Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-08 21:40:45 UTC |
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Update Date | 2023-02-21 17:18:41 UTC |
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HMDB ID | HMDB0029223 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | alpha-Methylphenylalanine |
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Description | alpha-Methylphenylalanine, also known as α-methyl-DL-phenylalanine, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Based on a literature review a significant number of articles have been published on alpha-Methylphenylalanine. |
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Structure | CC(N)(CC1=CC=CC=C1)C(O)=O InChI=1S/C10H13NO2/c1-10(11,9(12)13)7-8-5-3-2-4-6-8/h2-6H,7,11H2,1H3,(H,12,13) |
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Synonyms | Value | Source |
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a-Methylphenylalanine | Generator | Α-methylphenylalanine | Generator | 2-Amino-2-methyl-3-phenylpropanoate | HMDB | alpha-Methylphenylalanine, hydrochloride, (D-phe)-isomer | HMDB | alpha-Methylphenylalanine, hydrochloride, (DL-phe)-isomer | HMDB | alpha-Methylphenylalanine, hydrochloride, (L-phe)-isomer | HMDB | alpha-Methylphenylalanine, (D-phe)-isomer | HMDB | alpha-Methylphenylalanine, (DL-phe)-isomer | HMDB | alpha-Methylphenylalanine, (L-phe)-isomer | HMDB | a-Methyl-DL-phenylalanine | HMDB | Α-methyl-DL-phenylalanine | HMDB | alpha-Methylphenylalanine | MeSH |
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Chemical Formula | C10H13NO2 |
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Average Molecular Weight | 179.2157 |
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Monoisotopic Molecular Weight | 179.094628665 |
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IUPAC Name | 2-amino-2-methyl-3-phenylpropanoic acid |
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Traditional Name | 2-amino-2-methyl-3-phenylpropanoic acid |
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CAS Registry Number | Not Available |
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SMILES | CC(N)(CC1=CC=CC=C1)C(O)=O |
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InChI Identifier | InChI=1S/C10H13NO2/c1-10(11,9(12)13)7-8-5-3-2-4-6-8/h2-6H,7,11H2,1H3,(H,12,13) |
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InChI Key | HYOWVAAEQCNGLE-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Phenylpropanoic acids |
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Sub Class | Not Available |
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Direct Parent | Phenylpropanoic acids |
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Alternative Parents | |
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Substituents | - 3-phenylpropanoic-acid
- Alpha-amino acid
- Alpha-amino acid or derivatives
- Amphetamine or derivatives
- Phenylpropane
- Aralkylamine
- Monocyclic benzene moiety
- Benzenoid
- Amino acid or derivatives
- Amino acid
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organonitrogen compound
- Primary aliphatic amine
- Organooxygen compound
- Organic oxide
- Carbonyl group
- Organic nitrogen compound
- Organopnictogen compound
- Primary amine
- Amine
- Organic oxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | 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 | 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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alpha-Methylphenylalanine,1TMS,isomer #1 | CC(N)(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C | 1565.1 | Semi standard non polar | 33892256 | alpha-Methylphenylalanine,1TMS,isomer #2 | CC(CC1=CC=CC=C1)(N[Si](C)(C)C)C(=O)O | 1648.7 | Semi standard non polar | 33892256 | alpha-Methylphenylalanine,2TMS,isomer #1 | CC(CC1=CC=CC=C1)(N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1643.2 | Semi standard non polar | 33892256 | alpha-Methylphenylalanine,2TMS,isomer #1 | CC(CC1=CC=CC=C1)(N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1686.1 | Standard non polar | 33892256 | alpha-Methylphenylalanine,2TMS,isomer #2 | CC(CC1=CC=CC=C1)(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1840.4 | Semi standard non polar | 33892256 | alpha-Methylphenylalanine,2TMS,isomer #2 | CC(CC1=CC=CC=C1)(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1766.1 | Standard non polar | 33892256 | alpha-Methylphenylalanine,3TMS,isomer #1 | CC(CC1=CC=CC=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1860.0 | Semi standard non polar | 33892256 | alpha-Methylphenylalanine,3TMS,isomer #1 | CC(CC1=CC=CC=C1)(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1828.0 | Standard non polar | 33892256 | alpha-Methylphenylalanine,1TBDMS,isomer #1 | CC(N)(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C | 1812.7 | Semi standard non polar | 33892256 | alpha-Methylphenylalanine,1TBDMS,isomer #2 | CC(CC1=CC=CC=C1)(N[Si](C)(C)C(C)(C)C)C(=O)O | 1899.9 | Semi standard non polar | 33892256 | alpha-Methylphenylalanine,2TBDMS,isomer #1 | CC(CC1=CC=CC=C1)(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2109.0 | Semi standard non polar | 33892256 | alpha-Methylphenylalanine,2TBDMS,isomer #1 | CC(CC1=CC=CC=C1)(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2104.8 | Standard non polar | 33892256 | alpha-Methylphenylalanine,2TBDMS,isomer #2 | CC(CC1=CC=CC=C1)(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2302.8 | Semi standard non polar | 33892256 | alpha-Methylphenylalanine,2TBDMS,isomer #2 | CC(CC1=CC=CC=C1)(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2173.5 | Standard non polar | 33892256 | alpha-Methylphenylalanine,3TBDMS,isomer #1 | CC(CC1=CC=CC=C1)(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2532.8 | Semi standard non polar | 33892256 | alpha-Methylphenylalanine,3TBDMS,isomer #1 | CC(CC1=CC=CC=C1)(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2415.0 | 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 - alpha-Methylphenylalanine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9400000000-8693856b7ebd46028a63 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - alpha-Methylphenylalanine GC-MS (1 TMS) - 70eV, Positive | splash10-0006-9500000000-1c0774497a68191729b1 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - alpha-Methylphenylalanine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - alpha-Methylphenylalanine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - alpha-Methylphenylalanine GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - alpha-Methylphenylalanine GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - alpha-Methylphenylalanine GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-03 | 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 - alpha-Methylphenylalanine 10V, Positive-QTOF | splash10-001i-0900000000-0f6eecd6cec27b546600 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 20V, Positive-QTOF | splash10-001i-2900000000-c5666ae92da7850e89fe | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 40V, Positive-QTOF | splash10-0006-9400000000-24d32f10a470e037f6cc | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 10V, Negative-QTOF | splash10-004i-0900000000-b095d20c24fa61b85a40 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 20V, Negative-QTOF | splash10-005i-6900000000-b6240b2bfb4f9701787c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 40V, Negative-QTOF | splash10-00l6-8900000000-bbd41f94a7130dcb2077 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 10V, Negative-QTOF | splash10-004l-3900000000-13907a76b4a5975aee8a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 20V, Negative-QTOF | splash10-014i-4900000000-a58fdc5f38658c886c76 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 40V, Negative-QTOF | splash10-014l-9700000000-17cd851b9dd640f25961 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 10V, Positive-QTOF | splash10-001i-1900000000-490c647484a64a1b4bd3 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 20V, Positive-QTOF | splash10-014i-2900000000-4cfbe93b4c0531391d9e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - alpha-Methylphenylalanine 40V, Positive-QTOF | splash10-0006-9100000000-0be2b8f0f765d186e28e | 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 |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Disease References | Colorectal cancer |
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- 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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