Record Information |
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Version |
1.0 |
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Update Date |
1/22/2018 12:54:54 PM |
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Metabolite ID | PAMDB120103 |
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Identification |
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Name: |
seleno-L-methionine |
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Description: | An amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of L-selenomethionine; major species at pH 7.3. |
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Structure |
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Synonyms: | - (2S)-2-ammonio-4-(methylselanyl)butanoate
- L-selenomethionine
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Chemical Formula: |
C5H11NO2SE |
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Average Molecular Weight: |
196.107 |
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Monoisotopic Molecular
Weight: |
198.00333 |
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InChI Key: |
RJFAYQIBOAGBLC-BYPYZUCNSA-N |
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InChI: | InChI=1S/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1 |
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CAS
number: |
3211-76-5 |
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IUPAC Name: | (2S)-2-azaniumyl-4-(methylselanyl)butanoate |
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Traditional IUPAC Name: |
(+,-)-selenomethionine |
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SMILES: | C[Se]CCC(C([O-])=O)[N+] |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of chemical entities known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). |
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Kingdom |
Chemical entities |
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Super Class | Organic compounds |
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Class |
Organic acids and derivatives |
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Sub Class | Carboxylic acids and derivatives |
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Direct Parent |
Alpha amino acids |
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Alternative Parents |
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Substituents |
- Alpha-amino acid
- Fatty acid
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Selenoether
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Primary amine
- Organoselenium compound
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Primary aliphatic amine
- Organic oxygen compound
- Carbonyl group
- Amine
- Aliphatic acyclic compound
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Molecular Framework |
Aliphatic acyclic compounds |
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External Descriptors |
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Physical Properties |
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State: |
Solid |
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Charge: | 0 |
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Melting point: |
275 °C |
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Experimental Properties: |
Property | Value | Reference |
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Melting Point | 275 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties |
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Biological Properties |
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Cellular Locations: |
Not Available |
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Reactions: | |
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Pathways: |
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Spectra |
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Spectra: |
Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS | Not Available |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0f89-0900000000-4949659ad5c41236a070 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a4i-9500000000-dbac3b4e6e034ebd3855 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0a4i-9200000000-d58c983bc06091b8dd74 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f6t-1900000000-185fb006e1bba095a984 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udj-1900000000-d4cebd865ad12ea7d7a0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-8900000000-797a41add1f29f10c4dd | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0007-7900000000-60bc9ba77f492e1b35e1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0f95-5900000000-7b650680f083adef2064 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-006x-9200000000-027a3e15d6897c294431 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available |
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1D NMR | 1H NMR Spectrum | Not Available |
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1D NMR | 13C NMR Spectrum | Not Available |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available |
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References |
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References: |
- Greenwald P, Milner JA, Anderson DE, McDonald SS: Micronutrients in cancer chemoprevention. Cancer Metastasis Rev. 2002;21(3-4):217-30. [12549762 ]
- Pointner H, Kinast H, Flegel U: 75Se-selenomethionine excretion in bile and pancreatic juice. Digestion. 1975;12(1):61-4. [1175867 ]
- Seo YR, Sweeney C, Smith ML: Selenomethionine induction of DNA repair response in human fibroblasts. Oncogene. 2002 May 23;21(23):3663-9. [12032834 ]
- Yang X, Tian Y, Ha P, Gu L: [Determination of the selenomethionine content in grain and human blood] Wei Sheng Yan Jiu. 1997 Mar;26(2):113-6. [10325615 ]
- Hoang TT, Chen Y, May SW, Browner RF: Analysis of organoselenium compounds in human urine using active carbon and chemically modified silica sol-gel surface-assisted laser desorption/ionization high-resolution time-of-flight mass spectrometry. Anal Chem. 2004 Apr 1;76(7):2062-70. [15053672 ]
- Dorea JG: Selenium and breast-feeding. Br J Nutr. 2002 Nov;88(5):443-61. [12425725 ]
- Wally J, Halbrooks PJ, Vonrhein C, Rould MA, Everse SJ, Mason AB, Buchanan SK: The crystal structure of iron-free human serum transferrin provides insight into inter-lobe communication and receptor binding. J Biol Chem. 2006 Aug 25;281(34):24934-44. Epub 2006 Jun 22. [16793765 ]
- Cabanero AI, Madrid Y, Camara C: Selenium long-term administration and its effect on mercury toxicity. J Agric Food Chem. 2006 Jun 14;54(12):4461-8. [16756381 ]
- Wan XS, Zhou Z, Kennedy AR, Kopelovich L: In vitro evaluation of chemopreventive agents using cultured human prostate epithelial cells. Oncol Rep. 2003 Nov-Dec;10(6):2009-14. [14534735 ]
- Nakanishi F, Kasuga T, Kobayashi T, Miyabayashi H, Yano K: [Method of analysis of regional dynamics of the pancreas with 75Se-selenomethionine] Kaku Igaku. 1977 Apr;14(2):223-32. [559835 ]
- Agnew JE, McCarthy DM, Melmed RNBOUCHIER IA: Count rate analysis as an adjunct to the 75Se-selenomethionine pancreas scan. Br J Radiol. 1969 Oct;42(502):762-9. [5345341 ]
- Kuehnelt D, Kienzl N, Traar P, Le NH, Francesconi KA, Ochi T: Selenium metabolites in human urine after ingestion of selenite, L-selenomethionine, or DL-selenomethionine: a quantitative case study by HPLC/ICPMS. Anal Bioanal Chem. 2005 Sep;383(2):235-46. Epub 2005 Oct 12. [16132136 ]
- Whanger PD: Selenium and its relationship to cancer: an update. Br J Nutr. 2004 Jan;91(1):11-28. [14748935 ]
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Synthesis Reference: |
Jakubke, Hans D.; Fischer, J.; Jost, Karel; Rudinger, Josef. Amino acids and peptides. LXXXVI. Synthesis of L-selenomethionine, L-selenoethionine, and their tert-butoxy-carbonyl derivatives. Collection of Czechoslovak Chemical Communications (1968), 33(11), 3910-12. |
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Material Safety Data Sheet (MSDS) |
Download (PDF) |
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Links |
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External Links: |
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