Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-06-15 17:03:38 UTC |
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Update Date | 2021-09-14 15:40:14 UTC |
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HMDB ID | HMDB0060579 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ramiprilat |
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Description | Ramiprilat, also known as ramiprilic acid, 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. Ramiprilat is a very strong basic compound (based on its pKa). In humans, ramiprilat is involved in ramipril metabolism pathway. Ramiprilat is a metabolite of ramipril. |
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Structure | C[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1[C@H]2CCC[C@H]2C[C@H]1C(O)=O InChI=1S/C21H28N2O5/c1-13(22-16(20(25)26)11-10-14-6-3-2-4-7-14)19(24)23-17-9-5-8-15(17)12-18(23)21(27)28/h2-4,6-7,13,15-18,22H,5,8-12H2,1H3,(H,25,26)(H,27,28)/t13-,15-,16-,17-,18-/m0/s1 |
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Synonyms | Value | Source |
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Ramiprilate | ChEBI | Ramiprilatum | ChEBI | Ramiprilic acid | Generator |
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Chemical Formula | C21H28N2O5 |
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Average Molecular Weight | 388.4574 |
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Monoisotopic Molecular Weight | 388.199822016 |
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IUPAC Name | (2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid |
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Traditional Name | (2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | C[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1[C@H]2CCC[C@H]2C[C@H]1C(O)=O |
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InChI Identifier | InChI=1S/C21H28N2O5/c1-13(22-16(20(25)26)11-10-14-6-3-2-4-7-14)19(24)23-17-9-5-8-15(17)12-18(23)21(27)28/h2-4,6-7,13,15-18,22H,5,8-12H2,1H3,(H,25,26)(H,27,28)/t13-,15-,16-,17-,18-/m0/s1 |
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InChI Key | KEDYTOTWMPBSLG-HILJTLORSA-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
- N-acyl-l-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- Alpha-amino acid
- Alpha-amino acid or derivatives
- L-alpha-amino acid
- Pyrrolidine carboxylic acid or derivatives
- Pyrrolidine carboxylic acid
- N-acylpyrrolidine
- Aralkylamine
- Monocyclic benzene moiety
- Dicarboxylic acid or derivatives
- Benzenoid
- Tertiary carboxylic acid amide
- Pyrrolidine
- Amino acid or derivatives
- Carboxamide group
- Amino acid
- Organoheterocyclic compound
- Azacycle
- Secondary aliphatic amine
- Carboxylic acid
- Secondary amine
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Organic nitrogen compound
- Amine
- Organonitrogen compound
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | 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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Ramiprilat,1TMS,isomer #1 | C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@@H]21 | 3046.2 | Semi standard non polar | 33892256 | Ramiprilat,1TMS,isomer #2 | C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCC[C@@H]21 | 3073.5 | Semi standard non polar | 33892256 | Ramiprilat,1TMS,isomer #3 | C[C@@H](C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C | 3050.3 | Semi standard non polar | 33892256 | Ramiprilat,2TMS,isomer #1 | C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCC[C@@H]21 | 3035.6 | Semi standard non polar | 33892256 | Ramiprilat,2TMS,isomer #2 | C[C@@H](C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 3020.2 | Semi standard non polar | 33892256 | Ramiprilat,2TMS,isomer #3 | C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C | 3023.7 | Semi standard non polar | 33892256 | Ramiprilat,3TMS,isomer #1 | C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 3038.0 | Semi standard non polar | 33892256 | Ramiprilat,3TMS,isomer #1 | C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 3015.3 | Standard non polar | 33892256 | Ramiprilat,3TMS,isomer #1 | C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 3781.8 | Standard polar | 33892256 | Ramiprilat,1TBDMS,isomer #1 | C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@@H]21 | 3294.4 | Semi standard non polar | 33892256 | Ramiprilat,1TBDMS,isomer #2 | C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCC[C@@H]21 | 3320.8 | Semi standard non polar | 33892256 | Ramiprilat,1TBDMS,isomer #3 | C[C@@H](C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C | 3309.7 | Semi standard non polar | 33892256 | Ramiprilat,2TBDMS,isomer #1 | C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCC[C@@H]21 | 3505.8 | Semi standard non polar | 33892256 | Ramiprilat,2TBDMS,isomer #2 | C[C@@H](C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3527.6 | Semi standard non polar | 33892256 | Ramiprilat,2TBDMS,isomer #3 | C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C | 3540.5 | Semi standard non polar | 33892256 | Ramiprilat,3TBDMS,isomer #1 | C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3732.7 | Semi standard non polar | 33892256 | Ramiprilat,3TBDMS,isomer #1 | C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3608.3 | Standard non polar | 33892256 | Ramiprilat,3TBDMS,isomer #1 | C[C@@H](C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCC[C@@H]21)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3996.5 | 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 - Ramiprilat GC-MS (Non-derivatized) - 70eV, Positive | splash10-00lu-9323000000-940b006da9cc06b5fc6f | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ramiprilat GC-MS (2 TMS) - 70eV, Positive | splash10-01bc-9141420000-7b066a10b282ca037203 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ramiprilat 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 - Ramiprilat 10V, Positive-QTOF | splash10-05g3-0129000000-f89fdd99fb3669abd143 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ramiprilat 20V, Positive-QTOF | splash10-0btc-1953000000-dfe1ab2c8f9ea43b55d9 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ramiprilat 40V, Positive-QTOF | splash10-08fu-3910000000-087ef0850acdcd1f8f50 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ramiprilat 10V, Negative-QTOF | splash10-000l-0009000000-b5af622fa6177501b3e1 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ramiprilat 20V, Negative-QTOF | splash10-0frg-0649000000-fd1f4001ead8c583d80b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ramiprilat 40V, Negative-QTOF | splash10-11p0-1900000000-0b5f7e804738b6a5e86d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ramiprilat 10V, Negative-QTOF | splash10-000i-0009000000-e43abe228ffb93ba9251 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ramiprilat 20V, Negative-QTOF | splash10-01q3-1946000000-d8f9fa67c21f69549090 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ramiprilat 40V, Negative-QTOF | splash10-0udi-3910000000-7248ba42f7d521ea892f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ramiprilat 10V, Positive-QTOF | splash10-000i-0009000000-8ffcb38a7676a96d10df | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ramiprilat 20V, Positive-QTOF | splash10-01p6-1935000000-2b66e2a4796a046c7eff | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ramiprilat 40V, Positive-QTOF | splash10-066r-1900000000-13f50f12fb869bbe2aaa | 2021-10-12 | 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) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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General References | - Gupta VK, Jain R, Lukram O, Agarwal S, Dwivedi A: Simultaneous determination of ramipril, ramiprilat and telmisartan in human plasma using liquid chromatography tandem mass spectrometry. Talanta. 2011 Jan 15;83(3):709-16. doi: 10.1016/j.talanta.2010.10.011. Epub 2010 Nov 18. [PubMed:21147310 ]
- Efsen E, Saermark T, Hansen A, Bruun E, Brynskov J: Ramiprilate inhibits functional matrix metalloproteinase activity in Crohn's disease fistulas. Basic Clin Pharmacol Toxicol. 2011 Sep;109(3):208-16. doi: 10.1111/j.1742-7843.2011.00713.x. Epub 2011 Jun 3. [PubMed:21535409 ]
- Potier L, Waeckel L, Vincent MP, Chollet C, Gobeil F Jr, Marre M, Bruneval P, Richer C, Roussel R, Alhenc-Gelas F, Bouby N: Selective kinin receptor agonists as cardioprotective agents in myocardial ischemia and diabetes. J Pharmacol Exp Ther. 2013 Jul;346(1):23-30. doi: 10.1124/jpet.113.203927. Epub 2013 Apr 16. [PubMed:23591995 ]
- van Griensven JM, Schoemaker RC, Cohen AF, Luus HG, Seibert-Grafe M, Rothig HJ: Pharmacokinetics, pharmacodynamics and bioavailability of the ACE inhibitor ramipril. Eur J Clin Pharmacol. 1995;47(6):513-8. [PubMed:7768254 ]
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