3-O-Sulfogalactosylceramide (d18:1/20:0) (CHEM040778)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 00:33:11 UTC
Update Date2016-11-09 01:22:19 UTC
Accession NumberCHEM040778
Identification
Common Name3-O-Sulfogalactosylceramide (d18:1/20:0)
ClassSmall Molecule
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). [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-O-Sulphogalactosylceramide (D18:1/20:0)Generator
3'-O-SulphogalactosylceramideHMDB
3-O-SulfO-beta-D-galactosylceramideHMDB
3-O-SulfO-beta-delta-galactosylceramideHMDB
3-O-SulfogalactosylceramideHMDB
Cerebroside 3-sulfateHMDB
Cerebroside 3-sulphateHMDB
Galactosylceramide-sulfateHMDB
Galactosylceramide-sulphateHMDB
GalactosylceramidesulfateHMDB
GalactosylceramidesulphateHMDB
N-[(1S,2R,3E)-2-Hydroxy-1-[[(3-O-sulfO-b-D-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-eicosanamideHMDB
N-[(1S,2R,3E)-2-Hydroxy-1-[[(3-O-sulfO-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-eicosanamideHMDB
SulfatideHMDB
Sulfatide (D18:1/20:0)HMDB
[R-[R*,s*-(e)]]-N-[2-hydroxy-1-[[(3-O-sulfO-b-D-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-eicosanamideHMDB
[R-[R*,s*-(e)]]-N-[2-hydroxy-1-[[(3-O-sulfO-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-eicosanamideHMDB
(3'-SulphO)galbeta-cer(D18:1/20:0)Generator
Chemical FormulaC44H85NO11S
Average Molecular Mass836.211 g/mol
Monoisotopic Mass835.584 g/mol
CAS Registry Number265096-81-9
IUPAC Name[(2R,5S,6R)-3,5-dihydroxy-2-{[(2S,3R,4E)-3-hydroxy-2-icosanamidooctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid
Traditional NameC20 sulfatide
SMILESCCCCCCCCCCCCCCCCCCCC(=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 IdentifierInChI=1S/C44H85NO11S/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-40(48)45-37(38(47)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2)36-54-44-42(50)43(56-57(51,52)53)41(49)39(35-46)55-44/h31,33,37-39,41-44,46-47,49-50H,3-30,32,34-36H2,1-2H3,(H,45,48)(H,51,52,53)/b33-31+/t37-,38+,39+,41-,42?,43?,44+/m0/s1
InChI KeyAURCBSWGPREGRQ-VGNRXBDKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sulfatides. These are an hydrogen sulfate esters of glycosphingolipids.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassGlycosphingolipids
Direct ParentSulfatides
Alternative Parents
Substituents
  • Sulfoglycosphingolipid
  • Glycosyl-n-acylsphingosine
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • Oxane
  • Fatty acyl
  • Sulfuric acid monoester
  • Sulfate-ester
  • Alkyl sulfate
  • Sulfuric acid ester
  • Organic sulfuric acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00051 g/LALOGPS
logP5.45ALOGPS
logP8.88ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)0.025ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area192.08 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity226.58 m³·mol⁻¹ChemAxon
Polarizability102.45 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1000040090-8048ede7c7e7fb1781f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-5010090120-4326daf9290d70d8a7d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053v-9140020000-e42aa3dc0b7734bfa0d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000090-c3d2bb562361a113474fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1161030290-9c5d7587a62a04a7ad8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pca-9232020000-36fffe05a5cac1a03fc6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0012315
FooDB IDFDB028937
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDGALACTOSYLCERAMIDE-SULFATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24823253
ChEBI IDNot Available
PubChem Compound ID24779583
Kegg Compound IDC06125
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78.
2. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50.
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. Phospholipids Handbook
8. The lipid handbook with CD-ROM