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Showing Compound Ganglioside GM2 (d18:1/12:0) (FDB023524)

Record Information
Version1.0
Creation date2011-09-21 00:31:10 UTC
Update date2015-07-21 06:57:44 UTC
Primary IDFDB023524
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGanglioside GM2 (d18:1/12:0)
DescriptionA 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. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.078 g/LALOGPS
logP2.24ALOGPS
logP2.91ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.02ChemAxon
pKa (Strongest Basic)2.47ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count29ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area471.9 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity317.55 m³·mol⁻¹ChemAxon
Polarizability140.47 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC61H109N3O26
IUPAC name(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)-3-hydroxy-2-[(1-hydroxydodecylidene)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-carboxylic acid
InChI IdentifierInChI=1S/C61H109N3O26/c1-5-7-9-11-13-15-16-17-18-20-21-23-25-27-38(71)37(64-44(74)28-26-24-22-19-14-12-10-8-6-2)34-83-58-51(79)50(78)53(42(32-67)85-58)87-59-52(80)56(54(43(33-68)86-59)88-57-46(63-36(4)70)49(77)48(76)41(31-66)84-57)90-61(60(81)82)29-39(72)45(62-35(3)69)55(89-61)47(75)40(73)30-65/h25,27,37-43,45-59,65-68,71-73,75-80H,5-24,26,28-34H2,1-4H3,(H,62,69)(H,63,70)(H,64,74)(H,81,82)/t37-,38+,39-,40+,41+,42+,43+,45+,46+,47+,48-,49+,50+,51+,52+,53+,54-,55?,56+,57-,58+,59-,61-/m0/s1
InChI KeyUBCMQDIOEUZUPT-LSYNROPGSA-N
Isomeric SMILES[H][C@@](O)(CO)[C@@]([H])(O)C1O[C@@](C[C@]([H])(O)[C@@]1([H])NC(C)=O)(O[C@]1([H])[C@@]([H])(O)[C@]([H])(O[C@]2([H])[C@@]([H])(CO)O[C@@]([H])(OC[C@]([H])(NC(=O)CCCCCCCCCCC)[C@]([H])(O)C=CCCCCCCCCCCCCC)[C@]([H])(O)[C@@]2([H])O)O[C@]([H])(CO)[C@]1([H])O[C@]1([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])NC(C)=O)C(O)=O
Average Molecular Weight1300.5227
Monoisotopic Molecular Weight1299.729930675
Classification
Description 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
ClassSphingolipids
Sub ClassGlycosphingolipids
Direct ParentGalNAcb1-4Galb1-4Glc- (Ganglio series)
Alternative Parents
Substituents
  • Galnacb1-4galb1-4glcb-cer_backbone
  • Neuaca2-3galb1-4glcb-cer_backbone
  • Glycosyl-n-acylsphingosine
  • Oligosaccharide
  • N-acylneuraminic acid or derivatives
  • N-acylneuraminic acid
  • Neuraminic acid
  • N-acyl-alpha-hexosamine
  • Fatty acyl glycoside
  • C-glucuronide
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • C-glycosyl compound
  • Ketal
  • Fatty acyl
  • Pyran
  • Oxane
  • N-acyl-amine
  • Fatty amide
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • 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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
SpectraNot Available
ChemSpider ID16744922
ChEMBL IDNot Available
KEGG Compound IDC04884
Pubchem Compound ID20057332
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04936
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference