Showing metabocard for Propionylcarnitine (BMDB0000824)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:37:08 UTC
Update Date2020-06-04 20:41:37 UTC
MCDB ID BMDB0000824
Secondary Accession Numbers
  • BMDB00824
Metabolite Identification
Common NamePropionylcarnitine
DescriptionPropionylcarnitine 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, propionylcarnitine is considered to be a fatty ester lipid molecule. Propionylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Propionylcarnitine participates in a number of enzymatic reactions, within cattle. In particular, Propionylcarnitine can be biosynthesized from propionyl-CoA and L-carnitine; which is mediated by the enzyme carnitine O-acetyltransferase. In addition, Propionylcarnitine can be biosynthesized from propionyl-CoA and L-carnitine through its interaction with the enzyme carnitine O-acetyltransferase. In cattle, propionylcarnitine is involved in the metabolic pathway called the oxidation OF branched-chain fatty acids pathway. Propionylcarnitine is a potentially toxic compound. Propionylcarnitine has been found to be associated with several diseases known as crohn's disease, eosinophilic esophagitis, and obesity; also propionylcarnitine has been linked to several inborn metabolic disorders including propionic acidemia and celiac disease.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Carboxy-N,N,N-trimethyl-2-(1-oxopropoxy)-1-propanaminium inner saltChEBI
O-PropionylcarnitineChEBI
Propionyl carnitineChEBI
(+/-)-propionylcarnitine chlorideHMDB
(3-Carboxy-2-hydroxypropyl)trimethyl-hydroxide ammonium inner saltHMDB
L-PropionylcarnitineHMDB
O-PropanoylcarnitineHMDB
Propionyl-carnitineHMDB
Propionyl-L-carnitineHMDB
Propionylcarnitine, (+-)-isomerHMDB
Propionylcarnitine, (R)-isomerHMDB
Chemical FormulaC10H19NO4
Average Molecular Weight217.2622
Monoisotopic Molecular Weight217.131408101
IUPAC Name3-(propanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Namepropionyl-L-carnitine
CAS Registry Number17298-37-2
SMILES
CCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C10H19NO4/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4/h8H,5-7H2,1-4H3
InChI KeyUFAHZIUFPNSHSL-UHFFFAOYSA-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
logP-2.3ALOGPS
logP-3.7ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.19ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity77.26 m³·mol⁻¹ChemAxon
Polarizability22.72 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected and Quantified4.1 +/- 0.1 uM details
Detected and Quantified4.4 +/- 0.1 uM details
Detected and Quantified4 +/- 1 uM details
Detected and Quantified3.93 +/- 0.02 uM details
HMDB IDHMDB0000824
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022268
KNApSAcK IDNot Available
Chemspider ID96904
KEGG Compound IDC03017
BioCyc IDNot Available
BiGG ID1862604
Wikipedia LinkNot Available
METLIN ID5787
PubChem Compound107738
PDB IDNot Available
ChEBI ID28867
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]
  2. 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.
  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.