Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 06:38:07 UTC |
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Update Date | 2016-11-09 01:21:22 UTC |
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Accession Number | CHEM035797 |
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Identification |
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Common Name | Ganglioside GM2 (d18:1/16:0) |
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Class | Small Molecule |
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Description | |
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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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(2S,4S,5R)-2-{[(2R,3S,4R,5R,6S)-3-{[(2S,3R,4R,5R,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-[(1-hydroxyhexadecylidene)amino]octadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate | HMDB | GalNAc-beta1->4(neu5ac-alpha2->3)gal-beta1->4GLC-beta1->1'cer | HMDB | Ganglioside GM2 | HMDB | GM2 | HMDB | II3neuacggose3cer | HMDB | N-Acetyl-D-galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-1,4-beta-D-glucosyl-N-acylsphingosine | HMDB | N-Acetyl-D-galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-D-glucosylceramide | HMDB | N-Acetyl-delta-galactosaminyl-(N-acetylneuraminyl)-delta-galactosyl-1,4-beta-delta-glucosyl-N-acylsphingosine | HMDB | N-Acetyl-delta-galactosaminyl-(N-acetylneuraminyl)-delta-galactosyl-delta-glucosylceramide | HMDB | N-Acetyl-ganglioside GM2 | HMDB | N-Acetylganglioside GM2 | HMDB | NeuAc-GM2 | HMDB | Tay-sachs ganglioside | HMDB |
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Chemical Formula | C65H117N3O26 |
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Average Molecular Mass | 1356.629 g/mol |
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Monoisotopic Mass | 1355.793 g/mol |
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CAS Registry Number | Not Available |
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IUPAC Name | (2S,4S,5R)-5-acetamido-2-{[(2R,3S,4R,5R,6S)-3-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,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-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
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Traditional Name | (2S,4S,5R)-5-acetamido-2-{[(2R,3S,4R,5R,6S)-3-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,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-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
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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]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)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C65H117N3O26/c1-5-7-9-11-13-15-17-19-21-23-25-27-29-31-42(75)41(68-48(78)32-30-28-26-24-22-20-18-16-14-12-10-8-6-2)38-87-62-55(83)54(82)57(46(36-71)89-62)91-63-56(84)60(58(47(37-72)90-63)92-61-50(67-40(4)74)53(81)52(80)45(35-70)88-61)94-65(64(85)86)33-43(76)49(66-39(3)73)59(93-65)51(79)44(77)34-69/h29,31,41-47,49-63,69-72,75-77,79-84H,5-28,30,32-38H2,1-4H3,(H,66,73)(H,67,74)(H,68,78)(H,85,86)/b31-29+/t41-,42+,43-,44+,45+,46+,47+,49+,50+,51+,52-,53+,54+,55+,56+,57+,58-,59?,60+,61-,62+,63-,65-/m0/s1 |
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InChI Key | DQWHBRCKOXYCIY-QTUBRTPCSA-N |
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Chemical Taxonomy |
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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
- 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
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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 LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-6098000000-c587fd7994e92764b993 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0f89-3093002000-45035c62f7cb374ce6ef | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fl3-3191010100-504172675733a9e09b2f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0pi9-1139052000-9bd5526a64f3a02c6e2d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0adi-2295037000-dcc984abdc04fb6587ed | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pb9-1291210000-1c05389a47270ea96484 | 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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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0004938 |
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FooDB ID | FDB023526 |
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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 | CPD-1100 |
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METLIN ID | 7191 |
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PDB ID | Not Available |
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Wikipedia Link | Not Available |
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Chemspider ID | 16744924 |
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ChEBI ID | Not Available |
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PubChem Compound ID | 20057334 |
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Kegg Compound ID | C04884 |
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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. Okada N, Wu X, Mizokami M, Irie RF, Okada H: Human IgM monoclonal antibody to ganglioside GM2 and complement suppress virus propagation in ex vivo cultures of lymphocytes from HIV-1 infected patients. Microbiol Immunol. 1999;43(7):723-7. | 2. De Vriese SR, Matthys C, De Henauw S, De Backer G, Dhont M, Christophe AB: Maternal and umbilical fatty acid status in relation to maternal diet. Prostaglandins Leukot Essent Fatty Acids. 2002 Dec;67(6):389-96. | 3. Denny CA, Kasperzyk JL, Gorham KN, Bronson RT, Seyfried TN: Influence of caloric restriction on motor behavior, longevity, and brain lipid composition in Sandhoff disease mice. J Neurosci Res. 2006 May 1;83(6):1028-38. |
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