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Showing Compound Tetrahexosylceramide (d18:1/12:0) (FDB023545)

Record Information
Version1.0
Creation date2011-09-21 00:31:24 UTC
Update date2015-07-21 06:57:45 UTC
Primary IDFDB023545
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTetrahexosylceramide (d18:1/12:0)
DescriptionA glycosphingolipid (ceramide and oligosaccharide)or oligoglycosylceramide with one or more sialic acids (i.e. n-acetylneuraminic acid) linked on the sugar chain. Tetrahexosylceramide contains a tetrasaccharide moiety bound in glycosidic linkage to the hydroxyl group of ceramide as the polar head group. It is a component the cell plasma membrane which modulates cell signal transduction events. Gangliosides have been found to be highly important in immunology. Ganglioside Gb4 carries a net-negative charge at pH 7.0 and is acidic. Gangliosides can amount to 6% of the weight of lipids from brain, but they are found at low levels in all animal tissues. Globosides are glycosphingolipids. There are four types of glycosphingolipids, the cerebrosides, sulfatides, globosides and gangliosides. Globosides are cerebrosides that contain additional carbohydrates, predominantly galactose, glucose or GalNAc. Lactosyl ceramide is a globoside found in erythrocyte plasma membranes. Globotriaosylceramide (also called ceramide trihexoside) contains glucose and two moles of galactose and accumulates, primarily in the kidneys, of patients suffering from Fabry disease. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP2.73ALOGPS
logP3.35ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)5.36ChemAxon
pKa (Strongest Basic)2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area402.01 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity289.17 m³·mol⁻¹ChemAxon
Polarizability128.55 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC56H102N2O23
IUPAC nameN-[(2S,3R)-1-{[(2R,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]dodecanimidic acid
InChI IdentifierInChI=1S/C56H102N2O23/c1-4-6-8-10-12-14-15-16-17-19-20-22-24-26-35(64)34(58-40(65)27-25-23-21-18-13-11-9-7-5-2)32-74-54-47(71)45(69)50(38(30-61)77-54)79-55-48(72)46(70)51(39(31-62)78-55)80-56-49(73)52(43(67)37(29-60)76-56)81-53-41(57-33(3)63)44(68)42(66)36(28-59)75-53/h24,26,34-39,41-56,59-62,64,66-73H,4-23,25,27-32H2,1-3H3,(H,57,63)(H,58,65)/t34-,35+,36+,37+,38+,39+,41+,42-,43-,44+,45+,46+,47?,48+,49+,50+,51-,52-,53-,54+,55-,56+/m0/s1
InChI KeyMJVVJMMBLSKMDU-ZQEHVGIFSA-N
Isomeric SMILES[H][C@@](CO[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@]([H])(O[C@@]3([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O[C@]4([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]4([H])NC(C)=O)[C@@]3([H])O)[C@]([H])(O)[C@@]2([H])O)[C@]([H])(O)C1O)(NC(=O)CCCCCCCCCCC)[C@]([H])(O)C=CCCCCCCCCCCCCC
Average Molecular Weight1171.4087
Monoisotopic Molecular Weight1170.68733758
Classification
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
  • N-acyl-alpha-hexosamine
  • Fatty acyl glycoside
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Fatty acyl
  • Oxane
  • N-acyl-amine
  • Fatty amide
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
SpectraNot Available
ChemSpider ID16744943
ChEMBL IDNot Available
KEGG Compound IDC03272
Pubchem Compound ID20057343
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04958
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference