Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-11-30 19:02:44 UTC |
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HMDB ID | HMDB0004854 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ganglioside GM1 (18:1/9Z-18:1) |
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Description | Ganglioside GM1 (18:1/9Z-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 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. |
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Structure | 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@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@H](O3)[C@@H](O)[C@@H](O)CO)C(O)=O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C73H129N3O31/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-52(87)76-44(45(84)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)41-98-69-61(94)59(92)63(50(39-80)101-69)103-71-62(95)67(107-73(72(96)97)35-46(85)53(74-42(3)82)66(106-73)55(88)47(86)36-77)64(51(40-81)102-71)104-68-54(75-43(4)83)65(57(90)49(38-79)99-68)105-70-60(93)58(91)56(89)48(37-78)100-70/h19-20,31,33,44-51,53-71,77-81,84-86,88-95H,5-18,21-30,32,34-41H2,1-4H3,(H,74,82)(H,75,83)(H,76,87)(H,96,97)/b20-19-,33-31-/t44-,45+,46+,47+,48-,49-,50-,51-,53-,54-,55+,56+,57+,58+,59-,60-,61-,62-,63-,64+,65-,66+,67-,68+,69-,70+,71+,73+/m1/s1 |
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Synonyms | Value | Source |
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(2S,4S,5R,6S)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4Z)-3-hydroxy-2-{[(9Z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3-hydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylate | HMDB | 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 | HMDB | 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 | HMDB | 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 | HMDB | 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 | HMDB | D-Galactosyl-1,3-beta-N-acetyl-D galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-D-glucosyl-nacylsphingosine | HMDB | D-Galactosyl-N-acetyl-D galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-D-glucosylceramide | HMDB | delta-Galactosyl-1,3-beta-N-acetyl-D galactosaminyl-(N-acetylneuraminyl)-delta-galactosyl-delta-glucosyl-nacylsphingosine | HMDB | delta-Galactosyl-N-acetyl-D galactosaminyl-(N-acetylneuraminyl)-delta-galactosyl-delta-glucosylceramide | HMDB | Gal-beta1->3galnac-beta1->4(neu5ac-alpha2->3)gal-beta1->4GLC-beta1->1'cer | HMDB | Gal-beta1->3galnac-beta1->4(neu5ac-alpha2>3)gal-beta1->4GLC-beta1->1'cer | HMDB | Ganglioside GM1 | HMDB | GM1 | HMDB | GM1a | HMDB | II3neuacggose4cer | HMDB | N-Acetyl-ganglioside GM1 | HMDB | N-Acetylganglioside GM1 | HMDB | NeuAc-GM1a | HMDB |
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Chemical Formula | C73H129N3O31 |
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Average Molecular Weight | 1544.8069 |
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Monoisotopic Molecular Weight | 1543.861004425 |
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IUPAC Name | (2S,4S,5R,6S)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4Z)-3-hydroxy-2-[(9Z)-octadec-9-enamido]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-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-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
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Traditional Name | (2S,4S,5R,6S)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4Z)-3-hydroxy-2-[(9Z)-octadec-9-enamido]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-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-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1S,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
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CAS Registry Number | Not Available |
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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@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@H](O3)[C@@H](O)[C@@H](O)CO)C(O)=O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCC\C=C/CCCCCCCC |
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InChI Identifier | InChI=1S/C73H129N3O31/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-52(87)76-44(45(84)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)41-98-69-61(94)59(92)63(50(39-80)101-69)103-71-62(95)67(107-73(72(96)97)35-46(85)53(74-42(3)82)66(106-73)55(88)47(86)36-77)64(51(40-81)102-71)104-68-54(75-43(4)83)65(57(90)49(38-79)99-68)105-70-60(93)58(91)56(89)48(37-78)100-70/h19-20,31,33,44-51,53-71,77-81,84-86,88-95H,5-18,21-30,32,34-41H2,1-4H3,(H,74,82)(H,75,83)(H,76,87)(H,96,97)/b20-19-,33-31-/t44-,45+,46+,47+,48-,49-,50-,51-,53-,54-,55+,56+,57+,58+,59-,60-,61-,62-,63-,64+,65-,66+,67-,68+,69-,70+,71+,73+/m1/s1 |
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InChI Key | GKNKBTFUDIUEPH-DAJNGDRVSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Sphingolipids |
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Sub Class | Glycosphingolipids |
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Direct Parent | Gangliosides |
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Alternative Parents | |
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Substituents | - 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
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Oxane
- Pyran
- Acetamide
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxamide group
- Polyol
- Carboxylic acid derivative
- Carboxylic acid
- Acetal
- Oxacycle
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Primary alcohol
- Hydrocarbon derivative
- Organic nitrogen compound
- Organopnictogen compound
- Alcohol
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0 | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Kovats Retention IndicesNot Available |
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General References | - 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 ]
- 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 ]
- 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 ]
- Cacic M: Gangliosides of anencephalic and fetal brain--immunostaining on thin-layer chromatograms. Neuroreport. 1995 Jan 26;6(2):389-93. [PubMed:7538811 ]
- Mellgren SI: [Peripheral neuropathies]. Tidsskr Nor Laegeforen. 1995 May 30;115(14):1735-8. [PubMed:7785034 ]
- 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 ]
- Blennow K, Wallin A: Clinical heterogeneity of probable Alzheimer's disease. J Geriatr Psychiatry Neurol. 1992 Apr-Jun;5(2):106-13. [PubMed:1590911 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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