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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-04-22 23:31:01 UTC
HMDB IDHMDB0000770
Secondary Accession Numbers
  • HMDB00770
Metabolite Identification
Common NameN-Glycoloylganglioside GM2
DescriptionN-Glycoloylganglioside GM2 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 AII 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.
Structure
Data?1582752155
Synonyms
ValueSource
Ganglioside aiiHMDB
N-Glycoloyl-ganglioside GM2HMDB
N-Glycoloyl-GM2HMDB
NeuGc-GM2HMDB
N-[(2S,3S)-3-Hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}nonadecan-2-yl]octadecanimidateHMDB
Chemical FormulaC43H85NO8
Average Molecular Weight744.1369
Monoisotopic Molecular Weight743.627518701
IUPAC NameN-[(2S,3S)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}nonadecan-2-yl]octadecanamide
Traditional NameN-[(2S,3S)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}nonadecan-2-yl]octadecanamide
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@H](O)CCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C43H85NO8/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-39(47)44-36(35-51-43-42(50)41(49)40(48)38(34-45)52-43)37(46)32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h36-38,40-43,45-46,48-50H,3-35H2,1-2H3,(H,44,47)/t36-,37-,38+,40+,41-,42+,43+/m0/s1
InChI KeySYMIJCRAJBNLEL-YPQBUIQASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.g. S-,C-, or N-type) has been reported.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassGlycosphingolipids
Direct ParentGlycosphingolipids
Alternative Parents
Substituents
  • Glycosphingolipid
  • 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
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Polyol
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Organoleptic 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00051 g/LALOGPS
logP8.25ALOGPS
logP10.63ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)12.19ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area148.71 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity211.03 m³·mol⁻¹ChemAxon
Polarizability95.72 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue Locations
  • Brain
  • Neuron
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022233
KNApSAcK IDNot Available
Chemspider ID393427
KEGG Compound IDC01808
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5737
PubChem Compound445946
PDB IDGM2
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceSchmidt, Richard; Castro-Palomino, Julio C.; Doll, Andreas; Ritter, Gerd; Old, Lloyd J. Preparation of ganglioside GM2. PCT Int. Appl. (1997), 27 pp. CODEN: PIXXD2 WO 9730061 A1 19970821 CAN 127:248363 AN 1997:568133
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Cox EV, Robertson-Smith D, Small M, White AM: The excretion of propionate and acetate in vitamin B12 deficiency. Clin Sci. 1968 Aug;35(1):123-34. [PubMed:5679881 ]
  2. Hanibuchi M, Yano S, Nishioka Y, Yanagawa H, Kawano T, Sone S: Therapeutic efficacy of mouse-human chimeric anti-ganglioside GM2 monoclonal antibody against multiple organ micrometastases of human lung cancer in NK cell-depleted SCID mice. Int J Cancer. 1998 Nov 9;78(4):480-5. [PubMed:9797137 ]

Only showing the first 10 proteins. There are 46 proteins in total.

Enzymes

General function:
Involved in sialyltransferase activity
Specific function:
Involved in the production of gangliosides GD3 and GT3 from GM3; gangliosides are a subfamily of complex glycosphinglolipds that contain one or more residues of sialic acid.
Gene Name:
ST8SIA1
Uniprot ID:
Q92185
Molecular weight:
40518.655
General function:
Involved in exo-alpha-sialidase activity
Specific function:
Plays a role in modulating the ganglioside content of the lipid bilayer at the level of membrane-bound sialyl glycoconjugates
Gene Name:
NEU3
Uniprot ID:
Q9UQ49
Molecular weight:
48251.5
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Catalyzes the formation of some glycolipid via the addition of N-acetylgalactosamine (GalNAc) in alpha-1,3-linkage to some substrate. Glycolipids probably serve for adherence of some pathogens
Gene Name:
GBGT1
Uniprot ID:
Q8N5D6
Molecular weight:
40126.9
General function:
Involved in N-acetylglucosaminylphosphatidylinositol de
Specific function:
Involved in the second step of GPI biosynthesis. De-N-acetylation of N-acetylglucosaminyl-phosphatidylinositol.
Gene Name:
PIGL
Uniprot ID:
Q9Y2B2
Molecular weight:
28530.965
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:
ST3GAL5
Uniprot ID:
Q9UNP4
Molecular weight:
45584.69
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Involved in the biosynthesis of gangliosides GM2, GD2 and GA2.
Gene Name:
B4GALNT1
Uniprot ID:
Q00973
Molecular weight:
58881.78
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGQ
Uniprot ID:
Q9BRB3
Molecular weight:
65343.25
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 phosphatidylinositol N-acetylglucosaminyltr
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGH
Uniprot ID:
Q14442
Molecular weight:
21080.415
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGP
Uniprot ID:
P57054
Molecular weight:
18089.055

Only showing the first 10 proteins. There are 46 proteins in total.