| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2009-01-27 03:43:11 -0700 |
| Update Date |
2013-02-08 17:26:56 -0700 |
| HMDB ID |
HMDB11591 |
| Secondary Accession Numbers |
|
| Metabolite Identification |
|---|
| Common Name |
Lactosylceramide (d18:1/18:0) |
| Description |
Lactosylceramide (d18:1/18:0) is a lactosylceramide or LacCer. Lactosylceramides are the most important and abundant of the diosylceramides. Lactosylceramides (LacCer) were originally called 'cytolipin H'. It is found in small amounts only in most animal tissues, but it has a number of significant biological functions and it is of great importance as the biosynthetic precursor of most of the neutral oligoglycosylceramides, sulfatides and gangliosides. In animal tissues, biosynthesis of lactosylceramide involves addition of the second monosaccharides unit (galactose) as its nucleotide derivative to monoglucosylceramide, catalysed by a specific beta-1,4-galactosyltransferase on the lumenal side of the Golgi apparatus. The glucosylceramide precursor must first cross from the cytosolic side of the membrane, possibly via the action of a flippase. The lactosylceramide produced can be further glycosylated or transferred to the plasma membrane. Lactosylceramide may assist in stabilizing the plasma membrane and activating receptor molecules in the special micro-domains or rafts, as with the cerebrosides. It may also have its own specialized function in the immunological system in that it is known to bind to specific bacteria. In addition, it is believed that a number of pro-inflammatory factors activate lactosylceramide synthase to generate lactosylceramide, which in turn activates "oxygen-sensitive" signalling pathways that affect such cellular processes as proliferation, adhesion, migration and angiogenesis. Dysfunctions in these pathways can affect several diseases of the cardiovascular system, cancer and inflammatory states, so lactosylceramide metabolism is a potential target for new therapeutic treatments. beta-D-Galactosyl-1,4-beta-D-glucosylceramide is the second to last step in the synthesis of N-Acylsphingosine and is converted. from Glucosylceramide via the enzyme beta-1,4-galactosyltransferase 6(EC:2.4.1.-). It can be converted to Glucosylceramide via the enzyme beta-galactosidase (EC:3.2.1.23). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 1-O-(4-O-b-D-Galactopyranosyl-b-D-glucopyranosyl)-Ceramide
- 1-O-(4-O-beta-D-Galactopyranosyl-beta-glucopyranosyl)ceramide
- 1-O-(4-O-beta-delta-Galactopyranosyl-beta-delta-glucopyranosyl)-Ceramide
- 1-O-(4-O-beta-delta-Galactopyranosyl-beta-glucopyranosyl)ceramide
- 1ylce-O-(4-O-beta-delta-Galactopyranosyl-beta-glucopyranosyl)ceramide
- beta-D-Galactosyl-1,4-beta-D-Glucosylceramide
- beta-delta-Galactosyl-1,4-beta-delta-glucosramide
- beta-delta-Galactosyl-1,4-beta-delta-Glucosylceramide
- CDH
- CDw17 antigen
- Cytolipin H
- D-Galactosyl-1,4-beta-D-glucosylceramide
- delta-Galactosyl-1,4-beta-delta-glucosylceramide
- Gal-beta1->4Glc-beta1->1'Cer
- LacCer
- LacCer(d18:1/18:0)
- Lactosyl ceramide (d18:1/18:0)
- Lactosyl-N-acylsphingosine
- Lactosylceramide
- N-(Octadecanoyl)-1-b-lactosyl-sphing-4-enine
- N-(Octadecanoyl)-1-beta-lactosyl-sphing-4-enine
- N-Lignoceryl sphingosyl lactoside
|
| Chemical Formula |
C48H91NO13 |
| Average Molecular Weight |
890.235 |
| Monoisotopic Molecular Weight |
889.649042003 |
| IUPAC Name |
N-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]octadecanamide |
| Traditional IUPAC Name |
N-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]octadecanamide |
| CAS Registry Number |
Not Available |
| SMILES |
[H][C@@](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)(NC(=O)CCCCCCCCCCCCCCCCC)[C@]([H])(O)\C=C\CCCCCCCCCCCCC |
| InChI Identifier |
InChI=1S/C48H91NO13/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(53)49-36(37(52)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)35-59-47-45(58)43(56)46(39(34-51)61-47)62-48-44(57)42(55)41(54)38(33-50)60-48/h29,31,36-39,41-48,50-52,54-58H,3-28,30,32-35H2,1-2H3,(H,49,53)/b31-29+/t36-,37+,38+,39+,41-,42-,43+,44+,45+,46+,47+,48-/m0/s1 |
| InChI Key |
VOZHMDQUIRUFQW-LOTHNZFDSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Sphingolipids |
| Sub Class |
Neutral Glycosphingolipids |
| Other Descriptors |
- Aliphatic Heteropolycyclic Compounds
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| Substituents |
- 1,2 Diol
- Acetal
- Alkyl Glycoside
- Allyl Alcohol
- Carboxamide Group
- Ceramide
- Fatty Acyl Glycoside
- Glycosyl Compound
- Hexose Disaccharide
- N Acyl Amine
- O Glycosyl Compound
- Oxane
- Primary Alcohol
- Saccharide
- Secondary Alcohol
- Secondary Carboxylic Acid Amide
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| Direct Parent |
Gal- (Gala series) |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
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| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
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| 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 |
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| Predicted Properties |
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| Spectra |
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Not Available
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| Biological Properties |
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| Cellular Locations |
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| Biofluid Locations |
Not Available
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| Tissue Location |
Not Available
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| Pathways |
Not Available
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| Normal Concentrations |
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Not Available |
| Abnormal Concentrations |
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Not Available |
| Associated Disorders and Diseases |
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| 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 |
FDB028304 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
8435601  |
| KEGG Compound ID |
C01290 |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB11591 |
| Metagene Link |
HMDB11591 |
| METLIN ID |
Not Available |
| PubChem Compound |
10260120 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
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| General References |
Not Available |
| Enzymes |
|---|
| Name: |
Galactocerebrosidase
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| Reactions: |
- D-galactosyl-N-acylsphingosine + H2O = D-galactose + N-acylsphingosine [RN:R03617]
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| Gene Name: |
GALC |
| Uniprot ID: |
P54803 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Sialidase-1
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| Reactions: |
- Hydrolysis of alpha-(2->3)-, alpha-(2->6)-, alpha-(2->8)- glycosidic linkages of terminal sialic acid residues in oligosaccharides, glycoproteins, glycolipids, colominic acid and synthetic substrates ALL_REAC (other) R03491 R04018 R04634 R04650 R05115 R05117 R05996(G) R05998(G) R05999(G) R06012(G) R06147(G) R06253(G) INHIBITOR 2-Deoxy-2,3-dehydro-N-acetylneuraminic acid [CPD:C04580]
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| Gene Name: |
NEU1 |
| Uniprot ID: |
Q99519 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Lactosylceramide alpha-2,3-sialyltransferase
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| Reactions: |
- CMP-N-acetylneuraminate + beta-D-galactosyl-(1->4)-beta-D-glucosyl-(11)-ceramide = CMP + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D- glucosyl-(11)-ceramide [RN:R03488 R05937]
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| Gene Name: |
ST3GAL5 |
| Uniprot ID: |
Q9UNP4 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Beta-hexosaminidase subunit beta
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| Reactions: |
- Hydrolysis of terminal non-reducing N-acetyl-D-hexosamine residues in N-acetyl-beta-D-hexosaminides ALL_REAC (other) R00022 R03492 R04184 R04586 R05963(G) R06001(G) R06004(G) R06141(G) R07809(G) R07810(G)
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| Gene Name: |
HEXB |
| Uniprot ID: |
P07686 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Beta-hexosaminidase subunit alpha
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| Reactions: |
- Hydrolysis of terminal non-reducing N-acetyl-D-hexosamine residues in N-acetyl-beta-D-hexosaminides ALL_REAC (other) R00022 R03492 R04184 R04586 R05963(G) R06001(G) R06004(G) R06141(G) R07809(G) R07810(G)
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| Gene Name: |
HEXA |
| Uniprot ID: |
P06865 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Beta-1,4 N-acetylgalactosaminyltransferase 1
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| Reactions: |
- UDP-N-acetyl-D-galactosamine + 1-O-[O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D- galactopyranosyl-(1->4)-beta-D-glucopyranosyl]-ceramide = UDP + 1-O-[O-2-(acetylamino)-2-deoxy-beta-D-galactopyranosyl-(1->4)-O-[N- acetyl-alpha-neuraminosyl-(2->3)]-O-beta-D-galactopyranosyl-(1->4)- beta-D-glucopyranosyl]-ceramide [RN:R04584 R05939]
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| Gene Name: |
B4GALNT1 |
| Uniprot ID: |
Q00973 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Lactosylceramide 4-alpha-galactosyltransferase
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| 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]
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| Gene Name: |
A4GALT |
| Uniprot ID: |
Q9NPC4 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Acid ceramidase
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| Reactions: |
- N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
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| Gene Name: |
ASAH1 |
| Uniprot ID: |
Q13510 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Glucosylceramidase
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| Reactions: |
- D-glucosyl-N-acylsphingosine + H2O = D-glucose + N-acylsphingosine [RN:R01498]
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| Gene Name: |
GBA |
| Uniprot ID: |
P04062 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Alkaline ceramidase 2
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| Reactions: |
- N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
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| Gene Name: |
ACER2 |
| Uniprot ID: |
Q5QJU3 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Neutral ceramidase
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| Reactions: |
- N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
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| Gene Name: |
ASAH2 |
| Uniprot ID: |
Q9NR71 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Alkaline ceramidase 1
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| Reactions: |
- N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
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| Gene Name: |
ACER1 |
| Uniprot ID: |
Q8TDN7 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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