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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:21 UTC
HMDB IDHMDB00781
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Acetylgalactosamine 4-sulphate
DescriptionAlso known as GalNAc4S, this molecule is a key component of dermatan, keratan and chondroitin sulfate. It is also a substrate for the enzyme N-acteylgalactosamine-4-sulphate transferase. This molecule is found in elevated concentrations in the urine of patients suffering from muchopolysaccharidosis type III, IV and VI. Levels are typically 300-400 times normal values. GalNAc4S is thought to be derived from the action of beta-N-acetylhexosaminidase on sulphated GlcNAc or GalNAc residues at the non-reducing end of keratan sulphate, dermatan sulphate or chondroitin sulphate.
Structure
Thumb
Synonyms
ValueSource
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-sulfateHMDB
N-Acetylgalactosamine-4-sulphateHMDB
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 KeyInChIKey=WHCJUIFHMJFEFZ-UIAUGNHASA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Monosaccharide sulfate
  • Sulfuric acid monoester
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Oxane
  • Monosaccharide
  • Acetamide
  • Organic sulfuric acid or derivatives
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Hemiacetal
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected 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
Water Solubility42.9 mg/mLALOGPS
logP-2ALOGPS
logP-5ChemAxon
logS-0.85ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)-0.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area162.62 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.02 m3·mol-1ChemAxon
Polarizability26.15 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)FemaleEpithelial ovarian cancer details
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 IDFDB022238
KNApSAcK IDNot Available
Chemspider ID393546
KEGG Compound IDC16265
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00781
Metagene LinkHMDB00781
METLIN ID5747
PubChem Compound446101
PDB IDASG
ChEBI IDNot Available
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 References
  1. Hopwood JJ, Elliott H: Urinary excretion of sulphated N-acetylhexosamines in patients with various mucopolysaccharidoses. Biochem J. 1985 Aug 1;229(3):579-86. [3931626 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
May have a role in promoting tumor progression. May block the TGFB1-enhanced cell growth.
Gene Name:
HYAL1
Uniprot ID:
Q12794
Molecular weight:
Not Available
Reactions
+ Water → DWA-2 + N-Acetylgalactosamine 4-sulphatedetails
General function:
Involved in catalytic activity
Specific function:
Involved in sperm-egg adhesion. Upon fertilization sperm must first penetrate a layer of cumulus cells that surrounds the egg before reaching the zona pellucida. The cumulus cells are embedded in a matrix containing hyaluronic acid which is formed prior to ovulation. This protein aids in penetrating the layer of cumulus cells by digesting hyaluronic acid.
Gene Name:
SPAM1
Uniprot ID:
P38567
Molecular weight:
Not Available
Reactions
+ Water → DWA-2 + N-Acetylgalactosamine 4-sulphatedetails
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes high molecular weight hyaluronic acid to produce an intermediate-sized product which is further hydrolyzed by sperm hyaluronidase to give small oligosaccharides. Displays very low levels of activity. Associates with and negatively regulates MST1R.
Gene Name:
HYAL2
Uniprot ID:
Q12891
Molecular weight:
Not Available
Reactions
+ Water → DWA-2 + N-Acetylgalactosamine 4-sulphatedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
HYAL3
Uniprot ID:
O43820
Molecular weight:
Not Available
Reactions
+ Water → DWA-2 + N-Acetylgalactosamine 4-sulphatedetails
General function:
Not Available
Specific function:
Endo-hyaluronidase that degrades hyaluronan to smaller oligosaccharide fragments. Has also chondroitin sulfate hydrolase activity, The best substrate being the galactosaminidic linkage in the sequence of a trisulfated tetrasaccharide.
Gene Name:
HYAL4
Uniprot ID:
Q2M3T9
Molecular weight:
Not Available
Reactions
+ Water → DWA-2 + N-Acetylgalactosamine 4-sulphatedetails