Showing metabocard for Trihexosylceramide (d18:1/9Z-18:1) (BMDB0004878)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:11:49 UTC
Update Date2020-05-11 20:31:23 UTC
BMDB IDBMDB0004878
Secondary Accession Numbers
  • BMDB04878
Metabolite Identification
Common NameTrihexosylceramide (d18:1/9Z-18:1)
DescriptionTrihexosylceramide (d18:1/9Z-18:1), also known as globotriaosylceramide or ceramide trihexoside, 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. Trihexosylceramide (d18:1/9Z-18:1) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-[(4E)-1-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3-hydroxyoctadec-4-en-2-yl]octadec-9-enimidateHMDB
Ceramide trihexosideHMDB
D-Galactosyl-1,4-D-galactosyl-1,4-D-glucosylceramideHMDB
delta-Galactosyl-1,4-delta-galactosyl-1,4-delta-glucosylceramideHMDB
Fabry glycolipidHMDB
Gal-alpha1->4gal-beta1->4GLC-beta1->1'cerHMDB
Gal-alpha1->4laccerHMDB
Ganglioside GL3HMDB
Gb3HMDB
Globo-N-triaosylceramideHMDB
GlobotriaosylceramideHMDB
GlobotriglycosylceramideHMDB
GlobotriosylceramideHMDB
Shiga toxin receptorHMDB
Chemical FormulaC54H99NO18
Average Molecular Weight1050.3598
Monoisotopic Molecular Weight1049.686215369
IUPAC Name(9E)-N-[(4E)-1-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3-hydroxyoctadec-4-en-2-yl]octadec-9-enamide
Traditional Name(9E)-N-[(4E)-1-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3-hydroxyoctadec-4-en-2-yl]octadec-9-enamide
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC\C=C\C(O)C(COC1OC(CO)C(OC2OC(CO)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C(O)C1O)NC(=O)CCCCCCC\C=C\CCCCCCCC
InChI Identifier
InChI=1S/C54H99NO18/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-42(60)55-37(38(59)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)36-68-52-48(66)45(63)50(40(34-57)70-52)73-54-49(67)46(64)51(41(35-58)71-54)72-53-47(65)44(62)43(61)39(33-56)69-53/h17-18,29,31,37-41,43-54,56-59,61-67H,3-16,19-28,30,32-36H2,1-2H3,(H,55,60)/b18-17+,31-29+
InChI KeyXRPQSEBNLXORQZ-LSUSWXEESA-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
  • Oligosaccharide
  • Fatty acyl glycoside
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty amide
  • N-acyl-amine
  • Oxane
  • Fatty acyl
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Oxacycle
  • Polyol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Primary alcohol
  • Alcohol
  • Organopnictogen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic nitrogen 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
logP4.93ALOGPS
logP6.08ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)11.76ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area307.01 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity273.33 m³·mol⁻¹ChemAxon
Polarizability122.21 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-0w5a-9512020120-f38032a68e62d23c1316View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h61-3901020120-9e0b089f425ad828be7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-029x-5900020000-81d92690f9dde25b087bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000120-30de7c5e8d79ca081640View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9501000123-4db88328dcede6967ee7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-073c-7934131640-237243ecb1e3030f0902View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen Locations
  • Brain
  • Epidermis
  • Kidney
  • Liver
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected 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
Abnormal Concentrations
Not Available
HMDB IDHMDB0004878
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023471
KNApSAcK IDNot Available
Chemspider ID16744891
KEGG Compound IDC04737
BioCyc IDD-GALACTOSYL-14-D-GALACTOSYL-14-D-
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7135
PubChem Compound20057314
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available