Showing metabocard for Trihexosylceramide (d18:1/12:0) (BMDB0004877)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:11:48 UTC
Update Date2020-05-11 20:31:22 UTC
BMDB IDBMDB0004877
Secondary Accession Numbers
  • BMDB04877
Metabolite Identification
Common NameTrihexosylceramide (d18:1/12:0)
DescriptionTrihexosylceramide (d18:1/12:0), 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 (d18:1/12:0) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-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]dodecanimidateHMDB
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 FormulaC48H89NO18
Average Molecular Weight968.2162
Monoisotopic Molecular Weight967.607965049
IUPAC NameN-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-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]dodecanamide
Traditional NameN-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5R,6R)-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]dodecanamide
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCC
InChI Identifier
InChI=1S/C48H89NO18/c1-3-5-7-9-11-13-14-15-16-18-19-21-23-25-32(53)31(49-36(54)26-24-22-20-17-12-10-8-6-4-2)30-62-46-42(60)39(57)44(34(28-51)64-46)67-48-43(61)40(58)45(35(29-52)65-48)66-47-41(59)38(56)37(55)33(27-50)63-47/h23,25,31-35,37-48,50-53,55-61H,3-22,24,26-30H2,1-2H3,(H,49,54)/b25-23+/t31-,32+,33+,34+,35+,37-,38-,39+,40+,41+,42+,43+,44+,45-,46+,47+,48-/m0/s1
InChI KeyHJVQASFQICDJJP-GJXDXCKOSA-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
logP3.17ALOGPS
logP3.77ChemAxon
logS-4.3ALOGPS
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 Count35ChemAxon
Refractivity244.61 m³·mol⁻¹ChemAxon
Polarizability110.02 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, Positivesplash10-0ugu-0100408819-34a11a7e6e1fd70d3862View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g0-0300709501-ef8ac402e8d8041f34a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-0801409311-b691ef3b3a9d2f7985a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-0410403219-693a63badcb884ed8482View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dv-3712209416-14260e86f9064bbbeafbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-4911116000-5a70a7d6a9a8960e37d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0n2a-3702302119-8c26a66d0c4fa6705f6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gi-1901201102-d45beaa25e8b41859201View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r7-6900200000-fd918736c1c45d4e6a46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000001019-88b3e1b2524a342e4b71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2401101139-5ed70149659da5bbc457View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0m0y-4952815020-2a3aaef7e17eb0449a06View 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 IDHMDB0004877
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023470
KNApSAcK IDNot Available
Chemspider ID30776565
KEGG Compound IDC04737
BioCyc IDD-GALACTOSYL-14-D-GALACTOSYL-14-D-
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7134
PubChem Compound53477785
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceOgawa, Tomoya; Koike, Katsuya; Numata, Masaaki; Sugimoto, Mamoru; Nakahara, Yoshiaki. Preparation of a neutral glycosphingolipid as a globotriaosylceramide analog useful in diagnosis and treatment of malignancy. Jpn. Kokai Tokkyo Koho (1988), 18
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available