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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2010-02-17 09:53:39 UTC
Update Date2019-05-26 20:18:13 UTC
HMDB IDHMDB0013324
Secondary Accession Numbers
  • HMDB13324
Metabolite Identification
Common Name2-Octenoylcarnitine
Description2-Octenoylcarnitine is classified as a member of the fatty acid esters. Fatty acid esters are carboxylic ester derivatives of a fatty acid. 2-Octenoylcarnitine is considered to be practically insoluble (in water) and a weak acidic compound. 2-Octenoylcarnitine can be found in blood and urine. Within a cell, 2-octenoylcarnitine is primarily located in the extracellular space and near the membrane.
Structure
Data?1558901893
Synonyms
ValueSource
(3S)-3-[(2E)-Oct-2-enoyloxy]-4-(trimethylammonio)butanoateChEBI
(e)-2-Octenoyl-L-carnitineChEBI
2-OctenoylcarnitineChEBI
(3S)-3-[(2E)-Oct-2-enoyloxy]-4-(trimethylammonio)butanoic acidGenerator
Chemical FormulaC15H27NO4
Average Molecular Weight285.384
Monoisotopic Molecular Weight285.194008353
IUPAC Name(3S)-3-[(2E)-oct-2-enoyloxy]-4-(trimethylazaniumyl)butanoate
Traditional Name(3S)-3-[(2E)-oct-2-enoyloxy]-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
CCCCC\C=C\C(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C15H27NO4/c1-5-6-7-8-9-10-15(19)20-13(11-14(17)18)12-16(2,3)4/h9-10,13H,5-8,11-12H2,1-4H3/b10-9+/t13-/m0/s1
InChI KeyLOSHAHDSFZXVCT-LXKVQUBZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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 Solubility0.00055 g/LALOGPS
logP-1.2ALOGPS
logP-1.3ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)4.17ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity101.36 m³·mol⁻¹ChemAxon
Polarizability32.45 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.2 +/- 0.15 uMAdult (>18 years old)BothNormal details
BloodDetected but not Quantified Adult (>18 years old)Female
Normal
details
UrineDetected and Quantified0.50 (0.08-1.20) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.100 +/- 0.050 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.123 +/- 0.070 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
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.
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 Compound70679121
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.