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Human Metabolome Database Version 3.5

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Showing metabocard for Ganglioside GA2 (d18:1/9Z-18:1) (HMDB04889)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:13:30 -0700
HMDB ID HMDB04889
Secondary Accession Numbers None
Metabolite Identification
Common Name Ganglioside GA2 (d18:1/9Z-18:1)
Description Ganglioside GA2 (d18:1/9Z-18:1) 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C56H102N2O18
Average Molecular Weight 1091.4117
Monoisotopic Molecular Weight 1090.71276447
IUPAC Name (9Z)-N-[(2S,3R,4E)-1-{[(2R,3R,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]octadec-9-enamide
Traditional IUPAC Name (9Z)-N-[(2S,3R,4E)-1-{[(2R,3R,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
CAS Registry Number 88506-68-7
SMILES CCCCCCCCCCCCC\C=C\[C@@H](O)[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)[C@H]1O)NC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier InChI=1S/C56H102N2O18/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-44(64)58-39(40(63)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)37-71-55-50(69)48(67)53(42(35-60)73-55)76-56-51(70)49(68)52(43(36-61)74-56)75-54-45(57-38(3)62)47(66)46(65)41(34-59)72-54/h18-19,30,32,39-43,45-56,59-61,63,65-70H,4-17,20-29,31,33-37H2,1-3H3,(H,57,62)(H,58,64)/b19-18-,32-30+/t39-,40+,41+,42+,43+,45+,46-,47+,48+,49+,50+,51+,52-,53+,54-,55+,56-/m0/s1
InChI Key SUEZBAAUECMPJR-MQILXBOASA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Sphingolipids
Sub Class Neutral 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 Parent Arthro and Ganglio series
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Insoluble Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.017 g/L ALOGPS
LogP 5.00 ALOGPS
LogP 5.79 ChemAxon
LogS -4.80 ALOGPS
pKa (strongest acidic) 11.7 ChemAxon
pKa (strongest basic) -3.5 ChemAxon
Hydrogen Acceptor Count 18 ChemAxon
Hydrogen Donor Count 12 ChemAxon
Polar Surface Area 315.88 A2 ChemAxon
Rotatable Bond Count 41 ChemAxon
Refractivity 284.44 ChemAxon
Polarizability 124.8 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location
  • Brain
  • Nerve Cells
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023481
KNApSAcK ID Not Available
Chemspider ID 13628423 Link_out
KEGG Compound ID C06135 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04889 Link_out
Metagene Link HMDB04889 Link_out
METLIN ID 7146 Link_out
PubChem Compound 21252325 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not 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 Link_out
Enzymes
Name: Sialidase-2
Reactions:
  • Hydrolysis of alpha-(2->3)-, alpha-(2->6)-, alpha-(2->8)- glycosidic linkages of terminal sialic acid residues in oligosaccharides, glycoproteins, glycolipids, colominic acid and synthetic substrates ALL_REAC (other) R03491 R04018 R04634 R04650 R05115 R05117 R05996(G) R05998(G) R05999(G) R06012(G) R06147(G) R06253(G) INHIBITOR 2-Deoxy-2,3-dehydro-N-acetylneuraminic acid [CPD:C04580]
Gene Name: NEU2
Uniprot ID: Q9Y3R4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sialidase-4
Reactions:
  • Hydrolysis of alpha-(2->3)-, alpha-(2->6)-, alpha-(2->8)- glycosidic linkages of terminal sialic acid residues in oligosaccharides, glycoproteins, glycolipids, colominic acid and synthetic substrates ALL_REAC (other) R03491 R04018 R04634 R04650 R05115 R05117 R05996(G) R05998(G) R05999(G) R06012(G) R06147(G) R06253(G) INHIBITOR 2-Deoxy-2,3-dehydro-N-acetylneuraminic acid [CPD:C04580]
Gene Name: NEU4
Uniprot ID: Q8WWR8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lactase-phlorizin hydrolase
Reactions:
  • lactose + H2O = D-galactose + D-glucose [RN:R01100 R06114]
Gene Name: LCT
Uniprot ID: P09848 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lactosylceramide alpha-2,3-sialyltransferase
Reactions:
  • CMP-N-acetylneuraminate + beta-D-galactosyl-(1->4)-beta-D-glucosyl-(11)-ceramide = CMP + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D- glucosyl-(11)-ceramide [RN:R03488 R05937]
Gene Name: ST3GAL5
Uniprot ID: Q9UNP4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-galactosidase
Reactions:
  • Hydrolysis of terminal non-reducing beta-D-galactose residues in beta-D-galactosides ALL_REAC (other) R01100 R01105 R01678 R03355 R04633 R04783 R05112 R05994(G) R06010(G) R06098(G) R06099(G) R06114(G) R06144(G) R06202(G) R07807(G)
Gene Name: GLB1
Uniprot ID: P16278 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-hexosaminidase subunit beta
Reactions:
  • Hydrolysis of terminal non-reducing N-acetyl-D-hexosamine residues in N-acetyl-beta-D-hexosaminides ALL_REAC (other) R00022 R03492 R04184 R04586 R05963(G) R06001(G) R06004(G) R06141(G) R07809(G) R07810(G)
Gene Name: HEXB
Uniprot ID: P07686 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-hexosaminidase subunit alpha
Reactions:
  • Hydrolysis of terminal non-reducing N-acetyl-D-hexosamine residues in N-acetyl-beta-D-hexosaminides ALL_REAC (other) R00022 R03492 R04184 R04586 R05963(G) R06001(G) R06004(G) R06141(G) R07809(G) R07810(G)
Gene Name: HEXA
Uniprot ID: P06865 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-1,4 N-acetylgalactosaminyltransferase 1
Reactions:
  • UDP-N-acetyl-D-galactosamine + 1-O-[O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D- galactopyranosyl-(1->4)-beta-D-glucopyranosyl]-ceramide = UDP + 1-O-[O-2-(acetylamino)-2-deoxy-beta-D-galactopyranosyl-(1->4)-O-[N- acetyl-alpha-neuraminosyl-(2->3)]-O-beta-D-galactopyranosyl-(1->4)- beta-D-glucopyranosyl]-ceramide [RN:R04584 R05939]
Gene Name: B4GALNT1
Uniprot ID: Q00973 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ganglioside GM2 activator
Reactions:
    Gene Name: GM2A
    Uniprot ID: P17900 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NEU1 protein
    Reactions:
      Gene Name: NEU1
      Uniprot ID: Q5JQI0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA