Record Information
Version1.0
Creation date2011-09-21 01:31:04 UTC
Update date2019-11-26 03:21:26 UTC
Primary IDFDB027860
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGalactosylceramide (d18:1/20:0)
DescriptionGalactosylceramide (GalCer) is a non-acidic monoglycosphingolipid, i.e. a sphingolipid with one carbohydrate moiety attached to a ceramide unit. It is an intermediate in sphingolipid metabolism and is the second to last step in the synthesis of digalactosylceramidesulfate. GalCer is generated from ceramide via the enzyme UDP-galactose ceramide galactosyltransferase [EC:2.4.1.47]. It can be converted to digalactosylceramide via the enzyme glycosyltransferases [EC 2.4.1.-]. Galactosylceramide is the principal glycosphingolipid in brain tissue, hence the trivial name "cerebroside", which was first conferred on it in 1874. Galactosylceramides are found in all nervous tissues, but they can amount to 2% of the dry weight of grey matter and 12% of white matter. They are major constituents of oligodendrocytes. Synthesis of galactosylceramide takes place on the lumenal surface of the endoplasmic reticulum, although it has free access to the cytosolic surface by an energy-independent flip-flop process. GalCer sits in the extracellular leaflet of cell membranes in nanometer sized domains or rafts. The local clustering of GalCer within rafts is thought to facilitate the initial adhesion of certain viruses, including HIV-1 and bacteria to cells through multivalent interactions between receptor proteins and GalCer. A defect in the degradation of cerbrosides leads to a disorder called Krabbe disease. Krabbe disease (also known as globoid cell leukodystrophy or galactosylceramide lipidosis) is a rare, often fatal degenerative disorder that affects the myelin sheath of the nervous system. Krabbe disease is caused by mutations in the GALC gene, which causes a deficiency of galactosylceramidase. Infants with Krabbe disease are normal at birth. Symptoms begin between the ages of 3 and 6 months with irritability, fevers, limb stiffness, seizures, feeding difficulties, vomiting, and slowing of mental and motor development. There are also juvenile- and adult-onset cases of Krabbe disease, which have similar symptoms but slower progression. In infants, the disease is generally fatal before age 2. Patients with late-onset Krabbe disease tend to have a slower progression of the disease and live significantly longer. 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. [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
N-(eicosanoyl)-1-b-galactosyl-sphing-4-eninehmdb
N-(eicosanoyl)-1-beta-galactosyl-sphing-4-eninehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.00047 g/LALOGPS
logP8.5ALOGPS
logP10.87ChemAxon
logS-6.2ALOGPS
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 Count37ChemAxon
Refractivity216.59 m³·mol⁻¹ChemAxon
Polarizability97.06 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC44H85NO8
IUPAC nameN-(3-hydroxy-1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl)icosanamide
InChI IdentifierInChI=1S/C44H85NO8/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-40(48)45-37(36-52-44-43(51)42(50)41(49)39(35-46)53-44)38(47)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h31,33,37-39,41-44,46-47,49-51H,3-30,32,34-36H2,1-2H3,(H,45,48)/t37?,38?,39-,41+,42+,43-,44-/m1/s1
InChI KeyDFELABABMXOKTD-YPFHOHCESA-N
Isomeric SMILES[H][C@]1(CO)O[C@@]([H])(OCC(NC(=O)CCCCCCCCCCCCCCCCCCC)C(O)C=CCCCCCCCCCCCCC)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O
Average Molecular Weight756.1476
Monoisotopic Molecular Weight755.627518701
Classification
Description Belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines 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 of mono- or disaccharide
  • Fatty acyl glycoside
  • Hexose monosaccharide
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Fatty acyl
  • Oxane
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Acetal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID24765746
ChEMBL IDNot Available
KEGG Compound IDC02686
Pubchem Compound ID53480654
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10710
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Alpha-galactosidase AGLAP06280
GlucosylceramidaseGBAP04062
Sialidase-2NEU2Q9Y3R4
Sialidase-4NEU4Q8WWR8
Acid ceramidaseASAH1Q13510
Putative neutral ceramidase CASAH2CP0C7U2
Alkaline ceramidase 2ACER2Q5QJU3
Neutral ceramidaseASAH2Q9NR71
Alkaline ceramidase 1ACER1Q8TDN7
Galactosylceramide sulfotransferaseGAL3ST1Q99999
Ganglioside GM2 activatorGM2AP17900
GalactocerebrosidaseGALCP54803
N-acetylglucosaminyl-phosphatidylinositol de-N-acetylasePIGLQ9Y2B2
Sphingomyelin phosphodiesteraseSMPD1P17405
Ceramide glucosyltransferaseUGCGQ16739
Phosphatidylinositol N-acetylglucosaminyltransferase subunit QPIGQQ9BRB3
Phosphatidylinositol N-acetylglucosaminyltransferase subunit APIGAP37287
Phosphatidylinositol N-acetylglucosaminyltransferase subunit HPIGHQ14442
Phosphatidylinositol N-acetylglucosaminyltransferase subunit PPIGPP57054
Phosphatidylinositol N-acetylglucosaminyltransferase subunit CPIGCQ92535
2-hydroxyacylsphingosine 1-beta-galactosyltransferaseUGT8Q16880
Collagen type IV alpha-3-binding proteinCOL4A3BPQ9Y5P4
T-cell surface glycoprotein CD1e, membrane-associatedCD1EP15812
Epididymal secretory protein E1NPC2P61916
Ceramide synthase 1CERS1P27544
Antigen-presenting glycoprotein CD1dCD1DP15813
GPI mannosyltransferase 1PIGMQ9H3S5
Phosphatidylinositol-glycan biosynthesis class W proteinPIGWQ7Z7B1
Phosphatidylinositol-glycan biosynthesis class X proteinPIGXQ8TBF5
GPI mannosyltransferase 4PIGZQ86VD9
Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferaseB3GNT5Q9BYG0
Beta-1,3-galactosyltransferase 5B3GALT5Q9Y2C3
GPI mannosyltransferase 3PIGBQ92521
Phosphatidylinositol-glycan biosynthesis class F proteinPIGFQ07326
GPI ethanolamine phosphate transferase 2PIGGQ5H8A4
GPI ethanolamine phosphate transferase 1PIGNO95427
GPI ethanolamine phosphate transferase 3PIGOQ8TEQ8
GPI transamidase component PIG-SPIGSQ96S52
GPI transamidase component PIG-TPIGTQ969N2
Phosphatidylinositol glycan anchor biosynthesis class U proteinPIGUQ9H490
GPI mannosyltransferase 2PIGVQ9NUD9
Phosphatidylinositol N-acetylglucosaminyltransferase subunit YPIGYQ3MUY2
Non-lysosomal glucosylceramidaseGBA2Q9HCG7
GPI-anchor transamidasePIGKQ92643
Lactosylceramide 4-alpha-galactosyltransferaseA4GALTQ9NPC4
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference