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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-19 21:42:07 UTC
HMDB IDHMDB0000140
Secondary Accession Numbers
  • HMDB00140
Metabolite Identification
Common NameGlucosylceramide
DescriptionGlucosylceramide is 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. Glucosylceramide is found to be associated with hypobetalipoproteinemia, which is an inborn error of metabolism.
Structure
Thumb
Synonyms
ValueSource
1-O-b-D-Glucopyranosyl-ceramideHMDB
1-O-beta-delta-Glucopyranosyl-ceramideHMDB
Ganglioside GL1aHMDB
Gaucher cerebrosideHMDB
GLC-beta1->1'cerHMDB
GlcCeramideHMDB
GlucocerebrosideHMDB
Chemical FormulaC48H93NO8
Average Molecular Weight812.2539
Monoisotopic Molecular Weight811.690118957
IUPAC NameN-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]tetracosanamide
Traditional NameN-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]tetracosanamide
CAS Registry NumberNot Available
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=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/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
InChI KeyPOQRWMRXUOPCLD-XNWFPASESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. These are compounds containing a sphingosine linked to a simple glucosyl moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassGlycosphingolipids
Direct ParentGlycosyl-N-acylsphingosines
Alternative Parents
Substituents
  • Glycosyl-n-acylsphingosine
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty amide
  • Fatty acyl
  • Monosaccharide
  • N-acyl-amine
  • Oxane
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Organoleptic effect:

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0Not Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00019 g/LALOGPS
logP9.15ALOGPS
logP12.65ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)12.18ChemAxon
pKa (Strongest Basic)0.019ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area148.71 ŲChemAxon
Rotatable Bond Count41ChemAxon
Refractivity235 m³·mol⁻¹ChemAxon
Polarizability105.5 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0100605930-c40e2ce986f55d74b79fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qc-0122309300-3bd6c3acb66a3639f792View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ec-1445109500-6532e065ad4396ac578fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2502117490-24d6b571f83398715c6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-3904124310-92221e6efff09684df05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9313000000-d566c390829a6039f2dbView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6.0 +/- 2.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified6.0 +/- 1.0 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.0 (3.9-4.4) uMAdult (>18 years old)BothAbetalipoproteinemia details
BloodDetected and Quantified0.39 +/- 0.065 uMAdult (>18 years old)BothHypobetalipoproteinemia details
Associated Disorders and Diseases
Disease References
Abetalipoproteinemia
  1. Dawson G, Kruski AW, Scanu AM: Distribution of glycosphingolipids in the serum lipoproteins of normal human subjects and patients with hypo- and hyperlipidemias. J Lipid Res. 1976 Mar;17(2):125-31. [PubMed:178813 ]
Hypobetalipoproteinemia
  1. Dawson G, Kruski AW, Scanu AM: Distribution of glycosphingolipids in the serum lipoproteins of normal human subjects and patients with hypo- and hyperlipidemias. J Lipid Res. 1976 Mar;17(2):125-31. [PubMed:178813 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021900
KNApSAcK IDNot Available
Chemspider ID24765741
KEGG Compound IDC01190
BioCyc IDGLUCOSYL_CERAMIDE
BiGG IDNot Available
Wikipedia LinkGlucocerebroside
METLIN IDNot Available
PubChem Compound53477677
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceHazama, 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.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 62 proteins in total.

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Cleaves beta-linked terminal galactosyl residues from gangliosides, glycoproteins, and glycosaminoglycans. Isoform 2 has no beta-galactosidase catalytic activity, but plays functional roles in the formation of extracellular elastic fibers (elastogenesis) and in the development of connective tissue. Seems to be identical to the elastin-binding protein (EBP), a major component of the non-integrin cell surface receptor expressed on fibroblasts, smooth muscle cells, chondroblasts, leukocytes, and certain cancer cell types. In elastin producing cells, associates with tropoelastin intracellularly and functions as a recycling molecular chaperone which facilitates the secretions of tropoelastin and its assembly into elastic fibers.
Gene Name:
GLB1
Uniprot ID:
P16278
Molecular weight:
Not Available
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Catalyzes the first glycosylation step in glycosphingolipid biosynthesis, the transfer of glucose to ceramide. May also serve as a "flippase".
Gene Name:
UGCG
Uniprot ID:
Q16739
Molecular weight:
44853.255
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
LPH splits lactose in the small intestine.
Gene Name:
LCT
Uniprot ID:
P09848
Molecular weight:
218584.77
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GBA
Uniprot ID:
P04062
Molecular weight:
59715.745
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Required for the biosynthesis of glycosphingolipids.
Gene Name:
B4GALT6
Uniprot ID:
Q9UBX8
Molecular weight:
44913.315
Reactions
UDP-L-rhamnose + Glucosylceramide → Uridine 5'-diphosphate + Lactosylceramide (d18:1/24:0)details
General function:
Involved in cysteine-type endopeptidase activity
Specific function:
Mediates GPI anchoring in the endoplasmic reticulum, by replacing a protein's C-terminal GPI attachment signal peptide with a pre-assembled GPI. During this transamidation reaction, the GPI transamidase forms a carbonyl intermediate with the substrate protein
Gene Name:
PIGK
Uniprot ID:
Q92643
Molecular weight:
45251.4
General function:
Involved in biosynthetic process
Specific function:
Necessary for the synthesis of N-acetylglucosaminyl-phosphatidylinositol, the very early intermediate in GPI-anchor biosynthesis.
Gene Name:
PIGA
Uniprot ID:
P37287
Molecular weight:
54126.065
General function:
Involved in catalytic activity
Specific function:
Non-lysosomal glucosylceramidase that catalyzes the conversion of glucosylceramide to free glucose and ceramide. Involved in sphingomyelin generation and prevention of glycolipid accumulation. May also catalyze the hydrolysis of bile acid 3-O-glucosides, however, the relevance of such activity is unclear in vivo.
Gene Name:
GBA2
Uniprot ID:
Q9HCG7
Molecular weight:
104648.13
General function:
Involved in GPI anchor biosynthetic process
Specific function:
Component of the GPI transamidase complex. May be involved in the recognition of either the GPI attachment signal or the lipid portion of GPI
Gene Name:
PIGU
Uniprot ID:
Q9H490
Molecular weight:
50051.2
General function:
Involved in protein binding
Specific function:
Component of the GPI transamidase complex. Essential for transfer of GPI to proteins, particularly for formation of carbonyl intermediates
Gene Name:
PIGT
Uniprot ID:
Q969N2
Molecular weight:
65699.0

Only showing the first 10 proteins. There are 62 proteins in total.