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Human Metabolome Database Version 3.5

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Showing metabocard for Decanoylcarnitine (HMDB00651)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:01 -0700
HMDB ID HMDB00651
Secondary Accession Numbers None
Metabolite Identification
Common Name Decanoylcarnitine
Description Acylcarnitine useful in the diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of medium-chain acyl-CoA dehydrogenase (MCAD) deficiency deficiencyoxidation disorders.(PMID: 12385891 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Decanoyl-L-carnitine
  2. Decanoylcarnitine
Chemical Formula C17H33NO4
Average Molecular Weight 315.4482
Monoisotopic Molecular Weight 315.240958549
IUPAC Name 3-(decanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional IUPAC Name 3-(decanoyloxy)-4-(trimethylaminio)butanoate
CAS Registry Number 1492-27-9
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 Key LZOSYCMHQXPBFU-UHFFFAOYSA-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 1.350E-04 g/L ALOGPS
LogP -0.85 ALOGPS
LogP -0.63 ChemAxon
LogS -6.44 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 14 ChemAxon
Refractivity 109.47 ChemAxon
Polarizability 37.6 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.26 +/- 0.11 uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and Quantified
Article_icon
0.141 +/- 0.009 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
0.005 (0.0-0.124) uM Children (1-13 year old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.04 (0.02-0.06) 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
0.103 +/- 0.008 uM Adult (>18 years old) Both Celiac disease Not Available
Blood Detected and Quantified
Article_icon
0.005 (0.0-0.012) 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 FDB022162
      KNApSAcK ID Not Available
      Chemspider ID 8420677 Link_out
      KEGG Compound ID Not Available
      BioCyc ID PALMITOYL-CARNITINE Link_out
      BiGG ID Not Available
      Wikipedia Link Not Available
      NuGOwiki Link HMDB00651 Link_out
      Metagene Link HMDB00651 Link_out
      METLIN ID 5623 Link_out
      PubChem Compound 10245190 Link_out
      PDB ID Not Available
      ChEBI ID Not Available
      References
      Synthesis Reference Strack, 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 Link_out