Showing metabocard for N-Acetylglucosamine 6-sulfate (BMDB0000814)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:36:59 UTC
Update Date2020-04-22 15:05:27 UTC
BMDB IDBMDB0000814
Secondary Accession Numbers
  • BMDB00814
Metabolite Identification
Common NameN-Acetylglucosamine 6-sulfate
DescriptionN-Acetylglucosamine 6-sulfate, also known as (6S)glcnacb or beta-D-glcnac6S, 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. Based on a literature review a significant number of articles have been published on N-Acetylglucosamine 6-sulfate.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-4950000000-13940ac5e468432398b7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0uk9-9642360000-0556f57524c6e051ccceView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9000000000-817a28ce988569235755View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01vo-9340000000-504c36bfe143b4a7f463View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0229-9100000000-264590e50946f7a0d359View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-0195000000-af51c028ca94369e7900View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-2490000000-08e64b3e000c397dda1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-5900000000-3f03e4ada13ce3606f78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxr-1931000000-1fbdf0a6dbb5c47e4effView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc1-9650000000-3e144b064fa9aab04903View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-fc434687f458b9ffe5c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0059000000-051383097e9025ca37c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3941000000-a84f1b793e2c4952e0a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-9300000000-0de82fc7fb25dbc826ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1779000000-9a99656e709794566a74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9352000000-d2641968250788de1913View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9100000000-6969d41c96331cb033e6View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000814
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
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 ReferencesNot Available