N-Acetylgalactosamine 4-sulphate (CHEM022759)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:51:04 UTC
Update Date2016-11-09 01:17:34 UTC
Accession NumberCHEM022759
Identification
Common NameN-Acetylgalactosamine 4-sulphate
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-Acetyl-beta-D-galactosamine 4-sulphateChEBI
2-(Acetylamino)-2-deoxy-4-O-sulfO-beta-D-galactopyranoseChEBI
2-Deoxy-2-acetamido-beta-D-galactose-4-sulfateChEBI
beta-D-GalpNAc4SChEBI
N-Acetyl-beta-D-galactosamine 4-sulfuric acidChEBI
N-Acetyl-b-D-galactosamine 4-sulfateGenerator
N-Acetyl-b-D-galactosamine 4-sulfuric acidGenerator
N-Acetyl-b-D-galactosamine 4-sulphateGenerator
N-Acetyl-b-D-galactosamine 4-sulphuric acidGenerator
N-Acetyl-beta-D-galactosamine 4-sulfateGenerator
N-Acetyl-beta-D-galactosamine 4-sulphuric acidGenerator
N-Acetyl-β-D-galactosamine 4-sulfateGenerator
N-Acetyl-β-D-galactosamine 4-sulfuric acidGenerator
N-Acetyl-β-D-galactosamine 4-sulphateGenerator
N-Acetyl-β-D-galactosamine 4-sulphuric acidGenerator
2-(Acetylamino)-2-deoxy-4-O-sulfO-b-D-galactopyranoseGenerator
2-(Acetylamino)-2-deoxy-4-O-sulfO-β-D-galactopyranoseGenerator
2-(Acetylamino)-2-deoxy-4-O-sulphO-b-D-galactopyranoseGenerator
2-(Acetylamino)-2-deoxy-4-O-sulphO-beta-D-galactopyranoseGenerator
2-(Acetylamino)-2-deoxy-4-O-sulphO-β-D-galactopyranoseGenerator
2-Deoxy-2-acetamido-b-D-galactose-4-sulfateGenerator
2-Deoxy-2-acetamido-b-D-galactose-4-sulfuric acidGenerator
2-Deoxy-2-acetamido-b-D-galactose-4-sulphateGenerator
2-Deoxy-2-acetamido-b-D-galactose-4-sulphuric acidGenerator
2-Deoxy-2-acetamido-beta-D-galactose-4-sulfuric acidGenerator
2-Deoxy-2-acetamido-beta-D-galactose-4-sulphateGenerator
2-Deoxy-2-acetamido-beta-D-galactose-4-sulphuric acidGenerator
2-Deoxy-2-acetamido-β-D-galactose-4-sulfateGenerator
2-Deoxy-2-acetamido-β-D-galactose-4-sulfuric acidGenerator
2-Deoxy-2-acetamido-β-D-galactose-4-sulphateGenerator
2-Deoxy-2-acetamido-β-D-galactose-4-sulphuric acidGenerator
b-D-GalpNAc4SGenerator
Β-D-galpnac4SGenerator
N-Acetylgalactosamine 4-sulfateGenerator
N-Acetylgalactosamine 4-sulfuric acidGenerator
N-Acetylgalactosamine 4-sulphuric acidGenerator
2-(Acetylamino)-2-deoxy-D-galactose 4-(hydrogen sulfate)HMDB
2-(Acetylamino)-2-deoxy-D-galactose 4-(hydrogen sulphate)HMDB
GalNAc4SHMDB
N-Acetyl-D-galactosamine 4-sulfateHMDB
N-Acetyl-D-galactosamine 4-sulphateHMDB
N-Acetylgalactosamine-4-sulfateHMDB
N-Acetylgalactosamine-4-sulphateHMDB
NAG-4-SHMDB
N-[(2R,3R,4R,5R,6R)-2,4-Dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-3-yl]ethanimidateHMDB
N-[(2R,3R,4R,5R,6R)-2,4-Dihydroxy-6-(hydroxymethyl)-5-(sulphooxy)oxan-3-yl]ethanimidateHMDB
N-[(2R,3R,4R,5R,6R)-2,4-Dihydroxy-6-(hydroxymethyl)-5-(sulphooxy)oxan-3-yl]ethanimidic acidHMDB
Chemical FormulaC8H15NO9S
Average Molecular Mass301.271 g/mol
Monoisotopic Mass301.047 g/mol
CAS Registry Number45233-43-0
IUPAC Name[(2R,3R,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid
Traditional Name[(2R,3R,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid
SMILESCC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS(O)(=O)=O)[C@@H]1O
InChI IdentifierInChI=1S/C8H15NO9S/c1-3(11)9-5-6(12)7(18-19(14,15)16)4(2-10)17-8(5)13/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H,14,15,16)/t4-,5-,6-,7+,8-/m1/s1
InChI KeyWHCJUIFHMJFEFZ-UIAUGNHASA-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
  • Carboxamide group
  • Hemiacetal
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility42.9 g/LALOGPS
logP-2ALOGPS
logP-4.9ChemAxon
logS-0.85ALOGPS
pKa (Strongest Acidic)-2ChemAxon
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
Polarizability25.95 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05gr-5690000000-9999f4a9ad628f920f6eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0uk9-7274790000-51356389c283408fe702Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0fk9-0190000000-9873b0cf34b6a2d02305Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0059-5900000000-0a0f78bfc09ede96dc12Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9100000000-4309fcbb832ee8f8fe9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zgi-0095000000-9b84207cee0fb9a603c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uec-1190000000-6ac62541fed00ea34c8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udu-9610000000-8f949b47b6e8ba30243aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3793000000-b4c948ad4ba7a620e6d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9350000000-aa4efc17a9e76f1d628cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-0a15855482484fda6549Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-940928f9d0f78df7d01cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2974000000-ccb9995db976a2f25a26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9810000000-822c5da05677cfbdfdd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-0193000000-dc3a85b96a45405e85daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-4493000000-db92c062dc52b16910d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-9000000000-38775368e20d30c779e2Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01872
HMDB IDHMDB0000781
FooDB IDFDB022238
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-12516
METLIN ID5747
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID393546
ChEBI ID44391
PubChem Compound ID446101
Kegg Compound IDC16265
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Skelton, Timothy P.; Hooper, Lora V.; Srivastava, Vandana; Hindsgaul, Ole; Baenziger, Jacques U. Characterization of a sulfotransferase responsible for the 4-O-sulfation of terminal b-N-acetyl-D-galactosamine on asparagine-linked oligosaccharides of glycoprotein hormones. Journal of Biological Chemistry (1991), 266(26), 17142-50.
2. Hopwood JJ, Elliott H: Urinary excretion of sulphated N-acetylhexosamines in patients with various mucopolysaccharidoses. Biochem J. 1985 Aug 1;229(3):579-86.
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=10329456
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23385884
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25474621
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=30177144
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=712855