Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:31:10 UTC |
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Update date | 2015-07-21 06:57:44 UTC |
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Primary ID | FDB023523 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Ganglioside GD2 (d18:1/25:0) |
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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 GD2 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. The GD2 ganglioside is a cell surface component that appears on the surface of metastatic melanoma cells and is a marker for the progression of the disease.(PubMed ID 9216084)
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. [HMDB] |
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CAS Number | Not Available |
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Structure | |
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Synonyms | Synonym | Source |
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Not Available | Not Available |
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Predicted Properties | |
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Chemical Formula | C85H152N4O34 |
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IUPAC name | (2S,4S,5R)-6-[(1S,2R)-2-{[(2S,4S,5R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-1,3-dihydroxypropyl]-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R)-3-hydroxy-2-pentacosanamidooctadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxyoxane-2-carboxylic acid |
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InChI Identifier | InChI=1S/C85H152N4O34/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-28-30-32-34-36-38-40-42-63(102)89-54(55(98)41-39-37-35-33-31-29-19-17-15-13-11-9-7-2)50-114-80-72(108)71(107)74(61(48-93)116-80)118-81-73(109)78(75(62(49-94)117-81)119-79-66(88-53(5)97)70(106)68(104)59(46-91)115-79)123-85(83(112)113)44-57(100)65(87-52(4)96)77(122-85)69(105)60(47-92)120-84(82(110)111)43-56(99)64(86-51(3)95)76(121-84)67(103)58(101)45-90/h39,41,54-62,64-81,90-94,98-101,103-109H,6-38,40,42-50H2,1-5H3,(H,86,95)(H,87,96)(H,88,97)(H,89,102)(H,110,111)(H,112,113)/t54-,55+,56-,57-,58+,59+,60+,61+,62+,64+,65+,66+,67+,68-,69+,70+,71+,72+,73+,74+,75-,76?,77?,78+,79-,80+,81-,84+,85-/m0/s1 |
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InChI Key | JBVRGVXYPMEGLV-MOHVIDLJSA-N |
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Isomeric SMILES | [H][C@@](O)(CO)[C@@]([H])(O)C1O[C@@](C[C@]([H])(O)[C@@]1([H])NC(C)=O)(O[C@]([H])(CO)[C@@]([H])(O)C1O[C@@](C[C@]([H])(O)[C@@]1([H])NC(C)=O)(O[C@]1([H])[C@@]([H])(O)[C@]([H])(O[C@]2([H])[C@@]([H])(CO)O[C@@]([H])(OC[C@]([H])(NC(=O)CCCCCCCCCCCCCCCCCCCCCCCC)[C@]([H])(O)C=CCCCCCCCCCCCCC)[C@]([H])(O)[C@@]2([H])O)O[C@]([H])(CO)[C@]1([H])O[C@]1([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])NC(C)=O)C(O)=O)C(O)=O |
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Average Molecular Weight | 1774.1228 |
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Monoisotopic Molecular Weight | 1773.028798032 |
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Classification |
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Description | 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. |
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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 | GalNAcb1-4Galb1-4Glc- (Ganglio series) |
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Alternative Parents | |
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Substituents | - 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
- Dicarboxylic acid or derivatives
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Oxane
- Pyran
- Acetamide
- Secondary alcohol
- Secondary carboxylic acid amide
- Carboxamide group
- Organoheterocyclic compound
- Polyol
- Oxacycle
- Carboxylic acid derivative
- Carboxylic acid
- Acetal
- Organonitrogen compound
- Organic oxide
- Alcohol
- Hydrocarbon derivative
- Carbonyl group
- Organooxygen compound
- Organic oxygen compound
- Organic nitrogen compound
- Primary alcohol
- Organopnictogen compound
- 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 | Organoleptic effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Not Available |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0uk9-0090000200-8b219e62fd394562d184 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01x0-1191302400-a446c34f93dfe332bd89 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00e9-4093407320-da9cac937a58c54a4de6 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0pi1-2031303913-d90ff9fb98bfe12af631 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05fr-4140117965-978e67f067f0a7ba8a33 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ukc-7792327701-802b9a5958b2d151fd05 | 2021-09-25 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 17216312 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 22833645 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB04934 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Ganglioside GM2 activator | GM2A | P17900 | N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase | PIGL | Q9Y2B2 | Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q | PIGQ | Q9BRB3 | Phosphatidylinositol N-acetylglucosaminyltransferase subunit A | PIGA | P37287 | Phosphatidylinositol N-acetylglucosaminyltransferase subunit H | PIGH | Q14442 | Phosphatidylinositol N-acetylglucosaminyltransferase subunit P | PIGP | P57054 | Phosphatidylinositol N-acetylglucosaminyltransferase subunit C | PIGC | Q92535 | T-cell surface glycoprotein CD1e, membrane-associated | CD1E | P15812 | Epididymal secretory protein E1 | NPC2 | P61916 | Antigen-presenting glycoprotein CD1d | CD1D | P15813 | GPI mannosyltransferase 1 | PIGM | Q9H3S5 | Phosphatidylinositol-glycan biosynthesis class W protein | PIGW | Q7Z7B1 | Phosphatidylinositol-glycan biosynthesis class X protein | PIGX | Q8TBF5 | GPI mannosyltransferase 4 | PIGZ | Q86VD9 | Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase | B3GNT5 | Q9BYG0 | Beta-1,3-galactosyltransferase 5 | B3GALT5 | Q9Y2C3 | GPI mannosyltransferase 3 | PIGB | Q92521 | Phosphatidylinositol-glycan biosynthesis class F protein | PIGF | Q07326 | GPI ethanolamine phosphate transferase 2 | PIGG | Q5H8A4 | GPI ethanolamine phosphate transferase 1 | PIGN | O95427 | GPI ethanolamine phosphate transferase 3 | PIGO | Q8TEQ8 | GPI transamidase component PIG-S | PIGS | Q96S52 | GPI transamidase component PIG-T | PIGT | Q969N2 | Phosphatidylinositol glycan anchor biosynthesis class U protein | PIGU | Q9H490 | GPI mannosyltransferase 2 | PIGV | Q9NUD9 | Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y | PIGY | Q3MUY2 | Non-lysosomal glucosylceramidase | GBA2 | Q9HCG7 | GPI-anchor transamidase | PIGK | Q92643 |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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