2.0 2012-05-31 14:54:17 -0600 2015-09-13 12:56:14 -0600 ECMDB21009 M2MDB001427 Se-Methylselenocysteine 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. 3-(Methylseleno)-L-Alanine Methylselenocysteine Se-Methyl-L-selenocysteine Selenium-methylselenocystine C4H9NO2Se 182.08 182.979850365 (2R)-2-amino-3-(methylselanyl)propanoic acid methylselenocysteine 26046-90-2 C[Se]C[C@H](N)C(O)=O InChI=1S/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1 XDSSPSLGNGIIHP-VKHMYHEASA-N Solid Cytoplasm Periplasm logp -2.83 ALOGPS logs -0.07 ALOGPS solubility 1.56e+02 g/l ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 1.46 ChemAxon pka_strongest_basic 8.4 ChemAxon iupac (2R)-2-amino-3-(methylselanyl)propanoic acid ChemAxon average_mass 182.08 ChemAxon mono_mass 182.979850365 ChemAxon smiles C[Se]C[C@H](N)C(O)=O ChemAxon formula C4H9NO2Se ChemAxon inchi InChI=1S/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1 ChemAxon inchikey XDSSPSLGNGIIHP-VKHMYHEASA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 38.2 ChemAxon polarizability 12.89 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Selenoamino acid metabolism ec00450 Specdb::CMs 1070 Specdb::CMs 1163 Specdb::CMs 3284 Specdb::CMs 31504 Specdb::CMs 31505 Specdb::CMs 38717 Specdb::CMs 160877 Specdb::NmrOneD 41642 Specdb::NmrOneD 41643 Specdb::NmrOneD 41644 Specdb::NmrOneD 41645 Specdb::NmrOneD 41646 Specdb::NmrOneD 41647 Specdb::NmrOneD 41648 Specdb::NmrOneD 41649 Specdb::NmrOneD 41650 Specdb::NmrOneD 41651 Specdb::NmrOneD 41652 Specdb::NmrOneD 41653 Specdb::NmrOneD 41654 Specdb::NmrOneD 41655 Specdb::NmrOneD 41656 Specdb::NmrOneD 41657 Specdb::NmrOneD 41658 Specdb::NmrOneD 41659 Specdb::NmrOneD 41660 Specdb::NmrOneD 41661 Specdb::MsMs 26873 Specdb::MsMs 26874 Specdb::MsMs 26875 Specdb::MsMs 33431 Specdb::MsMs 33432 Specdb::MsMs 33433 Specdb::MsMs 2797280 Specdb::MsMs 2797281 Specdb::MsMs 2797282 Specdb::MsMs 2881733 Specdb::MsMs 2881734 Specdb::MsMs 2881735 HMDB04113 147004 129633 C05689 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. 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. 15213307 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. http://hmdb.ca/system/metabolites/msds/000/003/694/original/HMDB04113.pdf?1358461408 Gamma-glutamyltranspeptidase P18956 GGT_ECOLI ggt http://ecmdb.ca/proteins/P18956.xml Cysteine desulfurase_ P77444 SUFS_ECOLI sufS http://ecmdb.ca/proteins/P77444.xml (5-L-Glutamyl)-peptide + Se-Methylselenocysteine <> Peptide + gamma-Glutamyl-Se-methylselenocysteine R04935 Se-Methylselenocysteine + Water <> Pyruvic acid + Ammonia + Methaneselenol R09366