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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2010-02-22 11:10:56 UTC
Update Date2018-05-20 08:48:35 UTC
HMDB IDHMDB0013331
Secondary Accession Numbers
  • HMDB13331
Metabolite Identification
Common Name3, 5-Tetradecadiencarnitine
Description 3, 5-tetradecadiencarnitine is considered to be a practically insoluble (in water) and a weak acidic compound. 3, 5-tetradecadiencarnitine can be found in blood and urine. Within a cell, 3, 5-tetradecadiencarnitine is primarily located in the extracellular space and near the membrane.
Structure
Thumb
Synonyms
ValueSource
3-Hydroxy-9(Z)-octadecenoylcarnitineHMDB
Chemical FormulaC21H37NO4
Average Molecular Weight367.5228
Monoisotopic Molecular Weight367.272258677
IUPAC Name(4S)-4-{[(9Z)-3-hydroxyoctadec-9-enoyl]oxy}-4-(trimethylazaniumyl)butanoate
Traditional Name(4S)-4-{[(9Z)-3-hydroxyoctadec-9-enoyl]oxy}-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C\C=C\CC(=O)O[C@H]([N+](C)(C)C)CCC([O-])=O
InChI Identifier
InChI=1S/C21H37NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-21(25)26-19(22(2,3)4)17-18-20(23)24/h12-15,19H,5-11,16-18H2,1-4H3/b13-12+,15-14+/t19-/m0/s1
InChI KeyHXOGMKPCIDSSKJ-NKBLVAAJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • 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 Solubility2.6e-05 g/LALOGPS
logP0.73ALOGPS
logP1.66ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)4.06ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area86.66 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity148.84 m³·mol⁻¹ChemAxon
Polarizability53.75 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, Positivesplash10-0006-6961000000-3e4b80a846ff081cdb6cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9703100000-cae256fab3e9a5e1ea6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-1123900000-da5b3930b3b290d8a9ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-2920100000-5e2da4c2c317c1231b02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-6961000000-1d72839df4094e7c623dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0060900000-7e2b3f8f770e222956f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-005c-1092100000-c8a6de69d2c6551466b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f9g-4090000000-616d13b76b7323e5cca5View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.012-0.080 uMAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0023 (0.0010-0.0050) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0039 +/- 0.0012 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.030 +/- 0.014 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.032 +/- 0.013 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
UrineDetected and Quantified0.0045 +/- 0.0015 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.0085 +/- 0.0081 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Obesity
  1. 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.
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029400
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481699
PDB IDNot Available
ChEBI IDNot Available
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.