| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:13:26 -0700 |
| HMDB ID |
HMDB04851 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Ganglioside GM3 (d18:1/24:0) |
| Description |
Ganglioside GM3 (d18:1/24:0) 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 GM3 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 tissuesGangliosides 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. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (N-Acetylneuraminyl)-D-galactosyl-D-glucosylceramide
- (N-Acetylneuraminyl)-delta-galactosyl-delta-glucosylceramide
- alpha-N-Acetylneuraminyl-2,3-beta-D-galactosyl-1,4-beta-D-glucosylceramide
- alpha-N-Acetylneuraminyl-2,3-beta-delta-galactosyl-1,4-beta-delta-glucosylceramide
- Ganglioside GM3
- Ganglioside M3
- GLac1
- GM3
- Hematoside
- N-Acetylneuraminyl-2,3-alpha-D-galactosyl-1,4-beta-D-glucosylceramide
- N-Acetylneuraminyl-2,3-alpha-delta-galactosyl-1,4-beta-delta-glucosylceramide
- Neu5Ac-alpha2->3Gal-beta1->4Glc-beta1->1'Cer
- Sialosyllactosylceramide
|
| Chemical Formula |
C65H120N2O21 |
| Average Molecular Weight |
1265.6491 |
| Monoisotopic Molecular Weight |
1264.838358912 |
| IUPAC Name |
(2S,4S,5R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-tetracosanamidooctadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
| Traditional IUPAC Name |
(2S,4S,5R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,6R)-4,5-dihydroxy-6-{[(2S,3R,4E)-3-hydroxy-2-tetracosanamidooctadec-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydrox |
| CAS Registry Number |
54827-14-4 |
| SMILES |
CCCCCCCCCCCCCCCCCCCCCCCC(=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](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)C1O)[C@H](O)\C=C\CCCCCCCCCCCCC |
| InChI Identifier |
InChI=1S/C65H120N2O21/c1-4-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-29-31-33-35-37-39-52(75)67-46(47(72)38-36-34-32-30-28-26-17-15-13-11-9-7-5-2)44-83-62-57(79)56(78)59(51(43-70)85-62)86-63-58(80)61(55(77)50(42-69)84-63)88-65(64(81)82)40-48(73)53(66-45(3)71)60(87-65)54(76)49(74)41-68/h36,38,46-51,53-63,68-70,72-74,76-80H,4-35,37,39-44H2,1-3H3,(H,66,71)(H,67,75)(H,81,82)/b38-36+/t46-,47+,48-,49+,50+,51+,53+,54+,55-,56+,57?,58+,59+,60?,61-,62+,63-,65-/m0/s1 |
| InChI Key |
JUZJEIYRVNAPCT-MVZMHTFCSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Sphingolipids |
| Sub Class |
Gangliosides |
| Other Descriptors |
- Aliphatic Heteropolycyclic Compounds
|
| Substituents |
- 1,2 Diol
- 1,3 Aminoalcohol
- Acetal
- Alkyl Glycoside
- Allyl Alcohol
- Carboxamide Group
- Carboxylic Acid
- Ceramide
- Fatty Acyl Glycoside
- Glyco Amino Acid
- Glycosyl Compound
- Hexose Trisaccharide
- N Acetylneuraminic Acid
- N Acyl Amine
- Neuraminic Acid
- O Glycosyl Compound
- Oxane
- Primary Alcohol
- Pyranoid Amino Acid
- Saccharide
- Secondary Alcohol
- Secondary Carboxylic Acid Amide
- Simple Glycosylsphingosine
- Sugar Acid
|
| Direct Parent |
Gangliosides |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Membrane component
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Insoluble |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
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| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
Not Available
|
| Tissue Location |
- Fibroblasts
- Testes
- Brain
- Myelin
- Adrenal Gland
- Stratum Corneum
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB023452 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
16744868  |
| KEGG Compound ID |
C04730 |
| BioCyc ID |
ACETYLNEURAMINYL-ETCETERA-GLUCOS |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB04851 |
| Metagene Link |
HMDB04851 |
| METLIN ID |
7110 |
| PubChem Compound |
20057292 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- Ishii A, Ohta M, Watanabe Y, Matsuda K, Ishiyama K, Sakoe K, Nakamura M, Inokuchi J, Sanai Y, Saito M: Expression cloning and functional characterization of human cDNA for ganglioside GM3 synthase. J Biol Chem. 1998 Nov 27;273(48):31652-5.
Pubmed: 9822625
- Toledo MS, Suzuki E, Handa K, Hakomori S: Effect of ganglioside and tetraspanins in microdomains on interaction of integrins with fibroblast growth factor receptor. J Biol Chem. 2005 Apr 22;280(16):16227-34. Epub 2005 Feb 14.
Pubmed: 15710618
- Caudie C, Vial C, Petiot P, Bancel J, Lombard C, Gonnaud PM: [Monoclonal IgM autoantibody activity vis-a-vis glycoconjugates of peripheral nerves: apropos of 112 cases] Ann Biol Clin (Paris). 2001 Sep-Oct;59(5):567-77.
Pubmed: 11602387
- Paller AS, Siegel JN, Spalding DE, Bremer EG: Absence of a stratum corneum antigen in disorders of epidermal cell proliferation: detection with an anti-ganglioside GM3 antibody. J Invest Dermatol. 1989 Feb;92(2):240-6.
Pubmed: 2645370
- Dawson G: Glycosphingolipid levels in an unusual neurovisceral storage disease characterized by lactosylceramide galactosyl hydrolase deficiency: lactosylceramidosis. J Lipid Res. 1972 Mar;13(2):207-19.
Pubmed: 5016302
- Schriever F, Dennis RD, Pallmann B, Riethmuller G, Johnson JP: Monoclonal antibody MACG1 distinguishes between different molecular species of the ganglioside GM3. Hybridoma. 1989 Apr;8(2):153-9.
Pubmed: 2714813
- Valaperta R, Chigorno V, Basso L, Prinetti A, Bresciani R, Preti A, Miyagi T, Sonnino S: Plasma membrane production of ceramide from ganglioside GM3 in human fibroblasts. FASEB J. 2006 Jun;20(8):1227-9. Epub 2006 Apr 27.
Pubmed: 16645048
|
| Enzymes |
|---|
| Name: |
Sialidase-2
|
| Reactions: |
- Hydrolysis of alpha-(2->3)-, alpha-(2->6)-, alpha-(2->8)- glycosidic linkages of terminal sialic acid residues in oligosaccharides, glycoproteins, glycolipids, colominic acid and synthetic substrates ALL_REAC (other) R03491 R04018 R04634 R04650 R05115 R05117 R05996(G) R05998(G) R05999(G) R06012(G) R06147(G) R06253(G) INHIBITOR 2-Deoxy-2,3-dehydro-N-acetylneuraminic acid [CPD:C04580]
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| Gene Name: |
NEU2 |
| Uniprot ID: |
Q9Y3R4 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Sialidase-4
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| Reactions: |
- Hydrolysis of alpha-(2->3)-, alpha-(2->6)-, alpha-(2->8)- glycosidic linkages of terminal sialic acid residues in oligosaccharides, glycoproteins, glycolipids, colominic acid and synthetic substrates ALL_REAC (other) R03491 R04018 R04634 R04650 R05115 R05117 R05996(G) R05998(G) R05999(G) R06012(G) R06147(G) R06253(G) INHIBITOR 2-Deoxy-2,3-dehydro-N-acetylneuraminic acid [CPD:C04580]
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| Gene Name: |
NEU4 |
| Uniprot ID: |
Q8WWR8 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Lactosylceramide alpha-2,3-sialyltransferase
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| Reactions: |
- CMP-N-acetylneuraminate + beta-D-galactosyl-(1->4)-beta-D-glucosyl-(11)-ceramide = CMP + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D- glucosyl-(11)-ceramide [RN:R03488 R05937]
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| Gene Name: |
ST3GAL5 |
| Uniprot ID: |
Q9UNP4 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Beta-hexosaminidase subunit beta
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| Reactions: |
- Hydrolysis of terminal non-reducing N-acetyl-D-hexosamine residues in N-acetyl-beta-D-hexosaminides ALL_REAC (other) R00022 R03492 R04184 R04586 R05963(G) R06001(G) R06004(G) R06141(G) R07809(G) R07810(G)
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| Gene Name: |
HEXB |
| Uniprot ID: |
P07686 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Beta-hexosaminidase subunit alpha
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| Reactions: |
- Hydrolysis of terminal non-reducing N-acetyl-D-hexosamine residues in N-acetyl-beta-D-hexosaminides ALL_REAC (other) R00022 R03492 R04184 R04586 R05963(G) R06001(G) R06004(G) R06141(G) R07809(G) R07810(G)
|
| Gene Name: |
HEXA |
| Uniprot ID: |
P06865 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Beta-1,4 N-acetylgalactosaminyltransferase 1
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| Reactions: |
- UDP-N-acetyl-D-galactosamine + 1-O-[O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D- galactopyranosyl-(1->4)-beta-D-glucopyranosyl]-ceramide = UDP + 1-O-[O-2-(acetylamino)-2-deoxy-beta-D-galactopyranosyl-(1->4)-O-[N- acetyl-alpha-neuraminosyl-(2->3)]-O-beta-D-galactopyranosyl-(1->4)- beta-D-glucopyranosyl]-ceramide [RN:R04584 R05939]
|
| Gene Name: |
B4GALNT1 |
| Uniprot ID: |
Q00973 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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