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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-03-26 21:30:24 UTC
Update Date2021-09-14 15:18:08 UTC
HMDB IDHMDB0005817
Secondary Accession Numbers
  • HMDB05817
Metabolite Identification
Common Name2-Acetamido-2-deoxy-6-O-a-L-fucopyranosyl-D-glucose
Description2-Acetamido-2-deoxy-6-O-a-L-fucopyranosyl-D-glucose is an oligosaccharide isolated from the urine of patients with fucosidosis (Fucosidosis is an autosomal recessive lysosomal storage disease caused by defective alpha-L-fucosidase with accumulation of fucose in the tissues. Different phenotypes include clinical features such as neurologic deterioration, growth retardation, visceromegaly, and seizures in a severe early form; coarse facial features, angiokeratoma corporis diffusum, spasticity and delayed psychomotor development in a longer surviving form; and an unusual spondylometaphyseoepiphyseal dysplasia in yet another form. OMIM 230000 ). (PMID 728478 ).
Structure
Thumb
Synonyms
ValueSource
2-(acetylamino)-2-Deoxy-6-O-(6-deoxy-a-L-galactopyranosyl)-D-glucoseHMDB
2-(acetylamino)-2-Deoxy-6-O-(6-deoxy-alpha-L-galactopyranosyl)-D-glucoseHMDB
2-(acetylamino)-2-Deoxy-6-O-(6-deoxy-alpha-L-galactopyranosyl)-delta-glucoseHMDB
N-{3,4,5-trihydroxy-1-oxo-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]hexan-2-yl}ethanimidateGenerator, HMDB
2-Acetamido-2-deoxy-6-O-a-L-fucopyranosyl-D-glucoseGenerator
2-Acetamido-2-deoxy-6-O-α-L-fucopyranosyl-D-glucoseGenerator
Chemical FormulaC14H25NO10
Average Molecular Weight367.349
Monoisotopic Molecular Weight367.147846025
IUPAC NameN-{3,4,5-trihydroxy-1-oxo-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]hexan-2-yl}acetamide
Traditional NameN-{3,4,5-trihydroxy-1-oxo-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]hexan-2-yl}acetamide
CAS Registry Number37776-59-3
SMILES
CC1OC(OCC(O)C(O)C(O)C(NC(C)=O)C=O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C14H25NO10/c1-5-9(19)12(22)13(23)14(25-5)24-4-8(18)11(21)10(20)7(3-16)15-6(2)17/h3,5,7-14,18-23H,4H2,1-2H3,(H,15,17)
InChI KeyYBWAUUBLHOFOPK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Amino saccharide
  • Beta-hydroxy aldehyde
  • Monosaccharide
  • Oxane
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aldehyde
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023773
KNApSAcK IDNot Available
Chemspider ID17216351
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22833656
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Strecker G, Fournet B, Montreuil J: Structure of the three major fucosyl-glycoasparagines accumulating in the urine of a patient with fucosidosis. Biochimie. 1978;60(8):725-34. [PubMed:728478 ]