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Record Information
Version3.6
Creation Date2006-10-23 13:16:22 UTC
Update Date2013-05-29 19:41:39 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 IUPAC Name(3R)-3-(tetradecanoyloxy)-4-(trimethylaminio)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
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acid Esters
Sub ClassAcyl Carnitines
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
Substituents
  • Carboxylic Acid Ester
  • Carboxylic Acid Salt
  • Carnitine
  • Choline
  • Dicarboxylic Acid Derivative
  • Quaternary Ammonium Salt
Direct ParentAcyl Carnitines
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 solubility1.690E-05 g/LALOGPS
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 area66.43ChemAxon
rotatable bond count18ChemAxon
refractivity127.87ChemAxon
polarizability46.17ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.04 +/- 0.01 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.016 (0.002-0.043) uMChildren (1-13 years old)Both
Normal
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. Pubmed: 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. Pubmed: 16425363