L-Palmitoylcarnitine (YMDB01533)

Identification
YMDB IDYMDB01533
NameL-Palmitoylcarnitine
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionHexadecanoylcarnitine (palmitoylcarnitine) is a long-chain fatty acid ester of carnitine with palmitoleic acid. Carnitine is used for the transport of fatty acids during beta-oxidation, during what fatty acids are broken down to acetyl-CoA. Acetyl-CoA is then used in the glyoxylate cycle for gluconeogenesis and formation of carbohydrates, or transported to mitochondrion for the generation of metabolic energy through the citric acid cycle. [Biocyc PWY-6111]
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
CAS numberNot Available
WeightAverage: 385.5381
Monoisotopic: 385.282823363
InChI KeyBCZXLGKYFZTAJX-GGYWPGCISA-N
InChIInChI=1S/C21H39NO5/c1-5-6-7-8-9-10-11-12-13-14-18(23)17-21(26)27-19(22(2,3)4)15-16-20(24)25/h12-13,18-19,23H,5-11,14-17H2,1-4H3/t18?,19-/m0/s1
IUPAC Name(4S)-4-[(3-hydroxytetradec-5-enoyl)oxy]-4-(trimethylazaniumyl)butanoate
Traditional IUPAC Name(4S)-4-[(3-hydroxytetradec-5-enoyl)oxy]-4-(trimethylammonio)butanoate
Chemical FormulaC21H39NO5
SMILESCCCCCCCCC=CCC(O)CC(=O)O[C@@H](CCC([O-])=O)[N+](C)(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Secondary alcohol
  • Carboxylic acid salt
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organic zwitterion
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00044 g/LALOGPS
logP-0.29ALOGPS
logP-0.12ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area86.66 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity130.44 m³·mol⁻¹ChemAxon
Polarizability45.76 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Fatty acid metabolismPW002460 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fatty acid metabolismec00071 Map00071
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.3 ± 0.0 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-4911000000-3e751cc3ce8236c2126cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014u-0209000000-a90be786d498771ac2dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-2911000000-3dcdb260e04e1b73c006JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-4900000000-980035d868aafcb59581JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0049000000-c54ab11beccf671116a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00gl-2595000000-79c3a46aa74e5d28b652JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-6930000000-f8340bb30e24661c27e4JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB13330
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDPalmitoylcarnitine
BioCyc IDNot Available