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Bovine Metabolome Database



Showing metabocard for 3-O-Sulfogalactosylceramide (d18:1/24:0) (BMDB00024)

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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
  1. Sulfatide (d18:1/24:0)
  2. 3'-O-Sulphogalactosylceramide
  3. 3-O-Sulfogalactosylceramide
  4. 3-O-Sulphogalactosylceramide
  5. 3-O-sulfo-beta-D-galactosylceramide
  6. Cerebroside 3-sulfate
  7. Galactosylceramide-sulfate
  8. Galactosylceramidesulfate
  9. Sulfatide
  10. 3-O-sulfo-beta-delta-galactosylceramide
  11. N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-Tetracosanamide
  12. N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-Tetracosanamide
  13. [R-[R*,S*-(E)]]-N-[2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-Tetracosanamide
  14. N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-Tetracosanamide
  15. N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-Tetracosanamide
  16. [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 Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Lipids
Class
  • Glycolipids
Sub Class
  • Lactosylceramides
Family
  • Mammalian_Metabolite
Species
  • acetal; primary alcohol; secondary alcohol; secondary carboxylic acid amide; sulfuric acid monoester; alkene; heterocyclic compound
Biofunction
  • Component of Glycosphingolipid metabolism
Application
Source
  • Endogenous
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 Link Image
BioCyc ID GALACTOSYLCERAMIDE-SULFATE Link Image
BiGG ID Not Available
Wikipedia Link Sulfatide Link Image
METLIN ID 5096 Link Image
PubChem Compound 6451121 Link Image
PubChem Substance 10559604 Link Image
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
3D Structure
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
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Lysosome
  • membrane
Biofluid Location Not Available
Tissue Location
Tissue References
Brain
Kidney
Myelin
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Sphingolipid Metabolism
HMDB Pathways
Name Sphingolipid Metabolism
Image Show Link Image
KEGG Pathways
Name Sphingolipid Metabolism
Image Show Link Image
SimCell Pathways
Name Sphingolipid Metabolism
Image Show Link Image
Graph
SBML
General References
  1. Wikipedia Link Image
Metabolic Enzymes
  1. Galactosylceramide sulfotransferase
  2. Arylsulfatase A
Enzyme 1 [top]
Enzyme 1 ID 80
Enzyme 1 Name Galactosylceramide sulfotransferase
Enzyme 1 Synonyms
  1. GalCer sulfotransferase
  2. Cerebroside sulfotransferase
  3. 3'-phosphoadenylylsulfate:galactosylceramide 3'-sulfotransferase
  4. 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
  • None
Enzyme 1 Transmembrane Regions
  • 15-35
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 151553575 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID A6QNK1 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name G3ST1_BOVIN Link Image
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 Link Image
Enzyme 1 GeneCard ID GAL3ST1 Link Image
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 Link Image
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
  1. ASA
  2. 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
  • 1-18
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein 115304931 Link Image
Enzyme 2 UniProtKB/Swiss-Prot ID Q08DD1 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name ARSA_BOVIN Link Image
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 Link Image
Enzyme 2 GeneCard ID ARSA Link Image
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 Link Image
Enzyme 2 General References Not Available
Enzyme 2 Metabolite References Not Available