Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2014-06-23 10:26:39 UTC |
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Update Date | 2021-09-14 15:47:06 UTC |
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HMDB ID | HMDB0061720 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Temocapril |
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Description | Temocapril belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Temocapril is a very strong basic compound (based on its pKa). In humans, temocapril is involved in temocapril metabolism pathway. Temocapril can also be used in hemodialysis patients without risk of serious accumulation. When compared with other Angiotensin-converting Enzyme Inhibitors, temocapril's advantages include a rapid onset of action and what research suggests is tighter vascular ACE binding than enalaprilat. ACE inhibitors exert their hemodynamic effect mainly by inhibiting the renin-angiotensin system. Temocaprilat has slightly higher potency than enalaprilat in ACE inhibition isolated from rabbit lung. Temocapril is a prodrug-type angiotensin-I converting enzyme (ACE) inhibitor not approved for use in the United States, but is approved in Japan and South Korea. Temocapril is a prodrug of its active metabolite (and diacid form) temocaprilat which contains a thiazepine ring. They cause mainly vasodilation and mild natriuresis without affecting heart rate and contractility. They also modulate sympathetic nervous system activity and increase prostaglandin synthesis. |
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Structure | CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@@H](CN(CC(O)=O)C1=O)C1=CC=CS1 InChI=1S/C23H28N2O5S2/c1-2-30-23(29)17(11-10-16-7-4-3-5-8-16)24-18-15-32-20(19-9-6-12-31-19)13-25(22(18)28)14-21(26)27/h3-9,12,17-18,20,24H,2,10-11,13-15H2,1H3,(H,26,27)/t17-,18-,20-/m0/s1 |
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Synonyms | Value | Source |
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alpha-((2S,6R)-6-((1S)-1-Ethoxycarbonyl-3-phenylpropyl)amino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepin-4-yl)acetic acid.hcl | HMDB | Temocapril hydrochloride | HMDB |
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Chemical Formula | C23H28N2O5S2 |
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Average Molecular Weight | 476.609 |
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Monoisotopic Molecular Weight | 476.143963396 |
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IUPAC Name | 2-[(2S,6R)-6-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-4-yl]acetic acid |
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Traditional Name | [(2S,6R)-6-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-4-yl]acetic acid |
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CAS Registry Number | Not Available |
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SMILES | CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@@H](CN(CC(O)=O)C1=O)C1=CC=CS1 |
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InChI Identifier | InChI=1S/C23H28N2O5S2/c1-2-30-23(29)17(11-10-16-7-4-3-5-8-16)24-18-15-32-20(19-9-6-12-31-19)13-25(22(18)28)14-21(26)27/h3-9,12,17-18,20,24H,2,10-11,13-15H2,1H3,(H,26,27)/t17-,18-,20-/m0/s1 |
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InChI Key | FIQOFIRCTOWDOW-BJLQDIEVSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Dipeptides |
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Alternative Parents | |
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Substituents | - Alpha-dipeptide
- Alpha-amino acid ester
- Alpha-amino acid or derivatives
- Fatty acid ester
- Aralkylamine
- Monocyclic benzene moiety
- Dicarboxylic acid or derivatives
- Fatty acyl
- Benzenoid
- Tertiary carboxylic acid amide
- Heteroaromatic compound
- Thiophene
- Amino acid or derivatives
- Carboxamide group
- Carboxylic acid ester
- Amino acid
- Lactam
- Secondary amine
- Dialkylthioether
- Organoheterocyclic compound
- Azacycle
- Thioether
- Carboxylic acid
- Secondary aliphatic amine
- Organooxygen compound
- Organic oxide
- Amine
- Organic oxygen compound
- Carbonyl group
- Organopnictogen compound
- Hydrocarbon derivative
- Organic nitrogen compound
- Organonitrogen 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 | Not Available |
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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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Temocapril,1TMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C)C1=O | 3803.4 | Semi standard non polar | 33892256 | Temocapril,1TMS,isomer #2 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O)C1=O)[Si](C)(C)C | 3787.8 | Semi standard non polar | 33892256 | Temocapril,2TMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C)C1=O)[Si](C)(C)C | 3731.9 | Semi standard non polar | 33892256 | Temocapril,2TMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C)C1=O)[Si](C)(C)C | 3516.8 | Standard non polar | 33892256 | Temocapril,2TMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C)C1=O)[Si](C)(C)C | 4878.1 | Standard polar | 33892256 | Temocapril,1TBDMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O | 4037.4 | Semi standard non polar | 33892256 | Temocapril,1TBDMS,isomer #2 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O)C1=O)[Si](C)(C)C(C)(C)C | 3969.8 | Semi standard non polar | 33892256 | Temocapril,2TBDMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C | 4111.3 | Semi standard non polar | 33892256 | Temocapril,2TBDMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C | 3935.0 | Standard non polar | 33892256 | Temocapril,2TBDMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C | 4887.5 | 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 - Temocapril GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udi-3300900000-07c0bde728f9e7cad38a | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Temocapril GC-MS (1 TMS) - 70eV, Positive | splash10-004i-3200910000-b52f07bd2a96ae84f2c2 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Temocapril 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 - Temocapril 10V, Positive-QTOF | splash10-0fmi-2900400000-06af7a1143b5abccba26 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Temocapril 20V, Positive-QTOF | splash10-003u-4362900000-0743a982c0ed45c1affb | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Temocapril 40V, Positive-QTOF | splash10-00du-9300000000-2585084c57fba4d3130f | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Temocapril 10V, Negative-QTOF | splash10-004i-2921400000-ea6d0202eb7b0a7b86b4 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Temocapril 20V, Negative-QTOF | splash10-004i-3953400000-eea8b567695e04163132 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Temocapril 40V, Negative-QTOF | splash10-00ej-9430000000-053ca4271d92f5f59f9d | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Temocapril 10V, Positive-QTOF | splash10-004i-0000900000-55f39eb3922a0c1c8f26 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Temocapril 20V, Positive-QTOF | splash10-004i-0511900000-9d098ce150dd0dd4ee3e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Temocapril 40V, Positive-QTOF | splash10-08ir-0790000000-ef9ad031ca41af6d886f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Temocapril 10V, Negative-QTOF | splash10-004i-0000900000-2c8feffe734e85cdc085 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Temocapril 20V, Negative-QTOF | splash10-00fr-1091400000-22c4735d269f91570e2a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Temocapril 40V, Negative-QTOF | splash10-01zi-1490100000-9fff467ed2cf416a6dce | 2021-09-24 | Wishart Lab | View Spectrum |
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