Showing metabocard for N-Acetylgalactosamine 4-sulphate (BMDB0000781)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:36:27 UTC
Update Date2020-04-22 15:05:16 UTC
BMDB IDBMDB0000781
Secondary Accession Numbers
  • BMDB00781
Metabolite Identification
Common NameN-Acetylgalactosamine 4-sulphate
DescriptionN-Acetylgalactosamine 4-sulphate, also known as beta-D-galpnac4S or GALNAC4S, 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. N-Acetylgalactosamine 4-sulphate is an extremely weak basic (essentially neutral) compound (based on its pKa).
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 Weight301.271
Monoisotopic Molecular Weight301.046751773
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
CAS Registry Number45233-43-0
SMILES
CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS(O)(=O)=O)[C@@H]1O
InChI Identifier
InChI=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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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-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
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, Positivesplash10-05gr-5690000000-9999f4a9ad628f920f6eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0uk9-7274790000-51356389c283408fe702View 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 - Quattro_QQQ 10V, Positive (Annotated)splash10-0fk9-0190000000-9873b0cf34b6a2d02305View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0059-5900000000-0a0f78bfc09ede96dc12View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9100000000-4309fcbb832ee8f8fe9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zgi-0095000000-9b84207cee0fb9a603c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uec-1190000000-6ac62541fed00ea34c8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udu-9610000000-8f949b47b6e8ba30243aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3793000000-b4c948ad4ba7a620e6d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9350000000-aa4efc17a9e76f1d628cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-0a15855482484fda6549View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-940928f9d0f78df7d01cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2974000000-ccb9995db976a2f25a26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9810000000-822c5da05677cfbdfdd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-0193000000-dc3a85b96a45405e85daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-4493000000-db92c062dc52b16910d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-9000000000-38775368e20d30c779e2View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
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
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000781
DrugBank IDDB01872
Phenol Explorer Compound IDNot Available
FooDB IDFDB022238
KNApSAcK IDNot Available
Chemspider ID393546
KEGG Compound IDC16265
BioCyc IDCPD-12516
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5747
PubChem Compound446101
PDB IDNot Available
ChEBI ID44391
References
Synthesis ReferenceSkelton, 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.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available