Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2017-08-01 02:12:29 UTC |
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Update Date | 2022-09-22 18:34:30 UTC |
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HMDB ID | HMDB0094651 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Pyroglutamylvaline |
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Description | pyroglutamylvaline, also known as pyro-glu-val or 5-oxoprolylvaline, 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. pyroglutamylvaline is an extremely weak basic (essentially neutral) compound (based on its pKa). A dipeptide obtained by formal condensation of the carboxy group of pyroglutamic acid with the amino group of valine. |
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Structure | CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1)C(O)=O InChI=1S/C10H16N2O4/c1-5(2)8(10(15)16)12-9(14)6-3-4-7(13)11-6/h5-6,8H,3-4H2,1-2H3,(H,11,13)(H,12,14)(H,15,16)/t6-,8-/m0/s1 |
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Synonyms | Value | Source |
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5-Oxoprolylvaline | ChEBI | L-Pyroglutamyl-L-valine | ChEBI | p-Glu-val | ChEBI | Pyro-glu-val | ChEBI | Pyroglutamyl valine | ChEBI | N-(5-Oxo-L-prolyl)-L-valine | HMDB | N-(5-Oxo-L-prolyl)-valine | HMDB | 5-Oxo-L-prolyl-L-valine | HMDB | L-Pyrrolidonecarboxyl-L-valine | HMDB | Pyrrolidin-2-one-5-carbonylvaline | HMDB | Pyroglutamylvaline | HMDB |
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Chemical Formula | C10H16N2O4 |
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Average Molecular Weight | 228.248 |
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Monoisotopic Molecular Weight | 228.111007003 |
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IUPAC Name | (2S)-3-methyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanoic acid |
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Traditional Name | (2S)-3-methyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanoic acid |
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CAS Registry Number | 21282-10-0 |
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SMILES | CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1)C(O)=O |
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InChI Identifier | InChI=1S/C10H16N2O4/c1-5(2)8(10(15)16)12-9(14)6-3-4-7(13)11-6/h5-6,8H,3-4H2,1-2H3,(H,11,13)(H,12,14)(H,15,16)/t6-,8-/m0/s1 |
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InChI Key | DTSWLLBBGHRXQH-XPUUQOCRSA-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
- Valine or derivatives
- Proline or derivatives
- 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 or derivatives
- Pyrrolidine carboxylic acid or derivatives
- Pyrrolidine-2-carboxamide
- Branched fatty acid
- Heterocyclic fatty acid
- Methyl-branched fatty acid
- Fatty acyl
- Fatty acid
- Pyrrolidone
- 2-pyrrolidone
- Pyrrolidine
- Secondary carboxylic acid amide
- Carboxamide group
- Lactam
- Organoheterocyclic compound
- Carboxylic acid
- Azacycle
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organonitrogen compound
- Organooxygen compound
- Carbonyl group
- Organic oxygen compound
- Organopnictogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic 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 | Not Available |
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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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Pyroglutamylvaline,1TMS,isomer #1 | CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1)C(=O)O[Si](C)(C)C | 2019.7 | Semi standard non polar | 33892256 | Pyroglutamylvaline,1TMS,isomer #2 | CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C | 1966.5 | Semi standard non polar | 33892256 | Pyroglutamylvaline,1TMS,isomer #3 | CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)C(=O)O | 1963.6 | Semi standard non polar | 33892256 | Pyroglutamylvaline,2TMS,isomer #1 | CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C | 2008.6 | Semi standard non polar | 33892256 | Pyroglutamylvaline,2TMS,isomer #1 | CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C | 2006.9 | Standard non polar | 33892256 | Pyroglutamylvaline,2TMS,isomer #1 | CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C | 3048.4 | Standard polar | 33892256 | Pyroglutamylvaline,2TMS,isomer #2 | CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1980.0 | Semi standard non polar | 33892256 | Pyroglutamylvaline,2TMS,isomer #2 | CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2017.9 | Standard non polar | 33892256 | Pyroglutamylvaline,2TMS,isomer #2 | CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2785.2 | Standard polar | 33892256 | Pyroglutamylvaline,2TMS,isomer #3 | CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)[Si](C)(C)C | 1895.7 | Semi standard non polar | 33892256 | Pyroglutamylvaline,2TMS,isomer #3 | CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)[Si](C)(C)C | 2016.5 | Standard non polar | 33892256 | Pyroglutamylvaline,2TMS,isomer #3 | CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)[Si](C)(C)C | 2665.4 | Standard polar | 33892256 | Pyroglutamylvaline,3TMS,isomer #1 | CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)[Si](C)(C)C | 1960.5 | Semi standard non polar | 33892256 | Pyroglutamylvaline,3TMS,isomer #1 | CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)[Si](C)(C)C | 2097.4 | Standard non polar | 33892256 | Pyroglutamylvaline,3TMS,isomer #1 | CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C)[Si](C)(C)C | 2352.6 | Standard polar | 33892256 | Pyroglutamylvaline,1TBDMS,isomer #1 | CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1)C(=O)O[Si](C)(C)C(C)(C)C | 2246.6 | Semi standard non polar | 33892256 | Pyroglutamylvaline,1TBDMS,isomer #2 | CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C(C)(C)C | 2216.2 | Semi standard non polar | 33892256 | Pyroglutamylvaline,1TBDMS,isomer #3 | CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)C(=O)O | 2198.0 | Semi standard non polar | 33892256 | Pyroglutamylvaline,2TBDMS,isomer #1 | CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C(C)(C)C | 2452.1 | Semi standard non polar | 33892256 | Pyroglutamylvaline,2TBDMS,isomer #1 | CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C(C)(C)C | 2422.6 | Standard non polar | 33892256 | Pyroglutamylvaline,2TBDMS,isomer #1 | CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1)[Si](C)(C)C(C)(C)C | 3031.4 | Standard polar | 33892256 | Pyroglutamylvaline,2TBDMS,isomer #2 | CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2434.7 | Semi standard non polar | 33892256 | Pyroglutamylvaline,2TBDMS,isomer #2 | CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2444.4 | Standard non polar | 33892256 | Pyroglutamylvaline,2TBDMS,isomer #2 | CC(C)[C@H](NC(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2816.0 | Standard polar | 33892256 | Pyroglutamylvaline,2TBDMS,isomer #3 | CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2382.2 | Semi standard non polar | 33892256 | Pyroglutamylvaline,2TBDMS,isomer #3 | CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2425.5 | Standard non polar | 33892256 | Pyroglutamylvaline,2TBDMS,isomer #3 | CC(C)[C@@H](C(=O)O)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2755.2 | Standard polar | 33892256 | Pyroglutamylvaline,3TBDMS,isomer #1 | CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2640.3 | Semi standard non polar | 33892256 | Pyroglutamylvaline,3TBDMS,isomer #1 | CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2678.9 | Standard non polar | 33892256 | Pyroglutamylvaline,3TBDMS,isomer #1 | CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1CCC(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2683.9 | Standard polar | 33892256 |
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Spectra |
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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 - Pyroglutamylvaline GC-MS (Non-derivatized) - 70eV, Positive | splash10-001l-9200000000-9db84667672f6a505f45 | 2017-09-14 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Pyroglutamylvaline GC-MS (3 TMS) - 70eV, Positive | splash10-0a6r-6932300000-013d4bddc38160ccb236 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Pyroglutamylvaline 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 - Pyroglutamylvaline 10V, Negative-QTOF | splash10-0059-0490000000-c6f69f147e19e6d90c77 | 2017-09-14 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 20V, Negative-QTOF | splash10-07yi-3950000000-bce5cc05c920b36b4fdc | 2017-09-14 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 40V, Negative-QTOF | splash10-00kf-9200000000-add672a776175abea58c | 2017-09-14 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 10V, Positive-QTOF | splash10-02cr-3690000000-3bd2cf60b4176dafefff | 2017-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 20V, Positive-QTOF | splash10-0089-9300000000-e0b20d2fcc43e6cb45e5 | 2017-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 40V, Positive-QTOF | splash10-05gi-9100000000-987567c667aa950bbc60 | 2017-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 10V, Positive-QTOF | splash10-03gi-4980000000-ca77ede8584ae5157107 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 20V, Positive-QTOF | splash10-001i-9100000000-9b083dd619db45b224bd | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 40V, Positive-QTOF | splash10-001i-9300000000-bc014979775b6ec4a63e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 10V, Negative-QTOF | splash10-004i-0090000000-c8a3f11499151a4d3a87 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 20V, Negative-QTOF | splash10-004i-6900000000-fd52a1fe405d3f84c962 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyroglutamylvaline 40V, Negative-QTOF | splash10-0006-9100000000-544465ead7a4ca8f9b9b | 2021-09-22 | 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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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Cancer patients undergoing total body irradiation | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Cancer patients undergoing total body irradiation | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 152416 |
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PDB ID | Not Available |
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ChEBI ID | 132991 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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