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Human Metabolome Database Version 3.5

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Showing metabocard for Ganglioside GA1 (d18:1/26:1(17Z)) (HMDB04907)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:13:33 -0700
HMDB ID HMDB04907
Secondary Accession Numbers None
Metabolite Identification
Common Name Ganglioside GA1 (d18:1/26:1(17Z))
Description Ganglioside GA1 (d18:1/26:1(17Z)) 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 GA1 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 ganglioside GM1a
  2. Asialo GM1
  3. Asialo GM1 ganglioside
  4. Asialoganglioside G(M1) from bovine brain
  5. Asialoganglioside GM1
  6. Asialoganglioside GT1b
  7. GA1
  8. Gal-beta1->3GalNAc-beta1->4Gal-beta1->4Glc-beta1->1'Cer
  9. Gal-beta1->3GalNAc-beta1->4Gal-beta1->4Glc-beta1->1'Cer(d18:1/26:1
  10. Ganglio-N-tetraosylceramide
  11. Ganglioside GA1
  12. Gangliotetraosylceramide
Chemical Formula C70H128N2O23
Average Molecular Weight 1365.7649
Monoisotopic Molecular Weight 1364.890788412
IUPAC Name (17Z)-N-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-5-{[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}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]hexacos-17-enamide
Traditional IUPAC Name (17Z)-N-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-5-{[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-d
CAS Registry Number 71012-19-6
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]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H]3NC(C)=O)[C@H](O)[C@H]2O)[C@H](O)C1O)NC(=O)CCCCCCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier InChI=1S/C70H128N2O23/c1-4-6-8-10-12-14-16-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-41-54(79)72-48(49(78)40-38-36-34-32-30-28-17-15-13-11-9-7-5-2)46-88-68-62(86)59(83)65(52(44-75)91-68)94-70-63(87)60(84)64(53(45-76)92-70)93-67-55(71-47(3)77)66(57(81)51(43-74)89-67)95-69-61(85)58(82)56(80)50(42-73)90-69/h18-19,38,40,48-53,55-70,73-76,78,80-87H,4-17,20-37,39,41-46H2,1-3H3,(H,71,77)(H,72,79)/b19-18-,40-38+/t48-,49+,50+,51+,52+,53+,55+,56-,57-,58-,59+,60+,61+,62?,63+,64-,65+,66+,67-,68+,69-,70-/m0/s1
InChI Key IUMXYENFRLYSPF-HDWONUQSSA-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 Tetrasaccharide
  • 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 0.015 g/L ALOGPS
LogP 5.22 ALOGPS
LogP 7.58 ChemAxon
LogS -4.95 ALOGPS
pKa (strongest acidic) 11.61 ChemAxon
pKa (strongest basic) -3.6 ChemAxon
Hydrogen Acceptor Count 23 ChemAxon
Hydrogen Donor Count 15 ChemAxon
Polar Surface Area 395.03 A2 ChemAxon
Rotatable Bond Count 52 ChemAxon
Refractivity 353.66 ChemAxon
Polarizability 157.81 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location
  • Placenta
  • Brain
  • Nerve Cells
  • Spleen
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 FDB023498
KNApSAcK ID Not Available
Chemspider ID 17216298 Link_out
KEGG Compound ID C06136 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04907 Link_out
Metagene Link HMDB04907 Link_out
METLIN ID 7163 Link_out
PubChem Compound 22833631 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. Habu S, Fukui H, Shimamura K, Kasai M, Nagai Y, Okumura K, Tamaoki N: In vivo effects of anti-asialo GM1. I. Reduction of NK activity and enhancement of transplanted tumor growth in nude mice. J Immunol. 1981 Jul;127(1):34-8. Pubmed: 7240748 Link_out
  2. Nakamura K, Hashimoto Y, Suzuki M, Suzuki A, Yamakawa T: Characterization of GM1b in mouse spleen. J Biochem (Tokyo). 1984 Oct;96(4):949-57. Pubmed: 6520127 Link_out
  3. Nobile-Orazio E, Manfredini E, Carpo M, Meucci N, Monaco S, Ferrari S, Bonetti B, Cavaletti G, Gemignani F, Durelli L, et al.: Frequency and clinical correlates of anti-neural IgM antibodies in neuropathy associated with IgM monoclonal gammopathy. Ann Neurol. 1994 Sep;36(3):416-24. Pubmed: 8080249 Link_out
  4. Shpitz B, Chambers CA, Singhal AB, Hozumi N, Fernandes BJ, Roifman CM, Weiner LM, Roder JC, Gallinger S: High level functional engraftment of severe combined immunodeficient mice with human peripheral blood lymphocytes following pretreatment with radiation and anti-asialo GM1. J Immunol Methods. 1994 Feb 28;169(1):1-15. Pubmed: 7907638 Link_out
  5. Dasgupta S, Hogan EL, Spicer SS: Stage-specific expression of fuco-neolacto- (Lewis X) and ganglio-series neutral glycosphingolipids during brain development: characterization of Lewis X and related glycosphingolipids in bovine, human and rat brain. Glycoconj J. 1996 Jun;13(3):367-75. Pubmed: 8781967 Link_out
  6. Okamoto M, Kaji R, Kasetani H, Yoshida H, Moriya Y, Saito M, Sato M: Purification and characterization of interferon-gamma-inducing molecule of OK-432, a penicillin-killed streptococcal preparation, by monoclonal antibody neutralizing interferon-gamma-inducing activity of OK-432. J Immunother. 1993 May 4;13(4):232-42. Pubmed: 8334107 Link_out
  7. Ledvinova J, Poupetova H, Hanackova A, Pisacka M, Elleder M: Blood group B glycosphingolipids in alpha-galactosidase deficiency (Fabry disease): influence of secretor status. Biochim Biophys Acta. 1997 Apr 1;1345(2):180-7. Pubmed: 9106497 Link_out
  8. Yoshimura M, Ihara Y, Ohnishi A, Ijuhin N, Nishiura T, Kanakura Y, Matsuzawa Y, Taniguchi N: Bisecting N-acetylglucosamine on K562 cells suppresses natural killer cytotoxicity and promotes spleen colonization. Cancer Res. 1996 Jan 15;56(2):412-8. Pubmed: 8542600 Link_out
  9. Yuki N, Yanagisawa K, Saito Y, Aikawa M, Miyatake T: [Proximal lower motor neuron syndrome associated with serum antibodies to asialo-GM1, GM1 and LM1] Rinsho Shinkeigaku. 1993 Aug;33(8):891-4. Pubmed: 8261703 Link_out
  10. Gori AH, Ahmed K, Martinez G, Masaki H, Watanabe K, Nagatake T: Mediation of attachment of Burkholderia pseudomallei to human pharyngeal epithelial cells by the asialoganglioside GM1-GM2 receptor complex. Am J Trop Med Hyg. 1999 Sep;61(3):473-5. Pubmed: 10497993 Link_out
  11. Imundo L, Barasch J, Prince A, Al-Awqati Q: Cystic fibrosis epithelial cells have a receptor for pathogenic bacteria on their apical surface. Proc Natl Acad Sci U S A. 1995 Mar 28;92(7):3019-23. Pubmed: 7708767 Link_out
  12. Chaouat G, Tranchot Diallo J, Volumenie JL, Menu E, Gras G, Delage G, Mognetti B: Immune suppression and Th1/Th2 balance in pregnancy revisited: a (very) personal tribute to Tom Wegmann. Am J Reprod Immunol. 1997 Jun;37(6):427-34. Pubmed: 9228297 Link_out
  13. Ogawa-Goto K, Ohta Y, Kubota K, Funamoto N, Abe T, Taki T, Nagashima K: Glycosphingolipids of human peripheral nervous system myelins isolated from cauda equina. J Neurochem. 1993 Oct;61(4):1398-403. Pubmed: 7690848 Link_out
  14. Ito M, Hiramatsu H, Kobayashi K, Suzue K, Kawahata M, Hioki K, Ueyama Y, Koyanagi Y, Sugamura K, Tsuji K, Heike T, Nakahata T: NOD/SCID/gamma(c)(null) mouse: an excellent recipient mouse model for engraftment of human cells. Blood. 2002 Nov 1;100(9):3175-82. Pubmed: 12384415 Link_out
  15. Fujiwara S, Hashiba H, Hirota T, Forstner JF: Purification and characterization of a novel protein produced by Bifidobacterium longum SBT2928 that inhibits the binding of enterotoxigenic Escherichia coli Pb176 (CFA/II) to gangliotetraosylceramide. J Appl Microbiol. 1999 Apr;86(4):615-21. Pubmed: 10212407 Link_out
  16. Vukelic Z, Metelmann W, Muthing J, Kos M, Peter-Katalinic J: Anencephaly: structural characterization of gangliosides in defined brain regions. Biol Chem. 2001 Feb;382(2):259-74. Pubmed: 11308024 Link_out
  17. Matsuda J, Suzuki O, Oshima A, Ogura A, Noguchi Y, Yamamoto Y, Asano T, Takimoto K, Sukegawa K, Suzuki Y, Naiki M: Beta-galactosidase-deficient mouse as an animal model for GM1-gangliosidosis. Glycoconj J. 1997 Sep;14(6):729-36. Pubmed: 9337086 Link_out
  18. Okamoto M, Gohda H, Ohe G, Yoshida H, Matsuno T, Saito M, Sato M: Cytokine-inducing activity and antitumor effect of a liposome-incorporated interferon-gamma-inducing molecule derived from OK-432, a streptococcal preparation. J Immunother. 2000 Jan;23(1):94-103. Pubmed: 10687142 Link_out
  19. Imundo, L., Barasch, J., Prince, A., Al-Awqati, Q. Cystic fibrosis epithelial cells have a receptor for pathogenic bacteria on their apical surface. Proceedings of the National Academy of Sciences of the United States of America (1995), 92(7), 3019-23
Enzymes
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