Showing metabocard for Glucosylceramide (d18:1/9Z-18:1) (BMDB0004970)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:05 UTC
Update Date2020-05-11 20:54:18 UTC
BMDB IDBMDB0004970
Secondary Accession Numbers
  • BMDB04970
Metabolite Identification
Common NameGlucosylceramide (d18:1/9Z-18:1)
DescriptionGlucosylceramide (d18:1/9Z-18:1), also known as b-D-glucosyl-N-(oleoyl)sphing-4-enine or glccer(D18:1/18:1(9Z)), 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 (d18:1/9Z-18:1) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
beta-D-Glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enineChEBI
beta-D-Glucosyl-N-(oleoyl)sphing-4-enineChEBI
beta-D-Glucosyl-N-[(9Z)-octadecenoyl]-octadecasphing-4-enineChEBI
beta-D-Glucosyl-N-[(9Z)-octadecenoyl]-octadecasphingosineChEBI
GlcCer(D18:1/18:1(9Z))ChEBI
N-(9Z-Octadecenoyl)-1-beta-glucosyl-sphing-4-enineChEBI
b-D-Glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enineGenerator
Β-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enineGenerator
b-D-Glucosyl-N-(oleoyl)sphing-4-enineGenerator
Β-D-glucosyl-N-(oleoyl)sphing-4-enineGenerator
b-D-Glucosyl-N-[(9Z)-octadecenoyl]-octadecasphing-4-enineGenerator
Β-D-glucosyl-N-[(9Z)-octadecenoyl]-octadecasphing-4-enineGenerator
b-D-Glucosyl-N-[(9Z)-octadecenoyl]-octadecasphingosineGenerator
Β-D-glucosyl-N-[(9Z)-octadecenoyl]-octadecasphingosineGenerator
N-(9Z-Octadecenoyl)-1-b-glucosyl-sphing-4-enineGenerator
N-(9Z-Octadecenoyl)-1-β-glucosyl-sphing-4-enineGenerator
b-D-Glucosyl-N-(oleoyl)sphingosineHMDB
Β-D-glucosyl-N-(oleoyl)sphingosineHMDB
1-O-b-D-Glucopyranosyl-ceramideHMDB
1-O-beta-delta-Glucopyranosyl-ceramideHMDB
Ganglioside GL1aHMDB
Gaucher cerebrosideHMDB
GLC-beta1->1'cerHMDB
GlcCeramideHMDB
GlucocerebrosideHMDB
GlucosylceramideHMDB
Glucosylceramide (D18:1/9Z-18:1)ChEBI
Chemical FormulaC42H79NO8
Average Molecular Weight726.0786
Monoisotopic Molecular Weight725.580568509
IUPAC Name(9Z)-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]octadec-9-enamide
Traditional Name(9Z)-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]octadec-9-enamide
CAS Registry Number85305-87-9
SMILES
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)NC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C42H79NO8/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/h17-18,29,31,35-37,39-42,44-45,47-49H,3-16,19-28,30,32-34H2,1-2H3,(H,43,46)/b18-17-,31-29+/t35-,36+,37+,39+,40-,41+,42+/m0/s1
InChI KeyMVGFIPNJBNBHNC-HVFXMTMESA-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 DescriptorsNot Available
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
logP8.12ALOGPS
logP9.62ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)12.18ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area148.71 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity208.51 m³·mol⁻¹ChemAxon
Polarizability90.9 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000900-1eab8439ececedae3757View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0229-6210136900-93748df163fc0c653248View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-074l-9445010000-3615f847930b2b132c68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1010061900-aab15f2353759a4f9238View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-2100093400-fe9a62d5427a03e7f023View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9400030000-295e197659e345f08e17View 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 IDHMDB0004970
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023557
KNApSAcK IDNot Available
Chemspider ID16744955
KEGG Compound IDC01190
BioCyc IDGLUCOSYL_CERAMIDE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7223
PubChem Compound20057355
PDB ID03F
ChEBI ID139140
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available