Record Information
Creation date2011-09-21 00:29:55 UTC
Update date2015-07-21 06:57:43 UTC
Primary IDFDB023434
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGalabiosylceramide (d18:1/16:0)
DescriptionGalabiosylceramide is a non-acidic diglycosphingolipids, i.e. a sphingolipid with two or more carbohydrate moieties attached to a ceramide unit. It is a vital component of cellular membranes of most eukaryotic organisms and some bacteria. Its abundance relative to other lipids is usually low other than in epithelial and neuronal cells. Galabiosylceramide has also been found in small amounts in kidney and pancreas, for example. Galabiosylceramide is one of the lipids that accumulates in excessive amounts in Fabry's disease. It is the precursor of the gala series of oligoglycosylceramides. n animal tissues, biosynthesis involves addition of a second monosaccharides unit from the appropriate sugar nucleotide to a monoglycosylceramide, catalysed by a glycosyl transferase, in the lumen of the Golgi apparatus. Glycolipids are important components of the body's immune defense system, either in haptenic reactivity or in antibody-producing potency, i.e. as cellular immunogens or antigens. Certain glycolipids are involved in the antigenicity of blood group determinants, while others bind to specific toxins or bacteria. Some also function as receptors for cellular recognition, and they can be specific for particular tissues or tumours. [HMDB]
CAS NumberNot Available
Predicted Properties
Water Solubility0.012 g/LALOGPS
pKa (Strongest Acidic)5.81ChemAxon
pKa (Strongest Basic)2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area231.35 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity231.12 m³·mol⁻¹ChemAxon
Polarizability103.46 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC46H87NO13
IUPAC nameN-(1-{[(2R,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl)hexadecanimidic acid
InChI IdentifierInChI=1S/C46H87NO13/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-35(50)34(47-38(51)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)33-57-45-43(56)41(54)44(37(32-49)59-45)60-46-42(55)40(53)39(52)36(31-48)58-46/h27,29,34-37,39-46,48-50,52-56H,3-26,28,30-33H2,1-2H3,(H,47,51)/t34?,35?,36-,37-,39+,40+,41-,42-,43-,44+,45-,46-/m1/s1
Isomeric SMILES[H][C@]1(CO)O[C@]([H])(O[C@@]2([H])[C@@]([H])(CO)O[C@@]([H])(OCC(NC(=O)CCCCCCCCCCCCCCC)C(O)C=CCCCCCCCCCCCCC)[C@]([H])(O)[C@@]2([H])O)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O
Average Molecular Weight862.1819
Monoisotopic Molecular Weight861.617741875
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
Sub ClassGlycosphingolipids
Direct ParentGlycosyl-N-acylsphingosines
Alternative Parents
  • Glycosyl-n-acylsphingosine
  • Fatty acyl glycoside of mono- or disaccharide
  • Fatty acyl glycoside
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Fatty acyl
  • Oxane
  • N-acyl-amine
  • 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
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
SpectraNot Available
ChemSpider ID16744850
ChEMBL IDNot Available
KEGG Compound IDC06126
Pubchem Compound ID20057274
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2267787
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
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
NameGene NameUniProt ID
Alpha-galactosidase AGLAP06280
Acid ceramidaseASAH1Q13510
Putative neutral ceramidase CASAH2CP0C7U2
Alkaline ceramidase 2ACER2Q5QJU3
Neutral ceramidaseASAH2Q9NR71
Alkaline ceramidase 1ACER1Q8TDN7
Galactosylceramide sulfotransferaseGAL3ST1Q99999
Ganglioside GM2 activatorGM2AP17900
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
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
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
MSDSNot Available
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference