| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:14:15 UTC |
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| Update Date | 2020-05-11 20:54:23 UTC |
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| BMDB ID | BMDB0004977 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Glucosylceramide (d18:1/26:0) |
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| Description | GlcCer(d18:1/26:0), also known as cerebroside (CB), glycosphingolipid or glycoceramide, is a glucosylceramide (GlcCer). Glucosylceramides are members of the class of compounds known as sphingolipids (SPs), or glycosylceramides. SPs are lipids containing a backbone of sphingoid bases (e.g. sphingosine or sphinganine) that are often covalently bound to a fatty acid derivative through N-acylation. SPs are found in cell membranes, particularly in peripheral nerve cells and the cells found in the central nervous system (including the brain and spinal cord). Sphingolipids are extremely versatile molecules that have functions controlling fundamental cellular processes such as cell division, differentiation, and cell death. Impairments associated with sphingolipid metabolism are associated with many common human diseases such as diabetes, various cancers, microbial infections, diseases of the cardiovascular and respiratory systems, Alzheimer’s disease and other neurological syndromes. The biosynthesis and catabolism of sphingolipids involves a large number of intermediate metabolites where many different enzymes are involved. Simple sphingolipids, which include the sphingoid bases and ceramides, make up the early products of the sphingolipid synthetic pathways, while complex sphingolipids may be formed by the addition of head groups to the ceramide template (Wikipedia). Cerebroside is the common name for monoglycosylceramides which are important components in animal muscle and nerve cell membranes. In terms of their chemical structure, GlcCers can either be glycosphingolipids (ceramide and oligosaccharide) or oligoglycosylceramides with one or more sialic acids (i.e. n-acetylneuraminic acid) linked on the sugar chain. GlcCers are important components of the cell plasma membrane, which modulates cell signal transduction events. Gangliosides have been found to be very important in immunology. Gangliosides can amount to 6% of the weight of lipids from brain, but they are found at lower levels in other animal tissues. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. CBs consist of a ceramide with a single sugar residue which could be either glucose or galactose; the two major types are therefore called glucocerebrosides (glucosylceramides; containing glucose) and galactocerebrosides (galactosylceramides; containing galactose). Galactocerebrosides are the most common and are typically found in neuronal cell membrane, while glucocerebrosides are the least common and are found in other tissues such as the spleen and erythrocytes. Glucocerebrosides are not normally found in cell membranes. Instead, they are typically intermediates in the synthesis or degradation of more complex glycosphingolipids. In humans, glucosylceramide is produced by the enzyme ceramide glucosyltransferase from a ceramide or by the enzyme beta-galactosidase from a lactosylceramides (LacCer). The latter could also be produced from glucosylceramides by the enzyme beta-1,4-galactosyltransferase 6. Glucosylceramide could be hydrolyzed by the enzyme glucosylceramidase to produce a ceramide. Galactosylceramide on the other hand could undergo sulfoglycolipid biosynthesis to produce a sulfatide which in turn can be catalyzed by the enzyme arylsulfatase A to generate a galactosylceramide. Galactosylceramide could also be hydrolyzed to produce a ceramide by the enzyme galactosylceramidase. Other sources for galactosylceramide are ganglioside and digalactosylceramide, which are processed by the enzymes sialidase-2/3/4 and alpha-galactosidase respectively. Excess lysosomal accumulation of glucocerebrosides is found in Gaucher disease, which is an inborn error of metabolism. In terms of its appearance and structure, GlcCer(d18:1/26:0) is a colorless solid that consists of an unsaturated 18-carbon sphingoid base with an attached saturated hexacosanoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| beta-D-Glucopyranosyl-N-(hexacosanoyl)sphingosine | ChEBI | | beta-D-Glucosyl-N-docosanoylsphingosine | ChEBI | | beta-GlcCer | ChEBI | | beta-Glucosylceramide | ChEBI | | Glucosylceramide (D18:1/26:0) | ChEBI | | N-(Hexacosanoyl)-1-beta-glucosyl-sphing-4-enine | ChEBI | | b-D-Glucopyranosyl-N-(hexacosanoyl)sphingosine | Generator | | Β-D-glucopyranosyl-N-(hexacosanoyl)sphingosine | Generator | | b-D-Glucosyl-N-docosanoylsphingosine | Generator | | Β-D-glucosyl-N-docosanoylsphingosine | Generator | | b-GlcCer | Generator | | Β-glccer | Generator | | b-Glucosylceramide | Generator | | Β-glucosylceramide | Generator | | N-(Hexacosanoyl)-1-b-glucosyl-sphing-4-enine | Generator | | N-(Hexacosanoyl)-1-β-glucosyl-sphing-4-enine | Generator | | b-D-Glucosyl-N-(hexacosanoyl)sphingosine | HMDB | | Β-D-glucosyl-N-(hexacosanoyl)sphingosine | HMDB | | 1-O-b-D-Glucopyranosyl-ceramide | HMDB | | 1-O-beta-delta-Glucopyranosyl-ceramide | HMDB | | Ganglioside GL1a | HMDB | | Gaucher cerebroside | HMDB | | GLC-beta1->1'cer | HMDB | | GlcCeramide | HMDB | | Glucocerebroside | HMDB | | Glucosylceramide | HMDB | | Glucosylceramide(D18:1/26:0) | MetBuilder | | N-(Hexacosanoyl)-1-β-glucosyl-sphingosine | MetBuilder | | N-(Hexacosanoyl)-1-β-glucosyl-D-erythro-sphingosine | MetBuilder | | N-(Hexacosanoyl)-1-β-glucosyl-4-sphingenine | MetBuilder | | N-(Hexacosanoyl)-1-β-glucosyl-D-sphingosine | MetBuilder | | N-(Hexacosanoyl)-1-β-glucosyl-sphingenine | MetBuilder | | N-(Hexacosanoyl)-1-β-glucosyl-erythro-4-sphingenine | MetBuilder |
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| Chemical Formula | C50H97NO8 |
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| Average Molecular Weight | 840.3071 |
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| Monoisotopic Molecular Weight | 839.721419085 |
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| IUPAC Name | N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]hexacosanamide |
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| Traditional Name | N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]hexacosanamide |
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| CAS Registry Number | 85305-87-9 |
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| SMILES | CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCC |
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| InChI Identifier | InChI=1S/C50H97NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-46(54)51-43(42-58-50-49(57)48(56)47(55)45(41-52)59-50)44(53)39-37-35-33-31-29-27-16-14-12-10-8-6-4-2/h37,39,43-45,47-50,52-53,55-57H,3-36,38,40-42H2,1-2H3,(H,51,54)/b39-37+/t43-,44+,45+,47+,48-,49+,50+/m0/s1 |
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| InChI Key | DOIOUJPHIXRQFM-WBOUPBNQSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Sphingolipids |
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| Sub Class | Glycosphingolipids |
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| Direct Parent | Glycosyl-N-acylsphingosines |
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| Alternative Parents | |
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| Substituents | - Glycosyl-n-acylsphingosine
- Fatty acyl glycoside
- Fatty acyl glycoside of mono- or disaccharide
- Alkyl glycoside
- Hexose monosaccharide
- Glycosyl compound
- O-glycosyl compound
- Fatty amide
- Fatty acyl
- Monosaccharide
- N-acyl-amine
- Oxane
- Carboxamide group
- Secondary carboxylic acid amide
- Secondary alcohol
- Acetal
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Alcohol
- Organic oxygen compound
- Organic nitrogen compound
- Primary alcohol
- Carbonyl group
- Organooxygen compound
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Expected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cell membrane
- Endosome
- Membrane
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Insoluble | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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