Record Information
Version1.0
Creation date2011-09-21 00:08:57 UTC
Update date2015-10-09 22:30:47 UTC
Primary IDFDB022132
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlucosamine 6-sulfate
DescriptionGlucosamine 6-sulfate is a naturally occurring compound present in many of the body's tissues, and belongs to a class of compounds known as glycosaminoglycans (GAGs). Glucosamine 6-sulfate is being used in the treatment of arthritis. Glucosamine for arthritis products is usually formulated as the hydrochloride salt or glucosamine sulfate and often combined with chondroitin sulphate. It is notable that while both the hydrochloride salt and glucosamine sulfate are used in pharmaceutical preparations, glucosamine sulfate is thought to have a higher biological activity due to the presence of the sulfate. It should also be noted that there is a large cost difference between the two salts, with the hydrochloride salt being significantly less expensive. (PMID: 15925239) [HMDB]
CAS Number91674-26-9
Structure
Thumb
Synonyms
SynonymSource
2-Amino-2-deoxy-beta-D-glucopyranose 6-sulfateChEBI
2-Amino-2-deoxy-D-glucose 6-sulfateChEBI
2-Amino-2-deoxy-D-glucose 6-sulphateChEBI
6-O-SulfO-beta-D-glucosamineChEBI
beta-D-Glucosamine 6-O-sulfateChEBI
D-Glucosamine-6-sulfateChEBI
D-Glucosamine-6-sulphateChEBI
GLCN-6SChEBI
Glucosamine 6-O-sulfateChEBI
Glucosamine 6-O-sulphateChEBI
Glucosamine 6-sulphateChEBI
2-Amino-2-deoxy-b-D-glucopyranose 6-sulfateGenerator
2-Amino-2-deoxy-b-D-glucopyranose 6-sulfuric acidGenerator
2-Amino-2-deoxy-b-D-glucopyranose 6-sulphateGenerator
2-Amino-2-deoxy-b-D-glucopyranose 6-sulphuric acidGenerator
2-Amino-2-deoxy-beta-D-glucopyranose 6-sulfuric acidGenerator
2-Amino-2-deoxy-beta-D-glucopyranose 6-sulphateGenerator
2-Amino-2-deoxy-beta-D-glucopyranose 6-sulphuric acidGenerator
2-Amino-2-deoxy-β-D-glucopyranose 6-sulfateGenerator
2-Amino-2-deoxy-β-D-glucopyranose 6-sulfuric acidGenerator
2-Amino-2-deoxy-β-D-glucopyranose 6-sulphateGenerator
2-Amino-2-deoxy-β-D-glucopyranose 6-sulphuric acidGenerator
2-Amino-2-deoxy-D-glucose 6-sulfuric acidGenerator
2-Amino-2-deoxy-D-glucose 6-sulphuric acidGenerator
6-O-SulfO-b-D-glucosamineGenerator
6-O-SulfO-β-D-glucosamineGenerator
6-O-SulphO-b-D-glucosamineGenerator
6-O-SulphO-beta-D-glucosamineGenerator
6-O-SulphO-β-D-glucosamineGenerator
b-D-Glucosamine 6-O-sulfateGenerator
b-D-Glucosamine 6-O-sulfuric acidGenerator
b-D-Glucosamine 6-O-sulphateGenerator
b-D-Glucosamine 6-O-sulphuric acidGenerator
beta-D-Glucosamine 6-O-sulfuric acidGenerator
beta-D-Glucosamine 6-O-sulphateGenerator
beta-D-Glucosamine 6-O-sulphuric acidGenerator
Β-D-glucosamine 6-O-sulfateGenerator
Β-D-glucosamine 6-O-sulfuric acidGenerator
Β-D-glucosamine 6-O-sulphateGenerator
Β-D-glucosamine 6-O-sulphuric acidGenerator
D-Glucosamine-6-sulfuric acidGenerator
D-Glucosamine-6-sulphuric acidGenerator
Glucosamine 6-O-sulfuric acidGenerator
Glucosamine 6-O-sulphuric acidGenerator
Glucosamine 6-sulfuric acidGenerator
Glucosamine 6-sulphuric acidGenerator
b-D-Glucosamine 6-sulfateHMDB
b-D-Glucosamine 6-sulfuric acidHMDB
b-D-Glucosamine 6-sulphateHMDB
b-D-Glucosamine 6-sulphuric acidHMDB
beta-D-Glucosamine 6-sulfuric acidHMDB
beta-D-Glucosamine 6-sulphateHMDB
beta-D-Glucosamine 6-sulphuric acidHMDB
Β-D-glucosamine 6-sulfateHMDB
Β-D-glucosamine 6-sulfuric acidHMDB
Β-D-glucosamine 6-sulphateHMDB
Β-D-glucosamine 6-sulphuric acidHMDB
Glucosamine 6-sulfateGenerator
2-amino-2-deoxy-D-Glucose 6-sulfatehmdb
2-amino-2-Deoxy-D-glucose 6-sulphateHMDB
Glucosamine 6-sulfic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility129 g/LALOGPS
logP-2.3ALOGPS
logP-4ChemAxon
logS-0.3ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)8.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area159.54 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.57 m³·mol⁻¹ChemAxon
Polarizability22.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H13NO8S
IUPAC name{[(2R,3S,4R,5R,6R)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}sulfonic acid
InChI IdentifierInChI=1S/C6H13NO8S/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H,11,12,13)/t2-,3-,4-,5-,6-/m1/s1
InChI KeyMTDHILKWIRSIHB-QZABAPFNSA-N
Isomeric SMILESN[C@H]1[C@H](O)O[C@H](COS(O)(=O)=O)[C@@H](O)[C@@H]1O
Average Molecular Weight259.234
Monoisotopic Molecular Weight259.036187087
Classification
Description Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Monosaccharide sulfate
  • Amino saccharide
  • Oxane
  • Sulfuric acid monoester
  • Sulfate-ester
  • Alkyl sulfate
  • Sulfuric acid ester
  • Organic sulfuric acid or derivatives
  • Hemiacetal
  • 1,2-diol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGlucosamine 6-sulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004u-9730000000-70576e4f34730bd11b36Spectrum
Predicted GC-MSGlucosamine 6-sulfate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0h2r-7986600000-5b5175e6891f55edf068Spectrum
Predicted GC-MSGlucosamine 6-sulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_3_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucosamine 6-sulfate, TMS_3_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-6970000000-009d2ce27a1136ae62992012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00lr-9400000000-8aa8e83725fd2209af682012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0gz0-3900000000-2fc5556359b0a81414a02012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-03l3-9730000000-18899d8301ceb9f277a52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-01vo-9000000000-f6d3abd918ff1f2825422021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0002-9200000000-d6e4a53d78b7aeb01f632021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0229-9200000000-dae70870d5a8ff4487d72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01ox-4690000000-39e1a100bf62422031562021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03l3-9730000000-015caba1d680f2a331f02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0230-9200000000-856d105b38cc83c2d9162021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-ee43794c6edbd6c968602021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-4490000000-cc9089e44d1b4d9eb4472021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0390000000-81e2f32b467d86796fcd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-3910000000-7eba3117f55467e8f5502021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0190000000-39f760bc9dbc41c02a702017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-7930000000-4464d045ff43e6cc091c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c0r-9400000000-33a1a2d302a56e55d1b62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-066r-2950000000-6d9cab81302970f1e2192017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03la-6940000000-c181e63cb661eaf9a55e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-01102593189e8bacc7e72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0190000000-549c6b338079dc20e0872021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9200000000-1ed446aec03069aacf4b2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01vo-9100000000-26a23911c4053ac8c9dc2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-1690000000-8ee96cfc324aa66678022021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9330000000-7b55e68c175be9b010bf2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID65298
ChEMBL IDCHEMBL1162001
KEGG Compound IDC04132
Pubchem Compound ID72361
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00592
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference