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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:19:13 UTC
HMDB IDHMDB0000651
Secondary Accession Numbers
  • HMDB00651
Metabolite Identification
Common NameDecanoylcarnitine
DescriptionDecanoylcarnitine, is a member of the class of compounds known as acyl carnitines. Acyl carnitines are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Thus, decanoylcarnitine is considered to be a fatty ester lipid molecule. Decanoylcarnitine is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Decanoylcarnitine can be found primarily in blood, feces, and urine. Within the cell, decanoylcarnitine is primarily located in the membrane. It can also be found in the extracellular space. Acyl carnitines 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 (PMID: 12385891 ). Moreover, decanoylcarnitine is found to be associated with very long chain acyl-CoA dehydrogenase (VLAD) deficiency, glutaric aciduria II, and celiac disease, which are inborn errors of metabolism.
Structure
Thumb
Synonyms
ValueSource
Decanoyl-L-carnitineHMDB
Decanoylcarnitine, (+-)-isomerMeSH
Decanoylcarnitine, (R)-isomerMeSH
Decanoylcarnitine, (S)-isomerMeSH
Chemical FormulaC17H33NO4
Average Molecular Weight315.4482
Monoisotopic Molecular Weight315.240958549
IUPAC Name3-(decanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Name(+-)-decanoylcarnitine
CAS Registry Number1492-27-9
SMILES
CCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C17H33NO4/c1-5-6-7-8-9-10-11-12-17(21)22-15(13-16(19)20)14-18(2,3)4/h15H,5-14H2,1-4H3
InChI KeyLZOSYCMHQXPBFU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

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 Solubility0.00014 g/LALOGPS
logP-0.85ALOGPS
logP-0.63ChemAxon
logS-6.4ALOGPS
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 Count14ChemAxon
Refractivity109.47 m³·mol⁻¹ChemAxon
Polarizability37.6 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014r-7029000000-c5e89a545ccedb00aa9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-9100000000-51ec5fbc3590afaa7d94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-e8d414ba473e4495a085View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.26 +/- 0.11 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.141 +/- 0.009 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified<0.3 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.16-0.55 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.23(0.09) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.31 +/- 0.13 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.16-0.55 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.005 (0.0-0.124) uMChildren (1-13 years old)BothNormal details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedNormal details
UrineDetected and Quantified4.5 (0.62-15.2) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0699 +/- 0.0206 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.103 +/- 0.008 uMAdult (>18 years old)BothCeliac disease details
BloodDetected and Quantified0.72 uMAdolescent (13-18 years old)Male
Glutaric aciduria II
details
BloodDetected and Quantified1.09 uMAdolescent (13-18 years old)MaleGlutaric aciduria II details
BloodDetected and Quantified0.1267 (0.0743) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified0.2449 (0.1076) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified0.31(0.13) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified0.005 (0.0-0.012) uMAdult (>18 years old)BothVery long-chain acyl-CoA dehydrogenase deficiency (vLCAD) details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUnclassified IBD details
UrineDetected and Quantified0.0673 +/- 0.0193 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.0821 +/- 0.0263 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Celiac disease
  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 ]
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
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022162
KNApSAcK IDNot Available
Chemspider ID8420677
KEGG Compound IDNot Available
BioCyc IDPALMITOYL-CARNITINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5623
PubChem Compound10245190
PDB IDNot Available
ChEBI ID68830
References
Synthesis ReferenceStrack, Erich; Mueller, Detlef M. Preparation of O-acylcarnitines. Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie (1970), 351(1), 95-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  2. 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 ]