Version |
1.0 |
Creation Date |
2005-11-16 15:48:42 |
Update Date |
2009-05-05 20:57:38 |
Accession Number |
BMDB00024 |
Common Name |
3-O-Sulfogalactosylceramide (d18:1/24:0) |
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). |
Synonyms |
- Sulfatide (d18:1/24:0)
- 3'-O-Sulphogalactosylceramide
- 3-O-Sulfogalactosylceramide
- 3-O-Sulphogalactosylceramide
- 3-O-sulfo-beta-D-galactosylceramide
- Cerebroside 3-sulfate
- Galactosylceramide-sulfate
- Galactosylceramidesulfate
- Sulfatide
- 3-O-sulfo-beta-delta-galactosylceramide
- N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-Tetracosanamide
- N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-Tetracosanamide
- [R-[R*,S*-(E)]]-N-[2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-Tetracosanamide
- N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-Tetracosanamide
- N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-Tetracosanamide
- [R-[R*,S*-(E)]]-N-[2-hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-Tetracosanamide
|
Chemical IUPAC Name |
[(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(tetracosanoylamino)octadec-4-enoxy]oxan-4-yl] hydrogen sulfate |
Chemical Formula |
C48H93NO11S |
Chemical Structure |
 |
Chemical Taxonomy |
Kingdom |
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Super Class |
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Class |
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Sub Class |
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Family |
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Species |
- acetal; primary alcohol; secondary alcohol; secondary carboxylic acid amide; sulfuric acid monoester; alkene; heterocyclic compound
|
Biofunction |
- Component of Glycosphingolipid metabolism
|
Application |
— |
Source |
|
|
Average Molecular Weight |
892.317 |
Monoisotopic Molecular Weight |
891.646912 |
Isomeric SMILES |
CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](OS(O)(=O)=O)[C@H]1O)[C@H](O)C=CCCCCCCCCCCCCC |
Canonical SMILES |
CCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(COC1OC(CO)C(O)C(OS(O)(=O)=O)C1O)C(O)C=CCCCCCCCCCCCCC |
KEGG Compound ID |
C06125  |
BioCyc ID |
GALACTOSYLCERAMIDE-SULFATE  |
BiGG ID |
Not Available |
Wikipedia Link |
Sulfatide  |
METLIN ID |
5096  |
PubChem Compound |
6451121  |
PubChem Substance |
10559604  |
ChEBI ID |
Not Available |
CAS Registry Number |
151122-71-3 |
InChI Identifier |
InChI=1/C48H93NO11S/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/h35,37,41-43,45-48,50-51,53-54H,3-34,36,38-40H2,1-2H3,(H,49,52)(H,55,56,57)/b37-35+/t41-,42+,43+,45-,46+,47-,48+/m0/s1 |
Synthesis Reference |
Hakomori, Senichiro; Ishimoda, Taiko; Nakamura, Kiyoshi. Separation and characterization of two sulfatides of brain. Journal of Biochemistry (Tokyo, Japan) (1962), 52 468-9. |
Melting Point (Experimental) |
Not Available |
Experimental Water Solubility |
Not Available
Source: PhysProp
|
Predicted Water Solubility |
2.09e-04 mg/mL [Predicted by ALOGPS]
Calculated using ALOGPS
|
Physiological Charge |
0 |
State |
Solid |
Experimental LogP/Hydrophobicity |
Not Available
Source: PhysProp
|
Predicted LogP/Hydrophobicity |
6.01 [Predicted by ALOGPS]; 12.1 [Predicted by PubChem via XLOGP]
Calculated using ALOGPS
|
Material Safety Data Sheet (MSDS) |
Not Available |
MOL File |
Show |
SDF File |
Show |
PDB File |
Show |
2D Structure |
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3D Structure |
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Experimental PDB ID |
Not Available |
Experimental 1H NMR Spectrum |
Not Available |
Experimental 13C NMR Spectrum |
Not Available |
Experimental 13C HSQC Spectrum |
Not Available |
Predicted 1H NMR Spectrum |
Show Image Show Peaklist
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Predicted 13C NMR Spectrum |
Show Image Show Peaklist
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Mass Spectrum |
Not Available |
Simplified TOCSY Spectrum |
Not Available |
BMRB Spectrum |
Not Available |
Cellular Location |
|
Biofluid Location |
Not Available |
Tissue Location |
Tissue |
References |
Brain |
— |
Kidney |
— |
Myelin |
— |
|
Concentrations (Normal) |
Not Available |
Concentrations (Abnormal) |
Not Available |
Pathway Names |
|
HMDB Pathways |
Name
|
Sphingolipid Metabolism
|
Image
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Show  |
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KEGG Pathways |
Name
|
Sphingolipid Metabolism
|
Image
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Show  |
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SimCell Pathways |
Name
|
Sphingolipid Metabolism
|
Image
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Show  |
Graph
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SBML
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General References |
- Wikipedia

|
Metabolic Enzymes |
- Galactosylceramide sulfotransferase
- Arylsulfatase A
|
Enzyme 1
[top]
|
Enzyme 1 ID |
80 |
Enzyme 1 Name |
Galactosylceramide sulfotransferase |
Enzyme 1 Synonyms |
- GalCer sulfotransferase
- Cerebroside sulfotransferase
- 3'-phosphoadenylylsulfate:galactosylceramide 3'-sulfotransferase
- 3'-phosphoadenosine-5'-phosphosulfate:GalCer sulfotransferase
|
Enzyme 1 Gene Name |
GAL3ST1 |
Enzyme 1 Protein Sequence |
>Galactosylceramide sulfotransferase
MPLPQKKRWESMAKGLVLGALFTSFLLLLYSYAVPPLYTGLASTTPEGAAPCSPAPREPE
APTSANGSAGGCQPRRDIVFMKTHKTASSTLLNILFRFGQKHGLKFAFPNGRNDFDYPAF
FARSLVQDYRPGACFNIICNHMRFHYDEVRGLVAPNATFITVLRDPARLFESSFHYFGSV
VPFTWKLSGRDKLAEFLQDPDRYYDARGYNAHYLRNLLFFDLGYDSDLDPSSPQVQEHIL
EVERHFHLVLLQEYFDESLVLLKDLLCWELEDVLYFKLNARRASAVPRLSGELYRRATAW
NVLDARLYRHFNASFWRKVEAFGRERMAREVAALRRANERMRRICIDGGRAVDAAAIEDS
AMQPWQPLGAKSILGYNLKKSIGQRHAQLCRRMLTPEIQYLMDLGANLWITKLWKFIRDF
LRW |
Enzyme 1 Number of Residues |
423 |
Enzyme 1 Molecular Weight |
48753.6 |
Enzyme 1 Theoretical pI |
9.53 |
Enzyme 1 GO Classification |
Function |
— |
Process |
— |
Component |
— |
|
Enzyme 1 General Function |
Involved in galactosylceramide sulfotransferase activity |
Enzyme 1 Specific Function |
Catalyzes the sulfation of membrane glycolipids. Seems to prefer beta-glycosides at the non-reducing termini of sugar chains attached to a lipid moiety. Catalyzes the synthesis of HSO3-3-galactosylceramide (sulfatide), a major lipid component of the myelin sheath and of HSO3-3-monogalactosylalkylacylglycerol (seminolipid), present in spermatocytes. Also acts on lactosylceramide, galactosyl 1-alkyl-2-sn-glycerol and galactosyl diacylglycerol (in vitro) |
Enzyme 1 Pathways |
- Lipid metabolism
- sphingolipid metabolism
|
Enzyme 1 Reactions |
Not Available |
Enzyme 1 Pfam Domain Function |
|
Enzyme 1 Signals |
|
Enzyme 1 Transmembrane Regions |
|
Enzyme 1 Essentiality |
Not Available |
Enzyme 1 GenBank ID Protein |
151553575  |
Enzyme 1 UniProtKB/Swiss-Prot ID |
A6QNK1  |
Enzyme 1 UniProtKB/Swiss-Prot Entry Name |
G3ST1_BOVIN  |
Enzyme 1 PDB ID |
Not Available |
Enzyme 1 Cellular Location |
Not Available |
Enzyme 1 Gene Sequence |
>1272 bp
ATGCCGCTGCCACAGAAGAAGCGCTGGGAGTCCATGGCCAAGGGGCTGGTGCTGGGAGCG
CTCTTCACCAGCTTCCTGCTACTGCTGTACTCCTATGCTGTCCCCCCACTGTACACTGGC
CTGGCTTCCACGACCCCCGAGGGCGCGGCACCCTGCTCTCCGGCCCCGAGGGAGCCAGAG
GCTCCCACCTCGGCCAACGGCTCGGCGGGAGGCTGCCAGCCGCGGCGGGACATCGTGTTC
ATGAAGACGCACAAGACGGCCAGCAGCACGCTGCTCAACATCCTGTTCCGCTTCGGCCAG
AAGCACGGGCTCAAGTTCGCCTTCCCCAACGGCCGCAACGACTTCGACTACCCCGCCTTC
TTCGCGCGCAGCCTGGTGCAGGACTACCGGCCCGGGGCCTGCTTCAACATCATCTGCAAC
CACATGCGCTTCCACTACGACGAGGTGCGGGGCCTGGTGGCGCCCAACGCCACCTTCATC
ACCGTGCTGCGCGACCCCGCCCGCCTCTTCGAGTCCTCCTTCCACTACTTCGGCTCCGTG
GTGCCCTTCACGTGGAAGCTCTCGGGCCGCGACAAGCTGGCCGAGTTCCTGCAGGACCCC
GACCGCTACTACGACGCCCGCGGCTACAACGCCCACTACCTCCGCAACCTGCTCTTCTTC
GACCTGGGCTACGACAGCGACCTGGACCCCAGCAGCCCGCAGGTGCAGGAGCACATCCTG
GAGGTGGAGCGCCACTTCCACCTGGTGCTGCTGCAGGAGTACTTCGACGAGTCGCTCGTG
CTGCTCAAGGACCTGCTGTGCTGGGAGCTGGAGGACGTGCTCTACTTCAAGCTCAACGCC
CGCCGCGCCTCGGCCGTGCCGCGCCTCTCGGGCGAGCTGTACCGGCGCGCCACGGCCTGG
AACGTGCTGGACGCGCGCCTCTACCGCCACTTCAACGCCAGCTTCTGGCGCAAGGTGGAG
GCCTTCGGGCGCGAGCGCATGGCCCGCGAGGTGGCCGCCCTGCGGCGCGCCAACGAGCGC
ATGCGCCGCATCTGCATCGACGGCGGCCGCGCGGTGGACGCGGCGGCCATCGAGGACTCG
GCCATGCAGCCCTGGCAGCCGCTGGGCGCCAAGTCCATCCTGGGCTACAACCTCAAGAAG
AGCATCGGGCAGCGGCATGCGCAGCTCTGCCGGCGCATGCTCACGCCGGAGATCCAGTAC
CTGATGGACCTGGGCGCCAACCTGTGGATCACCAAGCTCTGGAAGTTCATCCGGGACTTC
CTGCGGTGGTGA |
Enzyme 1 GenBank Gene ID |
BC148870  |
Enzyme 1 GeneCard ID |
GAL3ST1  |
Enzyme 1 GenAtlas ID |
Not Available |
Enzyme 1 HGNC ID |
Not Available |
Enzyme 1 Chromosome Location |
Chromosome:2 |
Enzyme 1 Locus |
22q12.2 |
Enzyme 1 SNPs |
SNPJam Report  |
Enzyme 1 General References |
Not Available |
Enzyme 1 Metabolite References |
Not Available |
Enzyme 2
[top]
|
Enzyme 2 ID |
81 |
Enzyme 2 Name |
Arylsulfatase A |
Enzyme 2 Synonyms |
- ASA
- Cerebroside-sulfatase
|
Enzyme 2 Gene Name |
ARSA |
Enzyme 2 Protein Sequence |
>Arylsulfatase A
MEALWTLTLALAAGLAAASPPNILLIFADDLGYGDLGSYGHPSSTTPNLDQLAAGGLRFT
DFYVPVSLCTPSRAALLTGRLPVRMGLYPGVLEPSSRGGLPLDEVTLAEVLAAQGYLTGI
AGKWHLGVGPEGAFLPPHHGFHRFLGIPYSHDQGPCQNLTCFPPATPCEGICDQGLVPIP
LLANLSVEAQPPWLPGLEARYVAFARDLMTDAQHQGRPFFLYYASHHTHYPQFSGQSFPG
HSGRGPFGDSLMELDAAVGALMTAVGDLGLLGETLVFFTADNGPETMRMSHGGCSGLLRC
GKGTTFEGGVREPALAFWPGHIAPGVTHELASSLDLLPTLAALAGAQLPNITLDGVDLSP
LLLGTGKSPRHTLFFYSAYPDEVRGVFAVRSGKYKAHFFTQGSVHSDTTADPACHASNPL
TAHEPPLLFDLSEDPGENYNLLDSVDEVAPEALQAVKQLELLKAQFDAAMTFGPSQMAQG
EDPTLQVCCQPSCTPRPSCCHCPEFQP |
Enzyme 2 Number of Residues |
507 |
Enzyme 2 Molecular Weight |
53806.6 |
Enzyme 2 Theoretical pI |
4.90 |
Enzyme 2 GO Classification |
Function |
— |
Process |
— |
Component |
— |
|
Enzyme 2 General Function |
Inorganic ion transport and metabolism |
Enzyme 2 Specific Function |
Hydrolyzes cerebroside sulfate |
Enzyme 2 Pathways |
Not Available |
Enzyme 2 Reactions |
Not Available |
Enzyme 2 Pfam Domain Function |
|
Enzyme 2 Signals |
|
Enzyme 2 Transmembrane Regions |
|
Enzyme 2 Essentiality |
Not Available |
Enzyme 2 GenBank ID Protein |
115304931  |
Enzyme 2 UniProtKB/Swiss-Prot ID |
Q08DD1  |
Enzyme 2 UniProtKB/Swiss-Prot Entry Name |
ARSA_BOVIN  |
Enzyme 2 PDB ID |
Not Available |
Enzyme 2 Cellular Location |
Not Available |
Enzyme 2 Gene Sequence |
>1524 bp
ATGGAGGCTCTGTGGACCCTCACTCTGGCCTTGGCCGCAGGTCTGGCTGCTGCCAGCCCA
CCTAACATCCTGCTGATCTTTGCTGATGACCTGGGCTACGGGGACCTGGGCTCCTATGGG
CACCCCAGCTCCACCACTCCCAATCTGGACCAGTTGGCCGCAGGGGGTCTGCGGTTCACA
GACTTCTACGTGCCTGTGTCTCTGTGCACACCCTCCCGGGCTGCCCTCCTGACCGGCCGA
CTCCCAGTTCGGATGGGTTTGTACCCTGGAGTTCTGGAGCCCAGCTCCCGAGGGGGCCTG
CCCCTGGATGAGGTGACCTTGGCTGAGGTCCTGGCTGCCCAAGGCTACCTCACAGGGATA
GCTGGCAAGTGGCACCTTGGGGTGGGGCCTGAGGGGGCCTTTCTGCCCCCCCACCACGGC
TTCCATCGATTCCTGGGCATCCCATACTCCCATGACCAGGGCCCTTGCCAGAACCTGACC
TGCTTCCCCCCGGCCACCCCCTGCGAAGGCATCTGCGACCAGGGCCTGGTCCCTATCCCA
CTGTTGGCCAACCTGTCGGTGGAGGCACAGCCCCCTTGGCTGCCTGGACTCGAGGCTCGC
TACGTGGCCTTTGCCCGCGACCTCATGACTGACGCCCAACACCAAGGCCGCCCGTTCTTC
CTGTACTACGCCTCCCACCACACCCACTACCCCCAGTTCAGTGGGCAGAGCTTCCCAGGG
CACTCAGGCCGAGGGCCATTTGGGGACTCCCTGATGGAGCTGGACGCGGCTGTGGGGGCC
CTGATGACAGCTGTGGGGGACCTGGGGCTGCTTGGAGAGACGCTCGTCTTCTTCACTGCA
GACAACGGGCCTGAGACGATGCGGATGTCCCATGGTGGCTGCTCTGGCCTCCTGCGATGC
GGAAAAGGAACCACTTTCGAAGGGGGCGTCCGAGAGCCTGCCTTGGCCTTCTGGCCAGGT
CACATCGCTCCCGGTGTGACCCATGAGCTGGCCAGCTCCCTGGACCTGCTGCCCACCCTG
GCAGCCCTGGCGGGGGCCCAACTGCCCAATATCACCTTGGATGGCGTTGACCTCAGCCCC
CTGCTGTTGGGCACAGGCAAGAGCCCCCGGCACACCCTCTTCTTCTACTCGGCCTACCCG
GATGAGGTCCGAGGGGTCTTTGCAGTGCGGAGCGGGAAGTACAAGGCACACTTCTTTACC
CAGGGCTCTGTCCACAGCGACACCACTGCAGACCCTGCCTGCCACGCCTCTAATCCTCTG
ACTGCCCATGAGCCCCCGCTGCTCTTTGACCTGTCTGAGGACCCTGGTGAGAACTACAAC
CTTCTGGACAGTGTGGATGAGGTTGCCCCAGAGGCGCTGCAGGCAGTGAAGCAACTTGAG
CTGCTCAAGGCCCAGTTTGATGCTGCCATGACCTTCGGACCCAGCCAGATGGCGCAGGGT
GAGGACCCCACCCTGCAGGTCTGCTGCCAGCCCAGCTGCACCCCCCGGCCGTCCTGCTGC
CACTGCCCTGAGTTCCAGCCCTGA |
Enzyme 2 GenBank Gene ID |
BC123816  |
Enzyme 2 GeneCard ID |
ARSA  |
Enzyme 2 GenAtlas ID |
Not Available |
Enzyme 2 HGNC ID |
Not Available |
Enzyme 2 Chromosome Location |
Chromosome:2 |
Enzyme 2 Locus |
22q13.31-qter|22q13.33 |
Enzyme 2 SNPs |
SNPJam Report  |
Enzyme 2 General References |
Not Available |
Enzyme 2 Metabolite References |
Not Available |