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Bovine Metabolome Database



Showing metabocard for Glucosylceramide (BMDB00140)

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Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:42
Accession Number BMDB00140
Common Name Glucosylceramide
Description A glycosphingolipid (ceramide and oligosaccharide)or oligoglycosylceramide with one or more sialic acids (i.e. n-acetylneuraminic acid) linked on the sugar chain. It is a component the cell plasma membrane which modulates cell signal transduction events. Gangliosides have been found to be highly important in immunology. Ganglioside GL1a carries a net-negative charge at pH 7.0 and is acidic. Gangliosides can amount to 6% of the weight of lipids from brain, but they are found at low levels in all animal tissues. Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease.
Synonyms
  1. 1-O-b-D-glucopyranosyl-Ceramide
  2. Ganglioside GL1a
  3. Gaucher cerebroside
  4. GlcCeramide
  5. Glucocerebroside
  6. Glucosylceramide
  7. Glc-beta1->1'Cer
  8. 1-O-beta-delta-glucopyranosyl-Ceramide
Chemical IUPAC Name N-[(E,2S,3R)-3-hydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadec-4-en-2-yl]tetracosanamide
Chemical Formula C48H93NO8
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Lipids
Class
  • Glycolipids
Sub Class
  • Gangliosides
Family
  • Mammalian_Metabolite
Species
  • acetal; primary alcohol; secondary alcohol; 1,2-diol; secondary carboxylic acid amide; alkene; heterocyclic compound
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 812.254
Monoisotopic Molecular Weight 811.690125
Isomeric SMILES CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)C(O)[C@H](O)[C@H]1O)[C@H](O)C=CCCCCCCCCCCCCC
Canonical SMILES CCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(COC1OC(CO)C(O)C(O)C1O)C(O)C=CCCCCCCCCCCCCC
KEGG Compound ID C01190 Link Image
BioCyc ID GLUCOSYL_CERAMIDE Link Image
BiGG ID Not Available
Wikipedia Link Glucosylceramide Link Image
METLIN ID Not Available
PubChem Compound 6475228 Link Image
PubChem Substance 628522 Link Image
ChEBI ID Not Available
CAS Registry Number 85305-87-9
InChI Identifier InChI=1/C48H93NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-44(52)49-41(40-56-48-47(55)46(54)45(53)43(39-50)57-48)42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h35,37,41-43,45-48,50-51,53-55H,3-34,36,38-40H2,1-2H3,(H,49,52)/b37-35+/t41-,42+,43+,45-,46-,47+,48+/m0/s1
Synthesis Reference Hazama, Kazuhiko; Kinoshita, Mikio; Onishi, Masao; Ono, Jisaburo. Glucosylceramide fractions from plant and cereals as colon cancer inhibitors and health foods. Jpn. Kokai Tokkyo Koho (2005), 11 pp.
Melting Point (Experimental) Not Available
Experimental Water Solubility Insoluble [Technical Appendix B Physicochemical Properties for TRI Chemicals and Chemical] Source: PhysProp
Predicted Water Solubility 1.86e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 9.15 [Predicted by ALOGPS]; 13.4 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane
Biofluid Location Not Available
Tissue Location
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Sphingolipid Metabolism
HMDB Pathways
Name Sphingolipid Metabolism
Image Show Link Image
KEGG Pathways
Name Sphingolipid Metabolism
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SimCell Pathways
Name Sphingolipid Metabolism
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Graph
SBML
General References
  1. Wikipedia Link Image