Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 14:54:17 -0600 |
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Update Date | 2015-09-13 12:56:14 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | Se-Methylselenocysteine |
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Description | Se-Methylselenocysteine (SeMSC) is a naturally occurring seleno-amino acid that is synthesized by plants such as garlic, astragalus, onions and broccoli. SeMSC is an intermediate in selenoamino acid metabolism. Unlike selenomethionine, which is incorporated into proteins in place of methionine, SeMSC is not incorporated into any proteins, thereby being fully available for the synthesis of selenium-containing enzymes such as glutathione peroxidase. |
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Structure | |
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Synonyms: | - 3-(Methylseleno)-L-Alanine
- Methylselenocysteine
- Se-Methyl-L-selenocysteine
- Selenium-methylselenocystine
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Chemical Formula: | C4H9NO2Se |
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Weight: | Average: 182.08 Monoisotopic: 182.979850365 |
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InChI Key: | XDSSPSLGNGIIHP-VKHMYHEASA-N |
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InChI: | InChI=1S/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1 |
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CAS number: | 26046-90-2 |
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IUPAC Name: | (2R)-2-amino-3-(methylselanyl)propanoic acid |
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Traditional IUPAC Name: | methylselenocysteine |
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SMILES: | C[Se]C[C@H](N)C(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. |
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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 | L-alpha-amino acids |
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Alternative Parents | |
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Substituents | - L-alpha-amino acid
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Selenoether
- Amine
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Primary amine
- Organoselenium compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Primary aliphatic amine
- Organic nitrogen compound
- Carbonyl group
- 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: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | - Selenoamino acid metabolism ec00450
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-000i-2900000000-584579d62a5c494d1ad4 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0i00-1960000000-c1d9d3d6c03ef447c682 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-000i-2900000000-584579d62a5c494d1ad4 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0i00-1960000000-c1d9d3d6c03ef447c682 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9400000000-b52de18849d5860694de | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00dl-9110000000-370afb49a49bc4836d3e | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001r-0900000000-87ae6338ccd9513f5db0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001r-1900000000-204e0c71178a372a67d0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000f-9800000000-f08ef5fe840b11c1330b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00lu-5900000000-267cb39ae0470e212ce2 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0079-9400000000-7ae0b50471ba90d5656c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9300000000-7580c3589d69535a4bb7 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-9000000000-f9689d19a8a4fb34dc2c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9000000000-f9689d19a8a4fb34dc2c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-f9689d19a8a4fb34dc2c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00lr-0900000000-d519041b7fbf3920f7ee | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00y0-0900000000-88e1671d699eb2ba3233 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00dl-5900000000-c1dd9e6e9d3616306ddc | View in MoNA |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Yin MB, Li ZR, Cao S, Durrani FA, Azrak RG, Frank C, Rustum YM: Enhanced 7-ethyl-10-hydroxycamptothecin (SN-38) lethality by methylselenocysteine is associated with Chk2 phosphorylation at threonine-68 and down-regulation of Cdc6 expression. Mol Pharmacol. 2004 Jul;66(1):153-60. Pubmed: 15213307
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Synthesis Reference: | Spallholz, Julian E.; Reid, Ted W.; Walkup, Robert D. A method of using synthetic L-Se-methylselenocysteine as a nutriceutical. Eur. Pat. Appl. (2002), 21 pp. |
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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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