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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:38 UTC
HMDB IDHMDB01481
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Sulfo-D-glucosamine
DescriptionN-Sulfo-D-glucosamine is a structurally altered form of N-acetyl-D-glucosamine (a polysaccharide found in animal tissues) by heparan sulfate N-deacetylase /N-sulfotransferase enzymes.
Structure
Thumb
Synonyms
  1. N-Sulfo-D-glucosamine
Chemical FormulaC6H13NO8S
Average Molecular Weight259.234
Monoisotopic Molecular Weight259.036187087
IUPAC NameN-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]sulfamic acid
Traditional NameN-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]sulfamic acid
CAS Registry Number909257-48-3
SMILES
OC[C@H]1O[C@@H](O)[C@H](NS(O)(=O)=O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H13NO8S/c8-1-2-4(9)5(10)3(6(11)15-2)7-16(12,13)14/h2-11H,1H2,(H,12,13,14)/t2-,3-,4-,5-,6-/m1/s1
InChI KeyPRDZVHCOEWJPOB-QZABAPFNSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassHexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Amino Sugars
  • Carbohydrates and Carbohydrate Conjugates
Substituents
  • 1,2 Diol
  • Hemiacetal
  • Organic Sulfuric Acid Amide
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
  • Sulfamic Acid Derivative
Direct ParentHexoses
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 Solubility94.3 g/LALOGPS
logP-2.3ALOGPS
logP-4.9ChemAxon
logS-0.44ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.55ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.87ChemAxon
Polarizability22.08ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022646
KNApSAcK IDNot Available
Chemspider ID388505
KEGG Compound IDC01075
BioCyc IDCPD-550
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01481
Metagene LinkHMDB01481
METLIN ID6267
PubChem Compound439388
PDB IDNot Available
ChEBI ID16702
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Inorganic ion transport and metabolism
Specific function:
Not Available
Gene Name:
SGSH
Uniprot ID:
P51688
Molecular weight:
56694.875
Reactions
N-Sulfo-D-glucosamine + Water → Glucosamine + Oat gumdetails