Human Metabolome Database: Showing metabocard for 3-O-Sulfogalactosylceramide (d18:1/18:1(9Z)) (HMDB12317)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (62) Show 62 proteins XML

enzymes (62) Show 62 proteins

Record Information

Version

3.6

Creation Date

2009-04-30 09:39:38 UTC

Update Date

2013-02-09 00:28:47 UTC

HMDB ID

HMDB12317

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-O-Sulfogalactosylceramide (d18:1/18:1(9Z))

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

MOL SDF PDB SMILES InChI View Structure

Synonyms

3'-O-Sulphogalactosylceramide
3-O-Sulfo-beta-D-galactosylceramide
3-O-Sulfo-beta-delta-galactosylceramide
3-O-Sulfogalactosylceramide
Cerebroside 3-sulfate
Cerebroside 3-sulphate
Galactosylceramide-sulfate
Galactosylceramide-sulphate
Galactosylceramidesulfate
Galactosylceramidesulphate
N-[(1S,2R,3E)-2-Hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-9-Octadecenamide
N-[(1S,2R,3E)-2-Hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-9-Octadecenamide
Sulfatide
Sulfatide (d18:1/18:1(9Z))
[R-[R*,S*-(E)]]-N-[2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-9-Octadecenamide
[R-[R*,S*-(E)]]-N-[2-hydroxy-1-[[(3-O-sulfo-beta-delta-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-9-Octadecenamide

Chemical Formula

C₄₂H₇₉NO₁₁S

Average Molecular Weight

806.142

Monoisotopic Molecular Weight

805.537383065

IUPAC Name

[(2R,5S,6R)-3,5-dihydroxy-2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-octadec-9-enamido]octadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid

Traditional IUPAC Name

[(2R,5S,6R)-3,5-dihydroxy-2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-octadec-9-enamido]octadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

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)CCCCCCC\C=C/CCCCCCCC

InChI Identifier

InChI=1S/C42H79NO11S/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-38(46)43-35(36(45)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)34-52-42-40(48)41(54-55(49,50)51)39(47)37(33-44)53-42/h17-18,29,31,35-37,39-42,44-45,47-48H,3-16,19-28,30,32-34H2,1-2H3,(H,43,46)(H,49,50,51)/b18-17-,31-29+/t35-,36+,37+,39-,40?,41?,42+/m0/s1

InChI Key

NXJDPFSYOMFVES-SUTPNROZSA-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	0.0011 g/L	ALOGPS
logP	5.03	ALOGPS
logP	7.62	ChemAxon
logS	-5.8	ALOGPS
pKa (strongest acidic)	-1.9	ChemAxon
pKa (strongest basic)	0.025	ChemAxon
physiological charge	-1	ChemAxon
hydrogen acceptor count	10	ChemAxon
hydrogen donor count	6	ChemAxon
polar surface area	192.08	ChemAxon
rotatable bond count	36	ChemAxon
refractivity	218.5	ChemAxon
polarizability	96.27	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

External Links

DrugBank ID

Not Available

DrugBank Metabolite ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

FDB028939

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C06125

BioCyc ID

GALACTOSYLCERAMIDE-SULFATE

BiGG ID

Not Available

Wikipedia Link

Sulfatide

NuGOwiki Link

HMDB12317

Metagene Link

HMDB12317

METLIN ID

Not Available

PubChem Compound

53481403

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Only showing the first 50 proteins. There are 62 proteins in total.

Show all enzymes and transporters

Enzymes

1. Galactocerebrosidase

Gene Name:: GALC
Uniprot ID:: P54803

2. Galactosylceramide sulfotransferase

Gene Name:: GAL3ST1
Uniprot ID:: Q99999

3. Globoside alpha-1,3-N-acetylgalactosaminyltransferase 1

Gene Name:: GBGT1
Uniprot ID:: Q8N5D6

4. N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase

Gene Name:: PIGL
Uniprot ID:: Q9Y2B2

5. Sphingomyelin phosphodiesterase

Gene Name:: SMPD1
Uniprot ID:: P17405

6. Ceramide glucosyltransferase

Gene Name:: UGCG
Uniprot ID:: Q16739

7. Lactosylceramide 4-alpha-galactosyltransferase

Gene Name:: A4GALT
Uniprot ID:: Q9NPC4

8. Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q

Gene Name:: PIGQ
Uniprot ID:: Q9BRB3

9. Phosphatidylinositol N-acetylglucosaminyltransferase subunit A

Gene Name:: PIGA
Uniprot ID:: P37287

10. Phosphatidylinositol N-acetylglucosaminyltransferase subunit H

Gene Name:: PIGH
Uniprot ID:: Q14442

11. Phosphatidylinositol N-acetylglucosaminyltransferase subunit P

Gene Name:: PIGP
Uniprot ID:: P57054

12. Phosphatidylinositol N-acetylglucosaminyltransferase subunit C

Gene Name:: PIGC
Uniprot ID:: Q92535

13. Acid ceramidase

Gene Name:: ASAH1
Uniprot ID:: Q13510

14. Ectonucleotide pyrophosphatase/phosphodiesterase family member 7

Gene Name:: ENPP7
Uniprot ID:: Q6UWV6

15. Sphingomyelin phosphodiesterase 2

Gene Name:: SMPD2
Uniprot ID:: O60906

16. Collagen type IV alpha-3-binding protein

Gene Name:: COL4A3BP
Uniprot ID:: Q9Y5P4

17. Ganglioside GM2 activator

Gene Name:: GM2A
Uniprot ID:: P17900

18. Glucosylceramidase

Gene Name:: GBA
Uniprot ID:: P04062

19. T-cell surface glycoprotein CD1e, membrane-associated

Gene Name:: CD1E
Uniprot ID:: P15812

20. Epididymal secretory protein E1

Gene Name:: NPC2
Uniprot ID:: P61916

21. Ceramide synthase 1

Gene Name:: CERS1
Uniprot ID:: P27544

22. Antigen-presenting glycoprotein CD1d

Gene Name:: CD1D
Uniprot ID:: P15813

23. GPI mannosyltransferase 1

Gene Name:: PIGM
Uniprot ID:: Q9H3S5

24. Phosphatidylinositol-glycan biosynthesis class W protein

Gene Name:: PIGW
Uniprot ID:: Q7Z7B1

25. Phosphatidylinositol-glycan biosynthesis class X protein

Gene Name:: PIGX
Uniprot ID:: Q8TBF5

26. GPI mannosyltransferase 4

Gene Name:: PIGZ
Uniprot ID:: Q86VD9

27. Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase

Gene Name:: B3GNT5
Uniprot ID:: Q9BYG0

28. Sphingomyelin phosphodiesterase 3

Gene Name:: SMPD3
Uniprot ID:: Q9NY59

29. Beta-1,3-galactosyltransferase 5

Gene Name:: B3GALT5
Uniprot ID:: Q9Y2C3

30. Beta-1,4-galactosyltransferase 6

Gene Name:: B4GALT6
Uniprot ID:: Q9UBX8

31. GPI mannosyltransferase 3

Gene Name:: PIGB
Uniprot ID:: Q92521

32. Phosphatidylinositol-glycan biosynthesis class F protein

Gene Name:: PIGF
Uniprot ID:: Q07326

33. GPI ethanolamine phosphate transferase 2

Gene Name:: PIGG
Uniprot ID:: Q5H8A4

34. GPI ethanolamine phosphate transferase 1

Gene Name:: PIGN
Uniprot ID:: O95427

35. GPI ethanolamine phosphate transferase 3

Gene Name:: PIGO
Uniprot ID:: Q8TEQ8

36. GPI transamidase component PIG-S

Gene Name:: PIGS
Uniprot ID:: Q96S52

37. GPI transamidase component PIG-T

Gene Name:: PIGT
Uniprot ID:: Q969N2

38. Phosphatidylinositol glycan anchor biosynthesis class U protein

Gene Name:: PIGU
Uniprot ID:: Q9H490

39. GPI mannosyltransferase 2

Gene Name:: PIGV
Uniprot ID:: Q9NUD9

40. Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y

Gene Name:: PIGY
Uniprot ID:: Q3MUY2

41. Pleckstrin homology domain-containing family A member 8

Gene Name:: PLEKHA8
Uniprot ID:: Q96JA3

42. Sphingomyelin phosphodiesterase 4

Gene Name:: SMPD4
Uniprot ID:: Q9NXE4

43. Putative neutral ceramidase C

Gene Name:: ASAH2C
Uniprot ID:: P0C7U2

44. Alkaline ceramidase 2

Gene Name:: ACER2
Uniprot ID:: Q5QJU3

45. Neutral ceramidase

Gene Name:: ASAH2
Uniprot ID:: Q9NR71

46. Non-lysosomal glucosylceramidase

Gene Name:: GBA2
Uniprot ID:: Q9HCG7

47. Alkaline ceramidase 1

Gene Name:: ACER1
Uniprot ID:: Q8TDN7

48. Killer cell lectin-like receptor subfamily B member 1

Gene Name:: KLRB1
Uniprot ID:: Q12918

49. Ceramide synthase 5

Gene Name:: CERS5
Uniprot ID:: Q8N5B7

50. ATP-binding cassette sub-family A member 7

Gene Name:: ABCA7
Uniprot ID:: Q8IZY2

Only showing the first 50 proteins. There are 62 proteins in total.

Show all enzymes and transporters