Human Metabolome Database Version 3.5

Showing metabocard for 3-O-Sulfogalactosylceramide (d18:1/20:0) (HMDB12315)

Record Information
Version 3.5
Creation Date 2009-04-30 02:52:46 -0600
Update Date 2013-02-08 17:28:47 -0700
HMDB ID HMDB12315
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-O-Sulfogalactosylceramide (d18:1/20:0)
Description 3-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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]-Eicosanamide
  12. N-[(1S,2R,3E)-2-Hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-Eicosanamide
  13. Sulfatide
  14. Sulfatide (d18:1/20:0)
  15. [R-[R*,S*-(E)]]-N-[2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-Eicosanamide
  16. [R-[R*,S*-(E)]]-N-[2-hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-Eicosanamide
Chemical Formula C44H85NO11S
Average Molecular Weight 836.211
Monoisotopic Molecular Weight 835.584333257
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 IUPAC Name C20 sulfatide
CAS Registry Number 265096-81-9
SMILES CCCCCCCCCCCCCCCCCCCC(=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/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 Key AURCBSWGPREGRQ-VGNRXBDKSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Sphingolipids
Sub Class Sulfatides
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 Parent Sulfatides
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 5.060E-04 g/L ALOGPS
LogP 5.45 ALOGPS
LogP 8.88 ChemAxon
LogS -6.22 ALOGPS
pKa (strongest acidic) -1.9 ChemAxon
pKa (strongest basic) 0.025 ChemAxon
Hydrogen Acceptor Count 10 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 192.08 A2 ChemAxon
Rotatable Bond Count 39 ChemAxon
Refractivity 226.58 ChemAxon
Polarizability 102.45 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB028937
KNApSAcK ID Not Available
Chemspider ID 24823253 Link_out
KEGG Compound ID C06125 Link_out
BioCyc ID GALACTOSYLCERAMIDE-SULFATE Link_out
BiGG ID Not Available
Wikipedia Link Sulfatide Link_out
NuGOwiki Link HMDB12315 Link_out
Metagene Link HMDB12315 Link_out
METLIN ID Not Available
PubChem Compound 24779583 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes

Show all enzymes and transporters Important Only showing the first 50 enzymes. There are 62 enzymes in total.

Name: Galactocerebrosidase
Reactions: Not Available
Gene Name: GALC
Uniprot ID: P54803 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Galactosylceramide sulfotransferase
Reactions: Not Available
Gene Name: GAL3ST1
Uniprot ID: Q99999 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Globoside alpha-1,3-N-acetylgalactosaminyltransferase 1
Reactions: Not Available
Gene Name: GBGT1
Uniprot ID: Q8N5D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase
Reactions: Not Available
Gene Name: PIGL
Uniprot ID: Q9Y2B2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase
Reactions: Not Available
Gene Name: SMPD1
Uniprot ID: P17405 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ceramide glucosyltransferase
Reactions: Not Available
Gene Name: UGCG
Uniprot ID: Q16739 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lactosylceramide 4-alpha-galactosyltransferase
Reactions: Not Available
Gene Name: A4GALT
Uniprot ID: Q9NPC4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q
Reactions: Not Available
Gene Name: PIGQ
Uniprot ID: Q9BRB3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit A
Reactions: Not Available
Gene Name: PIGA
Uniprot ID: P37287 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit H
Reactions: Not Available
Gene Name: PIGH
Uniprot ID: Q14442 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit P
Reactions: Not Available
Gene Name: PIGP
Uniprot ID: P57054 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit C
Reactions: Not Available
Gene Name: PIGC
Uniprot ID: Q92535 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acid ceramidase
Reactions: Not Available
Gene Name: ASAH1
Uniprot ID: Q13510 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 7
Reactions: Not Available
Gene Name: ENPP7
Uniprot ID: Q6UWV6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase 2
Reactions: Not Available
Gene Name: SMPD2
Uniprot ID: O60906 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Collagen type IV alpha-3-binding protein
Reactions: Not Available
Gene Name: COL4A3BP
Uniprot ID: Q9Y5P4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ganglioside GM2 activator
Reactions: Not Available
Gene Name: GM2A
Uniprot ID: P17900 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucosylceramidase
Reactions: Not Available
Gene Name: GBA
Uniprot ID: P04062 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: T-cell surface glycoprotein CD1e, membrane-associated
Reactions: Not Available
Gene Name: CD1E
Uniprot ID: P15812 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Epididymal secretory protein E1
Reactions: Not Available
Gene Name: NPC2
Uniprot ID: P61916 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ceramide synthase 1
Reactions: Not Available
Gene Name: CERS1
Uniprot ID: P27544 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Antigen-presenting glycoprotein CD1d
Reactions: Not Available
Gene Name: CD1D
Uniprot ID: P15813 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI mannosyltransferase 1
Reactions: Not Available
Gene Name: PIGM
Uniprot ID: Q9H3S5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class W protein
Reactions: Not Available
Gene Name: PIGW
Uniprot ID: Q7Z7B1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class X protein
Reactions: Not Available
Gene Name: PIGX
Uniprot ID: Q8TBF5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI mannosyltransferase 4
Reactions: Not Available
Gene Name: PIGZ
Uniprot ID: Q86VD9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase
Reactions: Not Available
Gene Name: B3GNT5
Uniprot ID: Q9BYG0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase 3
Reactions: Not Available
Gene Name: SMPD3
Uniprot ID: Q9NY59 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-1,3-galactosyltransferase 5
Reactions: Not Available
Gene Name: B3GALT5
Uniprot ID: Q9Y2C3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-1,4-galactosyltransferase 6
Reactions: Not Available
Gene Name: B4GALT6
Uniprot ID: Q9UBX8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI mannosyltransferase 3
Reactions: Not Available
Gene Name: PIGB
Uniprot ID: Q92521 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class F protein
Reactions: Not Available
Gene Name: PIGF
Uniprot ID: Q07326 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI ethanolamine phosphate transferase 2
Reactions: Not Available
Gene Name: PIGG
Uniprot ID: Q5H8A4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI ethanolamine phosphate transferase 1
Reactions: Not Available
Gene Name: PIGN
Uniprot ID: O95427 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI ethanolamine phosphate transferase 3
Reactions: Not Available
Gene Name: PIGO
Uniprot ID: Q8TEQ8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI transamidase component PIG-S
Reactions: Not Available
Gene Name: PIGS
Uniprot ID: Q96S52 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI transamidase component PIG-T
Reactions: Not Available
Gene Name: PIGT
Uniprot ID: Q969N2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol glycan anchor biosynthesis class U protein
Reactions: Not Available
Gene Name: PIGU
Uniprot ID: Q9H490 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GPI mannosyltransferase 2
Reactions: Not Available
Gene Name: PIGV
Uniprot ID: Q9NUD9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y
Reactions: Not Available
Gene Name: PIGY
Uniprot ID: Q3MUY2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pleckstrin homology domain-containing family A member 8
Reactions: Not Available
Gene Name: PLEKHA8
Uniprot ID: Q96JA3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase 4
Reactions: Not Available
Gene Name: SMPD4
Uniprot ID: Q9NXE4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative neutral ceramidase C
Reactions: Not Available
Gene Name: ASAH2C
Uniprot ID: P0C7U2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alkaline ceramidase 2
Reactions: Not Available
Gene Name: ACER2
Uniprot ID: Q5QJU3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Neutral ceramidase
Reactions: Not Available
Gene Name: ASAH2
Uniprot ID: Q9NR71 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Non-lysosomal glucosylceramidase
Reactions: Not Available
Gene Name: GBA2
Uniprot ID: Q9HCG7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alkaline ceramidase 1
Reactions: Not Available
Gene Name: ACER1
Uniprot ID: Q8TDN7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Killer cell lectin-like receptor subfamily B member 1
Reactions: Not Available
Gene Name: KLRB1
Uniprot ID: Q12918 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ceramide synthase 5
Reactions: Not Available
Gene Name: CERS5
Uniprot ID: Q8N5B7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: ATP-binding cassette sub-family A member 7
Reactions: Not Available
Gene Name: ABCA7
Uniprot ID: Q8IZY2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA