Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-07-24 17:55:36 UTC
HMDB IDHMDB04855
Secondary Accession NumbersNone
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.
Structure
Thumb
Synonyms
  1. 1-O-[O-(N-Acetyl-a-neuraminosyl)-(2)-O-[O-b-D-galactopyranosyl-(1)-2-(acetylamino)-2-deoxy-b-D-galactopyranosyl-(1)]-O-b-D-galactopyranosyl-(1)-b-D-glucopyranosyl]-Ceramide
  2. 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]-Ceramide
  3. 1-O-[O-(N-Acetyl-alpha-neuraminosyl)-(2)-O-[O-beta-delta-galactopyranosyl-(1)-2-(acetylamino)-2-deoxy-beta-delta-galactopyranosyl-(1)]-O-beta-delta-galactopyranosyl-(1)-beta-delta-glucopyranosyl]-Ceramide
  4. 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]-Ceramide
  5. D-Galactosyl-1,3-beta-N-acetyl-D galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-D-glucosyl-Nacylsphingosine
  6. D-Galactosyl-N-acetyl-D galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-D-glucosylceramide
  7. delta-Galactosyl-1,3-beta-N-acetyl-D galactosaminyl-(N-acetylneuraminyl)-delta-galactosyl-delta-glucosyl-Nacylsphingosine
  8. delta-Galactosyl-N-acetyl-D galactosaminyl-(N-acetylneuraminyl)-delta-galactosyl-delta-glucosylceramide
  9. Gal-beta1->3GalNAc-beta1->4(Neu5Ac-alpha2->3)Gal-beta1->4Glc-beta1->1'Cer
  10. Gal-beta1->3GalNAc-beta1->4(Neu5Ac-alpha2>3)Gal-beta1->4Glc-beta1->1'Cer
  11. Ganglioside GM1
  12. GM1
  13. GM1a
  14. II3NeuAcGgOse4Cer
  15. N-Acetyl-Ganglioside GM1
  16. N-Acetylganglioside GM1
  17. NeuAc-GM1a
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 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
CAS Registry Number104443-62-1
SMILES
CCCCCCCCCCCCCCCC(=O)N[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@@]3(C[C@H](O)[C@@H](NC(C)=O)C(O3)[C@@H](O)[C@@H](O)CO)C(O)=O)[C@H]2O)[C@H](O)C1O)[C@H](O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C71H127N3O31/c1-5-7-9-11-13-15-17-19-21-23-25-27-29-31-43(82)42(74-50(85)32-30-28-26-24-22-20-18-16-14-12-10-8-6-2)39-96-67-59(92)57(90)61(48(37-78)99-67)101-69-60(93)65(105-71(70(94)95)33-44(83)51(72-40(3)80)64(104-71)53(86)45(84)34-75)62(49(38-79)100-69)102-66-52(73-41(4)81)63(55(88)47(36-77)97-66)103-68-58(91)56(89)54(87)46(35-76)98-68/h29,31,42-49,51-69,75-79,82-84,86-93H,5-28,30,32-39H2,1-4H3,(H,72,80)(H,73,81)(H,74,85)(H,94,95)/b31-29+/t42-,43+,44-,45-,46+,47+,48+,49+,51+,52+,53-,54-,55-,56-,57+,58+,59?,60+,61+,62-,63+,64?,65+,66-,67+,68-,69-,71-/m0/s1
InChI KeyBWZAKDPPVXHOTB-TWDSFERASA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSphingolipids
Sub ClassNeutral Glycosphingolipids
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • Gangliosides
  • Hexose Oligosaccharides
Substituents
  • 1,2 Diol
  • 1,3 Aminoalcohol
  • Acetal
  • Alkyl Glycoside
  • Allyl Alcohol
  • Carboxamide Group
  • Carboxylic Acid
  • Ceramide
  • Fatty Acyl Glycoside
  • Glucosamine
  • Glyco Amino Acid
  • Glycosyl Compound
  • Mannosamine
  • N Acetylneuraminic Acid
  • N Acyl Amine
  • Neuraminic Acid
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Pyranoid Amino Acid
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Sugar Acid
Direct ParentArthro and Ganglio series
Ontology
StatusExpected 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityInsolubleNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.28 g/LALOGPS
logP1.73ALOGPS
logP1.09ChemAxon
logS-3.7ALOGPS
pKa (strongest acidic)2.8ChemAxon
pKa (strongest basic)-3.7ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count31ChemAxon
hydrogen donor count20ChemAxon
polar surface area540.58ChemAxon
rotatable bond count50ChemAxon
refractivity366.8ChemAxon
polarizability165.5ChemAxon
Spectra
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023456
KNApSAcK IDNot Available
Chemspider ID16744872
KEGG Compound IDC04911
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGM1
NuGOwiki LinkHMDB04855
Metagene LinkHMDB04855
METLIN IDNot Available
PubChem Compound20057296
PDB IDNot Available
ChEBI IDNot Available
References
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 50 proteins. There are 52 proteins in total.

Enzymes

Gene Name:
NEU2
Uniprot ID:
Q9Y3R4
Gene Name:
NEU3
Uniprot ID:
Q9UQ49
Gene Name:
NEU4
Uniprot ID:
Q8WWR8
Gene Name:
LCT
Uniprot ID:
P09848
Gene Name:
GLB1
Uniprot ID:
P16278
Gene Name:
B3GALT4
Uniprot ID:
O96024
Gene Name:
GM2A
Uniprot ID:
P17900
Gene Name:
NPC2
Uniprot ID:
P61916
Gene Name:
CD1D
Uniprot ID:
P15813
Gene Name:
PIGM
Uniprot ID:
Q9H3S5
Gene Name:
PIGZ
Uniprot ID:
Q86VD9
Gene Name:
B3GALT5
Uniprot ID:
Q9Y2C3
Gene Name:
PIGB
Uniprot ID:
Q92521
Gene Name:
PIGS
Uniprot ID:
Q96S52
Gene Name:
PIGT
Uniprot ID:
Q969N2
Gene Name:
PIGV
Uniprot ID:
Q9NUD9
Gene Name:
GBA2
Uniprot ID:
Q9HCG7
Gene Name:
NEU1
Uniprot ID:
Q5JQI0
Gene Name:
PIGK
Uniprot ID:
Q92643
Gene Name:
PLEKHA9
Uniprot ID:
O95397
Gene Name:
PLEKHA8
Uniprot ID:
B5MDU3
Gene Name:
CD1A
Uniprot ID:
P06126
Gene Name:
CD1C
Uniprot ID:
P29017
Gene Name:
LBP
Uniprot ID:
P18428
Gene Name:
DKFZp434L0435
Uniprot ID:
Q9UFH6

Only showing the first 50 proteins. There are 52 proteins in total.