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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-11-30 19:02:46 UTC
HMDB IDHMDB0004944
Secondary Accession Numbers
  • HMDB04944
Metabolite Identification
Common NameGanglioside GM2 (d18:1/26:0)
DescriptionGanglioside GM2 (d18:1/26:0) 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 GM2 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. G(M2) Ganglioside accumulates due to a deficiency of hexosaminidase A or B (beta-N-acetylhexosaminidase), or GM2 activator protein, resulting in Gangliosidoses. Gangliosidoses include heredity metabolic disorders that include Tay-Sachs disease and Sandhoff disease. Gangliosides GM2 is especially common in the nervous tissue of the brain. In the United States, about 1 in 27 to 1 in 30 Ashkenazi Jews is a recessive carrier. French Canadians and the Cajun community of Louisiana have an occurrence similar to the Ashkenazi Jews.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
Data?1582752332
Synonyms
ValueSource
(2S,4S,5R)-2-{[(2R,3S,4R,5R,6S)-3-{[(2S,3R,4R,5R,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-[(1-hydroxyhexacosylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateHMDB
GalNAc-beta1->4(neu5ac-alpha2->3)gal-beta1->4GLC-beta1->1'cerHMDB
Ganglioside GM2HMDB
GM2HMDB
II3neuacggose3cerHMDB
N-Acetyl-D-galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-1,4-beta-D-glucosyl-N-acylsphingosineHMDB
N-Acetyl-D-galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-D-glucosylceramideHMDB
N-Acetyl-delta-galactosaminyl-(N-acetylneuraminyl)-delta-galactosyl-1,4-beta-delta-glucosyl-N-acylsphingosineHMDB
N-Acetyl-delta-galactosaminyl-(N-acetylneuraminyl)-delta-galactosyl-delta-glucosylceramideHMDB
N-Acetyl-ganglioside GM2HMDB
N-Acetylganglioside GM2HMDB
NeuAc-GM2HMDB
Tay-sachs gangliosideHMDB
Chemical FormulaC75H137N3O26
Average Molecular Weight1496.8948
Monoisotopic Molecular Weight1495.949031571
IUPAC Name(2S,4S,5R)-5-acetamido-2-{[(2R,3S,4R,5R,6S)-3-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-6-{[(2S,3R,4E)-2-hexacosanamido-3-hydroxyoctadec-4-en-1-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2S,4S,5R)-5-acetamido-2-{[(2R,3S,4R,5R,6S)-3-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-6-{[(2S,3R,4E)-2-hexacosanamido-3-hydroxyoctadec-4-en-1-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCCCCCC(=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@@]3(C[C@H](O)[C@@H](NC(C)=O)C(O3)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]2O)[C@H](O)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C75H137N3O26/c1-5-7-9-11-13-15-17-19-20-21-22-23-24-25-26-27-28-30-32-34-36-38-40-42-58(88)78-51(52(85)41-39-37-35-33-31-29-18-16-14-12-10-8-6-2)48-97-72-65(93)64(92)67(56(46-81)99-72)101-73-66(94)70(68(57(47-82)100-73)102-71-60(77-50(4)84)63(91)62(90)55(45-80)98-71)104-75(74(95)96)43-53(86)59(76-49(3)83)69(103-75)61(89)54(87)44-79/h39,41,51-57,59-73,79-82,85-87,89-94H,5-38,40,42-48H2,1-4H3,(H,76,83)(H,77,84)(H,78,88)(H,95,96)/b41-39+/t51-,52+,53-,54+,55+,56+,57+,59+,60+,61+,62-,63+,64+,65+,66+,67+,68-,69?,70+,71-,72+,73-,75-/m0/s1
InChI KeyMSUCTRZPJLOZLE-KKBFWMGOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassCeramides
Direct ParentCeramides
Alternative Parents
Substituents
  • Ceramide
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0Not Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP4.27ALOGPS
logP7.31ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)2.8ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count26ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area461.43 ŲChemAxon
Rotatable Bond Count57ChemAxon
Refractivity380.4 m³·mol⁻¹ChemAxon
Polarizability171.9 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GM2 (d18:1/26:0) 10V, Positive-QTOFsplash10-01ti-0210901030-98119b84d884fb97f7d72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GM2 (d18:1/26:0) 20V, Positive-QTOFsplash10-000i-3941103060-cdbd75e1d5c3342b3ffa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GM2 (d18:1/26:0) 40V, Positive-QTOFsplash10-03dl-4777812091-93d6c495b0f3b4b103af2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GM2 (d18:1/26:0) 10V, Negative-QTOFsplash10-00di-2946800020-45840894feab5caa36c42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GM2 (d18:1/26:0) 20V, Negative-QTOFsplash10-0550-9575501030-ff99dac94d142d2843db2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GM2 (d18:1/26:0) 40V, Negative-QTOFsplash10-0a4i-9355000010-a7609659d30d5e97c0f22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GM2 (d18:1/26:0) 10V, Positive-QTOFsplash10-0gxw-1240907010-5b54d87dccaae8800e442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GM2 (d18:1/26:0) 20V, Positive-QTOFsplash10-00fr-1181519020-20a3f8ef7b13d0c9be972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GM2 (d18:1/26:0) 40V, Positive-QTOFsplash10-0ka2-2092402000-33a2e5744398f07806cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GM2 (d18:1/26:0) 10V, Negative-QTOFsplash10-0006-5050900000-edeadddb6223d04c94172021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GM2 (d18:1/26:0) 20V, Negative-QTOFsplash10-008c-2091702020-95bb39d787f0c0dac73d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GM2 (d18:1/26:0) 40V, Negative-QTOFsplash10-00dl-4193201110-785e04792158ac6dcca52021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Breast Milk
Tissue Locations
  • Brain
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Breast MilkDetected and Quantified0.1738168 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023532
KNApSAcK IDNot Available
Chemspider ID16744930
KEGG Compound IDC04884
BioCyc IDCPD-1100
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20057340
PDB IDNot Available
ChEBI ID89635
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Okada N, Wu X, Mizokami M, Irie RF, Okada H: Human IgM monoclonal antibody to ganglioside GM2 and complement suppress virus propagation in ex vivo cultures of lymphocytes from HIV-1 infected patients. Microbiol Immunol. 1999;43(7):723-7. [PubMed:10529115 ]
  2. De Vriese SR, Matthys C, De Henauw S, De Backer G, Dhont M, Christophe AB: Maternal and umbilical fatty acid status in relation to maternal diet. Prostaglandins Leukot Essent Fatty Acids. 2002 Dec;67(6):389-96. [PubMed:12468259 ]
  3. 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 ]

Only showing the first 10 proteins. There are 53 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:
Hydrolyzes sialylated compounds.
Gene Name:
NEU2
Uniprot ID:
Q9Y3R4
Molecular weight:
Not Available
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 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:
NEU4
Uniprot ID:
Q8WWR8
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:
LCT
Uniprot ID:
P09848
Molecular weight:
218584.77
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 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:
GLB1
Uniprot ID:
P16278
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:
HEXB
Uniprot ID:
P07686
Molecular weight:
Not Available

Only showing the first 10 proteins. There are 53 proteins in total.