Showing metabocard for Dodecanoylcarnitine (BMDB0002250)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:53:11 UTC
Update Date2020-06-04 19:49:46 UTC
MCDB ID BMDB0002250
Secondary Accession Numbers
  • BMDB02250
Metabolite Identification
Common NameDodecanoylcarnitine
DescriptionDodecanoylcarnitine, also known as lauroylcarnitine or O-C12:0-L-carnitine, 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, dodecanoylcarnitine is considered to be a fatty ester lipid molecule. Dodecanoylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Dodecanoylcarnitine exists in all eukaryotes, ranging from yeast to humans. Dodecanoylcarnitine has been found to be associated with several diseases known as pregnancy and obesity; also dodecanoylcarnitine has been linked to several inborn metabolic disorders including celiac disease and very long chain acyl-coa dehydrogenase deficiency.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-LauroylcarnitineChEBI
(3R)-3-(Dodecanoyloxy)-4-(trimethylammonio)butanoateChEBI
(R)-DodecanoylcarnitineChEBI
Dodecanoyl-L-carnitineChEBI
L-Carnitine dodecanoyl esterChEBI
Lauroyl-L(-)-carnitinChEBI
Lauroyl-L-carnitineChEBI
LauroylcarnitineChEBI
LaurylcarnitineChEBI
O-C12:0-L-CarnitineChEBI
O-Dodecanoyl-R-carnitineChEBI
(3R)-3-(Dodecanoyloxy)-4-(trimethylammonio)butanoic acidGenerator
C12 CarnitineHMDB
L-LauroylcarnitineHMDB
Lauroyl-L(-)-carnitineHMDB
DodecanoylcarnitineHMDB
O-DodecanoylcarnitineChEBI, HMDB
O-LauroylcarnitineChEBI, HMDB
O-Lauroyl-L-carnitineChEBI, HMDB
Chemical FormulaC19H37NO4
Average Molecular Weight343.5014
Monoisotopic Molecular Weight343.272258677
IUPAC Name(3R)-3-(dodecanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Namelauroyl-L(-)-carnitin
CAS Registry Number25518-54-1
SMILES
CCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C19H37NO4/c1-5-6-7-8-9-10-11-12-13-14-19(23)24-17(15-18(21)22)16-20(2,3)4/h17H,5-16H2,1-4H3/t17-/m1/s1
InChI KeyFUJLYHJROOYKRA-QGZVFWFLSA-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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.03ALOGPS
logP0.26ChemAxon
logS-7ALOGPS
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 Count16ChemAxon
Refractivity118.67 m³·mol⁻¹ChemAxon
Polarizability41.85 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9300000000-0cd49618a50984aad9822016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0002-0900000000-1c57ff1372236d823d802017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9000000000-ef35ea7a4d61bac8cb202017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-ce07549e40447c69729f2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9005000000-ce18984499544d19b7392021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-24View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified3.75 +/- 0.03 uM details
Detected and Quantified4.3 +/- 0.1 uM details
Detected and Quantified4.43 +/- 0.04 uM details
Detected and Quantified3.4 +/- 0.1 uM details
HMDB IDHMDB0002250
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022928
KNApSAcK IDC00052268
Chemspider ID147288
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6573
PubChem Compound168381
PDB IDNot Available
ChEBI ID77086
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.