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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-07-24 17:55:39 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameGanglioside GA2 (d18:1/24:0)
DescriptionGanglioside GA2 (d18:1/24:0) 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 GA2 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. Gangliosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Gangliosides are very similar to globosides except that they also contain N-acetyl neuraminic acid (NANA) in varying amounts. The specific names for the gangliosides provide information about their structure. The letter G refers to ganglioside, and the subscripts M, D, T and Q indicate that the molecule contains mono-, di-, tri and quatra-sialic acid. The numbered subscripts 1, 2 and 3 refer to the carbohydrate sequence that is attached to the ceramide. In particular, 1 stands for GalGalNAcGalGlc-ceramide, 2 stands for GalNAcGalGlc-ceramide and 3 stands for GalGlc-ceramide. Deficiencies in lysosomal enzymes that degrade the carbohydrate portions of various gangliosides are responsible for a number of lysosomal storage diseases such as Tay-Sachs disease, Sandhoff disease, and GM1 gangliosidosis. The carbohydrate portion of the ganglioside GM1 is the site of attachment of cholera toxin, the protein secreted by Vibrio cholerae.
  1. Asialo GM2
  2. Bissulfogangliotetraosylceramide
  3. G(A2) Ganglioside
  4. GA2
  5. GA2 Ganglioside
  6. GalNAc-beta1->4Gal-beta1->4Glc-beta1->1'Cer
  7. Ganglio-N-triaosylceramide
  8. Gangliotriosylceramide
  9. Glycolipid G
Chemical FormulaC62H116N2O18
Average Molecular Weight1177.587
Monoisotopic Molecular Weight1176.822314918
IUPAC NameN-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-5-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracosanamide
Traditional NameN-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-5-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracosanamide
CAS Registry Number88506-68-7
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as galnacb1-4galb1-4glc- (ganglio series). These are neutral glycosphingolipids in which the root sequence is GalNAcb1-4Galb1-4Glc.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
Sub ClassGlycosphingolipids
Direct ParentGalNAcb1-4Galb1-4Glc- (Ganglio series)
Alternative Parents
  • Galnacb1-4galb1-4glcb-cer_backbone
  • Oligosaccharide
  • Fatty acyl glycoside
  • N-acyl-alpha-hexosamine
  • Glucosamine
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Amino saccharide
  • Fatty acyl
  • Oxane
  • N-acyl-amine
  • Fatty amide
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
StatusExpected but not Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityInsolubleNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.0098 mg/mLALOGPS
pKa (Strongest Acidic)11.7ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area315.88 Å2ChemAxon
Rotatable Bond Count48ChemAxon
Refractivity310.92 m3·mol-1ChemAxon
Polarizability140.48 Å3ChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Location
  • Brain
  • Nerve Cells
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023489
KNApSAcK IDNot Available
Chemspider ID17216289
KEGG Compound IDC06135
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04897
Metagene LinkHMDB04897
PubChem Compound22833622
PDB IDNot Available
ChEBI IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Denny CA, Kasperzyk JL, Gorham KN, Bronson RT, Seyfried TN: Influence of caloric restriction on motor behavior, longevity, and brain lipid composition in Sandhoff disease mice. J Neurosci Res. 2006 May 1;83(6):1028-38. [16521125 ]


General function:
Involved in exo-alpha-sialidase activity
Specific function:
Hydrolyzes sialylated compounds.
Gene Name:
Uniprot ID:
Molecular weight:
Not Available
General function:
Involved in exo-alpha-sialidase activity
Specific function:
May function in lysosomal catabolism of sialylated glycoconjugates. Has sialidase activity towards synthetic substrates, such as 2'-(4-methylumbelliferyl)-alpha-D-N-acetylneuraminic acid (4-MU-NANA or 4MU-NeuAc). Has a broad substrate specificity being active on glycoproteins, oligosaccharides and sialylated glycolipids.
Gene Name:
Uniprot ID:
Molecular weight:
Not Available
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
LPH splits lactose in the small intestine.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in sialyltransferase activity
Specific function:
Catalyzes the formation of ganglioside GM3 (alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1, 4-beta-D-glucosylceramide).
Gene Name:
Uniprot ID:
Molecular weight:
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:
Uniprot ID:
Molecular weight:
Not Available
General function:
Involved in beta-N-acetylhexosaminidase activity
Specific function:
Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues.
Gene Name:
Uniprot ID:
Molecular weight:
Not Available
General function:
Involved in beta-N-acetylhexosaminidase activity
Specific function:
Responsible for the degradation of GM2 gangliosides, and a variety of other molecules containing terminal N-acetyl hexosamines, in the brain and other tissues. The form B is active against certain oligosaccharides. The form S has no measurable activity.
Gene Name:
Uniprot ID:
Molecular weight:
Not Available
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Involved in the biosynthesis of gangliosides GM2, GD2 and GA2.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in sphingolipid activator protein activity
Specific function:
Binds gangliosides and stimulates ganglioside GM2 degradation. It stimulates only the breakdown of ganglioside GM2 and glycolipid GA2 by beta-hexosaminidase A. It extracts single GM2 molecules from membranes and presents them in soluble form to beta-hexosaminidase A for cleavage of N-acetyl-D-galactosamine and conversion to GM3
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Not Available
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight: