Showing metabocard for Glucosylceramide (d18:1/24:1(15Z)) (BMDB0004975)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:12 UTC
Update Date2020-05-11 20:54:22 UTC
BMDB IDBMDB0004975
Secondary Accession Numbers
  • BMDB04975
Metabolite Identification
Common NameGlucosylceramide (d18:1/24:1(15Z))
DescriptionGlucosylceramide (d18:1/24:1(15Z)), also known as N-nervonoyl-beta-D-glucosylsphingosine or beta-glccer (C24:1), 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 (d18:1/24:1(15Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-O-beta-D-Glucopyranosyl-N-(nervonoyl)sphingosineChEBI
beta-D-Glucosyl-N-(15Z-tetracosenoyl)-sphing-4E-enineChEBI
beta-GlcCer (C24:1)ChEBI
C24:1 beta-D-Glucosyl ceramideChEBI
C24:1 beta-GlcCerChEBI
C24:1 GlcCerChEBI
C24:1-beta-Glucosyl ceramideChEBI
D-Glucosyl-beta-1,1' N-(15Z-tetracosenoyl)-D-erythro-sphingosineChEBI
GlcCer(D18:1/24:1(15Z))ChEBI
Glucosyl(beta) ceramide (D18:1/24:1(15Z))ChEBI
N-(15Z-Tetracosenoyl)-1-beta-glucosyl-sphing-4-eneChEBI
N-(15Z-Tetracosenoyl)-1-beta-glucosyl-sphing-4-enineChEBI
N-Nervonoyl-beta-D-glucosylsphingosineChEBI
N-Nervonoyl-beta-glucosylsphingosineChEBI
N-NervonoylglucosylsphingosineChEBI
N-Nervonyl-beta-D-glucosylsphingosineChEBI
N-Nervonyl-beta-glucosylsphingosineChEBI
N-NervonylglucosylsphingosineChEBI
1-O-b-D-Glucopyranosyl-N-(nervonoyl)sphingosineGenerator
1-O-Β-D-glucopyranosyl-N-(nervonoyl)sphingosineGenerator
b-D-Glucosyl-N-(15Z-tetracosenoyl)-sphing-4E-enineGenerator
Β-D-glucosyl-N-(15Z-tetracosenoyl)-sphing-4E-enineGenerator
b-GlcCer (C24:1)Generator
Β-glccer (C24:1)Generator
C24:1 b-D-Glucosyl ceramideGenerator
C24:1 Β-D-glucosyl ceramideGenerator
C24:1 b-GlcCerGenerator
C24:1 Β-glccerGenerator
C24:1-b-Glucosyl ceramideGenerator
C24:1-Β-glucosyl ceramideGenerator
D-Glucosyl-b-1,1' N-(15Z-tetracosenoyl)-D-erythro-sphingosineGenerator
D-Glucosyl-β-1,1' N-(15Z-tetracosenoyl)-D-erythro-sphingosineGenerator
Glucosyl(b) ceramide (D18:1/24:1(15Z))Generator
Glucosyl(β) ceramide (D18:1/24:1(15Z))Generator
N-(15Z-Tetracosenoyl)-1-b-glucosyl-sphing-4-eneGenerator
N-(15Z-Tetracosenoyl)-1-β-glucosyl-sphing-4-eneGenerator
N-(15Z-Tetracosenoyl)-1-b-glucosyl-sphing-4-enineGenerator
N-(15Z-Tetracosenoyl)-1-β-glucosyl-sphing-4-enineGenerator
N-Nervonoyl-b-D-glucosylsphingosineGenerator
N-Nervonoyl-β-D-glucosylsphingosineGenerator
N-Nervonoyl-b-glucosylsphingosineGenerator
N-Nervonoyl-β-glucosylsphingosineGenerator
N-Nervonyl-b-D-glucosylsphingosineGenerator
N-Nervonyl-β-D-glucosylsphingosineGenerator
N-Nervonyl-b-glucosylsphingosineGenerator
N-Nervonyl-β-glucosylsphingosineGenerator
b-D-Glucosyl-N-(nervonoyl)sphingosineHMDB
Β-D-glucosyl-N-(nervonoyl)sphingosineHMDB
1-O-b-D-Glucopyranosyl-ceramideHMDB
1-O-beta-delta-Glucopyranosyl-ceramideHMDB
Ganglioside GL1aHMDB
Gaucher cerebrosideHMDB
GLC-beta1->1'cerHMDB
GLC-beta1->1'cer(D18:1/24:1HMDB
GlcCeramideHMDB
GlucocerebrosideHMDB
GlucosylceramideHMDB
Chemical FormulaC48H91NO8
Average Molecular Weight810.238
Monoisotopic Molecular Weight809.674468893
IUPAC Name(15Z)-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]tetracos-15-enamide
Traditional Name(15Z)-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]tetracos-15-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)CCCCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C48H91NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-44(52)49-41(40-56-48-47(55)46(54)45(53)43(39-50)57-48)42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h17-18,35,37,41-43,45-48,50-51,53-55H,3-16,19-34,36,38-40H2,1-2H3,(H,49,52)/b18-17-,37-35+/t41-,42+,43+,45+,46-,47+,48+/m0/s1
InChI KeyWBOZIXHPUPAOIA-JZZPSRGZSA-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
logP9.12ALOGPS
logP12.29ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)12.18ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area148.71 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity236.11 m³·mol⁻¹ChemAxon
Polarizability103.89 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, Positivesplash10-01ox-0102305930-ee1d5a4cd66ba5a9bb04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0223309400-ea1c0d9959363b4ffca6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ed-1498206700-1c79a2c1fc53b1b4f2d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2400106590-abce0af2b0cec9640d00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ml-6916268410-900aa3aa1b25d15ffa86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9414001000-ef9e5f3dfac2764f2457View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-f50e2b4ec00e9f49c1feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-7210104790-bdf0c08b1ba9b4e32f67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9415320000-a289b61abf581d8881adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2002009560-655411d55f2feb31a3deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-2100009310-662ca4397c6119825e93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9500004000-9ff06df0fe9afa39b9eaView 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 IDHMDB0004975
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023562
KNApSAcK IDNot Available
Chemspider ID16744960
KEGG Compound IDC01190
BioCyc IDGLUCOSYL_CERAMIDE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7228
PubChem Compound20057357
PDB IDNot Available
ChEBI ID76302
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available