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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-10-23 13:16:22 UTC
Update Date2018-05-20 19:10:57 UTC
HMDB IDHMDB0005066
Secondary Accession Numbers
  • HMDB05066
Metabolite Identification
Common NameTetradecanoylcarnitine
DescriptionTetradecanoylcarnitine is a human carnitine involved in b-oxidation of long-chain fatty acids (PMID: 16425363 ). Tetradecanoylcarnitine is found to be associated with glutaric aciduria II, which is an inborn error of metabolism.
Structure
Thumb
Synonyms
ValueSource
(-)-MyristoylcarnitineChEBI
(-)-TetradecanoylcarnitineChEBI
(R)-MyristoylcarnitineChEBI
(R)-TetradecanoylcarnitineChEBI
L-MyristoylcarnitineChEBI
Myristoyl-L-(-)-carnitineChEBI
Myristoyl-L-carnitineChEBI
MyristoylcarnitineChEBI
O-Tetradecanoyl-(R)-carnitineChEBI
Tetradecanoyl-L-carnitineChEBI
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
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
  • 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility1.7e-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 Area66.43 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity127.87 m³·mol⁻¹ChemAxon
Polarizability46.17 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9310000000-80762110d17332491ce0View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.04 +/- 0.01 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.030-0.070 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.030-0.070 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.02 +/- 0.02 uMChildren (1-13 years old)Both
Normal
details
BloodDetected and Quantified0.01 +/- 0.01 uMChildren (1-13 years old)Both
Normal
details
BloodDetected and Quantified0.05(0.01) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified<0.18 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.016 (0.002-0.043) uMChildren (1-13 years old)Both
Normal
details
FecesDetected and Quantified0.54 +/- 0.47 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.32 +/- 0.29 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.056 +/- 0.056 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.018 (0.001-0.088) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.719 (0.478-0.983) uMAdult (>18 years old)Both
Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)
details
BloodDetected and Quantified0.02 +/- 0.02 uMChildren (1-13 years old)Both
Acetaminophen overdose
details
BloodDetected and Quantified0.05(0.01) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified0.0337 (0.0126) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified0.0403 (0.0065) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified0.043 +/- 0.015 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.047 +/- 0.018 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.3 uMAdolescent (13-18 years old)Male
Glutaric aciduria II
details
BloodDetected and Quantified0.92 uMAdolescent (13-18 years old)MaleGlutaric aciduria II 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 ]
Pregnancy
  1. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Obesity
  1. Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Glutaric aciduria II
  1. Prasad M, Hussain S: Glutaric aciduria type II presenting as myopathy and rhabdomyolysis in a teenager. J Child Neurol. 2015 Jan;30(1):96-9. doi: 10.1177/0883073813516676. Epub 2014 Jan 21. [PubMed:24453145 ]
Associated OMIM IDs
  • 201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
  • 231680 (Glutaric aciduria II)
  • 601665 (Obesity)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023615
KNApSAcK IDNot Available
Chemspider IDNot Available
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. 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 ]