Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 05:21:54 UTC |
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Update Date | 2016-11-09 01:21:13 UTC |
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Accession Number | CHEM034954 |
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Identification |
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Common Name | N-Glycoloylganglioside GM2 |
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Class | Small Molecule |
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Description | 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 AII 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. [HMDB] |
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Contaminant Sources | |
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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Ganglioside aii | HMDB | N-Glycoloyl-ganglioside GM2 | HMDB | N-Glycoloyl-GM2 | HMDB | NeuGc-GM2 | HMDB | N-[(2S,3S)-3-Hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}nonadecan-2-yl]octadecanimidate | HMDB |
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Chemical Formula | C43H85NO8 |
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Average Molecular Mass | 744.137 g/mol |
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Monoisotopic Mass | 743.628 g/mol |
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CAS Registry Number | Not Available |
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IUPAC Name | N-[(2S,3S)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}nonadecan-2-yl]octadecanamide |
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Traditional Name | N-[(2S,3S)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}nonadecan-2-yl]octadecanamide |
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SMILES | CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@H](O)CCCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C43H85NO8/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-39(47)44-36(35-51-43-42(50)41(49)40(48)38(34-45)52-43)37(46)32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h36-38,40-43,45-46,48-50H,3-35H2,1-2H3,(H,44,47)/t36-,37-,38+,40+,41-,42+,43+/m0/s1 |
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InChI Key | SYMIJCRAJBNLEL-YPQBUIQASA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.g. S-,C-, or N-type) has been reported. |
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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 | Glycosphingolipids |
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Alternative Parents | |
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Substituents | - Glycosphingolipid
- Fatty acyl glycoside
- Fatty acyl glycoside of mono- or disaccharide
- Alkyl glycoside
- Hexose monosaccharide
- Glycosyl compound
- O-glycosyl compound
- Fatty amide
- Fatty acyl
- Monosaccharide
- N-acyl-amine
- Oxane
- Carboxamide group
- Secondary carboxylic acid amide
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Acetal
- Carboxylic acid derivative
- Polyol
- Organonitrogen compound
- Organopnictogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Organooxygen compound
- Primary alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive | Not Available | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0000000900-bee4faa9bf515e17d408 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-5110034900-2a1a5346081aa4105b58 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0pk9-9146020000-ab530060298036935dbb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-052f-7000050900-1218e90887b4b8572e2a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06r6-9110081500-7652a75532fc12dd16a0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9032010000-b4d90ec8bb1244b11d2a | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0000770 |
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FooDB ID | FDB022233 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | Not Available |
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METLIN ID | 5737 |
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PDB ID | GM2 |
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Wikipedia Link | Not Available |
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Chemspider ID | 393427 |
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ChEBI ID | Not Available |
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PubChem Compound ID | 445946 |
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Kegg Compound ID | C01808 |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. Schmidt, Richard; Castro-Palomino, Julio C.; Doll, Andreas; Ritter, Gerd; Old, Lloyd J. Preparation of ganglioside GM2. PCT Int. Appl. (1997), 27 pp. CODEN: PIXXD2 WO 9730061 A1 19970821 CAN 127:248363 AN 1997:568133 | 2. Cox EV, Robertson-Smith D, Small M, White AM: The excretion of propionate and acetate in vitamin B12 deficiency. Clin Sci. 1968 Aug;35(1):123-34. | 3. Hanibuchi M, Yano S, Nishioka Y, Yanagawa H, Kawano T, Sone S: Therapeutic efficacy of mouse-human chimeric anti-ganglioside GM2 monoclonal antibody against multiple organ micrometastases of human lung cancer in NK cell-depleted SCID mice. Int J Cancer. 1998 Nov 9;78(4):480-5. |
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