Showing metabocard for N-Stearoylsphingosine (BMDB0000829)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:37:14 UTC
Update Date2020-04-22 15:05:31 UTC
BMDB IDBMDB0000829
Secondary Accession Numbers
  • BMDB00829
Metabolite Identification
Common NameN-Stearoylsphingosine
DescriptionN-Stearoylsphingosine belongs to the class of organic compounds known as ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid. N-Stearoylsphingosine is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-(1,3-Dihydroxyoctadec-4-en-2-yl)octadecanimidateHMDB
Chemical FormulaC36H71NO3
Average Molecular Weight565.968
Monoisotopic Molecular Weight565.54339515
IUPAC NameN-(1,3-dihydroxyoctadec-4-en-2-yl)octadecanamide
Traditional NameN-(1,3-dihydroxyoctadec-4-en-2-yl)octadecanamide
CAS Registry Number2304-81-6
SMILES
CCCCCCCCCCCCCCCCCC(=O)NC(CO)C(O)C=CCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C36H71NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38-39H,3-28,30,32-33H2,1-2H3,(H,37,40)
InChI KeyVODZWWMEJITOND-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassCeramides
Direct ParentCeramides
Alternative Parents
Substituents
  • Ceramide
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Endosome
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.78ALOGPS
logP11.75ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count32ChemAxon
Refractivity174.98 m³·mol⁻¹ChemAxon
Polarizability77.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ds-3279585000-475f0b589de62ad351dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000090000-3f6fc7446d90939e1273View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-0050090000-a5eb5a9f2cf3055ba7f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ea-0090060000-096de6b49933a090b7ecView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Intracellular membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000829
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022270
KNApSAcK IDNot Available
Chemspider ID2843374
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3607830
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceJulina, Radomir; Herzig, Thomas; Bernet, Bruno; Vasella, Andrea. Enantioselective synthesis of D-erythro-sphingosine and of ceramide. Helvetica Chimica Acta (1986), 69(2), 368-73.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available