Showing metabocard for Butyrylcarnitine (BMDB0002013)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:49:55 UTC
Update Date2020-06-04 20:04:02 UTC
BMDB IDBMDB0002013
Secondary Accession Numbers
  • BMDB02013
Metabolite Identification
Common NameButyrylcarnitine
DescriptionButyrylcarnitine, also known as O-butanoylcarnitine, 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, butyrylcarnitine is considered to be a fatty ester lipid molecule. Butyrylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Butyrylcarnitine exists in all eukaryotes, ranging from yeast to humans. Butyrylcarnitine is a potentially toxic compound. Butyrylcarnitine has been found to be associated with several diseases known as obesity, eosinophilic esophagitis, and pregnancy; also butyrylcarnitine has been linked to several inborn metabolic disorders including short chain acyl-coa dehydrogenase deficiency and very long chain acyl-coa dehydrogenase deficiency.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3R)-3-(Butyryloxy)-4-(trimethylammonio)butanoateChEBI
Butyryl-L-carnitineChEBI
L-Carnitine butyryl esterChEBI
N-Butyryl-L-(-)-carnitinChEBI
O-Butanoyl-(R)-carnitineChEBI
(3R)-3-(Butyryloxy)-4-(trimethylammonio)butanoic acidGenerator
ButylcarnitineHMDB
O-Butanoyl-carnitineHMDB
O-ButanoylcarnitineHMDB
ButyrylcarnitineChEBI
Chemical FormulaC11H21NO4
Average Molecular Weight231.292
Monoisotopic Molecular Weight231.14705816
IUPAC Name(3R)-3-(butanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional NameO-butanoylcarnitine
CAS Registry Number25576-40-3
SMILES
CCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C11H21NO4/c1-5-6-11(15)16-9(7-10(13)14)8-12(2,3)4/h9H,5-8H2,1-4H3/t9-/m1/s1
InChI KeyQWYFHHGCZUCMBN-SECBINFHSA-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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.1ALOGPS
logP-3.3ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4.27ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity81.86 m³·mol⁻¹ChemAxon
Polarizability24.8 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
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, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-9000000000-a5dda83cb139267daf89View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001r-8390000000-ceb4241ebded9660319eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-001i-0090000000-5c14cfc2ec68c45a3c6dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-001i-0090000000-ffb54886a9c9e0dd59c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-9000000000-45000c412d54fe872024View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001r-6290000000-a53c2ce500986fed88fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-cf95ec9e05e8b6c1a98fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-9050000000-ebf3a8e1eb1d0ceaaebaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-e9262cbaff8cb4ad0ba6View in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Fibroblasts
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Placenta
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.2 +/- 0.1 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected and Quantified0.36 +/- 0.08 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Longissimus Thoracis MuscleDetected and Quantified16 +/- 6 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Characterization ...
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
 details
MilkDetected and Quantified4.4 +/- 0.2 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified5.8 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified6.6 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified3.99 +/- 0.04 uMNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected and Quantified0.05 +/- 0.02 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Semimembranosus MuscleDetected and Quantified22 +/- 8 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified2.8 +/- 0.7 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0002013
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022795
KNApSAcK IDC00052220
Chemspider ID184820
KEGG Compound IDC02862
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6436
PubChem Compound213144
PDB IDNot Available
ChEBI ID21949
References
Synthesis ReferenceLozano Pedro; Daz Mirta; de Diego Teresa; Iborra Jose L Ester synthesis from trimethylammonium alcohols in dry organic media catalyzed by immobilized Candida antarctica lipase B. Biotechnology and bioengineering (2003), 82(3), 352-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  2. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals (2009). Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics.
  3. 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.