Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-04 19:02:22 UTC |
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Update Date | 2021-09-14 14:59:44 UTC |
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HMDB ID | HMDB0060831 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | meta-O-Dealkylated flecainide |
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Description | meta-O-Dealkylated flecainide is a metabolite of flecainide. Flecainide acetate is a class Ic antiarrhythmic agent used to prevent and treat tachyarrhythmias (abnormal fast rhythms of the heart). It is used to treat a variety of cardiac arrhythmias including paroxysmal atrial fibrillation (episodic irregular heartbeat originating in the upper chamber of the heart), paroxysmal supraventricular tachycardia (episodic rapid but regular heartbeat originating in the atrium), and ventricular tachycardia (rapid rhythms of the lower chambers of the heart). (Wikipedia) |
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Structure | OC1=CC=C(OCC(F)(F)F)C(=C1)C(=O)NCC1CCCCN1 InChI=1S/C15H19F3N2O3/c16-15(17,18)9-23-13-5-4-11(21)7-12(13)14(22)20-8-10-3-1-2-6-19-10/h4-5,7,10,19,21H,1-3,6,8-9H2,(H,20,22) |
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Synonyms | Value | Source |
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5-Hydroxy-N-(2-piperidinylmethyl)-2-(2,2,2-trifluoroethoxy)benzamide | HMDB | MODF | HMDB |
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Chemical Formula | C15H19F3N2O3 |
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Average Molecular Weight | 332.3182 |
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Monoisotopic Molecular Weight | 332.134777099 |
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IUPAC Name | 5-hydroxy-N-(piperidin-2-ylmethyl)-2-(2,2,2-trifluoroethoxy)benzamide |
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Traditional Name | 5-hydroxy-N-(piperidin-2-ylmethyl)-2-(2,2,2-trifluoroethoxy)benzamide |
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CAS Registry Number | Not Available |
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SMILES | OC1=CC=C(OCC(F)(F)F)C(=C1)C(=O)NCC1CCCCN1 |
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InChI Identifier | InChI=1S/C15H19F3N2O3/c16-15(17,18)9-23-13-5-4-11(21)7-12(13)14(22)20-8-10-3-1-2-6-19-10/h4-5,7,10,19,21H,1-3,6,8-9H2,(H,20,22) |
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InChI Key | FVJPPEWHZCSTAC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring. |
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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 | Benzamides |
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Alternative Parents | |
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Substituents | - 4-alkoxyphenol
- Benzamide
- Phenoxy compound
- Benzoyl
- Phenol ether
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Piperidine
- Amino acid or derivatives
- Carboxamide group
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Secondary aliphatic amine
- Ether
- Azacycle
- Organoheterocyclic compound
- Secondary amine
- Organohalogen compound
- Alkyl halide
- Alkyl fluoride
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organofluoride
- Organonitrogen compound
- Organooxygen compound
- Amine
- Organic oxygen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic 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 | |
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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 SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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meta-O-Dealkylated flecainide,1TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)NCC2CCCCN2)=C1 | 2360.4 | Semi standard non polar | 33892256 | meta-O-Dealkylated flecainide,1TMS,isomer #2 | C[Si](C)(C)N(CC1CCCCN1)C(=O)C1=CC(O)=CC=C1OCC(F)(F)F | 2301.4 | Semi standard non polar | 33892256 | meta-O-Dealkylated flecainide,1TMS,isomer #3 | C[Si](C)(C)N1CCCCC1CNC(=O)C1=CC(O)=CC=C1OCC(F)(F)F | 2401.6 | Semi standard non polar | 33892256 | meta-O-Dealkylated flecainide,2TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)N(CC2CCCCN2)[Si](C)(C)C)=C1 | 2311.2 | Semi standard non polar | 33892256 | meta-O-Dealkylated flecainide,2TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)N(CC2CCCCN2)[Si](C)(C)C)=C1 | 2424.3 | Standard non polar | 33892256 | meta-O-Dealkylated flecainide,2TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)N(CC2CCCCN2)[Si](C)(C)C)=C1 | 2581.2 | Standard polar | 33892256 | meta-O-Dealkylated flecainide,2TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)NCC2CCCCN2[Si](C)(C)C)=C1 | 2431.0 | Semi standard non polar | 33892256 | meta-O-Dealkylated flecainide,2TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)NCC2CCCCN2[Si](C)(C)C)=C1 | 2427.2 | Standard non polar | 33892256 | meta-O-Dealkylated flecainide,2TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)NCC2CCCCN2[Si](C)(C)C)=C1 | 2787.6 | Standard polar | 33892256 | meta-O-Dealkylated flecainide,2TMS,isomer #3 | C[Si](C)(C)N(CC1CCCCN1[Si](C)(C)C)C(=O)C1=CC(O)=CC=C1OCC(F)(F)F | 2374.0 | Semi standard non polar | 33892256 | meta-O-Dealkylated flecainide,2TMS,isomer #3 | C[Si](C)(C)N(CC1CCCCN1[Si](C)(C)C)C(=O)C1=CC(O)=CC=C1OCC(F)(F)F | 2542.4 | Standard non polar | 33892256 | meta-O-Dealkylated flecainide,2TMS,isomer #3 | C[Si](C)(C)N(CC1CCCCN1[Si](C)(C)C)C(=O)C1=CC(O)=CC=C1OCC(F)(F)F | 2798.8 | Standard polar | 33892256 | meta-O-Dealkylated flecainide,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)N(CC2CCCCN2[Si](C)(C)C)[Si](C)(C)C)=C1 | 2418.3 | Semi standard non polar | 33892256 | meta-O-Dealkylated flecainide,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)N(CC2CCCCN2[Si](C)(C)C)[Si](C)(C)C)=C1 | 2509.7 | Standard non polar | 33892256 | meta-O-Dealkylated flecainide,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)N(CC2CCCCN2[Si](C)(C)C)[Si](C)(C)C)=C1 | 2604.7 | Standard polar | 33892256 | meta-O-Dealkylated flecainide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)NCC2CCCCN2)=C1 | 2563.4 | Semi standard non polar | 33892256 | meta-O-Dealkylated flecainide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(CC1CCCCN1)C(=O)C1=CC(O)=CC=C1OCC(F)(F)F | 2516.4 | Semi standard non polar | 33892256 | meta-O-Dealkylated flecainide,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1CCCCC1CNC(=O)C1=CC(O)=CC=C1OCC(F)(F)F | 2616.9 | Semi standard non polar | 33892256 | meta-O-Dealkylated flecainide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)N(CC2CCCCN2)[Si](C)(C)C(C)(C)C)=C1 | 2710.2 | Semi standard non polar | 33892256 | meta-O-Dealkylated flecainide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)N(CC2CCCCN2)[Si](C)(C)C(C)(C)C)=C1 | 2829.5 | Standard non polar | 33892256 | meta-O-Dealkylated flecainide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)N(CC2CCCCN2)[Si](C)(C)C(C)(C)C)=C1 | 2758.4 | Standard polar | 33892256 | meta-O-Dealkylated flecainide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)NCC2CCCCN2[Si](C)(C)C(C)(C)C)=C1 | 2848.5 | Semi standard non polar | 33892256 | meta-O-Dealkylated flecainide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)NCC2CCCCN2[Si](C)(C)C(C)(C)C)=C1 | 2827.1 | Standard non polar | 33892256 | meta-O-Dealkylated flecainide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)NCC2CCCCN2[Si](C)(C)C(C)(C)C)=C1 | 2924.7 | Standard polar | 33892256 | meta-O-Dealkylated flecainide,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N(CC1CCCCN1[Si](C)(C)C(C)(C)C)C(=O)C1=CC(O)=CC=C1OCC(F)(F)F | 2809.6 | Semi standard non polar | 33892256 | meta-O-Dealkylated flecainide,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N(CC1CCCCN1[Si](C)(C)C(C)(C)C)C(=O)C1=CC(O)=CC=C1OCC(F)(F)F | 2932.3 | Standard non polar | 33892256 | meta-O-Dealkylated flecainide,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N(CC1CCCCN1[Si](C)(C)C(C)(C)C)C(=O)C1=CC(O)=CC=C1OCC(F)(F)F | 2957.0 | Standard polar | 33892256 | meta-O-Dealkylated flecainide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)N(CC2CCCCN2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1 | 3031.5 | Semi standard non polar | 33892256 | meta-O-Dealkylated flecainide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)N(CC2CCCCN2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1 | 3040.8 | Standard non polar | 33892256 | meta-O-Dealkylated flecainide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(OCC(F)(F)F)C(C(=O)N(CC2CCCCN2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1 | 2858.2 | Standard polar | 33892256 |
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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 - meta-O-Dealkylated flecainide GC-MS (Non-derivatized) - 70eV, Positive | splash10-00sj-9272000000-82f100221b0a392c9032 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - meta-O-Dealkylated flecainide GC-MS (1 TMS) - 70eV, Positive | splash10-00ej-9125000000-8396432eef72e6e7b8c6 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - meta-O-Dealkylated flecainide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - meta-O-Dealkylated flecainide 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 - meta-O-Dealkylated flecainide 10V, Positive-QTOF | splash10-001i-4229000000-daa21495bf6c565e5c7d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - meta-O-Dealkylated flecainide 20V, Positive-QTOF | splash10-000t-9332000000-0b112630dd47c34d2f1a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - meta-O-Dealkylated flecainide 40V, Positive-QTOF | splash10-0002-9000000000-5720c7eb1f5a890af12c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - meta-O-Dealkylated flecainide 10V, Negative-QTOF | splash10-001i-0019000000-3b132af0c25abae1d5f3 | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - meta-O-Dealkylated flecainide 20V, Negative-QTOF | splash10-001i-3569000000-63563a7909396b71cb6c | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - meta-O-Dealkylated flecainide 40V, Negative-QTOF | splash10-000x-9840000000-766b0c57f2cba44c8c28 | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - meta-O-Dealkylated flecainide 10V, Positive-QTOF | splash10-001i-0009000000-318d87a7239d505d8538 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - meta-O-Dealkylated flecainide 20V, Positive-QTOF | splash10-001i-2039000000-f496315bf07af39a8531 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - meta-O-Dealkylated flecainide 40V, Positive-QTOF | splash10-053s-9210000000-e08baee95664de30a43c | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - meta-O-Dealkylated flecainide 10V, Negative-QTOF | splash10-001i-0009000000-6630515278d3adcc5e77 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - meta-O-Dealkylated flecainide 20V, Negative-QTOF | splash10-001j-1981000000-d0992e6c9c07d46d7460 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - meta-O-Dealkylated flecainide 40V, Negative-QTOF | splash10-0wms-0950000000-d63497edee71b3500dd7 | 2021-10-12 | Wishart Lab | View Spectrum |
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