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Record Information
Version3.6
Creation Date2006-10-23 13:16:22 UTC
Update Date2015-04-22 22:46:36 UTC
HMDB IDHMDB05066
Secondary Accession NumbersNone
Metabolite Identification
Common NameTetradecanoylcarnitine
DescriptionTetradecanoylcarnitine is a human carnitine involved in b-oxidation of long-chain fatty acids (PMID: 16425363 ).
Structure
Thumb
Synonyms
  1. (-)-Myristoylcarnitine
  2. (-)-Tetradecanoylcarnitine
  3. (R)-Tetradecanoylcarnitine
  4. L-Myristoylcarnitine
  5. Myristoyl-L-(-)-carnitine
  6. Myristoyl-L-carnitine
  7. Myristoylcarnitine
  8. Tetradecanoyl-L-carnitine
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 KeyInChIKey=PSHXNVGSVNEJBD-LJQANCHMSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Carnitine
  • Acyl choline
  • Choline
  • Dicarboxylic acid or derivatives
  • Quaternary ammonium salt
  • Carboxylic acid salt
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic zwitterion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.69e-05 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity127.87 m3·mol-1ChemAxon
Polarizability46.17 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.04 +/- 0.01 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.016 (0.002-0.043) uMChildren (1-13 years old)Both
Normal
details
SalivaDetected and Quantified0.056 +/- 0.056 uMAdult (>18 years old)BothNormal
    • Dame, ZT. et al. ...
details
UrineDetected and Quantified0.018 (0.001-0.088) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.719 (0.478-0.983) uMAdult (>18 years old)Both
Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)
details
Associated Disorders and Diseases
Disease References
Very Long Chain Acyl-CoA Dehydrogenase Deficiency
  1. Costa CG, Struys EA, Bootsma A, ten Brink HJ, Dorland L, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of plasma acylcarnitines using gas chromatography chemical ionization mass fragmentography. J Lipid Res. 1997 Jan;38(1):173-82. [9034211 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023615
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05066
Metagene LinkHMDB05066
METLIN IDNot Available
PubChem Compound53477791
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bene J, Komlosi K, Gasztonyi B, Juhasz M, Tulassay Z, Melegh B: Plasma carnitine ester profile in adult celiac disease patients maintained on long-term gluten free diet. World J Gastroenterol. 2005 Nov 14;11(42):6671-5. [16425363 ]