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Record Information
Version4.0
Creation Date2006-05-22 14:17:44 UTC
Update Date2017-09-27 08:24:14 UTC
HMDB IDHMDB0002250
Secondary Accession Numbers
  • HMDB02250
Metabolite Identification
Common NameDodecanoylcarnitine
DescriptionDodecanoylcarnitine is an acylcarnitine is present in fatty acid oxidation disorders such as long-chain acyl CoA dehydrogenase deficiency, carnitine palmitoyltransferase I deficiency, and carnitine palmitoyltransferase II deficiency. (PMID 12828998 ).
Structure
Thumb
Synonyms
ValueSource
(-)-LauroylcarnitineChEBI
(3R)-3-(Dodecanoyloxy)-4-(trimethylammonio)butanoateChEBI
(R)-DodecanoylcarnitineChEBI
Dodecanoyl-L-carnitineChEBI
L-Carnitine dodecanoyl esterChEBI
Lauroyl-L(-)-carnitinChEBI
Lauroyl-L-carnitineChEBI
LauroylcarnitineChEBI
LaurylcarnitineChEBI
O-C12:0-L-CarnitineChEBI
O-Dodecanoyl-R-carnitineChEBI
(3R)-3-(Dodecanoyloxy)-4-(trimethylammonio)butanoic acidGenerator
Chemical FormulaC19H37NO4
Average Molecular Weight343.5014
Monoisotopic Molecular Weight343.272258677
IUPAC Name(3R)-3-(dodecanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Name(-)-lauroylcarnitine
CAS Registry Number25518-54-1
SMILES
CCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C19H37NO4/c1-5-6-7-8-9-10-11-12-13-14-19(23)24-17(15-18(21)22)16-20(2,3)4/h17H,5-16H2,1-4H3/t17-/m1/s1
InChI KeyFUJLYHJROOYKRA-QGZVFWFLSA-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:

  Organ and components:

  Cell and elements:

    Cell:

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 Solubility3.9e-05 g/LALOGPS
logP0.03ALOGPS
logP0.26ChemAxon
logS-7ALOGPS
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 Count16ChemAxon
Refractivity118.67 m³·mol⁻¹ChemAxon
Polarizability41.88 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, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0002-0900000000-1c57ff1372236d823d80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9000000000-ef35ea7a4d61bac8cb20View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.1 +/- 0.03 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.057-0.190 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.052 +/- 0.004 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.1(0.04) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.038 (0.005-0.069) uMChildren (1-13 years old)BothNormal details
UrineDetected and Quantified0.02 (0.01-0.04) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.032 +/- 0.002 uMAdult (>18 years old)BothCeliac disease details
BloodDetected and Quantified0.15(0.07) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified0.045 (0.0197) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified0.0651 (0.0228) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified0.124 (0.090-0.162) uMAdult (>18 years old)BothVery 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 ]
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 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022928
KNApSAcK IDNot Available
Chemspider ID147288
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6573
PubChem Compound168381
PDB IDNot Available
ChEBI ID77086
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Moder M, Kiessling A, Loster H, Bruggemann L: The pattern of urinary acylcarnitines determined by electrospray mass spectrometry: a new tool in the diagnosis of diabetes mellitus. Anal Bioanal Chem. 2003 Jan;375(2):200-10. Epub 2003 Jan 4. [PubMed:12560963 ]
  2. Shigematsu Y, Hirano S, Hata I, Tanaka Y, Sudo M, Tajima T, Sakura N, Yamaguchi S, Takayanagi M: Selective screening for fatty acid oxidation disorders by tandem mass spectrometry: difficulties in practical discrimination. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):63-72. [PubMed:12828998 ]
  3. Morrow RJ, Rose ME: Isolation of acylcarnitines from urine: a comparison of methods and application to long-chain acyl-CoA dehydrogenase deficiency. Clin Chim Acta. 1992 Oct 15;211(1-2):73-81. [PubMed:1468155 ]
  4. Vianey-Saban C, Divry P, Brivet M, Nada M, Zabot MT, Mathieu M, Roe C: Mitochondrial very-long-chain acyl-coenzyme A dehydrogenase deficiency: clinical characteristics and diagnostic considerations in 30 patients. Clin Chim Acta. 1998 Jan 12;269(1):43-62. [PubMed:9498103 ]