Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-06 15:16:50 UTC |
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Update Date | 2022-03-07 02:51:43 UTC |
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HMDB ID | HMDB0014722 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Enalapril |
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Description | Enalapril is a prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly metabolized in the liver to enalaprilat following oral administration. Enalaprilat is a potent, competitive inhibitor of ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Enalapril may be used to treat essential or renovascular hypertension and symptomatic congestive heart failure. |
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Structure | CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O InChI=1S/C20H28N2O5/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25)/t14-,16-,17-/m0/s1 |
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Synonyms | Value | Source |
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(S)-1-(N-(1-(Ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-L-proline | ChEBI | (S)-1-{(S)-2-[1-((S)-ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylic acid | ChEBI | 1-(N-((S)-1-Carboxy-3-phenylpropyl)-L-alanyl)-L-proline 1'-ethyl ester | ChEBI | Analapril | ChEBI | Enalaprila | ChEBI | Enalaprilum | ChEBI | (S)-1-{(S)-2-[1-((S)-ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylate | Generator | Enalapril maleate | HMDB | Enalaprilat | HMDB | Renitek | HMDB | Maleate, enalapril | HMDB | Renitec | HMDB |
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Chemical Formula | C20H28N2O5 |
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Average Molecular Weight | 376.4467 |
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Monoisotopic Molecular Weight | 376.199822016 |
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IUPAC Name | (2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid |
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Traditional Name | enalapril |
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CAS Registry Number | 75847-73-3 |
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SMILES | CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O |
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InChI Identifier | InChI=1S/C20H28N2O5/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25)/t14-,16-,17-/m0/s1 |
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InChI Key | GBXSMTUPTTWBMN-XIRDDKMYSA-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
- N-acyl-alpha amino acid or derivatives
- N-acyl-alpha-amino acid
- N-acyl-l-alpha-amino acid
- Proline or derivatives
- Alpha-amino acid ester
- Alpha-amino acid amide
- Alpha-amino acid or derivatives
- Pyrrolidine carboxylic acid or derivatives
- Pyrrolidine carboxylic acid
- N-acylpyrrolidine
- Fatty acid ester
- Aralkylamine
- Dicarboxylic acid or derivatives
- Fatty acyl
- Benzenoid
- Monocyclic benzene moiety
- Pyrrolidine
- Tertiary carboxylic acid amide
- Amino acid or derivatives
- Carboxamide group
- Carboxylic acid ester
- Amino acid
- Azacycle
- Secondary aliphatic amine
- Carboxylic acid
- Organoheterocyclic compound
- Secondary amine
- Hydrocarbon derivative
- Amine
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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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 | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 143 - 144.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.21 g/L | Not Available | LogP | 2.1 | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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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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Enalapril,1TMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C | 2851.6 | Semi standard non polar | 33892256 | Enalapril,1TMS,isomer #2 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C | 2822.5 | Semi standard non polar | 33892256 | Enalapril,2TMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)[Si](C)(C)C | 2827.9 | Semi standard non polar | 33892256 | Enalapril,2TMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)[Si](C)(C)C | 2778.1 | Standard non polar | 33892256 | Enalapril,2TMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)[Si](C)(C)C | 3564.9 | Standard polar | 33892256 | Enalapril,1TBDMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 3073.1 | Semi standard non polar | 33892256 | Enalapril,1TBDMS,isomer #2 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C | 3080.9 | Semi standard non polar | 33892256 | Enalapril,2TBDMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3306.9 | Semi standard non polar | 33892256 | Enalapril,2TBDMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3165.0 | Standard non polar | 33892256 | Enalapril,2TBDMS,isomer #1 | CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3724.7 | 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 - Enalapril GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udi-4329000000-0ccc991d6f82c8023381 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Enalapril GC-MS (1 TMS) - 70eV, Positive | splash10-004i-4139100000-e739549506767919633f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Enalapril 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - Enalapril LC-ESI-QFT , negative-QTOF | splash10-004i-0809000000-0e192d1573028e60641c | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Enalapril LC-ESI-QFT , positive-QTOF | splash10-003r-1859000000-8b202071e8860792a59f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Enalapril 40V, Positive-QTOF | splash10-02ai-0920000000-a43751d817c0f98bc5b6 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Enalapril 30V, Positive-QTOF | splash10-001i-0591000000-1e07b9fe2aaace58211e | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Enalapril 10V, Positive-QTOF | splash10-004i-0009000000-e737fba7359f446dfefa | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Enalapril 20V, Positive-QTOF | splash10-001i-0096000000-f899a068af97bea539ac | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Enalapril 35V, Positive-QTOF | splash10-003r-1859000000-a8e3ac5e4d170e35772c | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Enalapril 50V, Positive-QTOF | splash10-02t9-0900000000-0f67eb2d8b2e7821015c | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Enalapril 30V, Positive-QTOF | splash10-001i-0591000000-9695db764f080d9ae857 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Enalapril 35V, Negative-QTOF | splash10-004i-0809000000-0e192d1573028e60641c | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Enalapril 20V, Positive-QTOF | splash10-001i-0095000000-f899a068af97bea539ac | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Enalapril 10V, Positive-QTOF | splash10-0059-0239000000-feb01e2c02b331eea247 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Enalapril 20V, Positive-QTOF | splash10-001i-5893000000-141cda4f7233f214c8dc | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Enalapril 40V, Positive-QTOF | splash10-0296-6910000000-189f3dddcaf5004e885f | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Enalapril 10V, Negative-QTOF | splash10-004i-1019000000-ae65ecb00dc3ab6e3701 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Enalapril 20V, Negative-QTOF | splash10-03gs-5559000000-d8643ca2f50322b85449 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Enalapril 40V, Negative-QTOF | splash10-01ot-8921000000-5383f963d934648ca615 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Enalapril 10V, Positive-QTOF | splash10-004i-0129000000-f7705eec0d29efd988c2 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Enalapril 20V, Positive-QTOF | splash10-01sl-3944000000-04f3a7836b5b57821688 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Enalapril 40V, Positive-QTOF | splash10-0903-3900000000-cb0bc55987e5b9460684 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Enalapril 10V, Negative-QTOF | splash10-004i-0109000000-ec7a71512e90259b372c | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Enalapril 20V, Negative-QTOF | splash10-03di-3913000000-89b99fdc1118ca034b01 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Enalapril 40V, Negative-QTOF | splash10-03di-3900000000-294402e5b0098d7dc45e | 2021-10-11 | Wishart Lab | View Spectrum |
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