Showing metabocard for Isobutyrylcarnitine (BMDB0062101)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-06-25 21:50:46 UTC
Update Date2020-05-05 18:38:38 UTC
BMDB IDBMDB0062101
Secondary Accession Numbers
  • BMDB62101
Metabolite Identification
Common NameIsobutyrylcarnitine
Description[(2R)-3-carboxy-2-[(2-methylpropanoyl)oxy]propyl]trimethylazanium 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. [(2R)-3-carboxy-2-[(2-methylpropanoyl)oxy]propyl]trimethylazanium is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Isobutyryl-1-carnitineMeSH, HMDB
(R)-IsobutyrylcarnitineHMDB
iso-Butyryl-L(-)-carnitinHMDB
Isobutyryl-carnitineHMDB
Isobutyryl-L-(-)-carnitineHMDB
Isobutyryl-L-carnitineHMDB
IsobutyrylcarnitineHMDB
O-Isobutanoyl-(R)-carnitineHMDB
O-Isobutyryl-L-carnitineHMDB
Chemical FormulaC11H22NO4
Average Molecular Weight232.299
Monoisotopic Molecular Weight232.154334613
IUPAC Name[(2R)-3-carboxy-2-[(2-methylpropanoyl)oxy]propyl]trimethylazanium
Traditional Nameisobutyryl-carnitine
CAS Registry NumberNot Available
SMILES
[H][C@@](CC(O)=O)(C[N+](C)(C)C)OC(=O)C(C)C
InChI Identifier
InChI=1S/C11H21NO4/c1-8(2)11(15)16-9(6-10(13)14)7-12(3,4)5/h8-9H,6-7H2,1-5H3/p+1/t9-/m1/s1
InChI KeyLRCNOZRCYBNMEP-SECBINFHSA-O
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
  • Branched fatty acid
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic salt
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.77e-01 g/lALOGPS
LogP-1.79ALOGPS
Predicted Properties
PropertyValueSource
logP-1.8ALOGPS
logP-3.2ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.27ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity71 m³·mol⁻¹ChemAxon
Polarizability25.01 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, Positivesplash10-006x-9100000000-d4f2ec588392ed5cb87aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9020000000-59d336aa488f4f024e00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-5290000000-baab610a0cdc91406addView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-8d180efb75e39baa17aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-6311075865704b40d294View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01zd-2960000000-d58673805618579862b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fg7-5910000000-901a5442cd8f2d47a601View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9200000000-cf8ccce66b3680a8c957View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
Biospecimen Locations
  • Liver
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
    • Kurt J. Boudonck,...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000736
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022213
KNApSAcK IDNot Available
Chemspider ID147286
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound168380
PDB IDNot Available
ChEBI ID84838
References
Synthesis ReferenceNot Available
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, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8. Metabolomics.