L-Octanoylcarnitine (CHEM022389)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:30:53 UTC
Update Date2016-11-09 01:17:29 UTC
Accession NumberCHEM022389
Identification
Common NameL-Octanoylcarnitine
ClassSmall Molecule
DescriptionL-Octanoylcarnitine 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. Thus, L-octanoylcarnitine is considered to be a fatty ester lipid molecule. L-Octanoylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. L-Octanoylcarnitine has been found to be associated with several diseases known as pregnancy, colorectal cancer, and ulcerative colitis; also l-octanoylcarnitine has been linked to several inborn metabolic disorders including celiac disease and very long chain acyl-coa dehydrogenase deficiency.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
L-Octanoyl-L-carnitineChEBI
O-Octanoyl-(R)-carnitineChEBI
O-Octanoyl-R-carnitineChEBI
(-)-OctanoylcarnitineHMDB
L-Carnitine octanoyl esterHMDB
L-O-OctanoylcarnitineHMDB
Octanoic acid ester with L-(3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner saltHMDB
Octanoyl-L-carnitineHMDB
OctanoylcarnitineHMDB
Octanoylcarnitine chloride, (R)-isomerHMDB
Octanoylcarnitine, (R)-isomerHMDB
Octanoylcarnitine chlorideHMDB
Octanoylcarnitine chloride, (+-)-isomerHMDB
Octanoylcarnitine, (+-)-isomerHMDB
C8-CarnitineHMDB
L-OctanoylcarnitineChEBI
Chemical FormulaC15H29NO4
Average Molecular Mass287.395 g/mol
Monoisotopic Mass287.210 g/mol
CAS Registry Number25243-95-2
IUPAC Name(3R)-3-(octanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional NameL-octanoylcarnitine
SMILESCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
InChI IdentifierInChI=1S/C15H29NO4/c1-5-6-7-8-9-10-15(19)20-13(11-14(17)18)12-16(2,3)4/h13H,5-12H2,1-4H3/t13-/m1/s1
InChI KeyCXTATJFJDMJMIY-CYBMUJFWSA-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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00085 g/LALOGPS
logP-1.2ALOGPS
logP-1.5ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity100.27 m³·mol⁻¹ChemAxon
Polarizability33.28 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-6090000000-f5427438c18b619c6d12Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-0ffd63a09867f6b170e5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-558ce1fa555823e95479Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-9c0281b8f2959b51e65eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9050000000-5fd4264c445d0a035113Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-e9262cbaff8cb4ad0ba6Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000791
FooDB IDFDB022246
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDL-OCTANOYLCARNITINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID10128115
ChEBI ID18102
PubChem Compound ID11953814
Kegg Compound IDC02838
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.
2. Duhr, Edward F.; Mauro, J. Matthew; Clennan, Edward L.; Barden, Roland E. The synthesis and biological activity of thiolcarnitine and its thiolesters. Lipids (1983), 18(5), 382-6.
3. Chace DH, DiPerna JC, Adam BW, Hannon WH: Errors caused by the use of D,L-octanoylcarnitine for blood-spot calibrators. Clin Chem. 2001 Apr;47(4):758-60.
4. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23078175
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=6888266