Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2019-05-29 15:12:59 UTC |
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Update Date | 2022-03-07 03:18:16 UTC |
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HMDB ID | HMDB0240365 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | N,N,N-Trimethyl-L-alanyl-L-proline betaine |
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Description | N,N,N-Trimethyl-L-alanyl-L-proline betaine (TMAP) 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. TMAP was previously an unknown potential plasma biomarker for glomerular filtration rate (GFR) but its structure has since been elucidated (PMID: 28706470 ). TMAP has also been identified as a potential plasma biomarker of reduced kidney function in early chronic kidney disease (CKD), end stage renal disease (ESRD), and hemodialytic clearance (PMID: 31048706 ). |
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Structure | C[C@@H](C(=O)N1CCC[C@H]1C([O-])=O)[N+](C)(C)C InChI=1S/C11H20N2O3/c1-8(13(2,3)4)10(14)12-7-5-6-9(12)11(15)16/h8-9H,5-7H2,1-4H3/t8-,9-/m0/s1 |
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Synonyms | Value | Source |
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N,N,N-Trimethylalanylproline betaine | HMDB | TMAP | HMDB | L,L-TMAP | HMDB | N,N,N-Trimethyl-L-alanyl-L-proline betaine | HMDB |
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Chemical Formula | C11H20N2O3 |
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Average Molecular Weight | 228.292 |
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Monoisotopic Molecular Weight | 228.147392512 |
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IUPAC Name | (2S)-1-[(2S)-2-(trimethylazaniumyl)propanoyl]pyrrolidine-2-carboxylate |
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Traditional Name | (2S)-1-[(2S)-2-(trimethylammonio)propanoyl]pyrrolidine-2-carboxylate |
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CAS Registry Number | 2177265-93-7 |
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SMILES | C[C@@H](C(=O)N1CCC[C@H]1C([O-])=O)[N+](C)(C)C |
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InChI Identifier | InChI=1S/C11H20N2O3/c1-8(13(2,3)4)10(14)12-7-5-6-9(12)11(15)16/h8-9H,5-7H2,1-4H3/t8-,9-/m0/s1 |
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InChI Key | KXONJPJIFNGMCN-IUCAKERBSA-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-l-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- N-acyl-alpha-amino acid
- Alpha-amino acid or derivatives
- Pyrrolidine carboxylic acid or derivatives
- Pyrrolidine carboxylic acid
- N-acylpyrrolidine
- Tetraalkylammonium salt
- Tertiary carboxylic acid amide
- Quaternary ammonium salt
- Pyrrolidine
- Carboxylic acid salt
- Carboxamide group
- Azacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organic salt
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Amine
- 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 SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M+H]+ | 164.433 | 30932474 | DeepCCS | [M-H]- | 160.605 | 30932474 | DeepCCS | [M-2H]- | 197.023 | 30932474 | DeepCCS | [M+Na]+ | 173.199 | 30932474 |
Predicted Kovats Retention IndicesUnderivatized |
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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 - N,N,N-Trimethyl-L-alanyl-L-proline betaine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N,N,N-Trimethyl-L-alanyl-L-proline betaine 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 - N,N,N-Trimethyl-L-alanyl-L-proline betaine 10V, Positive-QTOF | splash10-016r-5940000000-6d0d451f2c6db62f385e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N,N-Trimethyl-L-alanyl-L-proline betaine 20V, Positive-QTOF | splash10-03xr-9310000000-c799146b357185c32857 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N,N-Trimethyl-L-alanyl-L-proline betaine 40V, Positive-QTOF | splash10-08mi-9000000000-bb62e1b4fa8b95671a10 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N,N-Trimethyl-L-alanyl-L-proline betaine 10V, Negative-QTOF | splash10-01t9-1690000000-367dc372f9e3b4388f38 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N,N-Trimethyl-L-alanyl-L-proline betaine 20V, Negative-QTOF | splash10-03di-4900000000-c9910ad3d7b2beb31bb1 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N,N,N-Trimethyl-L-alanyl-L-proline betaine 40V, Negative-QTOF | splash10-03di-6900000000-0c540d8e8429f8856d34 | 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 | - Velenosi TJ, Thomson BKA, Tonial NC, RaoPeters AAE, Mio MA, Lajoie GA, Garg AX, House AA, Urquhart BL: Untargeted metabolomics reveals N, N, N-trimethyl-L-alanyl-L-proline betaine (TMAP) as a novel biomarker of kidney function. Sci Rep. 2019 May 2;9(1):6831. doi: 10.1038/s41598-019-42992-3. [PubMed:31048706 ]
- Zhang Q, Ford LA, Evans AM, Toal DR: Structure elucidation of metabolite x17299 by interpretation of mass spectrometric data. Metabolomics. 2017;13(8):92. doi: 10.1007/s11306-017-1231-x. Epub 2017 Jun 24. [PubMed:28706470 ]
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