Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 21:02:39 UTC |
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Update Date | 2021-09-14 15:37:04 UTC |
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HMDB ID | HMDB0028827 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Glutamylproline |
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Description | Glutamylproline is a dipeptide composed of glutamate and proline, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Glutamylproline is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. |
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Structure | N[C@@H](CCC(O)=O)C(=O)N1CCC[C@H]1C(O)=O InChI=1S/C10H16N2O5/c11-6(3-4-8(13)14)9(15)12-5-1-2-7(12)10(16)17/h6-7H,1-5,11H2,(H,13,14)(H,16,17)/t6-,7-/m0/s1 |
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Synonyms | Value | Source |
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E-P | ChEBI | EP | ChEBI | L-Glu-L-pro | ChEBI | e-p Dipeptide | HMDB | EP dipeptide | HMDB | Glu-pro | HMDB | Glutamate proline dipeptide | HMDB | Glutamate-proline dipeptide | HMDB | L-Glutamyl-L-proline | HMDB | Α-glu-pro | HMDB | Α-L-glu-L-pro | HMDB | Α-glutamylproline | HMDB | Α-L-glutamyl-L-proline | HMDB | L-Α-glutamyl-L-proline | HMDB | alpha-Glu-pro | HMDB | alpha-L-Glu-L-pro | HMDB | alpha-Glutamylproline | HMDB | alpha-L-Glutamyl-L-proline | HMDB | L-alpha-Glutamyl-L-proline | HMDB | Glutamyl-proline | HMDB | Glutamic acid proline dipeptide | HMDB | Glutamic acid-proline dipeptide | HMDB | Glutamylproline | HMDB |
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Chemical Formula | C10H16N2O5 |
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Average Molecular Weight | 244.247 |
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Monoisotopic Molecular Weight | 244.105921623 |
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IUPAC Name | (2S)-1-[(2S)-2-amino-4-carboxybutanoyl]pyrrolidine-2-carboxylic acid |
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Traditional Name | (2S)-1-[(2S)-2-amino-4-carboxybutanoyl]pyrrolidine-2-carboxylic acid |
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CAS Registry Number | 41745-47-5 |
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SMILES | N[C@@H](CCC(O)=O)C(=O)N1CCC[C@H]1C(O)=O |
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InChI Identifier | InChI=1S/C10H16N2O5/c11-6(3-4-8(13)14)9(15)12-5-1-2-7(12)10(16)17/h6-7H,1-5,11H2,(H,13,14)(H,16,17)/t6-,7-/m0/s1 |
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InChI Key | YBTCBQBIJKGSJP-BQBZGAKWSA-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
- Proline or derivatives
- N-acyl-alpha amino acid or derivatives
- N-acyl-alpha-amino acid
- N-acyl-l-alpha-amino acid
- Alpha-amino acid amide
- Alpha-amino acid or derivatives
- N-acylpyrrolidine
- Pyrrolidine carboxylic acid
- Pyrrolidine carboxylic acid or derivatives
- Amino fatty acid
- Heterocyclic fatty acid
- Dicarboxylic acid or derivatives
- Fatty acyl
- Fatty acid
- Pyrrolidine
- Tertiary carboxylic acid amide
- Amino acid
- Amino acid or derivatives
- Carboxamide group
- Carboxylic acid
- Azacycle
- Organoheterocyclic compound
- Primary aliphatic amine
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organopnictogen compound
- Amine
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic 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 | Not Available |
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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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | -3.73 | Extrapolated |
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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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Glutamylproline,1TMS,isomer #1 | C[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O | 2218.4 | Semi standard non polar | 33892256 | Glutamylproline,1TMS,isomer #2 | C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CCC(=O)O | 2192.8 | Semi standard non polar | 33892256 | Glutamylproline,1TMS,isomer #3 | C[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)O | 2246.9 | Semi standard non polar | 33892256 | Glutamylproline,2TMS,isomer #1 | C[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C | 2231.2 | Semi standard non polar | 33892256 | Glutamylproline,2TMS,isomer #2 | C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O | 2262.2 | Semi standard non polar | 33892256 | Glutamylproline,2TMS,isomer #3 | C[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C | 2245.9 | Semi standard non polar | 33892256 | Glutamylproline,2TMS,isomer #4 | C[Si](C)(C)N([C@@H](CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C | 2368.2 | Semi standard non polar | 33892256 | Glutamylproline,3TMS,isomer #1 | C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C | 2270.1 | Semi standard non polar | 33892256 | Glutamylproline,3TMS,isomer #1 | C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C | 2336.0 | Standard non polar | 33892256 | Glutamylproline,3TMS,isomer #2 | C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 2388.9 | Semi standard non polar | 33892256 | Glutamylproline,3TMS,isomer #2 | C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 2377.1 | Standard non polar | 33892256 | Glutamylproline,3TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 2387.3 | Semi standard non polar | 33892256 | Glutamylproline,3TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 2364.9 | Standard non polar | 33892256 | Glutamylproline,4TMS,isomer #1 | C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 2441.6 | Semi standard non polar | 33892256 | Glutamylproline,4TMS,isomer #1 | C[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 2407.4 | Standard non polar | 33892256 | Glutamylproline,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O | 2478.0 | Semi standard non polar | 33892256 | Glutamylproline,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CCC(=O)O | 2448.3 | Semi standard non polar | 33892256 | Glutamylproline,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)O | 2494.5 | Semi standard non polar | 33892256 | Glutamylproline,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 2692.8 | Semi standard non polar | 33892256 | Glutamylproline,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O | 2747.3 | Semi standard non polar | 33892256 | Glutamylproline,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 2736.5 | Semi standard non polar | 33892256 | Glutamylproline,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N([C@@H](CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C | 2822.3 | Semi standard non polar | 33892256 | Glutamylproline,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 2955.4 | Semi standard non polar | 33892256 | Glutamylproline,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 2877.1 | Standard non polar | 33892256 | Glutamylproline,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3089.8 | Semi standard non polar | 33892256 | Glutamylproline,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2937.6 | Standard non polar | 33892256 | Glutamylproline,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3066.2 | Semi standard non polar | 33892256 | Glutamylproline,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2901.5 | Standard non polar | 33892256 | Glutamylproline,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3312.0 | Semi standard non polar | 33892256 | Glutamylproline,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3113.1 | Standard non 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 - Glutamylproline 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 - Glutamylproline 10V, Positive-QTOF | splash10-004j-0290000000-d16857feda5a4823de9d | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamylproline 20V, Positive-QTOF | splash10-0fa2-6940000000-b7f91157a68d9fb1dd99 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamylproline 40V, Positive-QTOF | splash10-0aou-9200000000-73ff64e7d2a8a35ac556 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamylproline 10V, Negative-QTOF | splash10-0007-0690000000-f834be1f54a737d5176f | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamylproline 20V, Negative-QTOF | splash10-01rt-2930000000-7869ef082678b0019a02 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamylproline 40V, Negative-QTOF | splash10-08mi-9800000000-e8e5c97f369195c093fb | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamylproline 10V, Positive-QTOF | splash10-0002-0290000000-95e0403d7d0aba1af04c | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamylproline 20V, Positive-QTOF | splash10-00lr-9510000000-2193ae1f63be955d3510 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamylproline 40V, Positive-QTOF | splash10-05fr-9000000000-69c5865049770eec3514 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamylproline 10V, Negative-QTOF | splash10-0006-0390000000-9e627bb1f7ff8232af64 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamylproline 20V, Negative-QTOF | splash10-03di-4900000000-13c94e33e653daf7ce9c | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamylproline 40V, Negative-QTOF | splash10-03dj-9500000000-e8ef6624a8b520d9c1bc | 2021-10-11 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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