Showing Compound Glucosylceramide (d18:1/26:0) (FDB023564)

Record Information

Version

1.0

Creation date

2011-09-21 00:31:40 UTC

Update date

2017-03-11 23:00:32 UTC

Primary ID

FDB023564

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Glucosylceramide (d18:1/26:0)

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).

CAS Number

85305-87-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
1-O-b-D-Glucopyranosyl-ceramide	HMDB
1-O-beta-delta-Glucopyranosyl-ceramide	HMDB
b-D-Glucopyranosyl-N-(hexacosanoyl)sphingosine	Generator
b-D-Glucosyl-N-(hexacosanoyl)sphingosine	HMDB
b-D-Glucosyl-N-docosanoylsphingosine	Generator
b-GlcCer	Generator
b-Glucosylceramide	Generator
beta-D-Glucopyranosyl-N-(hexacosanoyl)sphingosine	ChEBI
beta-D-Glucosyl-N-docosanoylsphingosine	ChEBI
beta-GlcCer	ChEBI

Showing 1 to 10 of 34 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.00013 g/L	ALOGPS
logP	9.39	ALOGPS
logP	13.54	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	0.019	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	148.71 Å²	ChemAxon
Rotatable Bond Count	43	ChemAxon
Refractivity	244.2 m³·mol⁻¹	ChemAxon
Polarizability	109.84 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C50H97NO8

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

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

InChI Key

DOIOUJPHIXRQFM-WBOUPBNQSA-N

Isomeric 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

Average Molecular Weight

840.3071

Monoisotopic Molecular Weight

839.721419085

Classification

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Glycosphingolipids

Direct Parent

Glycosyl-N-acylsphingosines

Alternative Parents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

beta-D-glucosyl-N-acylsphingosine (CHEBI:75344 )

Ontology

Physiological effect

Organoleptic effect:

Touch:

Smooth

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Organ and components:

Biofluid and excreta:

Blood

Cell and elements:

Extracellular

Cell:

Nerve cell

Subcellular:

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Biochemical process:

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Biological role:

Molecular messenger:

Signaling molecule

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-4100006090-96198f40116ec3c0e9ee	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-6200109340-940617b342629e98a798	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000x-9141002000-082a82cfa78961eb1830	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000000090-6d352cdb0a1a98891569	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-5110103590-b1cc9381f523b306baec	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-9242603000-0ead7a22d6777d89d778	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

16744962

ChEMBL ID

Not Available

KEGG Compound ID

C01190

Pubchem Compound ID

20057359

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB04977

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Glucocerebroside

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
Acid ceramidase	ASAH1	Q13510
Alkaline ceramidase 1	ACER1	Q8TDN7
Alkaline ceramidase 2	ACER2	Q5QJU3
Antigen-presenting glycoprotein CD1d	CD1D	P15813
Beta-1,3-galactosyltransferase 5	B3GALT5	Q9Y2C3
Beta-galactosidase	GLB1	P16278
Ceramide glucosyltransferase	UGCG	Q16739
Ceramide synthase 1	CERS1	P27544
Collagen type IV alpha-3-binding protein	COL4A3BP	Q9Y5P4
Epididymal secretory protein E1	NPC2	P61916