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Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2020-06-05 20:16:03 UTC |
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Update Date | 2022-09-22 18:34:33 UTC |
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HMDB ID | HMDB0240664 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | Benzoylcarnitine |
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Description | Benzoylcarnitine belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Benzoylcarnitine is a member of the class of compounds known as acylcarnitines. Acylcarnitines are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Acylcarnitines are useful in the diagnosis of genetic disorders such as fatty acid oxidation disorders and differentiation between biochemical phenotypes of medium-chain acyl-CoA dehydrogenase (MCAD) deficiency disorders (PMID: 12385891 ). Benzoylcarnitine is a metabolite of benzoate and has been identified in the urine of hyperammonemia patients treated with sodium benzoate and L-carnitine (PMID: 2609332 ). |
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Structure | C[N+](C)(C)C[C@@H](CC([O-])=O)OC(=O)C1=CC=CC=C1 InChI=1S/C14H19NO4/c1-15(2,3)10-12(9-13(16)17)19-14(18)11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3/t12-/m1/s1 |
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Synonyms | Value | Source |
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Benzoyl carnitine | HMDB | Benzoylcarnitine | HMDB |
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Chemical Formula | C14H20NO4 |
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Average Molecular Weight | 266.316 |
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Monoisotopic Molecular Weight | 266.138684548 |
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IUPAC Name | (3R)-3-(benzoyloxy)-4-(trimethylazaniumyl)butanoate |
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Traditional Name | (3R)-3-(benzoyloxy)-4-(trimethylammonio)butanoate |
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CAS Registry Number | 105450-08-6 |
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SMILES | C[N+](C)(C)C[C@@H](CC(O)=O)OC(=O)C1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C14H19NO4/c1-15(2,3)10-12(9-13(16)17)19-14(18)11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3/p+1/t12-/m1/s1 |
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InChI Key | AWUHAZDZHNWQAG-GFCCVEGCSA-O |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzoic acids and derivatives |
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Direct Parent | Benzoic acid esters |
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Alternative Parents | |
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Substituents | - Benzoate ester
- Benzoyl
- Dicarboxylic acid or derivatives
- Tetraalkylammonium salt
- Quaternary ammonium salt
- Carboxylic acid salt
- Carboxylic acid ester
- Carboxylic acid
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organic salt
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Amine
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Not Available |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M+H]+ | 161.585 | 30932474 | DeepCCS | [M-H]- | 159.227 | 30932474 | DeepCCS | [M-2H]- | 192.874 | 30932474 | DeepCCS | [M+Na]+ | 168.101 | 30932474 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Benzoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzoylcarnitine 10V, Positive-QTOF | splash10-014l-2790000000-6292d825b649662058d6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzoylcarnitine 20V, Positive-QTOF | splash10-0btj-9800000000-1bea2cef004dfb0665b7 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzoylcarnitine 40V, Positive-QTOF | splash10-052r-9300000000-c83160bcfdf30fc87776 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Cancer patients undergoing total body irradiation | | details | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Cancer patients undergoing total body irradiation | | details |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 114314 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 129022 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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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 | - Okun JG, Kolker S, Schulze A, Kohlmuller D, Olgemoller K, Lindner M, Hoffmann GF, Wanders RJ, Mayatepek E: A method for quantitative acylcarnitine profiling in human skin fibroblasts using unlabelled palmitic acid: diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of MCAD deficiency. Biochim Biophys Acta. 2002 Oct 10;1584(2-3):91-8. [PubMed:12385891 ]
- Sakuma T, Asai K, Ichiki T, Sugiyama N, Kidouchi K, Wada Y: Identification of benzoylcarnitine in the urine of a patient of hyperammonemia. Tohoku J Exp Med. 1989 Oct;159(2):147-51. doi: 10.1620/tjem.159.147. [PubMed:2609332 ]
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