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 19:04:27 UTC |
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Update Date | 2021-09-14 14:57:12 UTC |
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HMDB ID | HMDB0060867 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Phenytoin methylcatechol |
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Description | Phenytoin methylcatechol belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. Phenytoin acts to suppress the abnormal brain activity seen in seizure by reducing electrical conductance among brain cells by stabilizing the inactive state of voltage-gated sodium channels. Phenytoin methylcatechol is an extremely weak basic (essentially neutral) compound (based on its pKa). phenytoin methylcatechol and S-adenosylhomocysteine can be biosynthesized from phenytoin catechol and S-adenosylmethionine; which is mediated by the enzyme catechol O-methyltransferase. In humans, phenytoin methylcatechol is involved in the metabolic disorder called the phenytoin (antiarrhythmic) action pathway. It is sometimes considered a class 1b antiarrhythmic. Aside from seizures, it is an option in the treatment of trigeminal neuralgia in the event that carbamazepine or other first-line treatment seems inappropriate. Phenytoin sodium is a commonly used antiepileptic. Phenytoin methylcatechol is a metabolite of phenytoin. |
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Structure | OC1=C(C=O)C=C(C=C1)C1(NC(=O)NC1=O)C1=CC=CC=C1 InChI=1S/C16H12N2O4/c19-9-10-8-12(6-7-13(10)20)16(11-4-2-1-3-5-11)14(21)17-15(22)18-16/h1-9,20H,(H2,17,18,21,22) |
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Synonyms | Not Available |
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Chemical Formula | C16H12N2O4 |
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Average Molecular Weight | 296.2775 |
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Monoisotopic Molecular Weight | 296.079706882 |
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IUPAC Name | 5-(2,5-dioxo-4-phenylimidazolidin-4-yl)-2-hydroxybenzaldehyde |
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Traditional Name | 5-(2,5-dioxo-4-phenylimidazolidin-4-yl)-2-hydroxybenzaldehyde |
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CAS Registry Number | Not Available |
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SMILES | OC1=C(C=O)C=C(C=C1)C1(NC(=O)NC1=O)C1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C16H12N2O4/c19-9-10-8-12(6-7-13(10)20)16(11-4-2-1-3-5-11)14(21)17-15(22)18-16/h1-9,20H,(H2,17,18,21,22) |
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InChI Key | IVKHYRHKQDQYFC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Azolidines |
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Sub Class | Imidazolidines |
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Direct Parent | Phenylhydantoins |
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Alternative Parents | |
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Substituents | - Diphenylmethane
- 5-phenylhydantoin
- Phenylimidazolidine
- Alpha-amino acid or derivatives
- Hydroxybenzaldehyde
- Benzaldehyde
- Benzoyl
- 5-monosubstituted hydantoin
- 1-hydroxy-2-unsubstituted benzenoid
- N-acyl urea
- Phenol
- Aryl-aldehyde
- Ureide
- Monocyclic benzene moiety
- Benzenoid
- Dicarboximide
- Vinylogous acid
- Carbonic acid derivative
- Urea
- Azacycle
- Carboxylic acid derivative
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Aldehyde
- Carbonyl group
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen 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 | |
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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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Phenytoin methylcatechol,1TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)NC2=O)C=C1C=O | 3047.8 | Semi standard non polar | 33892256 | Phenytoin methylcatechol,1TMS,isomer #2 | C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=C(O)C(C=O)=C1 | 2856.3 | Semi standard non polar | 33892256 | Phenytoin methylcatechol,1TMS,isomer #3 | C[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O | 2850.2 | Semi standard non polar | 33892256 | Phenytoin methylcatechol,2TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)C=C1C=O | 2895.7 | Semi standard non polar | 33892256 | Phenytoin methylcatechol,2TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)C=C1C=O | 2842.7 | Standard non polar | 33892256 | Phenytoin methylcatechol,2TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C)C=C1C=O | 4055.2 | Standard polar | 33892256 | Phenytoin methylcatechol,2TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)C=C1C=O | 2931.7 | Semi standard non polar | 33892256 | Phenytoin methylcatechol,2TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)C=C1C=O | 2802.6 | Standard non polar | 33892256 | Phenytoin methylcatechol,2TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C)C2=O)C=C1C=O | 3862.0 | Standard polar | 33892256 | Phenytoin methylcatechol,2TMS,isomer #3 | C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O | 2537.3 | Semi standard non polar | 33892256 | Phenytoin methylcatechol,2TMS,isomer #3 | C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O | 2811.4 | Standard non polar | 33892256 | Phenytoin methylcatechol,2TMS,isomer #3 | C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O | 3555.3 | Standard polar | 33892256 | Phenytoin methylcatechol,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)C=C1C=O | 2643.0 | Semi standard non polar | 33892256 | Phenytoin methylcatechol,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)C=C1C=O | 2806.4 | Standard non polar | 33892256 | Phenytoin methylcatechol,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)C=C1C=O | 3320.4 | Standard polar | 33892256 | Phenytoin methylcatechol,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)NC2=O)C=C1C=O | 3308.2 | Semi standard non polar | 33892256 | Phenytoin methylcatechol,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=C(O)C(C=O)=C1 | 3153.7 | Semi standard non polar | 33892256 | Phenytoin methylcatechol,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O | 3175.1 | Semi standard non polar | 33892256 | Phenytoin methylcatechol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)C=C1C=O | 3428.0 | Semi standard non polar | 33892256 | Phenytoin methylcatechol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)C=C1C=O | 3241.8 | Standard non polar | 33892256 | Phenytoin methylcatechol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)NC(=O)N2[Si](C)(C)C(C)(C)C)C=C1C=O | 4021.1 | Standard polar | 33892256 | Phenytoin methylcatechol,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1C=O | 3452.0 | Semi standard non polar | 33892256 | Phenytoin methylcatechol,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1C=O | 3219.7 | Standard non polar | 33892256 | Phenytoin methylcatechol,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)NC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1C=O | 3924.4 | Standard polar | 33892256 | Phenytoin methylcatechol,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O | 3101.0 | Semi standard non polar | 33892256 | Phenytoin methylcatechol,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O | 3228.0 | Standard non polar | 33892256 | Phenytoin methylcatechol,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=C(O)C(C=O)=C2)C1=O | 3576.2 | Standard polar | 33892256 | Phenytoin methylcatechol,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)C=C1C=O | 3396.3 | Semi standard non polar | 33892256 | Phenytoin methylcatechol,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)C=C1C=O | 3415.2 | Standard non polar | 33892256 | Phenytoin methylcatechol,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)C=C1C=O | 3454.5 | 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 - Phenytoin methylcatechol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0v00-0960000000-bda3f49ea38924bfc1bd | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Phenytoin methylcatechol GC-MS (1 TMS) - 70eV, Positive | splash10-00b9-2893000000-5cfff8f48221b1f4f758 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Phenytoin methylcatechol 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 - Phenytoin methylcatechol 10V, Positive-QTOF | splash10-004j-0090000000-89e8077f74c6891cd4ac | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 20V, Positive-QTOF | splash10-004i-0190000000-ca80aa4f8cf0ad545b2a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 40V, Positive-QTOF | splash10-05fr-0940000000-00d5e69231c0bf46dd19 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 10V, Negative-QTOF | splash10-0002-0090000000-90d05301f1b239e4a5e6 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 20V, Negative-QTOF | splash10-0fxw-3190000000-281651580bc4a38bea5e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 40V, Negative-QTOF | splash10-0udm-4920000000-05f9311da7a5c3b02614 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 10V, Positive-QTOF | splash10-0002-0090000000-0c95764557d19b6513e0 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 20V, Positive-QTOF | splash10-004i-0390000000-885fed503b67c278c72a | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 40V, Positive-QTOF | splash10-00fr-1790000000-54ce2dcc4b90f291fa63 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 10V, Negative-QTOF | splash10-0002-0090000000-8c0a37cb17704175d425 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 20V, Negative-QTOF | splash10-0007-9370000000-7802a8e4e264c3c4fc3a | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenytoin methylcatechol 40V, Negative-QTOF | splash10-0006-9500000000-ccb684269530162f2746 | 2021-10-12 | Wishart Lab | View Spectrum |
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