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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:38:30 UTC
HMDB IDHMDB0001481
Secondary Accession Numbers
  • HMDB01481
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
SynonymsNot Available
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
DescriptionThis compound belongs to the class of chemical entities known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Sulfuric acid monoamide
  • Oxane
  • Organic sulfuric acid or derivatives
  • Hemiacetal
  • Secondary alcohol
  • Oxacycle
  • Polyol
  • Organoheterocyclic compound
  • Alcohol
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

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 Area156.55 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.87 m³·mol⁻¹ChemAxon
Polarizability22.08 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0a4u-4940000000-f1177df811aad3e60337View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00e9-7139450000-622c5d01b8aa44f9d597View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1930000000-d8f58b6b8e1db71d7ce0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-1950000000-1148cfb329ec18207ca2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000g-9400000000-9e0348d47c4f10432e41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-9140000000-d89f189e462284b97b52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qd-9840000000-9d6931881edf0f15d067View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0032-9000000000-3254059c9b10d5a0b8d2View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
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