-d2628c9d8baf55923bf52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-D-glucosamine 35V, Negative-QTOFsplash10-0pb9-9500000000-76ab0b7c683cc252741d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-D-glucosamine 35V, Negative-QTOFsplash10-0pb9-9400000000-5b6f61c6f220e75c67362021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-D-glucosamine 35V, Negative-QTOFsplash10-0pb9-9500000000-17fd92d5a45dc38915af2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-D-glucosamine 40V, Negative-QTOFsplash10-0a4i-9300000000-ccb575a1c77c8addd5fe2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-D-glucosamine 35V, Negative-QTOFsplash10-0pb9-9500000000-bf8c7a4f84891bcf3eb22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-D-glucosamine 35V, Negative-QTOFsplash10-0a4i-9000000000-f38ecd220da0924d093c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-D-glucosamine 20V, Negative-QTOFsplash10-0ab9-9400000000-eaa89be4aad99c7a45032021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-D-glucosamine 35V, Positive-QTOFsplash10-000i-3900000000-819a6ad0f73785d9287c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-D-glucosamine 10V, Positive-QTOFsplash10-000i-1910000000-723db02c59f390b489a72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-D-glucosamine 40V, Positive-QTOFsplash10-0537-9000000000-735f54db3223e736c3372021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetyl-D-glucosamine 20V, Positive-QTOFsplash10-003e-9600000000-197c8bc76e52b96b98712021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 10V, Positive-QTOFsplash10-00di-1490000000-40dfe33adabe6ad7a7a82015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 20V, Positive-QTOFsplash10-0il0-2940000000-880c7b1fb58ed63f0ee22015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 40V, Positive-QTOFsplash10-01ox-9400000000-e1f07558d7921e9f24e12015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 10V, Negative-QTOFsplash10-05g0-8920000000-d504941e0508d1593f332015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 20V, Negative-QTOFsplash10-0pb9-9820000000-753556be259b7e745ba72015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 40V, Negative-QTOFsplash10-0a4i-9100000000-bad102d081eb3bbc006b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 10V, Negative-QTOFsplash10-0a4i-9500000000-2c2b09cb6bfb290390852021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 20V, Negative-QTOFsplash10-0abc-9540000000-a1f7d557237a521d306a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 40V, Negative-QTOFsplash10-0a4i-9000000000-18eabe9e3d36578883602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 10V, Positive-QTOFsplash10-0udi-0390000000-3820a7eec5a8c72f49d92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 20V, Positive-QTOFsplash10-0h90-9740000000-db880363194a3979c6372021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-D-glucosamine 40V, Positive-QTOFsplash10-0229-9200000000-cdcf015aa799dc7d6d8b2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
  • Lysosome
Biospecimen Locations
  • Blood
  • Breast Milk
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Intestine
  • Neuron
  • Placenta
  • Platelet
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
Breast MilkDetected and Quantified204.3278984 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified2.23 +/- 1.83 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified2.40 +/- 2.35 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified21.4 +/- 18.6 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified3.14 +/- 2.38 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified3.78 +/- 3.93 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified4.41 +/- 5.98 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
UrineDetected and Quantified2.96 +/- 1.85 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specifiedasymptomatic diverticulosis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specifiedsymptomatic uncomplicated diverticular disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Diverticular disease
  1. Tursi A, Mastromarino P, Capobianco D, Elisei W, Miccheli A, Capuani G, Tomassini A, Campagna G, Picchio M, Giorgetti G, Fabiocchi F, Brandimarte G: Assessment of Fecal Microbiota and Fecal Metabolome in Symptomatic Uncomplicated Diverticular Disease of the Colon. J Clin Gastroenterol. 2016 Oct;50 Suppl 1:S9-S12. doi: 10.1097/MCG.0000000000000626. [PubMed:27622378 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008032
KNApSAcK IDNot Available
Chemspider ID388319
KEGG Compound IDC00140
BioCyc IDNot Available
BiGG ID34006
Wikipedia LinkNot Available
METLIN ID3356
PubChem Compound439174
PDB IDNot Available
ChEBI ID506227
Food Biomarker OntologyNot Available
VMH IDACGAM
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceZhang, He; Qi, Shanlong; Yang, Shenggui. Production of N-acetyl-D-glucosamine from chitin. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 6pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Nakagawa F, Schulte BA, Spicer SS: Lectin cytochemical evaluation of somatosensory neurons and their peripheral and central processes in rat and man. Cell Tissue Res. 1986;245(3):579-89. [PubMed:3757018 ]
  3. Hatcher VB, Schwarzmann GO, Jeanloz RW, McArthur JW: Changes in the sialic acid concentration in the major cervical glycoprotein from the bonnet monkey (Macaca radiata) during a hormonally induced cycle. Fertil Steril. 1977 Jun;28(6):682-8. [PubMed:405259 ]
  4. Percheron F: [Beta-D-mannosidase]. Bull Acad Natl Med. 1995 May;179(5):881-91; discussion 892. [PubMed:7583460 ]
  5. Collard CD, Montalto MC, Reenstra WR, Buras JA, Stahl GL: Endothelial oxidative stress activates the lectin complement pathway: role of cytokeratin 1. Am J Pathol. 2001 Sep;159(3):1045-54. [PubMed:11549596 ]
  6. Mollicone R, Candelier JJ, Mennesson B, Couillin P, Venot AP, Oriol R: Five specificity patterns of (1----3)-alpha-L-fucosyltransferase activity defined by use of synthetic oligosaccharide acceptors. Differential expression of the enzymes during human embryonic development and in adult tissues. Carbohydr Res. 1992 Apr 10;228(1):265-76. [PubMed:1366057 ]
  7. Kottgen E, Hell B, Muller C, Kainer F, Tauber R: Developmental changes in the glycosylation and binding properties of human fibronectins. Characterization of the glycan structures and ligand binding of human fibronectins from adult plasma, cord blood and amniotic fluid. Biol Chem Hoppe Seyler. 1989 Dec;370(12):1285-94. [PubMed:2619923 ]
  8. Madrid JF, Castells MT, Martinez-Menarguez JA, Aviles M, Hernandez F, Ballesta J: Subcellular characterization of glycoproteins in the principal cells of human gallbladder. A lectin cytochemical study. Histochemistry. 1994 Mar;101(3):195-204. [PubMed:8056619 ]
  9. Weiner B, Fischer T, Waxman S: Hemostasis in the era of the chronic anticoagulated patient. J Invasive Cardiol. 2003 Nov;15(11):669-73; quiz 674. [PubMed:14608143 ]
  10. Yates AD, Watkins WM: Enzymes involved in the biosynthesis of glycoconjugates. A UDP-2-acetamido-2-deoxy-D-glucose: beta-D-galactopyranosyl-(1 leads to 4)-saccharide (1 leads to 3)-2-acetamido-2-deoxy-beta-D- glucopyranosyltransferase in human serum. Carbohydr Res. 1983 Aug 16;120:251-68. [PubMed:6226355 ]
  11. 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. [PubMed:16237703 ]
  12. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 23 proteins in total.

Enzymes

General function:
Involved in ATP binding
Specific function:
Regulates and initiates biosynthesis of N-acetylneuraminic acid (NeuAc), a precursor of sialic acids. Plays an essential role in early development (By similarity). Required for normal sialylation in hematopoietic cells. Sialylation is implicated in cell adhesion, signal transduction, tumorigenicity and metastatic behavior of malignant cells.
Gene Name:
GNE
Uniprot ID:
Q9Y223
Molecular weight:
83065.25
General function:
Involved in catalytic 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
Reactions
N-Acetyl-D-glucosamine → N-Acetylmannosaminedetails
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 ]
General function:
Involved in transferase activity, transferring glycosyl groups
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
Reactions
Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosaminedetails
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 ]
General function:
Involved in transferase activity, transferring glycosyl groups
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 during development and egg fertilization, by binding to specific oligosaccharide ligands on opposing cells or in the extracellular matrix.
Gene Name:
B4GALT1
Uniprot ID:
P15291
Molecular weight:
43919.895
Reactions
Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosaminedetails
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 ]
General function:
Involved in beta-N-acetylhexosaminidase activity
Specific function:
Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues.
Gene Name:
HEXB
Uniprot ID:
P07686
Molecular weight:
Not Available
General function:
Involved in beta-N-acetylhexosaminidase activity
Specific function:
Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues. The form B is active against certain oligosaccharides. The form S has no measurable activity.
Gene Name:
HEXA
Uniprot ID:
P06865
Molecular weight:
Not Available
General function:
Carbohydrate transport and metabolism
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 kinase activity.
Gene Name:
NAGK
Uniprot ID:
Q9UJ70
Molecular weight:
42037.295
Reactions
Adenosine triphosphate + N-Acetyl-D-glucosamine → ADP + N-Acetyl-D-Glucosamine 6-Phosphatedetails
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 ]
General function:
Involved in chitin binding
Specific function:
Degrades chitin and chitotriose. May participate in the defense against nematodes, fungi and other pathogens. Plays a role in T-helper cell type 2 (Th2) immune response. Contributes to the response to IL-13 and inflammation in response to IL-13. Stimulates chemokine production by pulmonary epithelial cells. Protects lung epithelial cells against apoptosis and promotes phosphorylation of AKT1. Its function in the inflammatory response and in protecting cells against apoptosis is inhibited by allosamidin, suggesting that the function of this protein depends on carbohydrate binding.
Gene Name:
CHIA
Uniprot ID:
Q9BZP6
Molecular weight:
Not Available
Reactions
Chitin + Water → N-Acetyl-D-glucosamine + Chitindetails
General function:
Involved in N-acetylglucosamine-1-phosphodiester alpha-
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.
Gene Name:
NAGPA
Uniprot ID:
Q9UK23
Molecular weight:
56072.49
Reactions
Glycoprotein N-acetyl-D-glucosaminyl-phospho-D-mannose + Water → N-Acetyl-D-glucosamine + glycoprotein phospho-D-mannosedetails
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 ]
General function:
Involved in chitin binding
Specific function:
Degrades chitin, chitotriose and chitobiose. May participate in the defense against nematodes and other pathogens. Isoform 3 has no enzymatic activity.
Gene Name:
CHIT1
Uniprot ID:
Q13231
Molecular weight:
Not Available
Reactions
Chitin + Water → N-Acetyl-D-glucosamine + Chitindetails

Only showing the first 10 proteins. There are 23 proteins in total.