Showing metabocard for N-Palmitoylsphingosine (BMDB0000790)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:36:36 UTC
Update Date2020-04-22 15:05:19 UTC
BMDB IDBMDB0000790
Secondary Accession Numbers
  • BMDB00790
Metabolite Identification
Common NameN-Palmitoylsphingosine
DescriptionN-Palmitoylsphingosine belongs to the class of organic compounds known as long-chain ceramides. These are ceramides bearing a long chain fatty acid. N-Palmitoylsphingosine is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
D-erythro-C16-CeramideHMDB
D-erythro-D4-CeramideHMDB
N-Palmitoyl 4-sphingenineHMDB
N-Palmitoyl-D-sphingosineHMDB
[R-[R*,s*-(e)]]-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-hexadecanamideHMDB
C(16)-CeramideMeSH
C16-CeramideMeSH
C16-PalmitoylceramideMeSH
N-Palmitoylsphingosine, (r*,s*-(e))-(+-)MeSH
N-Palmitoylsphingosine, R-(r*,s*-(e))MeSH
NFA(C16)cerMeSH
PCer CPDMeSH
PalmitoylceramideMeSH
N-(1,3-Dihydroxyoctadec-4-en-2-yl)hexadecanimidateGenerator
N-PalmitoylsphingosineMeSH
C16-0(Palmitoyl)ceramideMeSH
Ceramide-C16MeSH
Chemical FormulaC34H67NO3
Average Molecular Weight537.9007
Monoisotopic Molecular Weight537.512095015
IUPAC NameN-[(4E)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide
Traditional NameN-[(4E)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)NC(CO)C(O)\C=C\CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)32(31-36)35-34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)/b29-27+
InChI KeyYDNKGFDKKRUKPY-ORIPQNMZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain ceramides. These are ceramides bearing a long chain fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSphingolipids
Sub ClassCeramides
Direct ParentLong-chain ceramides
Alternative Parents
Substituents
  • Long-chain 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
logP9.49ALOGPS
logP10.87ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)0.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity165.78 m³·mol⁻¹ChemAxon
Polarizability73.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cell membrane
  • Endosome
  • Intracellular membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5353456
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceDuclos, R. I. The total syntheses of D-erythro-sphingosine, N-palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog. Chemistry and Physics of Lipids (2001), 111(2), 111-138.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available