Showing metabocard for cis-5-Tetradecenoylcarnitine (BMDB0002014)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:49:56 UTC
Update Date2020-06-04 19:15:37 UTC
MCDB ID BMDB0002014
Secondary Accession Numbers
  • BMDB02014
Metabolite Identification
Common Namecis-5-Tetradecenoylcarnitine
DescriptionTetradecenoylcarnitine 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. Thus, tetradecenoylcarnitine is considered to be a fatty ester lipid molecule. Tetradecenoylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Tetradecenoylcarnitine exists in all eukaryotes, ranging from yeast to humans. Tetradecenoylcarnitine has been found to be associated with several diseases known as obesity and eosinophilic esophagitis; also tetradecenoylcarnitine has been linked to the inborn metabolic disorders including very long chain acyl-coa dehydrogenase deficiency.
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
Physical Properties
StateSolid
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9210000000-d55933555203a81af3b02017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fkc-0729000000-b7724178fd672abeda7c2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1900000000-a2f60fad8c99a570c7b02017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02fx-4900000000-6ae1e898595b8e8b61f52017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-a5108e2a8a5c949c79422017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-1289000000-351e00d1ad0b6a3015e92017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-7590000000-8eeb0dac52aa2c1d62462017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-1a5965dc435463ee085f2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-9005000000-84dcf946c3b41ee8ec832021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-22View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.021 +/- 0.001 uM details
Detected and Quantified0.032 +/- 0.002 uM details
Detected and Quantified0.047 +/- 0.003 uM details
HMDB IDHMDB0002014
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022796
KNApSAcK IDNot Available
Chemspider ID17216151
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6437
PubChem Compound22833575
PDB IDNot Available
ChEBI ID73060
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.