| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:37:08 UTC |
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| Update Date | 2020-06-04 20:41:37 UTC |
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| BMDB ID | BMDB0000824 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Propionylcarnitine |
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| Description | Propionylcarnitine 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. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 3-Carboxy-N,N,N-trimethyl-2-(1-oxopropoxy)-1-propanaminium inner salt | ChEBI | | O-Propionylcarnitine | ChEBI | | Propionyl carnitine | ChEBI | | (+/-)-propionylcarnitine chloride | HMDB | | (3-Carboxy-2-hydroxypropyl)trimethyl-hydroxide ammonium inner salt | HMDB | | L-Propionylcarnitine | HMDB | | O-Propanoylcarnitine | HMDB | | Propionyl-carnitine | HMDB | | Propionyl-L-carnitine | HMDB | | Propionylcarnitine, (+-)-isomer | HMDB | | Propionylcarnitine, (R)-isomer | HMDB |
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| Chemical Formula | C10H19NO4 |
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| Average Molecular Weight | 217.2622 |
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| Monoisotopic Molecular Weight | 217.131408101 |
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| IUPAC Name | 3-(propanoyloxy)-4-(trimethylazaniumyl)butanoate |
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| Traditional Name | propionyl-L-carnitine |
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| CAS Registry Number | 17298-37-2 |
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| SMILES | CCC(=O)OC(CC([O-])=O)C[N+](C)(C)C |
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| 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 |
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| InChI Key | UFAHZIUFPNSHSL-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Fatty acid esters |
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| Direct Parent | Acyl carnitines |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cell membrane
- Cytoplasm
- Membrane
- Mitochondria
- Peroxisome
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | Not Available |
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| Biological Properties |
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| Cellular Locations | - Cell membrane
- Cytoplasm
- Membrane
- Mitochondria
- Peroxisome
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| Biospecimen Locations | - Blood
- Liver
- Longissimus Thoracis Muscle
- Milk
- Placenta
- Ruminal Fluid
- Semimembranosus Muscle
- Testis
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 0.06 +/- 0.03 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 0.2 +/- 0.04 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 3 +/- 1 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 6 +/- 2 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.1 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.4 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3.93 +/- 0.02 uM | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.016 +/- 0.006 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.016 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.011 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.023 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.017 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.017 +/- 0.01 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.01 +/- 0.01 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.02 +/- 0.01 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.02 +/- 0.01 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.036 +/- 0.006 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.09 +/- 0.02 uM | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 7 +/- 2 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 0.6 +/- 0.2 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Abnormal (male calves/vaccination biomarker) | | details | | Blood | Detected and Quantified | 0.3 +/- 0.08 uM | Not Specified | Not Specified | Transition disease/1 wk after parturition | | details |
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| External Links |
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| HMDB ID | HMDB0000824 |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB022268 |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | 96904 |
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| KEGG Compound ID | C03017 |
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| BioCyc ID | Not Available |
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| BiGG ID | 1862604 |
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| Wikipedia Link | Not Available |
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| METLIN ID | 5787 |
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| PubChem Compound | 107738 |
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| PDB ID | Not Available |
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| ChEBI ID | 28867 |
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| References |
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| Synthesis Reference | Not Available |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - 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 ]
- 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.
- 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.
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