| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-09-21 01:47:42 UTC |
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| Update date | 2015-07-21 06:59:35 UTC |
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| Primary ID | FDB028940 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | 3-O-Sulfogalactosylceramide (d18:1/24:1(15Z)) |
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| 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). [HMDB] |
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| CAS Number | 151057-28-2 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C48H91NO11S |
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| IUPAC name | [(2R,5S,6R)-3,5-dihydroxy-2-{[(2S,3R)-3-hydroxy-2-(tetracos-15-enamido)octadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid |
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| InChI Identifier | InChI=1S/C48H91NO11S/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-44(52)49-41(42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2)40-58-48-46(54)47(60-61(55,56)57)45(53)43(39-50)59-48/h17-18,35,37,41-43,45-48,50-51,53-54H,3-16,19-34,36,38-40H2,1-2H3,(H,49,52)(H,55,56,57)/t41-,42+,43+,45-,46?,47?,48+/m0/s1 |
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| InChI Key | ZZQWQNAZXFNSEP-YZKNQZQMSA-N |
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| Isomeric SMILES | [H][C@@](CO[C@]1([H])O[C@]([H])(CO)[C@]([H])(O)C(OS(O)(=O)=O)C1O)(NC(=O)CCCCCCCCCCCCCC=CCCCCCCCC)[C@]([H])(O)C=CCCCCCCCCCCCCC |
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| Average Molecular Weight | 890.301 |
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| Monoisotopic Molecular Weight | 889.631283449 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as sulfatides. These are an hydrogen sulfate esters of glycosphingolipids. |
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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 | Sulfatides |
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| Alternative Parents | |
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| Substituents | - Sulfoglycosphingolipid
- Glycosyl-n-acylsphingosine
- Fatty acyl glycoside of mono- or disaccharide
- Fatty acyl glycoside
- Hexose monosaccharide
- Alkyl glycoside
- O-glycosyl compound
- Glycosyl compound
- Fatty acyl
- Sulfuric acid ester
- Alkyl sulfate
- Sulfate-ester
- Sulfuric acid monoester
- Oxane
- N-acyl-amine
- Monosaccharide
- Fatty amide
- Organic sulfuric acid or derivatives
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxamide group
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Acetal
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Alcohol
- 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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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | Not Available |
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| External Links |
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| ChemSpider ID | 24823257 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C06125 |
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| Pubchem Compound ID | 24779587 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB12318 |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Sulfatide |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | |
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