Record Information
Version3.6
Creation Date2009-04-30 09:04:25 UTC
Update Date2013-02-09 00:28:47 UTC
HMDB IDHMDB12316
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-O-Sulfogalactosylceramide (d18:1/22:0)
Description3-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
Thumb
Synonyms
  1. 3'-O-Sulphogalactosylceramide
  2. 3-O-Sulfo-beta-D-galactosylceramide
  3. 3-O-Sulfo-beta-delta-galactosylceramide
  4. 3-O-Sulfogalactosylceramide
  5. Cerebroside 3-sulfate
  6. Cerebroside 3-sulphate
  7. Galactosylceramide-sulfate
  8. Galactosylceramide-sulphate
  9. Galactosylceramidesulfate
  10. Galactosylceramidesulphate
  11. N-[(1S,2R,3E)-2-Hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-Docosanamide
  12. N-[(1S,2R,3E)-2-Hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-Docosanamide
  13. Sulfatide
  14. Sulfatide (d18:1/22:0)
  15. [R-[R*,S*-(E)]]-N-[2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-Docosanamide
  16. [R-[R*,S*-(E)]]-N-[2-hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-Docosanamide
Chemical FormulaC46H89NO11S
Average Molecular Weight864.264
Monoisotopic Molecular Weight863.615633385
IUPAC Name[(2R,5S,6R)-2-{[(2S,3R,4E)-2-docosanamido-3-hydroxyoctadec-4-en-1-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid
Traditional IUPAC NameC22 sulfatide
CAS Registry Number265096-83-1
SMILES
CCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@]([H])(CO[C@@H]1O[C@H](CO)[C@H](O)C(OS(=O)(O)=O)C1O)[C@@](O)([H])\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C46H89NO11S/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-42(50)47-39(40(49)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2)38-56-46-44(52)45(58-59(53,54)55)43(51)41(37-48)57-46/h33,35,39-41,43-46,48-49,51-52H,3-32,34,36-38H2,1-2H3,(H,47,50)(H,53,54,55)/b35-33+/t39-,40+,41+,43-,44?,45?,46+/m0/s1
InChI KeyUAKYQMHTPLVMJD-GJOJTGTQSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSphingolipids
Sub ClassSulfatides
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 ParentSulfatides
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Glycosphingolipid metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility3.050E-04 g/LALOGPS
logP5.75ALOGPS
logP9.76ChemAxon
logS-6.5ALOGPS
pKa (strongest acidic)-1.9ChemAxon
pKa (strongest basic)0.025ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count10ChemAxon
hydrogen donor count6ChemAxon
polar surface area192.08ChemAxon
rotatable bond count41ChemAxon
refractivity235.79ChemAxon
polarizability106.8ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028938
KNApSAcK IDNot Available
Chemspider ID24823252
KEGG Compound IDC06125
BioCyc IDGALACTOSYLCERAMIDE-SULFATE
BiGG IDNot Available
Wikipedia LinkSulfatide
NuGOwiki LinkHMDB12316
Metagene LinkHMDB12316
METLIN IDNot Available
PubChem Compound24779582
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 50 proteins. There are 62 proteins in total.

Enzymes

Gene Name:
GALC
Uniprot ID:
P54803
Gene Name:
GAL3ST1
Uniprot ID:
Q99999
Gene Name:
SMPD1
Uniprot ID:
P17405
Gene Name:
UGCG
Uniprot ID:
Q16739
Gene Name:
ASAH1
Uniprot ID:
Q13510
Gene Name:
SMPD2
Uniprot ID:
O60906
Gene Name:
COL4A3BP
Uniprot ID:
Q9Y5P4
Gene Name:
GM2A
Uniprot ID:
P17900
Gene Name:
GBA
Uniprot ID:
P04062
Gene Name:
NPC2
Uniprot ID:
P61916
Gene Name:
CERS1
Uniprot ID:
P27544
Gene Name:
CD1D
Uniprot ID:
P15813
Gene Name:
PIGM
Uniprot ID:
Q9H3S5
Gene Name:
PIGZ
Uniprot ID:
Q86VD9
Gene Name:
SMPD3
Uniprot ID:
Q9NY59
Gene Name:
B3GALT5
Uniprot ID:
Q9Y2C3
Gene Name:
B4GALT6
Uniprot ID:
Q9UBX8
Gene Name:
PIGB
Uniprot ID:
Q92521
Gene Name:
PIGS
Uniprot ID:
Q96S52
Gene Name:
PIGT
Uniprot ID:
Q969N2
Gene Name:
PIGV
Uniprot ID:
Q9NUD9
Gene Name:
SMPD4
Uniprot ID:
Q9NXE4
Gene Name:
ASAH2C
Uniprot ID:
P0C7U2
Gene Name:
ACER2
Uniprot ID:
Q5QJU3
Gene Name:
ASAH2
Uniprot ID:
Q9NR71
Gene Name:
GBA2
Uniprot ID:
Q9HCG7
Gene Name:
ACER1
Uniprot ID:
Q8TDN7
Gene Name:
CERS5
Uniprot ID:
Q8N5B7

Only showing the first 50 proteins. There are 62 proteins in total.