Tetradecenoylcarnitine (YMDB01532)

Identification
YMDB IDYMDB01532
NameTetradecenoylcarnitine
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionTetradecenoylcarnitine is a long-chain fatty acid ester of carnitine with 5-tetradecenoic acid (C14:1). 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
Synonyms
  • 3-[(5Z)-Tetradec-5-enoyloxy]-4-(trimethylammonio)butanoate
  • 3-[(5Z)-Tetradec-5-enoyloxy]-4-(trimethylammonio)butanoic acid
  • cis-5-Tetradecenoylcarnitine
CAS number835598-21-5
WeightAverage: 369.5387
Monoisotopic: 369.287908741
InChI KeyNNCBVXBBLABOCB-UHFFFAOYSA-N
InChIInChI=1S/C21H39NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-21(25)26-19(17-20(23)24)18-22(2,3)4/h12-13,19H,5-11,14-18H2,1-4H3
IUPAC Name3-[(5Z)-tetradec-5-enoyloxy]-4-(trimethylazaniumyl)butanoate
Traditional IUPAC Namecis-5-tetradecenoylcarnitine
Chemical FormulaC21H39NO4
SMILESCCCCCCCCC=CCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.7e-05 g/LALOGPS
logP0.48ALOGPS
logP0.78ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)4.24ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity128.99 m³·mol⁻¹ChemAxon
Polarizability44.6 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 PathwaysNot Available
KEGG PathwaysNot Available
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, Positivesplash10-00di-9210000000-d55933555203a81af3b0JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fkc-0729000000-b7724178fd672abeda7cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1900000000-a2f60fad8c99a570c7b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02fx-4900000000-6ae1e898595b8e8b61f5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-a5108e2a8a5c949c7942JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-1289000000-351e00d1ad0b6a3015e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-7590000000-8eeb0dac52aa2c1d6246JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-1a5965dc435463ee085fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-9005000000-84dcf946c3b41ee8ec83JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-e9262cbaff8cb4ad0ba6JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID73060
HMDB IDHMDB02014
Pubchem Compound ID22833575
Kegg IDNot Available
ChemSpider ID21238313
FOODB IDFDB022796
Wikipedia IDNot Available
BioCyc IDNot Available