| 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 19:02:45 UTC |
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| HMDB ID | HMDB0004906 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Ganglioside GA1 (d18:1/24:1(15Z)) |
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| Description | Ganglioside GA1 (d18:1/24:1(15Z)) 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 GA1 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@H]2O)[C@H](O)C1O)NC(=O)CCCCCCCCCCCCC\C=C/CCCCCCCC InChI=1S/C68H124N2O23/c1-4-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-29-31-33-35-37-39-52(77)70-46(47(76)38-36-34-32-30-28-26-17-15-13-11-9-7-5-2)44-86-66-60(84)57(81)63(50(42-73)89-66)92-68-61(85)58(82)62(51(43-74)90-68)91-65-53(69-45(3)75)64(55(79)49(41-72)87-65)93-67-59(83)56(80)54(78)48(40-71)88-67/h18-19,36,38,46-51,53-68,71-74,76,78-85H,4-17,20-35,37,39-44H2,1-3H3,(H,69,75)(H,70,77)/b19-18-,38-36+/t46-,47+,48+,49+,50+,51+,53+,54-,55-,56-,57+,58+,59+,60?,61+,62-,63+,64+,65-,66+,67-,68-/m0/s1 |
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| Synonyms | | Value | Source |
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| (15Z)-N-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-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-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracos-15-enimidate | HMDB | | Asialo ganglioside GM1a | HMDB | | Asialo GM1 | HMDB | | Asialo GM1 ganglioside | HMDB | | Asialoganglioside g(m1) from bovine brain | HMDB | | Asialoganglioside GM1 | HMDB | | Asialoganglioside GT1b | HMDB | | GA1 | HMDB | | Gal-beta1->3galnac-beta1->4gal-beta1->4GLC-beta1->1'cer | HMDB | | Gal-beta1->3galnac-beta1->4gal-beta1->4GLC-beta1->1'cer(D18:1/24:1 | HMDB | | Ganglio-N-tetraosylceramide | HMDB | | Ganglioside ga1 | HMDB | | Gangliotetraosylceramide | HMDB |
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| Chemical Formula | C68H124N2O23 |
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| Average Molecular Weight | 1337.7118 |
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| Monoisotopic Molecular Weight | 1336.859488284 |
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| IUPAC Name | (15Z)-N-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-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}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracos-15-enamide |
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| Traditional Name | (15Z)-N-[(2S,3R,4E)-1-{[(2R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-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}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracos-15-enamide |
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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@H]2O)[C@H](O)C1O)NC(=O)CCCCCCCCCCCCC\C=C/CCCCCCCC |
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| InChI Identifier | InChI=1S/C68H124N2O23/c1-4-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-29-31-33-35-37-39-52(77)70-46(47(76)38-36-34-32-30-28-26-17-15-13-11-9-7-5-2)44-86-66-60(84)57(81)63(50(42-73)89-66)92-68-61(85)58(82)62(51(43-74)90-68)91-65-53(69-45(3)75)64(55(79)49(41-72)87-65)93-67-59(83)56(80)54(78)48(40-71)88-67/h18-19,36,38,46-51,53-68,71-74,76,78-85H,4-17,20-35,37,39-44H2,1-3H3,(H,69,75)(H,70,77)/b19-18-,38-36+/t46-,47+,48+,49+,50+,51+,53+,54-,55-,56-,57+,58+,59+,60?,61+,62-,63+,64+,65-,66+,67-,68-/m0/s1 |
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| InChI Key | HVSCPOORNCFFOM-FLSKXLKNSA-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
- Glycosyl-n-acylsphingosine
- Oligosaccharide
- Fatty acyl glycoside
- N-acyl-alpha-hexosamine
- Alkyl glycoside
- Glycosyl compound
- O-glycosyl compound
- Fatty amide
- N-acyl-amine
- Oxane
- Fatty acyl
- Acetamide
- Secondary alcohol
- Secondary carboxylic acid amide
- Carboxamide group
- Polyol
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Acetal
- Primary alcohol
- Alcohol
- Organopnictogen compound
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Carbonyl group
- Organooxygen compound
- Organic nitrogen 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 | 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 Collision Cross SectionsPredicted Kovats Retention IndicesNot Available |
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| General References | - Nobile-Orazio E, Manfredini E, Carpo M, Meucci N, Monaco S, Ferrari S, Bonetti B, Cavaletti G, Gemignani F, Durelli L, et al.: Frequency and clinical correlates of anti-neural IgM antibodies in neuropathy associated with IgM monoclonal gammopathy. Ann Neurol. 1994 Sep;36(3):416-24. [PubMed:8080249 ]
- Ledvinova J, Poupetova H, Hanackova A, Pisacka M, Elleder M: Blood group B glycosphingolipids in alpha-galactosidase deficiency (Fabry disease): influence of secretor status. Biochim Biophys Acta. 1997 Apr 1;1345(2):180-7. [PubMed:9106497 ]
- 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 ]
- Ogawa-Goto K, Ohta Y, Kubota K, Funamoto N, Abe T, Taki T, Nagashima K: Glycosphingolipids of human peripheral nervous system myelins isolated from cauda equina. J Neurochem. 1993 Oct;61(4):1398-403. [PubMed:7690848 ]
- Habu S, Fukui H, Shimamura K, Kasai M, Nagai Y, Okumura K, Tamaoki N: In vivo effects of anti-asialo GM1. I. Reduction of NK activity and enhancement of transplanted tumor growth in nude mice. J Immunol. 1981 Jul;127(1):34-8. [PubMed:7240748 ]
- Nakamura K, Hashimoto Y, Suzuki M, Suzuki A, Yamakawa T: Characterization of GM1b in mouse spleen. J Biochem. 1984 Oct;96(4):949-57. [PubMed:6520127 ]
- Shpitz B, Chambers CA, Singhal AB, Hozumi N, Fernandes BJ, Roifman CM, Weiner LM, Roder JC, Gallinger S: High level functional engraftment of severe combined immunodeficient mice with human peripheral blood lymphocytes following pretreatment with radiation and anti-asialo GM1. J Immunol Methods. 1994 Feb 28;169(1):1-15. [PubMed:7907638 ]
- Dasgupta S, Hogan EL, Spicer SS: Stage-specific expression of fuco-neolacto- (Lewis X) and ganglio-series neutral glycosphingolipids during brain development: characterization of Lewis X and related glycosphingolipids in bovine, human and rat brain. Glycoconj J. 1996 Jun;13(3):367-75. [PubMed:8781967 ]
- Okamoto M, Kaji R, Kasetani H, Yoshida H, Moriya Y, Saito M, Sato M: Purification and characterization of interferon-gamma-inducing molecule of OK-432, a penicillin-killed streptococcal preparation, by monoclonal antibody neutralizing interferon-gamma-inducing activity of OK-432. J Immunother Emphasis Tumor Immunol. 1993 May 4;13(4):232-42. [PubMed:8334107 ]
- Yoshimura M, Ihara Y, Ohnishi A, Ijuhin N, Nishiura T, Kanakura Y, Matsuzawa Y, Taniguchi N: Bisecting N-acetylglucosamine on K562 cells suppresses natural killer cytotoxicity and promotes spleen colonization. Cancer Res. 1996 Jan 15;56(2):412-8. [PubMed:8542600 ]
- Yuki N, Yanagisawa K, Saito Y, Aikawa M, Miyatake T: [Proximal lower motor neuron syndrome associated with serum antibodies to asialo-GM1, GM1 and LM1]. Rinsho Shinkeigaku. 1993 Aug;33(8):891-4. [PubMed:8261703 ]
- Gori AH, Ahmed K, Martinez G, Masaki H, Watanabe K, Nagatake T: Mediation of attachment of Burkholderia pseudomallei to human pharyngeal epithelial cells by the asialoganglioside GM1-GM2 receptor complex. Am J Trop Med Hyg. 1999 Sep;61(3):473-5. [PubMed:10497993 ]
- Chaouat G, Tranchot Diallo J, Volumenie JL, Menu E, Gras G, Delage G, Mognetti B: Immune suppression and Th1/Th2 balance in pregnancy revisited: a (very) personal tribute to Tom Wegmann. Am J Reprod Immunol. 1997 Jun;37(6):427-34. [PubMed:9228297 ]
- Ito M, Hiramatsu H, Kobayashi K, Suzue K, Kawahata M, Hioki K, Ueyama Y, Koyanagi Y, Sugamura K, Tsuji K, Heike T, Nakahata T: NOD/SCID/gamma(c)(null) mouse: an excellent recipient mouse model for engraftment of human cells. Blood. 2002 Nov 1;100(9):3175-82. [PubMed:12384415 ]
- Fujiwara S, Hashiba H, Hirota T, Forstner JF: Purification and characterization of a novel protein produced by Bifidobacterium longum SBT2928 that inhibits the binding of enterotoxigenic Escherichia coli Pb176 (CFA/II) to gangliotetraosylceramide. J Appl Microbiol. 1999 Apr;86(4):615-21. [PubMed:10212407 ]
- Vukelic Z, Metelmann W, Muthing J, Kos M, Peter-Katalinic J: Anencephaly: structural characterization of gangliosides in defined brain regions. Biol Chem. 2001 Feb;382(2):259-74. [PubMed:11308024 ]
- Okamoto M, Gohda H, Ohe G, Yoshida H, Matsuno T, Saito M, Sato M: Cytokine-inducing activity and antitumor effect of a liposome-incorporated interferon-gamma-inducing molecule derived from OK-432, a streptococcal preparation. J Immunother. 2000 Jan;23(1):94-103. [PubMed:10687142 ]
- Imundo L, Barasch J, Prince A, Al-Awqati Q: Cystic fibrosis epithelial cells have a receptor for pathogenic bacteria on their apical surface. Proc Natl Acad Sci U S A. 1995 Mar 28;92(7):3019-23. [PubMed:7708767 ]
- (). Imundo, L., Barasch, J., Prince, A., Al-Awqati, Q. Cystic fibrosis epithelial cells have a receptor for pathogenic bacteria on their apical surface. Proceedings of the National Academy of Sciences of the United States of America (1995), 92(7), 3019-23. .
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