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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2010-02-22 11:49:49 UTC
Update Date2017-10-23 19:06:09 UTC
HMDB IDHMDB0013334
Secondary Accession Numbers
  • HMDB13334
Metabolite Identification
Common Name9,12-Hexadecadienoylcarnitine
Description9,12-Hexadecadienoylcarnitine is an acylcarnitine with C16:2 fatty acid moiety. 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 ).
Structure
Thumb
Synonyms
ValueSource
(Z,Z)9,12-HexadecadienoylcarnitineHMDB
9(Z),12(Z)-HexadecadienoylcarnitineHMDB
9,12-HexadecadienylcarnitineHMDB
9Z,12Z-HexadecadienoylcarnitineHMDB
Acyl carnitine C16:2HMDB
Hexadecadienyl-L-carnitineHMDB
Chemical FormulaC23H41NO4
Average Molecular Weight395.5759
Monoisotopic Molecular Weight395.303558805
IUPAC Name(4S)-4-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]-4-(trimethylazaniumyl)butanoate
Traditional Name(4S)-4-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
CCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H]([N+](C)(C)C)CCC([O-])=O
InChI Identifier
InChI=1S/C23H41NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(24(2,3)4)19-20-22(25)26/h7-8,10-11,21H,5-6,9,12-20H2,1-4H3/b8-7-,11-10-/t21-/m0/s1
InChI KeyAHZCIODFJPNPKS-XBDLETADSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

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 Solubility1.6e-05 g/LALOGPS
logP0.54ALOGPS
logP1.64ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)4.17ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity139.24 m³·mol⁻¹ChemAxon
Polarizability48.22 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, Positivesplash10-0006-4931000000-bd89639adccb5f1bca93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f92-1109000000-eb5b74c30982e98fcaffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-3920000000-abf1ed22b7ded8c0b18dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-5920000000-bfbfb7b5568842d2ad72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-0059000000-3baa5346a9141b44eca5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-0094000000-a1ef9031a46b0f6a0600View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pc3-6290000000-19dd8a13b0880b16a400View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.01 +/- 0 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0080-0.0250 uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.011 +/- 0.002 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.0010 (0.0005-0.0040) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.011 (0.0057) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029394
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481687
PDB IDNot Available
ChEBI ID89745
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.