N-Acetylgalactosamine 6-sulfate (CHEM034976)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:23:12 UTC
Update Date2016-11-09 01:21:13 UTC
Accession NumberCHEM034976
Identification
Common NameN-Acetylgalactosamine 6-sulfate
ClassSmall Molecule
DescriptionN-Acetylgalactosamine 6-sulfate is found in keratan sulfate and chondroitin 6-sulfate. PMID: 12489154 Morquio syndrome is caused by an abnormal accumulation of mucopolysaccharides - in this case, keratan sulfate - in the body. Keratan sulfate is excreted in urine. The symptoms vary from patient to patient, and may include hearing loss, cataracts, skeletal dysplasia, spinal instability, and minor respiratory issues, among others. Two forms are recognized, type A and type B. Type A is a deficiency of the enzyme N-acetylgalactosamine-6-sulfate sulfatase. [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-Acetylgalactosamine 6-sulfuric acidGenerator
N-Acetylgalactosamine 6-sulphateGenerator
N-Acetylgalactosamine 6-sulphuric acidGenerator
N-Acetyl-chondrosamine 6-(hydrogen sulfate)HMDB
N-Acetyl-chondrosamine 6-(hydrogen sulphate)HMDB
Nag-6-SHMDB
N-[(2R,3R,4R,5R)-3,4,5-Trihydroxy-1-oxo-6-(sulfooxy)hexan-2-yl]ethanimidateHMDB
N-[(2R,3R,4R,5R)-3,4,5-Trihydroxy-1-oxo-6-(sulphooxy)hexan-2-yl]ethanimidateHMDB
N-[(2R,3R,4R,5R)-3,4,5-Trihydroxy-1-oxo-6-(sulphooxy)hexan-2-yl]ethanimidic acidHMDB
N-Acetylgalactosamine 6-sulfateMeSH
Chemical FormulaC8H15NO9S
Average Molecular Mass301.271 g/mol
Monoisotopic Mass301.047 g/mol
CAS Registry Number10357-00-3
IUPAC Name{[(2R,3R,4R,5R)-5-acetamido-2,3,4-trihydroxy-6-oxohexyl]oxy}sulfonic acid
Traditional Name[(2R,3R,4R,5R)-5-acetamido-2,3,4-trihydroxy-6-oxohexyl]oxysulfonic acid
SMILESCC(=O)N[C@@H](C=O)[C@@H](O)[C@@H](O)[C@H](O)COS(O)(=O)=O
InChI IdentifierInChI=1S/C8H15NO9S/c1-4(11)9-5(2-10)7(13)8(14)6(12)3-18-19(15,16)17/h2,5-8,12-14H,3H2,1H3,(H,9,11)(H,15,16,17)/t5-,6+,7+,8-/m0/s1
InChI KeyNHZWETQZLORZIR-OSMVPFSASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharide sulfates. These are monosaccharides that contain a sulfate group linked to the sugar moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide sulfates
Alternative Parents
Substituents
  • Monosaccharide sulfate
  • Amino saccharide
  • Beta-hydroxy aldehyde
  • Sulfuric acid monoester
  • Sulfate-ester
  • Sulfuric acid ester
  • Alkyl sulfate
  • Organic sulfuric acid or derivatives
  • Acetamide
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Polyol
  • Carboxylic acid derivative
  • Aldehyde
  • Organonitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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 Solubility18.9 g/LALOGPS
logP-1.9ALOGPS
logP-5.7ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)-2ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.46 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity58.44 m³·mol⁻¹ChemAxon
Polarizability26.16 ųChemAxon
Number of Rings0ChemAxon
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, Positivesplash10-001l-4930000000-3995205cfc86e324a9e0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03xr-6679430000-092e8c1002aa5cf900f1Spectrum
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_1_6) - 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_2_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uec-2496000000-96d63298ebd1e32237c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-8910000000-5568627b80a529b392e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r7-9500000000-48ef9d68c6da00796d65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-1159-0921000000-71152529ad1ded1d5361Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pba-4910000000-cf50abbc7698ce6c52caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5c-9400000000-9dcf49e83939f8b39debSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0942000000-a601e7eda15b712d2174Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3900000000-31f86402ac2cedefc6ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-9300000000-caf200bac62db11fd285Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxs-5945000000-fe7324f6d560f56aa7deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9400000000-a89e6a5b374abd7f5e9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-9200000000-7f7930f002365d4143aaSpectrum
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
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 IDNot Available
HMDB IDHMDB0000841
FooDB IDFDB022274
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5804
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID167877
ChEBI ID165235
PubChem Compound ID193456
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Eliakim R, Gilead L, Ligumsky M, Okon E, Rachmilewitz D, Razin E: Histamine and chondroitin sulfate E proteoglycan released by cultured human colonic mucosa: indication for possible presence of E mast cells. Proc Natl Acad Sci U S A. 1986 Jan;83(2):461-4.
2. Chambers WH, Oeltmann TN: The effects of hexose 6-O-sulfate esters on human natural killer cell lytic function. J Immunol. 1986 Sep 1;137(5):1469-74.
3. Sobue M, Takeuchi J, Fukatsu T, Nagasaka T, Nakashima N, Ogura T, Katoh T, Yoshida K: Immunohistochemical techniques for detection of dermatan sulfate proteoglycan in tissue sections. Stain Technol. 1989 Jan;64(1):43-7.
4. Yutaka T, Okada S, Kato T, Inui K, Yabuuhi H: Galactose 6-sulfate sulfatase activity in Morquio syndrome. Clin Chim Acta. 1982 Jul 1;122(2):169-80.
5. Yutaka T, Okada S, Kato T, Inui K, Yabuuchi H: Properties of sulfatases in cultured skin fibroblasts of multiple sulfatase deficient patients. Clin Genet. 1981 Oct;20(4):296-303.
6. Yamakoshi Y, Hu JC, Liu S, Sun X, Zhang C, Oida S, Fukae M, Simmer JP: Porcine N-acetylgalactosamine 6-sulfatase (GALNS) cDNA sequence and expression in developing teeth. Connect Tissue Res. 2002;43(2-3):167-75.