Showing metabocard for 3-O-Sulfogalactosylceramide (d18:1/24:0) (BMDB0000024)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:18:37 UTC
Update Date2020-05-19 22:01:33 UTC
BMDB IDBMDB0000024
Secondary Accession Numbers
  • BMDB00024
Metabolite Identification
Common Name3-O-Sulfogalactosylceramide (d18:1/24:0)
Description3-O-Sulfogalactosylceramide (d18:1/24:0) belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Thus, 3-O-sulfogalactosylceramide (D18:1/24:0) is considered to be an acidic glycosphingolipid lipid molecule. 3-O-Sulfogalactosylceramide (d18:1/24:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within cattle, 3-O-sulfogalactosylceramide (D18:1/24:0) participates in a number of enzymatic reactions. In particular, 3-O-sulfogalactosylceramide (D18:1/24:0) and adenosine 3',5'-diphosphate can be biosynthesized from galactosylceramide (D18:1/16:0) and phosphoadenosine phosphosulfate; which is mediated by the enzyme galactosylceramide sulfotransferase. In addition, 3-O-sulfogalactosylceramide (D18:1/24:0) can be converted into galactosylceramide (D18:1/16:0) and sulfate; which is catalyzed by the enzyme arylsulfatase a. In cattle, 3-O-sulfogalactosylceramide (D18:1/24:0) is involved in the metabolic pathway called the sphingolipid metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-O-Sulphogalactosylceramide (D18:1/24:0)Generator
Chemical FormulaC48H93NO11S
Average Molecular Weight892.33
Monoisotopic Molecular Weight891.646933993
IUPAC Name[(2R,5S,6R)-3,5-dihydroxy-2-{[(2S,3R,4E)-3-hydroxy-2-tetracosanamidooctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid
Traditional NameC24 sulfatide
CAS Registry Number151122-71-3
SMILES
[H][C@@](CO[C@@H]1O[C@H](CO)[C@H](O)C(OS(O)(=O)=O)C1O)(NC(=O)CCCCCCCCCCCCCCCCCCCCCCC)[C@]([H])(O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/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
InChI KeyMEAZTWJVOWHKJM-YQTIZROBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenethylamine
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 2-arylethylamine
  • Aralkylamine
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Primary amine
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Endosome
  • Lysosome
  • Membrane
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.01ALOGPS
logP10.93ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)-0.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area192.08 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity244.99 m³·mol⁻¹ChemAxon
Polarizability111.09 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, Negativesplash10-0006-0010000090-4009dca32137df81dfe1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000x-2093004070-440431caa30e54f5b02fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-9115315000-b669e31b7b81f310731fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000x-3001009080-1e911bc6ce858fa13092View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-4011009010-ee22cc729d52a1645af6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06dl-7951023000-4afdf97295dee65586e4View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Lysosome
  • Membrane
  • Myelin sheath
Biospecimen Locations
  • Brain
  • Kidney
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000024
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24823255
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24779585
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceHakomori, Senichiro; Ishimoda, Taiko; Nakamura, Kiyoshi. Separation and characterization of two sulfatides of brain. Journal of Biochemistry (Tokyo, Japan) (1962), 52 468-9.
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
Reactions
Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate → 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphatedetails
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
Reactions
3-O-Sulfogalactosylceramide (d18:1/24:0) + Water → Galactosylceramide (d18:1/16:0) + Sulfatedetails