| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2009-04-30 03:39:38 -0600 |
| Update Date |
2013-02-08 17:28:47 -0700 |
| HMDB ID |
HMDB12317 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
3-O-Sulfogalactosylceramide (d18:1/18:1(9Z)) |
| Description |
3-O-Sulfogalactosylceramide is an acidic, sulfated glycosphingolipid, often known as sulfatide. This lipid occurs in membranes of various cell types, but is found in particularly high concentrations in myelin where it constitutes 3-4% of total membrane lipids. This lipid is synthesized primarily in the oligodendrocytes in the central nervous system. Accumulation of this lipid in the lysosomes is a characteristic of metachromatic leukodystrophy, a lysosomal storage disease caused by the deficiency of arylsulfatase A. Alterations in sulfatide metabolism, trafficking, and homeostasis are present in the earliest clinically recognizable stages of Alzheimer's disease.Cerebrosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Cerebrosides have a single sugar group linked to ceramide. The most common are galactocerebrosides (containing galactose), the least common are glucocerebrosides (containing glucose). Galactocerebrosides are found predominantly in neuronal cell membranes. In contrast glucocerebrosides are not normally found in membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. Galactocerebrosides are synthesized from ceramide and UDP-galactose. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease. Sulfatides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Sulfatides are the sulfuric acid esters of galactocerebrosides. They are synthesized from galactocerebrosides and activated sulfate, 3'-phosphoadenosine 5'-phosphosulfate (PAPS). |
| Structure |
Download:
MOL |
SDF |
PDB |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 3'-O-Sulphogalactosylceramide
- 3-O-Sulfo-beta-D-galactosylceramide
- 3-O-Sulfo-beta-delta-galactosylceramide
- 3-O-Sulfogalactosylceramide
- Cerebroside 3-sulfate
- Cerebroside 3-sulphate
- Galactosylceramide-sulfate
- Galactosylceramide-sulphate
- Galactosylceramidesulfate
- Galactosylceramidesulphate
- N-[(1S,2R,3E)-2-Hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-9-Octadecenamide
- N-[(1S,2R,3E)-2-Hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-9-Octadecenamide
- Sulfatide
- Sulfatide (d18:1/18:1(9Z))
- [R-[R*,S*-(E)]]-N-[2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-9-Octadecenamide
- [R-[R*,S*-(E)]]-N-[2-hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-9-Octadecenamide
|
| Chemical Formula |
C42H79NO11S |
| Average Molecular Weight |
806.142 |
| Monoisotopic Molecular Weight |
805.537383065 |
| IUPAC Name |
[(2R,5S,6R)-3,5-dihydroxy-2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-octadec-9-enamido]octadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid |
| Traditional IUPAC Name |
[(2R,5S,6R)-3,5-dihydroxy-2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-octadec-9-enamido]octadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid |
| CAS Registry Number |
Not Available |
| SMILES |
CCCCCCCCCCCCC\C=C\[C@](O)([H])[C@]([H])(CO[C@@H]1O[C@H](CO)[C@H](O)C(OS(=O)(O)=O)C1O)NC(=O)CCCCCCC\C=C/CCCCCCCC |
| InChI Identifier |
InChI=1S/C42H79NO11S/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-38(46)43-35(36(45)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)34-52-42-40(48)41(54-55(49,50)51)39(47)37(33-44)53-42/h17-18,29,31,35-37,39-42,44-45,47-48H,3-16,19-28,30,32-34H2,1-2H3,(H,43,46)(H,49,50,51)/b18-17-,31-29+/t35-,36+,37+,39-,40?,41?,42+/m0/s1 |
| InChI Key |
NXJDPFSYOMFVES-SUTPNROZSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Sphingolipids |
| Sub Class |
Sulfatides |
| Other Descriptors |
- Aliphatic Heteromonocyclic Compounds
|
| Substituents |
- Acetal
- Alkyl Glycoside
- Allyl Alcohol
- Carboxamide Group
- Ceramide
- Fatty Acyl Glycoside
- Glycosyl Compound
- Hexose Monosaccharide
- N Acyl Amine
- O Glycosyl Compound
- Organic Sulfuric Acid Monoester
- Oxane
- Primary Alcohol
- Saccharide
- Secondary Alcohol
- Secondary Carboxylic Acid Amide
- Sulfate Ester
|
| Direct Parent |
Sulfatides |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Component of Glycosphingolipid metabolism
- Fuel and energy storage
- Fuel or energy source
- 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 |
Not Available |
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 |
Not Available
|
| 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 |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB028939 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
Not Available |
| KEGG Compound ID |
C06125  |
| BioCyc ID |
GALACTOSYLCERAMIDE-SULFATE |
| BiGG ID |
Not Available |
| Wikipedia Link |
Sulfatide |
| NuGOwiki Link |
HMDB12317 |
| Metagene Link |
HMDB12317 |
| METLIN ID |
Not Available |
| PubChem Compound |
53481403 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
Not Available |
