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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-25 08:24:05 UTC
Update Date2021-09-14 15:18:17 UTC
HMDB IDHMDB0006598
Secondary Accession Numbers
  • HMDB06598
Metabolite Identification
Common NameIsoglobotriaose
DescriptionIsoglobotriaose is a glycosphingolipid found in mammalian tissues; nonepithelial residue in the intestine, spleen, and spleen microsomes. (PMID: 7053385 , 893368 , 4690582 ). Globotriaosylceramide receptors bind to Verotoxin 1 (VT1) B subunits from Escherichia coli eliciting human vascular disease as a consequence of specific binding to these receptors on endothelial cell surfaces. (PMID: 10361298 , 10353828 ). Globotriaosylceramides accumulate in patients with Fabry disease. Fabry disease is a X-linked metabolic disorder caused by a deficiency of alpha-galactosidase leading to the systemic accumulation of glycosphingolipids with alpha-galactosyl moieties; glycolipid deposition in endothelial cells leads to renal failure and cardiac and cerebrovascular disease. (PMID: 10339603 ).
Structure
Thumb
Synonyms
ValueSource
alpha-D-Galp-(1-4)-beta-D-galp-(1-4)-D-GLCHMDB
alpha-delta-Galp-(1-4)-beta-delta-galp-(1-4)-delta-GLCHMDB
GloboisotriaoseHMDB
IsoglobotriglycosylceramideHMDB
O-alpha-D-Galactopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)- D-glucoseHMDB
O-alpha-delta-Galactopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)- D-glucoseHMDB
Chemical FormulaC19H34O15
Average Molecular Weight502.4643
Monoisotopic Molecular Weight502.189770418
IUPAC Name(2R,3R,4R,5R)-4-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(1S,2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxy}oxan-2-yl]oxy}-2,3,5,6-tetrahydroxyhexanal
Traditional Nameisoglobotriaose
CAS Registry Number41744-59-6
SMILES
[H][C@@](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O[C@@]2([H])C[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H]1O)([C@H](O)CO)[C@H](O)[C@@H](O)C=O
InChI Identifier
InChI=1S/C19H34O15/c20-2-6-1-9(13(28)15(30)11(6)26)32-18-14(29)10(5-23)33-19(16(18)31)34-17(8(25)4-22)12(27)7(24)3-21/h3,6-20,22-31H,1-2,4-5H2/t6-,7+,8-,9+,10-,11+,12-,13+,14+,15+,16-,17-,18+,19+/m1/s1
InChI KeyDRRWNKCTTZUPPM-FBSSLUAZSA-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
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty alcohol
  • Cyclohexanol
  • Cyclitol or derivatives
  • Beta-hydroxy aldehyde
  • Oxane
  • Cyclic alcohol
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Polyol
  • Ether
  • Acetal
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aldehyde
  • Alcohol
  • 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 IDFDB023993
KNApSAcK IDNot Available
Chemspider ID30776581
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477863
PDB IDNot Available
ChEBI ID165246
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSarkar, Arun K.; Matta, Khushi L. Synthetic studies in carbohydrates. LXXX. 2,3,4,6-Tetra-O-benzyl-b-D-galactopyranosyl phenyl sulfoxide as a glycosyl donor. Synthesis of some oligosaccharides containing an a-D-galactopyranosyl group. Carbohydrate Research (1992), 233 245-50.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Breimer ME, Hansson GC, Karlsson KA, Leffler H: Glycosphingolipids of rat tissues. Different composition of epithelial and nonepithelial cells of small intestine. J Biol Chem. 1982 Jan 10;257(1):557-68. [PubMed:7053385 ]
  2. Arita H, Kawanami J: Cytolipin R from rat spleen. J Biochem. 1977 Jun;81(6):1661-4. [PubMed:893368 ]
  3. Stoffyn P, Stoffyn A, Hauser G: Structure of trihexosylceramide biosynthesized in vitro. J Biol Chem. 1973 Mar 25;248(6):1920-3. [PubMed:4690582 ]
  4. Bast DJ, Banerjee L, Clark C, Read RJ, Brunton JL: The identification of three biologically relevant globotriaosyl ceramide receptor binding sites on the Verotoxin 1 B subunit. Mol Microbiol. 1999 Jun;32(5):953-60. [PubMed:10361298 ]
  5. Picking WD, McCann JA, Nutikka A, Lingwood CA: Localization of the binding site for modified Gb3 on verotoxin 1 using fluorescence analysis. Biochemistry. 1999 Jun 1;38(22):7177-84. [PubMed:10353828 ]
  6. Ohshima T, Schiffmann R, Murray GJ, Kopp J, Quirk JM, Stahl S, Chan CC, Zerfas P, Tao-Cheng JH, Ward JM, Brady RO, Kulkarni AB: Aging accentuates and bone marrow transplantation ameliorates metabolic defects in Fabry disease mice. Proc Natl Acad Sci U S A. 1999 May 25;96(11):6423-7. [PubMed:10339603 ]