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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2010-02-22 10:23:05 UTC
Update Date2019-05-26 20:13:26 UTC
HMDB IDHMDB0013326
Secondary Accession Numbers
  • HMDB13326
Metabolite Identification
Common Nametrans-2-Dodecenoylcarnitine
DescriptionTrans-2-dodecenoylcarnitine is classified as a member of the fatty acid esters. Fatty acid esters are carboxylic ester derivatives of a fatty acid. Trans-2-dodecenoylcarnitine is considered to be a practically insoluble (in water) and a weak acidic compound. Trans-2-dodecenoylcarnitine can be found in Cow milk, pasteurized, vitamin A + D added, 0% fats, Cow milk, pasteurized, vitamin A + D added, 1% fats, Cow milk, pasteurized, vitamin A + D added, 2% fats, and Cow milk, pasteurized, vitamin D added, 3.25% fats. Trans-2-dodecenoylcarnitine can be found in blood and urine. Within a cell, Trans-2-dodecenoylcarnitine is primarily located in the extracellular space and near the membrane. trans-2-Dodecenoylcarnitine is found to be associated with glutaric aciduria II, which is an inborn error of metabolism.
Structure
Data?1558901606
SynonymsNot Available
Chemical FormulaC19H35NO4
Average Molecular Weight341.492
Monoisotopic Molecular Weight341.256608611
IUPAC Name(4S)-4-[(2E)-dodec-2-enoyloxy]-4-(trimethylazaniumyl)butanoate
Traditional Name(4S)-4-[(2E)-dodec-2-enoyloxy]-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
CCCCCCCCC\C=C\C(=O)O[C@@H](CCC([O-])=O)[N+](C)(C)C
InChI Identifier
InChI=1S/C19H35NO4/c1-5-6-7-8-9-10-11-12-13-14-19(23)24-17(20(2,3)4)15-16-18(21)22/h13-14,17H,5-12,15-16H2,1-4H3/b14-13+/t17-/m0/s1
InChI KeyJEOZLTJHDSKQIT-CLVCIHKQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring 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 Solubility3.4e-05 g/LALOGPS
logP0.16ALOGPS
logP0.81ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity119.7 m³·mol⁻¹ChemAxon
Polarizability41.08 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.10-0.40 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.23(0.07) uMAdult (>18 years old)BothNormal details
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    BloodDetected and Quantified0.10 +/- 0.03 uMChildren (1-13 years old)BothNormal details
    BloodDetected and Quantified<0.12 uMAdolescent (13-18 years old)MaleNormal details
    FecesDetected and Quantified0.47 +/- 0.33 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified0.43 +/- 0.26 nmol/g wet fecesAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.028 (0.011-0.042) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified0.29(0.1) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
    BloodDetected and Quantified0.16 +/- 0.05 uMChildren (1-13 years old)Both
    Obese
    details
    BloodDetected and Quantified0.16 +/- 0.06 uMChildren (1-13 years old)Both
    Obese
    details
    BloodDetected and Quantified0.16 +/- 0.06 uMChildren (1-13 years old)Both
    Obese
    details
    BloodDetected and Quantified0.16 +/- 0.07 uMChildren (1-13 years old)Both
    Obese
    details
    BloodDetected and Quantified0.130 +/- 0.040 uMChildren (1-13 years old)Both
    Obesity
      • Metabolomics reve...
    details
    BloodDetected and Quantified0.131 +/- 0.046 uMChildren (1-13 years old)Both
    Obesity
      • Metabolomics reve...
    details
    BloodDetected and Quantified0.13 +/- 0.04 uMChildren (1-13 years old)Both
    Obese
    details
    BloodDetected and Quantified0.15 uMAdolescent (13-18 years old)Male
    Glutaric aciduria II
    details
    BloodDetected and Quantified0.22 uMAdolescent (13-18 years old)MaleGlutaric aciduria II details
    Associated Disorders and Diseases
    Disease References
    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 ]
    Obesity
    1. Reinehr T, Wolters B, Knop C, Lass N, Hellmuth C, Harder U, Peissner W, Wahl S, Grallert H, Adamski J, Illig T, Prehn C, Yu Z, Wang-Sattler R, Koletzko B: Changes in the serum metabolite profile in obese children with weight loss. Eur J Nutr. 2015 Mar;54(2):173-81. doi: 10.1007/s00394-014-0698-8. Epub 2014 Apr 17. [PubMed:24740590 ]
    2. Wahl S, Yu Z, Kleber M, Singmann P, Holzapfel C, He Y, Mittelstrass K, Polonikov A, Prehn C, Romisch-Margl W, Adamski J, Suhre K, Grallert H, Illig T, Wang-Sattler R, Reinehr T: Childhood obesity is associated with changes in the serum metabolite profile. Obes Facts. 2012;5(5):660-70. doi: 10.1159/000343204. Epub 2012 Oct 4. [PubMed:23108202 ]
    3. Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDNot Available
    KNApSAcK IDNot Available
    Chemspider IDNot Available
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound53481671
    PDB IDNot Available
    ChEBI ID89717
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
    2. 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 ]
    3. 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 ]
    4. 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 ]
    5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.