Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-07-24 17:55:39 UTC
HMDB IDHMDB04897
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.
Structure
Thumb
Synonyms
  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 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]tetr
CAS Registry Number88506-68-7
SMILES
CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3NC(C)=O)[C@H](O)[C@H]2O)[C@H](O)C1O)[C@H](O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C62H116N2O18/c1-4-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-29-31-33-35-37-39-50(70)64-45(46(69)38-36-34-32-30-28-26-17-15-13-11-9-7-5-2)43-77-61-56(75)54(73)59(48(41-66)79-61)82-62-57(76)55(74)58(49(42-67)80-62)81-60-51(63-44(3)68)53(72)52(71)47(40-65)78-60/h36,38,45-49,51-62,65-67,69,71-76H,4-35,37,39-43H2,1-3H3,(H,63,68)(H,64,70)/b38-36+/t45-,46+,47+,48+,49+,51+,52-,53+,54+,55+,56?,57+,58-,59+,60-,61+,62-/m0/s1
InChI KeyXHRLJIMJGVPKKZ-PHASZRSXSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSphingolipids
Sub ClassNeutral Glycosphingolipids
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • Gangliosides
Substituents
  • 1,2 Diol
  • Acetal
  • Alkyl Glycoside
  • Allyl Alcohol
  • Carboxamide Group
  • Ceramide
  • Fatty Acyl Glycoside
  • Glucosamine
  • Glycosyl Compound
  • Hexose Trisaccharide
  • Mannosamine
  • N Acyl Amine
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct ParentArthro and Ganglio series
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityInsolubleNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.0098 g/LALOGPS
logP5.9ALOGPS
logP8.82ChemAxon
logS-5.1ALOGPS
pKa (strongest acidic)11.7ChemAxon
pKa (strongest basic)-3.5ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count18ChemAxon
hydrogen donor count12ChemAxon
polar surface area315.88ChemAxon
rotatable bond count48ChemAxon
refractivity310.92ChemAxon
polarizability140.48ChemAxon
Spectra
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
METLIN ID7154
PubChem Compound22833622
PDB IDNot Available
ChEBI IDNot Available
References
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. Pubmed: 16521125

Enzymes

Gene Name:
NEU2
Uniprot ID:
Q9Y3R4
Gene Name:
NEU4
Uniprot ID:
Q8WWR8
Gene Name:
LCT
Uniprot ID:
P09848
Gene Name:
GLB1
Uniprot ID:
P16278
Gene Name:
HEXB
Uniprot ID:
P07686
Gene Name:
HEXA
Uniprot ID:
P06865
Gene Name:
GM2A
Uniprot ID:
P17900
Gene Name:
NEU1
Uniprot ID:
Q5JQI0