Showing metabocard for Tetrahexosylceramide (d18:1/9Z-18:1) (BMDB0004959)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:13:48 UTC
Update Date2020-05-11 20:32:26 UTC
BMDB IDBMDB0004959
Secondary Accession Numbers
  • BMDB04959
Metabolite Identification
Common NameTetrahexosylceramide (d18:1/9Z-18:1)
DescriptionTetrahexosylceramide (d18:1/9Z-18:1), also known as ganglioside GB4 or IGB4CER, 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. Tetrahexosylceramide (d18:1/9Z-18:1) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(9Z)-N-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-5-{[(2R,3R,4S,5S,6R)-4-{[(2S,3R,4R,5R,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]octadec-9-enimidateHMDB
GalNAc-beta1->3gal-alpha1->3gal-beta1->4GLC-beta1->1'cerHMDB
Ganglioside GB4HMDB
Ganglioside GL 4HMDB
Gb4HMDB
IGb4cerHMDB
N-Acetyl-D-galactosaminyl-1,3-D-galactosyl-1,4-D-galactosyl-1,4-D-glucosylceramideHMDB
N-Acetyl-delta-galactosaminyl-1,3-delta-galactosyl-1,4-delta-galactosyl-1,4-delta-glucosylceramideHMDB
N-Acetyl-galactosaminyl-1,3-D-galactosyl-1,4-D-galactosyl-1,4-D-glucosylceramideHMDB
N-Acetyl-galactosaminyl-1,3-delta-galactosyl-1,4-delta-galactosyl-1,4-delta-glucosylceramideHMDB
Parvovirus b19 receptorHMDB
Chemical FormulaC62H112N2O23
Average Molecular Weight1253.5523
Monoisotopic Molecular Weight1252.7655879
IUPAC Name(9Z)-N-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-5-{[(2R,3R,4S,5S,6R)-4-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]octadec-9-enamide
Traditional Name(9Z)-N-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-5-{[(2S,3R,4R,5R,6R)-5-{[(2R,3R,4S,5S,6R)-4-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]octadec-9-enamide
CAS Registry Number11034-93-8
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]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4NC(C)=O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)NC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C62H112N2O23/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-46(71)64-40(41(70)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)38-80-60-53(77)51(75)56(44(36-67)83-60)85-61-54(78)52(76)57(45(37-68)84-61)86-62-55(79)58(49(73)43(35-66)82-62)87-59-47(63-39(3)69)50(74)48(72)42(34-65)81-59/h18-19,30,32,40-45,47-62,65-68,70,72-79H,4-17,20-29,31,33-38H2,1-3H3,(H,63,69)(H,64,71)/b19-18-,32-30+/t40-,41+,42+,43+,44+,45+,47+,48-,49-,50+,51+,52+,53+,54+,55+,56+,57-,58-,59-,60+,61-,62+/m0/s1
InChI KeyRAYORSFMGOKRRF-GVCCHFOSSA-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
  • N-acyl-alpha-hexosamine
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Oxane
  • Acetamide
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Alcohol
  • 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
logP3.79ALOGPS
logP4.02ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)11.59ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area395.03 ŲChemAxon
Rotatable Bond Count44ChemAxon
Refractivity316.85 m³·mol⁻¹ChemAxon
Polarizability141 ųChemAxon
Number of Rings4ChemAxon
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, Negativesplash10-0udi-0290000120-4c4179b6e75635368bbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4951031110-3d62c7742b48c5414e95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0c29-8954224410-8f96b9ffdb13c7fc2458View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0v0a-1093050110-a37832b2e746a88690beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0faj-1968070310-5be3de1a432b49cc9a83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000w-5924140000-f550a818f6ca0c6f1d45View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Membrane
Biospecimen Locations
  • Brain
  • Erythrocyte
  • Fibroblasts
  • Kidney
  • Liver
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected 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 IDHMDB0004959
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023546
KNApSAcK IDNot Available
Chemspider ID16744944
KEGG Compound IDC03272
BioCyc IDN-ACETYL-D-GALACTOSAMINYL-13-D-GALACT
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7212
PubChem Compound20057344
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available