Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-05-24 15:59:23 UTC |
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Update Date | 2021-09-14 15:18:07 UTC |
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HMDB ID | HMDB0006588 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Disialosyl galactosyl globoside |
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Description | Disialylgalactosylgloboside is a renal cell carcinoma (RCC)-associated antigen which mediates adhesion of RCC TOS-1 cells to certain lung tissue target cells. This adhesion process may initiate preferential lung metastasis of RCC (PMID: 10675485 ). Biosynthesis of disialylgalactosylgloboside (DSGG) is mediated by sialyltransferases from MSGG (monosialylgalactosylgloboside) (PMID: 17123352 ). Antidisialosyl antibodies have been found in some patients with chronic idiopathic ataxic neuropathy (CIAN) (PMID: 12420092 ). Globosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Globosides are cerebrosides that contain additional carbohydrates, predominantly galactose, glucose or GalNAc. Lactosyl ceramide is a globoside found in erythrocyte plasma membranes. Globotriaosylceramide (also called ceramide trihexoside) contains glucose and two moles of galactose and accumulates, primarily in the kidneys, of patients suffering from Fabry disease. |
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Structure | [H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O[C@@]2(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O2)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]1O)[C@@H](NC(C)=O)C=O)C(O)=O)[C@H](O)[C@H](O)CO InChI=1S/C36H59N3O27/c1-11(44)37-14(6-40)28(25(54)19(51)10-61-35(33(57)58)4-15(47)21(38-12(2)45)29(64-35)23(52)17(49)7-41)63-32-27(56)31(26(55)20(9-43)62-32)66-36(34(59)60)5-16(48)22(39-13(3)46)30(65-36)24(53)18(50)8-42/h6,14-32,41-43,47-56H,4-5,7-10H2,1-3H3,(H,37,44)(H,38,45)(H,39,46)(H,57,58)(H,59,60)/t14-,15-,16-,17+,18+,19+,20+,21+,22+,23+,24+,25-,26-,27+,28+,29+,30+,31-,32-,35+,36-/m0/s1 |
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Synonyms | Value | Source |
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Disialosylgalactosylgloboside | HMDB | DSGG | HMDB | Neuacalpha2-3galbeta1-3(neuacalpha2-6)galnac | HMDB | O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-[O-(N-acetyl-alpha-neuraminosyl)-(2->3)-beta-D-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-D-galactose | HMDB | O-(N-Acetyl-alpha-neuraminosyl)-(2->6)-O-[O-(N-acetyl-alpha-neuraminosyl)-(2->3)-beta-delta-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-delta-galactose | HMDB | Disialylgalactosylgloboside | MeSH, HMDB | (2R,4S,5R,6R)-2-{[(2R,3S,4R,5R)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroxy-5-[(1-hydroxyethylidene)amino]-6-oxohexyl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate | Generator, HMDB | Disialosyl galactosyl globoside | MeSH |
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Chemical Formula | C36H59N3O27 |
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Average Molecular Weight | 965.8576 |
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Monoisotopic Molecular Weight | 965.333593697 |
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IUPAC Name | (2R,4S,5R,6R)-2-{[(2R,3S,4R,5R)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-acetamido-2,3-dihydroxy-6-oxohexyl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
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Traditional Name | (2R,4S,5R,6R)-2-{[(2R,3S,4R,5R)-4-{[(2R,3R,4S,5S,6R)-4-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-acetamido-2,3-dihydroxy-6-oxohexyl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
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CAS Registry Number | 71764-07-3 |
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SMILES | [H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O[C@@]2(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O2)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]1O)[C@@H](NC(C)=O)C=O)C(O)=O)[C@H](O)[C@H](O)CO |
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InChI Identifier | InChI=1S/C36H59N3O27/c1-11(44)37-14(6-40)28(25(54)19(51)10-61-35(33(57)58)4-15(47)21(38-12(2)45)29(64-35)23(52)17(49)7-41)63-32-27(56)31(26(55)20(9-43)62-32)66-36(34(59)60)5-16(48)22(39-13(3)46)30(65-36)24(53)18(50)8-42/h6,14-32,41-43,47-56H,4-5,7-10H2,1-3H3,(H,37,44)(H,38,45)(H,39,46)(H,57,58)(H,59,60)/t14-,15-,16-,17+,18+,19+,20+,21+,22+,23+,24+,25-,26-,27+,28+,29+,30+,31-,32-,35+,36-/m0/s1 |
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InChI Key | SKJCZIMWAATHMG-CZYIXMLQSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | N-acylneuraminic acids |
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Alternative Parents | |
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Substituents | - N-acylneuraminic acid
- Neuraminic acid
- Fatty acyl glycoside of mono- or disaccharide
- Fatty acyl glycoside
- C-glucuronide
- Alkyl glycoside
- C-glycosyl compound
- O-glycosyl compound
- Glycosyl compound
- Ketal
- Amino saccharide
- Pyran
- Dicarboxylic acid or derivatives
- Oxane
- Monosaccharide
- Fatty acyl
- Acetamide
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxamide group
- Acetal
- Carboxylic acid derivative
- Carboxylic acid
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Alcohol
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Aldehyde
- Organic nitrogen compound
- Primary alcohol
- Organopnictogen compound
- Organonitrogen 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 | 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 | Not Available | 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 Collision Cross SectionsPredicted Kovats Retention IndicesNot Available |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 10V, Positive-QTOF | splash10-052b-0000213009-b5afc95a9679009dfda2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 20V, Positive-QTOF | splash10-0a59-2114119001-63997878e38b8b3b3d01 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 40V, Positive-QTOF | splash10-03di-7189436001-dfe5ac83e6e05b29f69f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 10V, Negative-QTOF | splash10-059w-1611010109-d42a43930e46c8838531 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 20V, Negative-QTOF | splash10-0a4i-6549111113-2e571a92e098b8650355 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 40V, Negative-QTOF | splash10-0a4i-7359121100-6c9aa0b6e112328fd50c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 10V, Positive-QTOF | splash10-014i-0000112009-acd1278d76e2cc2fd17a | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 20V, Positive-QTOF | splash10-0fmj-2551905328-68cf4bab4557987c3d4a | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 40V, Positive-QTOF | splash10-069r-9630400122-5157de188ab207e61199 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 10V, Negative-QTOF | splash10-08mr-9051000045-d1d82c4a04bb93693932 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 20V, Negative-QTOF | splash10-053r-5090000053-10f39d35d81f67abec31 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Disialosyl galactosyl globoside 40V, Negative-QTOF | splash10-0pdi-8791211231-90f6bc39ee21fec16646 | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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General References | - Senda M, Ito A, Tsuchida A, Hagiwara T, Kaneda T, Nakamura Y, Kasama K, Kiso M, Yoshikawa K, Katagiri Y, Ono Y, Ogiso M, Urano T, Furukawa K, Oshima S, Furukawa K: Identification and expression of a sialyltransferase responsible for the synthesis of disialylgalactosylgloboside in normal and malignant kidney cells: downregulation of ST6GalNAc VI in renal cancers. Biochem J. 2007 Mar 15;402(3):459-70. [PubMed:17123352 ]
- Satoh M, Nejad FM, Ohtani H, Ito A, Ohyama C, Saito S, Orikasa S, Hakomori S: Association of renal cell carcinoma antigen, disialylgalactosylgloboside, with c-Src and Rho A in clustered domains at the surface membrane. Int J Oncol. 2000 Mar;16(3):529-36. [PubMed:10675485 ]
- Serrano-Munuera C, Rojas-Garcia R, Gallardo E, De Luna N, Buenaventura I, Ferrero M, Garcia T, Garcia-Merino JA, Gonzalez-Rodriguez C, Guerriero A, Marco M, Marquez C, Grau JM, Graus F, Illa I: Antidisialosyl antibodies in chronic idiopathic ataxic neuropathy. J Neurol. 2002 Nov;249(11):1525-8. [PubMed:12420092 ]
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