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Human Metabolome Database Version 3.5

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)

• Blood
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Record Information
Version	3.5
Creation Date	2009-04-30 03:39:38 -0600
Update Date	2013-02-08 17:28:47 -0700
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	Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure
Synonyms	3'-O-Sulphogalactosylceramide 3-O-Sulfo-beta-D-galactosylceramide 3-O-Sulfo-beta-delta-galactosylceramide 3-O-Sulfogalactosylceramide Cerebroside 3-sulfate Galactosylceramide-sulfate Galactosylceramidesulfate 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 -5.85 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 36 ChemAxon Refractivity 218.5 ChemAxon Polarizability 96.27 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
External Links
DrugBank 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

---

Enzymes
Name: Galactocerebrosidase Reactions: D-galactosyl-N-acylsphingosine + H2O = D-galactose + N-acylsphingosine [RN:R03617] Gene Name: GALC Uniprot ID: P54803 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Galactosylceramide sulfotransferase Reactions: 3'-phosphoadenylyl sulfate + a galactosylceramide = adenosine 3',5'-bisphosphate + a galactosylceramidesulfate [RN:R04017 R06279] Gene Name: GAL3ST1 Uniprot ID: Q99999 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Globoside alpha-1,3-N-acetylgalactosaminyltransferase 1 Reactions: Gene Name: GBGT1 Uniprot ID: Q8N5D6 Protein Sequence: FASTA Gene Sequence: FASTA
Name: N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase Reactions: 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O = 6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate [RN:R03482 R05917] Gene Name: PIGL Uniprot ID: Q9Y2B2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase Reactions: sphingomyelin + H2O = N-acylsphingosine + choline phosphate [RN:R02541] Gene Name: SMPD1 Uniprot ID: P17405 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Ceramide glucosyltransferase Reactions: UDP-glucose + an N-acylsphingosine = UDP + a D-glucosyl-N-acylsphingosine [RN:R01497 R06275] Gene Name: UGCG Uniprot ID: Q16739 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Lactosylceramide 4-alpha-galactosyltransferase Reactions: UDP-galactose + beta-D-galactosyl-(1->4)-D-glucosyl-(11)-ceramide = UDP + alpha-D-galactosyl-(1->4)-beta-D-galactosyl-(1->4)-D-glucosyl-(11)- ceramide [RN:R03486 R05960] Gene Name: A4GALT Uniprot ID: Q9NPC4 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q Reactions: UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol = UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol [RN:R02654 R05916] Gene Name: PIGQ Uniprot ID: Q9BRB3 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit A Reactions: UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol = UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol [RN:R02654 R05916] Gene Name: PIGA Uniprot ID: P37287 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit H Reactions: UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol = UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol [RN:R02654 R05916] Gene Name: PIGH Uniprot ID: Q14442 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit P Reactions: UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol = UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol [RN:R02654 R05916] Gene Name: PIGP Uniprot ID: P57054 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit C Reactions: UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol = UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol [RN:R02654 R05916] Gene Name: PIGC Uniprot ID: Q92535 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Acid ceramidase Reactions: N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493] Gene Name: ASAH1 Uniprot ID: Q13510 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 7 Reactions: sphingomyelin + H2O = N-acylsphingosine + choline phosphate [RN:R02541] Gene Name: ENPP7 Uniprot ID: Q6UWV6 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase 2 Reactions: sphingomyelin + H2O = N-acylsphingosine + choline phosphate [RN:R02541] Gene Name: SMPD2 Uniprot ID: O60906 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Collagen type IV alpha-3-binding protein Reactions: Gene Name: COL4A3BP Uniprot ID: Q9Y5P4 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Ganglioside GM2 activator Reactions: Gene Name: GM2A Uniprot ID: P17900 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Glucosylceramidase Reactions: D-glucosyl-N-acylsphingosine + H2O = D-glucose + N-acylsphingosine [RN:R01498] Gene Name: GBA Uniprot ID: P04062 Protein Sequence: FASTA Gene Sequence: FASTA
Name: T-cell surface glycoprotein CD1e, membrane-associated Reactions: Gene Name: CD1E Uniprot ID: P15812 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Epididymal secretory protein E1 Reactions: Gene Name: NPC2 Uniprot ID: P61916 Protein Sequence: FASTA Gene Sequence: FASTA
Name: LAG1 longevity assurance homolog 1 Reactions: Gene Name: LASS1 Uniprot ID: P27544 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Antigen-presenting glycoprotein CD1d Reactions: Gene Name: CD1D Uniprot ID: P15813 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI mannosyltransferase 1 Reactions: Gene Name: PIGM Uniprot ID: Q9H3S5 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class W protein Reactions: Gene Name: PIGW Uniprot ID: Q7Z7B1 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class X protein Reactions: Gene Name: PIGX Uniprot ID: Q8TBF5 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI mannosyltransferase 4 Reactions: Gene Name: PIGZ Uniprot ID: Q86VD9 Protein Sequence: FASTA Gene Sequence: FASTA
Name: UDP-GlcNAc:betaGal beta-1,3-N-acetylglucosaminyltransferase 5 Reactions: Gene Name: B3GNT5 Uniprot ID: Q9BYG0 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase 3 Reactions: sphingomyelin + H2O = N-acylsphingosine + choline phosphate [RN:R02541] Gene Name: SMPD3 Uniprot ID: Q9NY59 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Beta-1,3-galactosyltransferase 5 Reactions: Gene Name: B3GALT5 Uniprot ID: Q9Y2C3 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Beta-1,4-galactosyltransferase 6 Reactions: Gene Name: B4GALT6 Uniprot ID: Q9UBX8 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI mannosyltransferase 3 Reactions: Gene Name: PIGB Uniprot ID: Q92521 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan biosynthesis class F protein Reactions: Gene Name: PIGF Uniprot ID: Q07326 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI ethanolamine phosphate transferase 2 Reactions: Gene Name: PIGG Uniprot ID: Q5H8A4 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI ethanolamine phosphate transferase 1 Reactions: Gene Name: PIGN Uniprot ID: O95427 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI ethanolamine phosphate transferase 3 Reactions: Gene Name: PIGO Uniprot ID: Q8TEQ8 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI transamidase component PIG-S Reactions: Gene Name: PIGS Uniprot ID: Q96S52 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI transamidase component PIG-T Reactions: Gene Name: PIGT Uniprot ID: Q969N2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol glycan anchor biosynthesis class U protein Reactions: Gene Name: PIGU Uniprot ID: Q9H490 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI mannosyltransferase 2 Reactions: Gene Name: PIGV Uniprot ID: Q9NUD9 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y Reactions: Gene Name: PIGY Uniprot ID: Q3MUY2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Pleckstrin homology domain-containing family A member 8 Reactions: Gene Name: PLEKHA8 Uniprot ID: Q96JA3 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Sphingomyelin phosphodiesterase 4 Reactions: sphingomyelin + H2O = N-acylsphingosine + choline phosphate [RN:R02541] Gene Name: SMPD4 Uniprot ID: Q9NXE4 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Putative neutral ceramidase C Reactions: N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493] Gene Name: ASAH2C Uniprot ID: P0C7U2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Alkaline ceramidase 2 Reactions: N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493] Gene Name: ACER2 Uniprot ID: Q5QJU3 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Neutral ceramidase Reactions: N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493] Gene Name: ASAH2 Uniprot ID: Q9NR71 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Non-lysosomal glucosylceramidase Reactions: D-glucosyl-N-acylsphingosine + H2O = D-glucose + N-acylsphingosine [RN:R01498] Gene Name: GBA2 Uniprot ID: Q9HCG7 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Alkaline ceramidase 1 Reactions: N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493] Gene Name: ACER1 Uniprot ID: Q8TDN7 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Killer cell lectin-like receptor subfamily B member 1 Reactions: Gene Name: KLRB1 Uniprot ID: Q12918 Protein Sequence: FASTA Gene Sequence: FASTA
Name: LAG1 longevity assurance homolog 5 Reactions: Gene Name: LASS5 Uniprot ID: Q8N5B7 Protein Sequence: FASTA Gene Sequence: FASTA
Name: ATP-binding cassette sub-family A member 7 Reactions: Gene Name: ABCA7 Uniprot ID: Q8IZY2 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GPI-anchor transamidase Reactions: Gene Name: PIGK Uniprot ID: Q92643 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Glycosylphosphatidylinositol anchor attachment 1 protein Reactions: Gene Name: GPAA1 Uniprot ID: O43292 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Protein PLEKHA9 Reactions: Gene Name: PLEKHA9 Uniprot ID: O95397 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Glycolipid transfer protein domain-containing protein 2 Reactions: Gene Name: GLTPD2 Uniprot ID: A6NH11 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Putative uncharacterized protein PLEKHA8 Reactions: Gene Name: PLEKHA8 Uniprot ID: B5MDU3 Protein Sequence: FASTA Gene Sequence: FASTA
Name: T-cell surface glycoprotein CD1a Reactions: Gene Name: CD1A Uniprot ID: P06126 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Glycolipid transfer protein domain-containing protein 1 Reactions: Gene Name: GLTPD1 Uniprot ID: Q5TA50 Protein Sequence: FASTA Gene Sequence: FASTA
Name: T-cell surface glycoprotein CD1c Reactions: Gene Name: CD1C Uniprot ID: P29017 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Lipopolysaccharide-binding protein Reactions: Gene Name: LBP Uniprot ID: P18428 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Putative uncharacterized protein DKFZp434L0435 Reactions: Gene Name: DKFZp434L0435 Uniprot ID: Q9UFH6 Protein Sequence: FASTA Gene Sequence: FASTA
Name: T-cell surface glycoprotein CD1b Reactions: Gene Name: CD1B Uniprot ID: P29016 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Glycolipid transfer protein Reactions: Gene Name: GLTP Uniprot ID: Q9NZD2 Protein Sequence: FASTA Gene Sequence: FASTA

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