Showing metabocard for Tetradecanoylcarnitine (BMDB0005066)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:15:09 UTC
Update Date2020-06-04 22:49:00 UTC
MCDB ID BMDB0005066
Secondary Accession Numbers
  • BMDB05066
Metabolite Identification
Common NameTetradecanoylcarnitine
DescriptionTetradecanoylcarnitine, also known as (R)-myristoylcarnitine, 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, tetradecanoylcarnitine is considered to be a fatty ester lipid molecule. Tetradecanoylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Tetradecanoylcarnitine exists in all eukaryotes, ranging from yeast to humans. Tetradecanoylcarnitine has been found to be associated with several diseases known as pregnancy and obesity; also tetradecanoylcarnitine has been linked to several inborn metabolic disorders including glutaric aciduria II and very long chain acyl-coa dehydrogenase deficiency.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-MyristoylcarnitineChEBI
(-)-TetradecanoylcarnitineChEBI
(R)-MyristoylcarnitineChEBI
(R)-TetradecanoylcarnitineChEBI
L-MyristoylcarnitineChEBI
Myristoyl-L-(-)-carnitineChEBI
Myristoyl-L-carnitineChEBI
MyristoylcarnitineChEBI
O-Tetradecanoyl-(R)-carnitineChEBI
Tetradecanoyl-L-carnitineChEBI
C14 CarnitineHMDB
TetradecanoylcarnitineHMDB
Chemical FormulaC21H41NO4
Average Molecular Weight371.5545
Monoisotopic Molecular Weight371.303558805
IUPAC Name(3R)-3-(tetradecanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Name(3R)-3-(tetradecanoyloxy)-4-(trimethylammonio)butanoate
CAS Registry Number25597-07-3
SMILES
CCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C21H41NO4/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/h19H,5-18H2,1-4H3/t19-/m1/s1
InChI KeyPSHXNVGSVNEJBD-LJQANCHMSA-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
logP0.86ALOGPS
logP1.14ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity127.87 m³·mol⁻¹ChemAxon
Polarizability46.06 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-9310000000-80762110d17332491ce02016-09-22View 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, Positivesplash10-00di-0009000000-ebacd89483d3e5c1fe242021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-9005000000-55ccdfe0f242958229652021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-24View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected and Quantified0.124 +/- 0.003 uM details
Detected and Quantified0.149 +/- 0.003 uM details
Detected and Quantified0.171 +/- 0.004 uM details
Detected and Quantified0.10 +/- 0.01 uM details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0005066
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023615
KNApSAcK IDC00052417
Chemspider ID30776567
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477791
PDB IDNot Available
ChEBI ID84634
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  2. Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
  3. Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93. [PubMed:5409465 ]
  4. 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.