Showing metabocard for 3-O-Sulfogalactosylceramide (d18:1/12:0) (BMDB0012311)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:35:55 UTC
Update Date2020-04-22 15:49:35 UTC
BMDB IDBMDB0012311
Secondary Accession Numbers
  • BMDB12311
Metabolite Identification
Common Name3-O-Sulfogalactosylceramide (d18:1/12:0)
Description3-O-Sulfogalactosylceramide (d18:1/12:0), also known as galactosylceramide-sulfate or sulfatide, belongs to the class of organic compounds known as sulfatides. These are an hydrogen sulfate esters of glycosphingolipids. 3-O-Sulfogalactosylceramide (d18:1/12:0) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-O-Sulphogalactosylceramide (D18:1/12:0)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]-undecanamideHMDB
N-[(1S,2R,3E)-2-Hydroxy-1-[[(3-O-sulfO-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-undecanamideHMDB
SulfatideHMDB
Sulfatide (D18:1/12:0)HMDB
[R-[R*,s*-(e)]]-N-[2-hydroxy-1-[[(3-O-sulfO-b-D-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-undecanamideHMDB
[R-[R*,s*-(e)]]-N-[2-hydroxy-1-[[(3-O-sulfO-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-undecanamideHMDB
N-[(2S,3R,4E)-1-{[(2R,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(sulfooxy)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]dodecanimidateGenerator
N-[(2S,3R,4E)-1-{[(2R,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(sulphooxy)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]dodecanimidateGenerator
N-[(2S,3R,4E)-1-{[(2R,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(sulphooxy)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]dodecanimidic acidGenerator
Chemical FormulaC36H69NO11S
Average Molecular Weight723.998
Monoisotopic Molecular Weight723.459132745
IUPAC Name[(2R,5S,6R)-2-{[(2S,3R,4E)-2-dodecanamido-3-hydroxyoctadec-4-en-1-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid
Traditional Name[(2R,5S,6R)-2-{[(2S,3R,4E)-2-dodecanamido-3-hydroxyoctadec-4-en-1-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid
CAS Registry Number852100-88-0
SMILES
CCCCCCCCCCCCC\C=C\[C@](O)([H])[C@]([H])(CO[C@@H]1O[C@H](CO)[C@H](O)C(OS(=O)(O)=O)C1O)NC(=O)CCCCCCCCCCC
InChI Identifier
InChI=1S/C36H69NO11S/c1-3-5-7-9-11-13-14-15-16-18-19-21-23-25-30(39)29(37-32(40)26-24-22-20-17-12-10-8-6-4-2)28-46-36-34(42)35(48-49(43,44)45)33(41)31(27-38)47-36/h23,25,29-31,33-36,38-39,41-42H,3-22,24,26-28H2,1-2H3,(H,37,40)(H,43,44,45)/b25-23+/t29-,30+,31+,33-,34?,35?,36+/m0/s1
InChI KeyFWVDYZZBQLRRDU-YHVLGNOMSA-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 DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Endosome
  • 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
logP3.88ALOGPS
logP5.32ChemAxon
logS-5.2ALOGPS
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 Count31ChemAxon
Refractivity189.78 m³·mol⁻¹ChemAxon
Polarizability85.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0100400900-e6c33dfded202e9898a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3010922300-9cb8c8aaaf27e48a7c02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000y-9210100000-5ddfb0789570221b4b62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000900-346aba845c2defecb9b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2250102900-db34a44d7d8b7f5f4aefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5d-9240200000-2e85f62bd57739b1859dView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0012311
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028933
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06125
BioCyc IDGALACTOSYLCERAMIDE-SULFATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481401
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Galactosylceramide sulfotransferase
General function:
Involved in galactosylceramide sulfotransferase activity
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) (By similarity).
Gene Name:
GAL3ST1
Uniprot ID:
A6QNK1
Molecular weight:
48754.0
Enzyme Details
2. Arylsulfatase A
General function:
Inorganic ion transport and metabolism
Specific function:
Hydrolyzes cerebroside sulfate.
Gene Name:
ARSA
Uniprot ID:
Q08DD1
Molecular weight:
53807.0