Showing metabocard for Trihexosylceramide (d18:1/26:1(17Z)) (BMDB0004884)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:11:57 UTC
Update Date2020-05-11 20:31:28 UTC
BMDB IDBMDB0004884
Secondary Accession Numbers
  • BMDB04884
Metabolite Identification
Common NameTrihexosylceramide (d18:1/26:1(17Z))
DescriptionTrihexosylceramide (d18:1/26:1(17Z)), 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 (d18:1/26:1(17Z)) 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]hexacosanimidateHMDB
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->4gal-beta1->4GLC-beta1->1'cer(D18:1/26:1HMDB
Gal-alpha1->4laccerHMDB
Ganglioside GL3HMDB
Gb3HMDB
Globo-N-triaosylceramideHMDB
GlobotriaosylceramideHMDB
GlobotriglycosylceramideHMDB
GlobotriosylceramideHMDB
Shiga toxin receptorHMDB
Chemical FormulaC62H117NO18
Average Molecular Weight1164.5883
Monoisotopic Molecular Weight1163.827065945
IUPAC NameN-[(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]hexacosanamide
Traditional NameN-[(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]hexacosanamide
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(COC1OC(CO)C(OC2OC(CO)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C(O)C1O)C(O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C62H117NO18/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-50(68)63-45(46(67)39-37-35-33-31-29-27-16-14-12-10-8-6-4-2)44-76-60-56(74)53(71)58(48(42-65)78-60)81-62-57(75)54(72)59(49(43-66)79-62)80-61-55(73)52(70)51(69)47(41-64)77-61/h37,39,45-49,51-62,64-67,69-75H,3-36,38,40-44H2,1-2H3,(H,63,68)/b39-37+
InChI KeyYWHNDSBMLSKIRV-NHFVQZBWSA-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
logP6.2ALOGPS
logP10ChemAxon
logS-5.1ALOGPS
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 Count49ChemAxon
Refractivity309.03 m³·mol⁻¹ChemAxon
Polarizability140.81 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, Positivesplash10-03dj-3901002011-be2465bc5620184d6498View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-1901001011-f85e2495278b1256888dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-029y-5910001000-5d5bb39fda4e7ac06a4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-975e375012808bacb428View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3901000010-2e14ff3b4a7b71b3e93fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kds-6942134140-3bf18c3394dbffbe7249View 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 IDHMDB0004884
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023477
KNApSAcK IDNot Available
Chemspider ID16744897
KEGG Compound IDC04737
BioCyc IDD-GALACTOSYL-14-D-GALACTOSYL-14-D-
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7141
PubChem Compound20057319
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available