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 21:03:14 UTC |
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Update Date | 2021-09-14 15:45:52 UTC |
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HMDB ID | HMDB0028979 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Methionyl-Methionine |
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Description | Methionyl-Methionine is a dipeptied compoosed of two methionine residues. It 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. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite. |
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Structure | CSCCC(N)C(=O)NC(CCSC)C(O)=O InChI=1S/C10H20N2O3S2/c1-16-5-3-7(11)9(13)12-8(10(14)15)4-6-17-2/h7-8H,3-6,11H2,1-2H3,(H,12,13)(H,14,15) |
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Synonyms | Value | Source |
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L-Methionyl-L-methionine | HMDB | m-m Dipeptide | HMDB | Met-met | HMDB | Methionine methionine dipeptide | HMDB | Methionine-methionine dipeptide | HMDB | Methionylmethionine | HMDB | MM Dipeptide | HMDB | Methionylmethionine, (L-met-L-met)-isomer | HMDB | DL-Methionylmethionine | HMDB | 2-{[2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoate | HMDB | 2-{[2-amino-1-hydroxy-4-(methylsulphanyl)butylidene]amino}-4-(methylsulphanyl)butanoate | HMDB | 2-{[2-amino-1-hydroxy-4-(methylsulphanyl)butylidene]amino}-4-(methylsulphanyl)butanoic acid | HMDB |
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Chemical Formula | C10H20N2O3S2 |
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Average Molecular Weight | 280.407 |
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Monoisotopic Molecular Weight | 280.091533896 |
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IUPAC Name | 2-[2-amino-4-(methylsulfanyl)butanamido]-4-(methylsulfanyl)butanoic acid |
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Traditional Name | 2-[2-amino-4-(methylsulfanyl)butanamido]-4-(methylsulfanyl)butanoic acid |
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CAS Registry Number | Not Available |
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SMILES | CSCCC(N)C(=O)NC(CCSC)C(O)=O |
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InChI Identifier | InChI=1S/C10H20N2O3S2/c1-16-5-3-7(11)9(13)12-8(10(14)15)4-6-17-2/h7-8H,3-6,11H2,1-2H3,(H,12,13)(H,14,15) |
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InChI Key | ZYTPOUNUXRBYGW-UHFFFAOYSA-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
- Methionine or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- Alpha-amino acid or derivatives
- Thia fatty acid
- Fatty amide
- N-acyl-amine
- Fatty acid
- Fatty acyl
- Amino acid
- Secondary carboxylic acid amide
- Amino acid or derivatives
- Carboxamide group
- Sulfenyl compound
- Thioether
- Dialkylthioether
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organopnictogen compound
- Organic nitrogen compound
- Organic oxide
- Primary aliphatic amine
- Organonitrogen compound
- Organooxygen compound
- Carbonyl group
- Organosulfur compound
- Primary amine
- Organic oxygen compound
- Amine
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Not Available | 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 | -2.08 | 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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Methionyl-Methionine,1TMS,isomer #1 | CSCCC(N)C(=O)NC(CCSC)C(=O)O[Si](C)(C)C | 2343.2 | Semi standard non polar | 33892256 | Methionyl-Methionine,1TMS,isomer #2 | CSCCC(NC(=O)C(CCSC)N[Si](C)(C)C)C(=O)O | 2373.2 | Semi standard non polar | 33892256 | Methionyl-Methionine,1TMS,isomer #3 | CSCCC(N)C(=O)N(C(CCSC)C(=O)O)[Si](C)(C)C | 2301.9 | Semi standard non polar | 33892256 | Methionyl-Methionine,2TMS,isomer #1 | CSCCC(N[Si](C)(C)C)C(=O)NC(CCSC)C(=O)O[Si](C)(C)C | 2392.8 | Semi standard non polar | 33892256 | Methionyl-Methionine,2TMS,isomer #1 | CSCCC(N[Si](C)(C)C)C(=O)NC(CCSC)C(=O)O[Si](C)(C)C | 2304.1 | Standard non polar | 33892256 | Methionyl-Methionine,2TMS,isomer #2 | CSCCC(N)C(=O)N(C(CCSC)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 2304.8 | Semi standard non polar | 33892256 | Methionyl-Methionine,2TMS,isomer #2 | CSCCC(N)C(=O)N(C(CCSC)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 2313.2 | Standard non polar | 33892256 | Methionyl-Methionine,2TMS,isomer #3 | CSCCC(N[Si](C)(C)C)C(=O)N(C(CCSC)C(=O)O)[Si](C)(C)C | 2376.5 | Semi standard non polar | 33892256 | Methionyl-Methionine,2TMS,isomer #3 | CSCCC(N[Si](C)(C)C)C(=O)N(C(CCSC)C(=O)O)[Si](C)(C)C | 2343.6 | Standard non polar | 33892256 | Methionyl-Methionine,2TMS,isomer #4 | CSCCC(NC(=O)C(CCSC)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O | 2491.4 | Semi standard non polar | 33892256 | Methionyl-Methionine,2TMS,isomer #4 | CSCCC(NC(=O)C(CCSC)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O | 2410.5 | Standard non polar | 33892256 | Methionyl-Methionine,3TMS,isomer #1 | CSCCC(NC(=O)C(CCSC)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2492.4 | Semi standard non polar | 33892256 | Methionyl-Methionine,3TMS,isomer #1 | CSCCC(NC(=O)C(CCSC)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2441.8 | Standard non polar | 33892256 | Methionyl-Methionine,3TMS,isomer #2 | CSCCC(N[Si](C)(C)C)C(=O)N(C(CCSC)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 2358.1 | Semi standard non polar | 33892256 | Methionyl-Methionine,3TMS,isomer #2 | CSCCC(N[Si](C)(C)C)C(=O)N(C(CCSC)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 2393.0 | Standard non polar | 33892256 | Methionyl-Methionine,3TMS,isomer #3 | CSCCC(C(=O)O)N(C(=O)C(CCSC)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2524.0 | Semi standard non polar | 33892256 | Methionyl-Methionine,3TMS,isomer #3 | CSCCC(C(=O)O)N(C(=O)C(CCSC)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2477.7 | Standard non polar | 33892256 | Methionyl-Methionine,4TMS,isomer #1 | CSCCC(C(=O)O[Si](C)(C)C)N(C(=O)C(CCSC)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2530.1 | Semi standard non polar | 33892256 | Methionyl-Methionine,4TMS,isomer #1 | CSCCC(C(=O)O[Si](C)(C)C)N(C(=O)C(CCSC)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2527.9 | Standard non polar | 33892256 | Methionyl-Methionine,1TBDMS,isomer #1 | CSCCC(N)C(=O)NC(CCSC)C(=O)O[Si](C)(C)C(C)(C)C | 2603.2 | Semi standard non polar | 33892256 | Methionyl-Methionine,1TBDMS,isomer #2 | CSCCC(NC(=O)C(CCSC)N[Si](C)(C)C(C)(C)C)C(=O)O | 2615.7 | Semi standard non polar | 33892256 | Methionyl-Methionine,1TBDMS,isomer #3 | CSCCC(N)C(=O)N(C(CCSC)C(=O)O)[Si](C)(C)C(C)(C)C | 2545.3 | Semi standard non polar | 33892256 | Methionyl-Methionine,2TBDMS,isomer #1 | CSCCC(N[Si](C)(C)C(C)(C)C)C(=O)NC(CCSC)C(=O)O[Si](C)(C)C(C)(C)C | 2881.2 | Semi standard non polar | 33892256 | Methionyl-Methionine,2TBDMS,isomer #1 | CSCCC(N[Si](C)(C)C(C)(C)C)C(=O)NC(CCSC)C(=O)O[Si](C)(C)C(C)(C)C | 2722.4 | Standard non polar | 33892256 | Methionyl-Methionine,2TBDMS,isomer #2 | CSCCC(N)C(=O)N(C(CCSC)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2801.0 | Semi standard non polar | 33892256 | Methionyl-Methionine,2TBDMS,isomer #2 | CSCCC(N)C(=O)N(C(CCSC)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2725.9 | Standard non polar | 33892256 | Methionyl-Methionine,2TBDMS,isomer #3 | CSCCC(N[Si](C)(C)C(C)(C)C)C(=O)N(C(CCSC)C(=O)O)[Si](C)(C)C(C)(C)C | 2866.6 | Semi standard non polar | 33892256 | Methionyl-Methionine,2TBDMS,isomer #3 | CSCCC(N[Si](C)(C)C(C)(C)C)C(=O)N(C(CCSC)C(=O)O)[Si](C)(C)C(C)(C)C | 2723.8 | Standard non polar | 33892256 | Methionyl-Methionine,2TBDMS,isomer #4 | CSCCC(NC(=O)C(CCSC)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O | 2972.6 | Semi standard non polar | 33892256 | Methionyl-Methionine,2TBDMS,isomer #4 | CSCCC(NC(=O)C(CCSC)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O | 2788.4 | Standard non polar | 33892256 | Methionyl-Methionine,3TBDMS,isomer #1 | CSCCC(NC(=O)C(CCSC)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 3202.4 | Semi standard non polar | 33892256 | Methionyl-Methionine,3TBDMS,isomer #1 | CSCCC(NC(=O)C(CCSC)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2993.2 | Standard non polar | 33892256 | Methionyl-Methionine,3TBDMS,isomer #2 | CSCCC(N[Si](C)(C)C(C)(C)C)C(=O)N(C(CCSC)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3080.6 | Semi standard non polar | 33892256 | Methionyl-Methionine,3TBDMS,isomer #2 | CSCCC(N[Si](C)(C)C(C)(C)C)C(=O)N(C(CCSC)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2946.7 | Standard non polar | 33892256 | Methionyl-Methionine,3TBDMS,isomer #3 | CSCCC(C(=O)O)N(C(=O)C(CCSC)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3208.0 | Semi standard non polar | 33892256 | Methionyl-Methionine,3TBDMS,isomer #3 | CSCCC(C(=O)O)N(C(=O)C(CCSC)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2992.2 | Standard non polar | 33892256 | Methionyl-Methionine,4TBDMS,isomer #1 | CSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)C(CCSC)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3413.8 | Semi standard non polar | 33892256 | Methionyl-Methionine,4TBDMS,isomer #1 | CSCCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)C(CCSC)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3203.9 | 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 - Methionyl-Methionine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0kai-9850000000-bcd240fcfddae89a18d7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Methionyl-Methionine GC-MS (1 TMS) - 70eV, Positive | splash10-0fh0-9532000000-3fd2d36548011eadb705 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Methionyl-Methionine 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 - Methionyl-Methionine 10V, Positive-QTOF | splash10-0f89-0490000000-0b739651cd0ed96d7c02 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methionyl-Methionine 20V, Positive-QTOF | splash10-0udr-4930000000-d2b923d1666275aad6cf | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methionyl-Methionine 40V, Positive-QTOF | splash10-0zg3-9300000000-b39810113866582781e8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methionyl-Methionine 10V, Negative-QTOF | splash10-002b-5090000000-bac900dfe188caa0c268 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methionyl-Methionine 20V, Negative-QTOF | splash10-0002-9220000000-311c8c8b82f54ae9a610 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methionyl-Methionine 40V, Negative-QTOF | splash10-0002-9100000000-43e05d13d023b50dd1f3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methionyl-Methionine 10V, Positive-QTOF | splash10-001i-0390000000-5a6a2fdf5446de41a5c5 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methionyl-Methionine 20V, Positive-QTOF | splash10-0ue9-2960000000-116aa51a0b34ff981dd9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methionyl-Methionine 40V, Positive-QTOF | splash10-0ik9-9300000000-9ed3c136873d1bc79e5e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methionyl-Methionine 10V, Negative-QTOF | splash10-004i-0090000000-37cd336791050b66de3c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methionyl-Methionine 20V, Negative-QTOF | splash10-0002-9100000000-e909b3fce726e8224b05 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methionyl-Methionine 40V, Negative-QTOF | splash10-0002-9000000000-e1d92d2a30bee517d754 | 2021-09-24 | 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) | 2021-09-25 | Wishart Lab | View Spectrum | 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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 |
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General References | - Alfimova MV, Korovaitseva GI, Lezheiko TV, Golimbet VE: Effect of BDNF Val66Met polymorphism on normal variability of executive functions. Bull Exp Biol Med. 2012 Mar;152(5):606-9. [PubMed:22803145 ]
- Hug GL, Bobrowski K, Kozubek H, Marciniak B: Photo-oxidation of methionine-containing peptides by the 4-carboxybenzophenone triplet state in aqueous solution. Competition between intramolecular two-centered three-electron bonded (S...S)+ and (S...N)+ formation. Photochem Photobiol. 2000 Jul;72(1):1-9. [PubMed:10911722 ]
- Baker DH, Bafundo KW, Boebel KP, Czarnecki GL, Halpin KM: Methionine peptides as potential food supplements: efficacy and susceptibility to Maillard browning. J Nutr. 1984 Feb;114(2):292-7. [PubMed:6693991 ]
- Marco-Pallares J, Nager W, Kramer UM, Cunillera T, Camara E, Cucurell D, Schule R, Schols L, Rodriguez-Fornells A, Munte TF: Neurophysiological markers of novelty processing are modulated by COMT and DRD4 genotypes. Neuroimage. 2010 Nov 15;53(3):962-9. doi: 10.1016/j.neuroimage.2010.02.012. Epub 2010 Feb 12. [PubMed:20156565 ]
- Friedman M, Gumbmann MR: Nutritional value and safety of methionine derivatives, isomeric dipeptides and hydroxy analogs in mice. J Nutr. 1988 Mar;118(3):388-97. [PubMed:3351635 ]
- Boebel KP, Baker DH: Efficacy of methionine peptides as determined by chick bioassay. J Nutr. 1982 Jun;112(6):1130-2. [PubMed:7086542 ]
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