Showing metabocard for cis-5-Tetradecenoylcarnitine (LMDB00375)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:48:26 UTC
Update Date2016-07-20 20:39:54 UTC
LmdbLMDB00375
Secondary Accession NumbersNone
Metabolite Identification
Common Namecis-5-Tetradecenoylcarnitine
DescriptionTetradecenoylcarnitine (C14:1) is the most characteristic metabolic marker of very long chain acyl-dehydrogenase (VLCAD) deficiency (PubMed ID 11433098 ); beta-Oxidation of long-chain fatty acids provides the major source of energy in the heart. Defects in enzymes of the beta-oxidation pathway cause sudden, unexplained death in childhood, acute hepatic encephalopathy or liver failure, skeletal myopathy, and cardiomyopathy. ( PubMed ID 7479827 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-[(5Z)-Tetradec-5-enoyloxy]-4-(trimethylammonio)butanoateChEBI
3-[(5Z)-Tetradec-5-enoyloxy]-4-(trimethylammonio)butanoic acidGenerator
cis-5-TetradecenoylcarnitineChEBI
Chemical FormulaC21H39NO4
Average Molecular Weight369.5387
Monoisotopic Molecular Weight369.287908741
IUPAC Name3-[(5Z)-tetradec-5-enoyloxy]-4-(trimethylazaniumyl)butanoate
Traditional Namecis-5-tetradecenoylcarnitine
CAS Registry Number835598-21-5
SMILES
CCCCCCCC\C=C/CCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=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/b13-12-
InChI KeyNNCBVXBBLABOCB-SEYXRHQNSA-N
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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9210000000-d55933555203a81af3b0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fkc-0729000000-b7724178fd672abeda7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1900000000-a2f60fad8c99a570c7b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02fx-4900000000-6ae1e898595b8e8b61f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-a5108e2a8a5c949c7942Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-1289000000-351e00d1ad0b6a3015e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-7590000000-8eeb0dac52aa2c1d6246Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-1a5965dc435463ee085fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-9005000000-84dcf946c3b41ee8ec83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-e9262cbaff8cb4ad0ba6Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
  • Ruminal Fluid
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Ruminal FluidDetected and Quantified0.09 +/- 0.001 uMNot AvailableBovine
    • Saleem F, Bouatra...
 details
DrugBank IDNot Available
HMDB IDHMDB0002014
FooDB IDFDB022796
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6437
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17216151
ChEBI ID73060
PubChem Compound ID22833575
Kegg Compound IDNot Available
YMDB IDYMDB01532
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available