You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:38 UTC
HMDB IDHMDB0000814
Secondary Accession Numbers
  • HMDB00814
Metabolite Identification
Common NameN-Acetylglucosamine 6-sulfate
DescriptionN-acetylglucosamine 6-sulfate is a physiological intermediate during the degradation of keratan sulfate and it is usually hydrolyzed intralysosomally by N-acetylglucosamine-6-sulfate sulfatase. (PMID 3161730 ).
Structure
Data?1582752158
Synonyms
ValueSource
(6S)GlcNAcbChEBI
(6S)GlcNAcbetaChEBI
4[6OSO3]glcnacbetaChEBI
6-O-SulfO-N-acetyl-beta-D-glucosamineChEBI
beta-D-GlcNAc6SChEBI
beta-D-GlcpNAc6SChEBI
N-Acetyl-D-glucosamine 6-sulfateChEBI
N-Acetylglucosamine 6-sulfic acidChEBI
6-O-SulfO-N-acetyl-b-D-glucosamineGenerator
6-O-SulfO-N-acetyl-β-D-glucosamineGenerator
6-O-SulphO-N-acetyl-b-D-glucosamineGenerator
6-O-SulphO-N-acetyl-beta-D-glucosamineGenerator
6-O-SulphO-N-acetyl-β-D-glucosamineGenerator
b-D-GlcNAc6SGenerator
Β-D-glcnac6SGenerator
b-D-GlcpNAc6SGenerator
Β-D-glcpnac6SGenerator
N-Acetyl-D-glucosamine 6-sulfuric acidGenerator
N-Acetyl-D-glucosamine 6-sulphateGenerator
N-Acetyl-D-glucosamine 6-sulphuric acidGenerator
N-Acetylglucosamine 6-sulfuric acidGenerator
N-Acetylglucosamine 6-sulphateGenerator
N-Acetylglucosamine 6-sulphuric acidGenerator
Aga-6-SHMDB
N-Acetyl-glucosamine 6-(hydrogen sulfate)HMDB
N-Acetyl-glucosamine 6-(hydrogen sulphate)HMDB
N-Acetylglucosamine-6-sulfateHMDB
GlcNAc-6-O-sulfateHMDB
N-Acetyl-b-D-glucosamine 6-sulfateHMDB
N-Acetyl-b-D-glucosamine 6-sulfuric acidHMDB
N-Acetyl-b-D-glucosamine 6-sulphateHMDB
N-Acetyl-b-D-glucosamine 6-sulphuric acidHMDB
N-Acetyl-beta-D-glucosamine 6-sulfuric acidHMDB
N-Acetyl-beta-D-glucosamine 6-sulphateHMDB
N-Acetyl-beta-D-glucosamine 6-sulphuric acidHMDB
N-Acetyl-β-D-glucosamine 6-sulfateHMDB
N-Acetyl-β-D-glucosamine 6-sulfuric acidHMDB
N-Acetyl-β-D-glucosamine 6-sulphateHMDB
N-Acetyl-β-D-glucosamine 6-sulphuric acidHMDB
N-Acetylglucosamine 6-sulfateChEBI
Chemical FormulaC8H15NO9S
Average Molecular Weight301.271
Monoisotopic Molecular Weight301.046751773
IUPAC Name{[(2R,3S,4R,5R,6R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}sulfonic acid
Traditional Name[(2R,3S,4R,5R,6R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxysulfonic acid
CAS Registry Number10356-99-7
SMILES
CC(=O)N[C@H]1[C@H](O)O[C@H](COS(O)(=O)=O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C8H15NO9S/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H,14,15,16)/t4-,5-,6-,7-,8-/m1/s1
InChI KeyWJFVEEAIYIOATH-FMDGEEDCSA-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 sulfate
  • Monosaccharide
  • Oxane
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Acetamide
  • 1,2-diol
  • Carboxamide group
  • Hemiacetal
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility44.5 g/LALOGPS
logP-2ALOGPS
logP-5ChemAxon
logS-0.83ALOGPS
pKa (Strongest Acidic)-2.1ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area162.62 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.02 m³·mol⁻¹ChemAxon
Polarizability26.71 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-4950000000-13940ac5e468432398b7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0uk9-9642360000-0556f57524c6e051ccceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-0195000000-af51c028ca94369e7900Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-2490000000-08e64b3e000c397dda1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-5900000000-3f03e4ada13ce3606f78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxr-1931000000-1fbdf0a6dbb5c47e4effSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc1-9650000000-3e144b064fa9aab04903Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-fc434687f458b9ffe5c0Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified8031.0 umol/mmol creatinineAdult (>18 years old)BothMucopolysaccharidosis type IIID details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022261
KNApSAcK IDNot Available
Chemspider ID389219
KEGG Compound IDC04132
BioCyc IDCPD-13665
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5778
PubChem Compound440235
PDB IDNot Available
ChEBI ID28132
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceSaito, Tomoo; Noguchi, Junzo; Komatsu, Kiroku. The esterification of carbohydrates in concentrated sul-furic acid. III. The synthesis of 2-amino-2-deoxy-D-glucose O-sulfate, 2-acetamido-2-deoxy-D-glucose-6-sulfate and its calcium and barium salts. Nippon Kagaku Zasshi (1961), 82 472-4.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Freeman C, Hopwood JJ: Sanfilippo D syndrome: estimation of N-acetylglucosamine-6-sulfatase activity with a radiolabeled monosulfated disaccharide substrate. Anal Biochem. 1989 Feb 1;176(2):244-8. [PubMed:2500866 ]
  2. Chambers WH, Oeltmann TN: The effects of hexose 6-O-sulfate esters on human natural killer cell lytic function. J Immunol. 1986 Sep 1;137(5):1469-74. [PubMed:3462244 ]
  3. Hopwood JJ, Elliott H: N-acetylglucosamine 6-sulfate residues in keratan sulfate and heparan sulfate are desulfated by the same enzyme. Biochem Int. 1983 Feb;6(2):141-8. [PubMed:6236815 ]
  4. Fuchs W, Beck M, Kresse H: Intralysosomal formation and metabolic fate of N-acetylglucosamine 6-sulfate from keratan sulfate. Eur J Biochem. 1985 Sep 16;151(3):551-6. [PubMed:3161730 ]
  5. Basner R, Kresse H, von Figura K: N-Acetylglucosamine-6-sulfate sulfatase from human urine. J Biol Chem. 1979 Feb 25;254(4):1151-8. [PubMed:762121 ]
  6. Spiro RG, Bhoyroo VD: Occurrence of sulfate in the asparagine-linked complex carbohydrate units of thyroglobulin. Identification and localization of galactose 3-sulfate and N-acetylglucosamine 6-sulfate residues in the human and calf proteins. J Biol Chem. 1988 Oct 5;263(28):14351-8. [PubMed:3170547 ]
  7. Slomiany BL, Murty VL, Piotrowski J, Grabska M, Slomiany A: Glycosulfatase activity of H. pylori toward human gastric mucin: effect of sucralfate. Am J Gastroenterol. 1992 Sep;87(9):1132-7. [PubMed:1381553 ]
  8. Hopwood JJ, Elliott H: Isolation and characterization of N-acetylglucosamine 6-sulfate from the urine of a patient with Sanfilippo type D syndrome and its occurrence in normal urine. Biochem Int. 1983 Jun;6(6):831-6. [PubMed:6435628 ]