Showing metabocard for Glucosylceramide (d18:1/18:0) (BMDB0004972)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:08 UTC
Update Date2020-05-11 20:54:19 UTC
BMDB IDBMDB0004972
Secondary Accession Numbers
  • BMDB04972
Metabolite Identification
Common NameGlucosylceramide (d18:1/18:0)
DescriptionGlucosylceramide (d18:1/18:0), also known as b-D-glucosyl-N-stearoylsphingosine or C18 glccer, 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. Glucosylceramide (d18:1/18:0) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
beta-D-Glucosyl-(11)-N-octadecanoylsphing-4-enineChEBI
beta-D-Glucosyl-N-stearoylsphingosineChEBI
C18 GlcCerChEBI
GlcCer(D18:1/18:0)ChEBI
N-(Octadecanoyl)-1-beta-glucosyl-sphing-4-enineChEBI
b-D-Glucosyl-(11)-N-octadecanoylsphing-4-enineGenerator
Β-D-glucosyl-(11)-N-octadecanoylsphing-4-enineGenerator
b-D-Glucosyl-N-stearoylsphingosineGenerator
Β-D-glucosyl-N-stearoylsphingosineGenerator
N-(Octadecanoyl)-1-b-glucosyl-sphing-4-enineGenerator
N-(Octadecanoyl)-1-β-glucosyl-sphing-4-enineGenerator
b-D-Glucosyl-N-octadecanoylsphingosineHMDB
Β-D-glucosyl-N-octadecanoylsphingosineHMDB
1-O-b-D-Glucopyranosyl-ceramideHMDB
1-O-beta-delta-Glucopyranosyl-ceramideHMDB
Ganglioside GL1aHMDB
Gaucher cerebrosideHMDB
GLC-beta1->1'cerHMDB
GlcCeramideHMDB
GlucocerebrosideHMDB
GlucosylceramideHMDB
Chemical FormulaC42H81NO8
Average Molecular Weight728.0944
Monoisotopic Molecular Weight727.596218573
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]octadecanamide
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]octadecanamide
CAS Registry Number85305-87-9
SMILES
CCCCCCCCCCCCCCCCCC(=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/C42H81NO8/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-38(46)43-35(34-50-42-41(49)40(48)39(47)37(33-44)51-42)36(45)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,35-37,39-42,44-45,47-49H,3-28,30,32-34H2,1-2H3,(H,43,46)/b31-29+/t35-,36+,37+,39+,40-,41+,42+/m0/s1
InChI KeyYMYQEDCYNANIPI-DYJXBSQNSA-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
logP8.13ALOGPS
logP9.98ChemAxon
logS-6ALOGPS
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 Count35ChemAxon
Refractivity207.39 m³·mol⁻¹ChemAxon
Polarizability92.71 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 (TMS_1_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0130342900-6ffc5f3d01ce03c04951View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-029w-0170392100-49f66daed67f6bab7d8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001c-0190113000-a73a590cd5f679d848a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1310041900-27fa50bb9f596bb3676fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08pi-5860790400-a33108b27bb384d72fdbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9442010000-b6435f233c20a9fdfd9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ta-3000062900-5ef4db4827212a7ec310View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-5110193400-0c2eadd40ed34cfdb5a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9051020000-280774e07dab7928b2e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-a655397bdc68858249beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-5120136900-58b9f7cb5b3c0ecd8262View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0axr-9267120000-b3ceb137bfa88003084cView in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
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 IDHMDB0004972
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023559
KNApSAcK IDNot Available
Chemspider ID10132611
KEGG Compound IDC01190
BioCyc IDGLUCOSYL_CERAMIDE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7225
PubChem Compound11958364
PDB IDNot Available
ChEBI ID84719
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available