Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-10-23 13:16:22 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005066
Secondary Accession Numbers
  • HMDB05066
Metabolite Identification
Common NameTetradecanoylcarnitine
DescriptionTetradecanoylcarnitine, also known as myristoylcarnitine, is a member of the class of compounds known as acylcarnitines. Acylcarnitines are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Acylcarnitines are useful in the diagnosis of genetic disorders such as fatty acid oxidation disorders and differentiation between biochemical phenotypes of medium-chain acyl-CoA dehydrogenase (MCAD) deficiency disorders (PMID: 12385891 ). Tetradecanoylcarnitine is involved in the beta-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
Data?1614288679
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 FormulaC21H42NO4
Average Molecular Weight372.569
Monoisotopic Molecular Weight372.310835257
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/p+1/t19-/m1/s1
InChI KeyPSHXNVGSVNEJBD-LJQANCHMSA-O
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
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability46.06 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+206.75930932474
DeepCCS[M-H]-202.73930932474
DeepCCS[M-2H]-239.28230932474
DeepCCS[M+Na]+215.57430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TetradecanoylcarnitineCCCCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C3545.2Standard polar33892256
TetradecanoylcarnitineCCCCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C2350.4Standard non polar33892256
TetradecanoylcarnitineCCCCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C2582.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tetradecanoylcarnitine,1TMS,isomer #1CCCCCCCCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C2601.0Semi standard non polar33892256
Tetradecanoylcarnitine,1TBDMS,isomer #1CCCCCCCCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C2833.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tetradecanoylcarnitine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9310000000-80762110d17332491ce02016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetradecanoylcarnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanoylcarnitine 10V, Positive-QTOFsplash10-00di-0009000000-ebacd89483d3e5c1fe242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanoylcarnitine 20V, Positive-QTOFsplash10-0079-9005000000-55ccdfe0f242958229652021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanoylcarnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Placenta
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 but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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 but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.018 (0.001-0.088) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.01-0.09 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified0.02(0.01-0.09) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified0.02(0.01-0.07) umol/mmol creatinineNewborn (0-30 days old)MaleNormal 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 ]
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 ]
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.
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDM02973
MarkerDB IDMDB00000468
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Okun JG, Kolker S, Schulze A, Kohlmuller D, Olgemoller K, Lindner M, Hoffmann GF, Wanders RJ, Mayatepek E: A method for quantitative acylcarnitine profiling in human skin fibroblasts using unlabelled palmitic acid: diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of MCAD deficiency. Biochim Biophys Acta. 2002 Oct 10;1584(2-3):91-8. [PubMed:12385891 ]
  2. 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 ]
  3. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
  4. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]