Showing metabocard for Glucosylceramide (d18:1/16:0) (BMDB0004971)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:06 UTC
Update Date2020-05-11 20:54:18 UTC
BMDB IDBMDB0004971
Secondary Accession Numbers
  • BMDB04971
Metabolite Identification
Common NameGlucosylceramide (d18:1/16:0)
DescriptionGlcCer(d18:1/16:0), 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(d18:1/16:0) is a colorless solid that consists of an unsaturated 18-carbon sphingoid base with an attached saturated hexadecanoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
beta-D-Glucosyl-(11')-N-hexadecanoylsphing-4-enineChEBI
beta-D-Glucosyl-N-palmitoylsphinganineChEBI
N-(Hexadecanoyl)-1-beta-glucosyl-sphing-4-enineChEBI
b-D-Glucosyl-(11')-N-hexadecanoylsphing-4-enineGenerator
Β-D-glucosyl-(11')-N-hexadecanoylsphing-4-enineGenerator
b-D-Glucosyl-N-palmitoylsphinganineGenerator
Β-D-glucosyl-N-palmitoylsphinganineGenerator
N-(Hexadecanoyl)-1-b-glucosyl-sphing-4-enineGenerator
N-(Hexadecanoyl)-1-β-glucosyl-sphing-4-enineGenerator
GlucosylceramideMetBuilder
Glucosylceramide(D18:1/16:0)MetBuilder
N-(Hexadecanoyl)-1-β-glucosyl-sphingosineMetBuilder
N-(Hexadecanoyl)-1-β-glucosyl-D-erythro-sphingosineMetBuilder
N-(Hexadecanoyl)-1-β-glucosyl-4-sphingenineMetBuilder
N-(Hexadecanoyl)-1-β-glucosyl-D-sphingosineMetBuilder
N-(Hexadecanoyl)-1-β-glucosyl-sphingenineMetBuilder
N-(Hexadecanoyl)-1-β-glucosyl-erythro-4-sphingenineMetBuilder
GlcCer(D18:1/16:0)ChEBI
1-O-b-D-Glucopyranosyl-ceramideHMDB
1-O-beta-delta-Glucopyranosyl-ceramideHMDB
Ganglioside GL1aHMDB
Gaucher cerebrosideHMDB
GLC-beta1->1'cerHMDB
GlcCeramideHMDB
GlucocerebrosideHMDB
b-D-Glucosyl-N-hexadecanoylsphingosineGenerator, HMDB
Β-D-glucosyl-N-hexadecanoylsphingosineGenerator, HMDB
beta-D-Glucosyl-N-hexadecanoylsphing-4E-enineChEBI
b-D-Glucosyl-N-hexadecanoylsphing-4E-enineGenerator
Β-D-glucosyl-N-hexadecanoylsphing-4E-enineGenerator
Chemical FormulaC40H77NO8
Average Molecular Weight700.0413
Monoisotopic Molecular Weight699.564918445
IUPAC NameN-[(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]hexadecanamide
Traditional NameN-[(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]hexadecanamide
CAS Registry Number85305-87-9
SMILES
CCCCCCCCCCCCCCCC(=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
InChI Identifier
InChI=1S/C40H77NO8/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(43)33(32-48-40-39(47)38(46)37(45)35(31-42)49-40)41-36(44)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,33-35,37-40,42-43,45-47H,3-26,28,30-32H2,1-2H3,(H,41,44)/b29-27+/t33-,34+,35+,37+,38-,39+,40+/m0/s1
InChI KeyVJLLLMIZEJJZTE-NNTBDIJYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassGlycosphingolipids
Direct ParentGlycosyl-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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Endosome
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityInsolubleNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.7ALOGPS
logP9.09ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)12.18ChemAxon
pKa (Strongest Basic)0.019ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area148.71 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity198.19 m³·mol⁻¹ChemAxon
Polarizability88.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01qi-4710259000-de915798ee8c440169ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gx0-0130359300-e9c5a5cdef2412266c17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-023c-0160394000-232c038a22cf94a4947fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01x3-3590221000-868d81febe76f98cebb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1300049000-42b410d97f315072a1c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03yi-5860966000-eaed4e11cb5421c80d9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9442010000-7a47c02ac22fed32706fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000009000-2978eacc43b2095a745cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3100139000-c6d87f301eff13e5888dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052k-8293300000-a386569d1b8551f01a57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3100095800-caef332a980acf7e4187View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-2220193200-c8dd5cfe42a5062a250dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-7191210000-3f1adb45d7f91a2684b5View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen Locations
  • Bone Marrow
  • Brain
  • Liver
  • Neuron
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Bone MarrowExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004971
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023558
KNApSAcK IDNot Available
Chemspider ID16744956
KEGG Compound IDC01190
BioCyc IDGLUCOSYL_CERAMIDE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7224
PubChem Compound14035030
PDB IDNot Available
ChEBI ID84716
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available