Showing metabocard for 3-O-Sulfogalactosylceramide (d18:1/24:1(15Z)) (BMDB0012318)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:36:05 UTC
Update Date2020-04-22 15:49:38 UTC
BMDB IDBMDB0012318
Secondary Accession Numbers
  • BMDB12318
Metabolite Identification
Common Name3-O-Sulfogalactosylceramide (d18:1/24:1(15Z))
Description3-O-Sulfogalactosylceramide (d18:1/24:1(15Z)) belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.g. S-,C-, or N-type) has been reported. 3-O-Sulfogalactosylceramide (d18:1/24:1(15Z)) is a moderately basic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-O-Sulphogalactosylceramide (D18:1/24:1(15Z))Generator
(15Z)-N-[(2S,3R,4E)-1-{[(2R,5S)-3,5-dihydroxy-6-(hydroxymethyl)-4-(sulfooxy)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracos-15-enimidateGenerator
(15Z)-N-[(2S,3R,4E)-1-{[(2R,5S)-3,5-dihydroxy-6-(hydroxymethyl)-4-(sulphooxy)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracos-15-enimidateGenerator
(15Z)-N-[(2S,3R,4E)-1-{[(2R,5S)-3,5-dihydroxy-6-(hydroxymethyl)-4-(sulphooxy)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracos-15-enimidic acidGenerator
Chemical FormulaC48H91NO11S
Average Molecular Weight890.31
Monoisotopic Molecular Weight889.631283928
IUPAC Name(15Z)-N-[(2S,3R,4E)-1-{[(2R,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(sulfooxy)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracos-15-enimidic acid
Traditional Name(15Z)-N-[(2S,3R,4E)-1-{[(2R,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(sulfooxy)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]tetracos-15-enimidic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCCCCCC(O)=N[C@@]([H])(CO[C@]1([H])OC([H])(CO)[C@]([H])(O)C([H])(OS(O)(=O)=O)C1([H])O)[C@]([H])(O)C(\[H])=C(/[H])CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C48H91NO11S/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/h17-18,35,37,41-43,45-48,50-51,53-54H,3-16,19-34,36,38-40H2,1-2H3,(H,49,52)(H,55,56,57)/b18-17-,37-35+/t41-,42+,43?,45-,46?,47?,48+/m0/s1
InChI KeyZZQWQNAZXFNSEP-IKWJIQCSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.g. S-,C-, or N-type) has been reported.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassGlycosphingolipids
Direct ParentGlycosphingolipids
Alternative Parents
Substituents
  • Glycosphingolipid
  • Fatty acyl glycoside of mono- or disaccharide
  • Fatty acyl glycoside
  • Hexose monosaccharide
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Fatty acyl
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Sulfuric acid monoester
  • Oxane
  • Monosaccharide
  • Organic sulfuric acid or derivatives
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Acetal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • 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
logP5.98ALOGPS
logP11.77ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)-2ChemAxon
pKa (Strongest Basic)2.43ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area195.57 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity246.63 m³·mol⁻¹ChemAxon
Polarizability109.04 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, Positivesplash10-00dl-0010043090-b7053392356ac277ed61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-008a-0033049240-c7318fdd3d58a456d1b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-7298033880-3153459e59d1be6cb92fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-0021015090-929c15c134e4b8edfd4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-6164019580-ed89b4edbd0f1a824393View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9353101000-bf4aa0a6e659b100f815View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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