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Human Metabolome Database Version 3.5

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Showing metabocard for Dodecanoylcarnitine (HMDB02250)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:44 -0600
Update Date 2013-02-08 17:11:38 -0700
HMDB ID HMDB02250
Secondary Accession Numbers None
Metabolite Identification
Common Name Dodecanoylcarnitine
Description Dodecanoylcarnitine 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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (-)-Lauroylcarnitine
  2. (R)-Dodecanoylcarnitine
  3. Dodecanoyl-L-carnitine
  4. L-Carnitine dodecanoyl ester
  5. Lauroyl-L(-)-carnitin
  6. Lauroyl-L-carnitine
  7. Lauroylcarnitine
Chemical Formula C19H37NO4
Average Molecular Weight 343.5014
Monoisotopic Molecular Weight 343.272258677
IUPAC Name (3R)-3-(dodecanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional IUPAC Name (3R)-3-(dodecanoyloxy)-4-(trimethylaminio)butanoate
CAS Registry Number 25518-54-1
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 Key FUJLYHJROOYKRA-QGZVFWFLSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl Carnitines
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
Substituents
  • Carboxylic Acid Ester
  • Carboxylic Acid Salt
  • Carnitine
  • Choline
  • Dicarboxylic Acid Derivative
  • Quaternary Ammonium Salt
Direct Parent Acyl Carnitines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Lipid catabolism, Fatty acid transport, Energy production
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.850E-05 g/L ALOGPS
LogP 0.03 ALOGPS
LogP 0.26 ChemAxon
LogS -7.01 ALOGPS
pKa (strongest acidic) 4.22 ChemAxon
pKa (strongest basic) -7.1 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 66.43 A2 ChemAxon
Rotatable Bond Count 16 ChemAxon
Refractivity 118.67 ChemAxon
Polarizability 41.88 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Liver
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.1 +/- 0.03 uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and Quantified
Article_icon
0.052 +/- 0.004 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
0.038 (0.005-0.069) uM Children (1-13 year old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.02 (0.01-0.04) umol/mmol creatinine Adult (>18 years old) Both Normal by DF MS/MS (Biocrates kit)
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.032 +/- 0.002 uM Adult (>18 years old) Both Celiac disease Not Available
Blood Detected and Quantified
Article_icon
0.124 (0.090-0.162) uM Adult (>18 years old) Both Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD) Not Available
Associated Disorders and Diseases
Disease References
Celiac disease
  • 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 Link_out
    Very Long Chain Acyl-CoA Dehydrogenase Deficiency
    • 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 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB022928
      KNApSAcK ID Not Available
      Chemspider ID 147288 Link_out
      KEGG Compound ID Not Available
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Not Available
      NuGOwiki Link HMDB02250 Link_out
      Metagene Link HMDB02250 Link_out
      METLIN ID 6573 Link_out
      PubChem Compound 168381 Link_out
      PDB ID Not Available
      ChEBI ID Not Available
      References
      Synthesis Reference Not 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 Link_out
      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 Link_out
      3. 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 Link_out
      4. 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 Link_out