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Record Information
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-03-13 21:15:59 UTC
Secondary Accession Numbers
  • HMDB04855
Metabolite Identification
Common NameGanglioside GM1 (18:1/16:0)
DescriptionGanglioside GM1 (18:1/16:0) 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 GM1 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.
1-O-[O-(N-Acetyl-a-neuraminosyl)-(2->3)-O-[O-b-D galactopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-b-D-galactopyranosyl-(1->4)]-O-b-D-galactopyranosyl-(1->4)-b-D-glucopyranosyl]-ceramideHMDB
1-O-[O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-[O-beta-D galactopyranosyl-(1->3)-2-(acetylamino)-2-deoxy-beta-delta-galactopyranosyl-(1->4)]-O-beta-delta-galactopyranosyl-(1->4)-beta-delta-glucopyranosyl]-ceramideHMDB
D-Galactosyl-1,3-beta-N-acetyl-D galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-D-glucosyl-nacylsphingosineHMDB
D-Galactosyl-N-acetyl-D galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-D-glucosylceramideHMDB
delta-Galactosyl-1,3-beta-N-acetyl-D galactosaminyl-(N-acetylneuraminyl)-delta-galactosyl-delta-glucosyl-nacylsphingosineHMDB
delta-Galactosyl-N-acetyl-D galactosaminyl-(N-acetylneuraminyl)-delta-galactosyl-delta-glucosylceramideHMDB
Ganglioside GM1HMDB
N-Acetyl-ganglioside GM1HMDB
N-Acetylganglioside GM1HMDB
Chemical FormulaC71H127N3O31
Average Molecular Weight1518.7696
Monoisotopic Molecular Weight1517.845354361
IUPAC Name(2S,4S,5R)-5-acetamido-2-{[(2R,3S,4R,5R,6S)-3-{[(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}-6-{[(2R,3S,4R,6R)-6-{[(2S,3R,4E)-2-hexadecanamido-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-[(1S,2S)-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-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-{[(2R,3S,4R,6R)-6-{[(2S,3R,4E)-2-hexadecanamido-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-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
CAS Registry NumberNot Available
InChI Identifier
Chemical Taxonomy
DescriptionThis compound 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
Sub ClassGlycosphingolipids
Direct ParentGalNAcb1-4Galb1-4Glc- (Ganglio series)
Alternative Parents
  • Galnacb1-4galb1-4glcb-cer_backbone
  • Neuaca2-3galb1-4glcb-cer_backbone
  • Glycosyl-n-acylsphingosine
  • Oligosaccharide
  • N-acylneuraminic acid or derivatives
  • N-acylneuraminic acid
  • Neuraminic acid
  • Fatty acyl glycoside
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Oxane
  • Pyran
  • Acetamide
  • Secondary alcohol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic oxide
  • Primary alcohol
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available

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Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0Not Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.28 g/LALOGPS
pKa (Strongest Acidic)2.8ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count31ChemAxon
Hydrogen Donor Count20ChemAxon
Polar Surface Area540.58 ŲChemAxon
Rotatable Bond Count50ChemAxon
Refractivity366.8 m³·mol⁻¹ChemAxon
Polarizability165.5 ųChemAxon
Number of Rings5ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Location
  • Brain
  • Fibroblasts
  • Myelin
  • Nerve Cells
PathwaysNot Available
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
FoodDB IDFDB023456
KNApSAcK IDNot Available
Chemspider ID16744872
KEGG Compound IDC04911
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20057296
PDB IDNot Available
ChEBI IDNot Available
Synthesis ReferenceMikhalyov, I. I.; Molotkovsky, Jul. G. Synthesis and characteristics of fluorescent BODIPY-labeled gangliosides. Russian Journal of Bioorganic Chemistry (Translation of Bioorganicheskaya Khimiya) (2003), 29(2), 168-174.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
  2. Rost KL, Brockmoller J, Weber W, Roots I: Multiple-dose pharmacokinetics of ganglioside GM1 after intravenous and intramuscular administration to healthy volunteers. Clin Pharmacol Ther. 1991 Aug;50(2):141-9. [PubMed:1868675 ]
  3. Takaura N, Yagi T, Maeda M, Nanba E, Oshima A, Suzuki Y, Yamano T, Tanaka A: Attenuation of ganglioside GM1 accumulation in the brain of GM1 gangliosidosis mice by neonatal intravenous gene transfer. Gene Ther. 2003 Aug;10(17):1487-93. [PubMed:12900764 ]
  4. Cacic M: Gangliosides of anencephalic and fetal brain--immunostaining on thin-layer chromatograms. Neuroreport. 1995 Jan 26;6(2):389-93. [PubMed:7538811 ]
  5. Mellgren SI: [Peripheral neuropathies]. Tidsskr Nor Laegeforen. 1995 May 30;115(14):1735-8. [PubMed:7785034 ]
  6. Sadeghlar F, Remmel N, Breiden B, Klingenstein R, Schwarzmann G, Sandhoff K: Physiological relevance of sphingolipid activator proteins in cultured human fibroblasts. Biochimie. 2003 Mar-Apr;85(3-4):439-48. [PubMed:12770782 ]
  7. Blennow K, Wallin A: Clinical heterogeneity of probable Alzheimer's disease. J Geriatr Psychiatry Neurol. 1992 Apr-Jun;5(2):106-13. [PubMed:1590911 ]
  8. Vogel A, Furst W, Abo-Hashish MA, Lee-Vaupel M, Conzelmann E, Sandhoff K: Identity of the activator proteins for the enzymatic hydrolysis of sulfatide, ganglioside GM1, and globotriaosylceramide. Arch Biochem Biophys. 1987 Dec;259(2):627-38. [PubMed:3426245 ]
  9. Gregson NA, Koblar S, Hughes RA: Antibodies to gangliosides in Guillain-Barre syndrome: specificity and relationship to clinical features. Q J Med. 1993 Feb;86(2):111-7. [PubMed:8464986 ]
  10. 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 ]
  11. Avrova NF, Zakharova IO, Tyurin VA, Tyurina YY, Gamaley IA, Schepetkin IA: Different metabolic effects of ganglioside GM1 in brain synaptosomes and phagocytic cells. Neurochem Res. 2002 Aug;27(7-8):751-9. [PubMed:12374210 ]

Only showing the first 10 proteins. There are 52 proteins in total.


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:
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Molecular weight:
General function:
Involved in exo-alpha-sialidase activity
Specific function:
Hydrolyzes sialylated compounds.
Gene Name:
Uniprot ID:
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:
Uniprot ID:
Molecular weight:
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:
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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:
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Molecular weight:
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:
Uniprot ID:
Molecular weight:
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:
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:
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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
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
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Molecular weight:

Only showing the first 10 proteins. There are 52 proteins in total.