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Record Information
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-11-30 19:02:45 UTC
Secondary Accession Numbers
  • HMDB04910
Metabolite Identification
Common NameGanglioside GA1 (d18:1/25:0)
DescriptionGanglioside GA1 (d18:1/25:0) 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 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.
Asialo ganglioside GM1aHMDB
Asialo GM1HMDB
Asialo GM1 gangliosideHMDB
Asialoganglioside g(m1) from bovine brainHMDB
Asialoganglioside GM1HMDB
Asialoganglioside GT1bHMDB
Ganglioside ga1HMDB
Chemical FormulaC69H128N2O23
Average Molecular Weight1353.7542
Monoisotopic Molecular Weight1352.890788412
IUPAC NameN-[(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]pentacosanamide
Traditional NameN-[(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]pentacosanamide
CAS Registry NumberNot Available
InChI Identifier
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gangliosides. These are lipid molecules composed of a glycosphingolipid (ceramide and saccharide) with one or more sialic acids linked on the sugar chain. They are usually oligoglycosylceramides derived from lactosylceramide and containing a sialic acid residue such as N-acetylneuraminic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
Sub ClassGlycosphingolipids
Direct ParentGangliosides
Alternative Parents
  • Neuaca2-3galb1-4glcb-cer_backbone
  • Glycosyl-n-acylsphingosine
  • Oligosaccharide
  • N-acylneuraminic acid or derivatives
  • N-acylneuraminic acid
  • Neuraminic acid
  • Fatty acyl glycoside
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Oxane
  • Pyran
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Organooxygen compound
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organopnictogen compound
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physiological effectNot Available
ProcessNot Available
RoleNot Available
Physical Properties
Experimental Molecular Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0Not Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Water Solubility0.018 g/LALOGPS
pKa (Strongest Acidic)11.61ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area395.03 ŲChemAxon
Rotatable Bond Count52ChemAxon
Refractivity347.94 m³·mol⁻¹ChemAxon
Polarizability157.33 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference

Predicted Kovats Retention Indices

Not Available

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GA1 (d18:1/25:0) 10V, Positive-QTOFsplash10-0gds-1109013010-b4e6dfeb79ebad8d491a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GA1 (d18:1/25:0) 20V, Positive-QTOFsplash10-000t-1319072020-2c9eaa8aa65737442be72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GA1 (d18:1/25:0) 40V, Positive-QTOFsplash10-02ai-7945023000-a1f7c7187cf36a6f266e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GA1 (d18:1/25:0) 10V, Negative-QTOFsplash10-0udi-0009000000-bbcbb89fa9f581ebe3422021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GA1 (d18:1/25:0) 20V, Negative-QTOFsplash10-0zi0-1159031021-e7e3d5081388bbd59c1d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ganglioside GA1 (d18:1/25:0) 40V, Negative-QTOFsplash10-014r-3296324031-f696f9c841ae3447c5e62021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue Locations
  • Brain
  • Neuron
  • Placenta
  • Spleen
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 IDFDB023501
KNApSAcK IDNot Available
Chemspider ID17216301
KEGG Compound IDC06136
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
PubChem Compound22833634
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Nakamura K, Hashimoto Y, Suzuki M, Suzuki A, Yamakawa T: Characterization of GM1b in mouse spleen. J Biochem. 1984 Oct;96(4):949-57. [PubMed:6520127 ]
  7. 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 ]
  8. 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 ]
  9. 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 Emphasis Tumor Immunol. 1993 May 4;13(4):232-42. [PubMed:8334107 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  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 ]
  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 ]
  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 ]
  17. 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 ]
  18. 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 ]
  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. .


General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
LPH splits lactose in the small intestine.
Gene Name:
Uniprot ID:
Molecular weight:
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:
Uniprot ID:
Molecular weight:
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:
Uniprot ID:
Molecular weight:
Not Available