2.0 2012-05-31 13:58:24 -0600 2015-06-03 15:54:21 -0600 ECMDB03288 M2MDB000488 Selenocysteine Selenocysteine is considered to be the 21st proteinogenic amino acid. It exists naturally in all kingdoms of life as a building block of selenoproteins. Selenocysteine is a cysteine analogue with a selenium-containing selenol group in place of the sulfur-containing thiol group. Selenocysteine is present in several enzymes (for example glutathione peroxidases, tetraiodothyronine 5' deiodinases, thioredoxin reductases, formate dehydrogenases, glycine reductases, (2R)-2-amino-3-selanylpropanoate (2R)-2-amino-3-selanylpropanoic acid 3-Seleno-alanine 3-Selenoalanine 3-Selenyl-L-Alanine L-Selenocystein L-Selenocysteine L-Selenozystein U C3H7NO2Se 168.05 168.964200301 (2R)-2-amino-3-selanylpropanoic acid L-selenocysteine 3614-08-2 N[C@@H](C[SeH])C(O)=O InChI=1S/C3H7NO2Se/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1 ZKZBPNGNEQAJSX-REOHCLBHSA-N Solid Cytoplasm Periplasm logp -3.20 ALOGPS logs 0.29 ALOGPS solubility 3.25e+02 g/l ALOGPS logp -4.1 ChemAxon pka_strongest_acidic 1.27 ChemAxon pka_strongest_basic 8.4 ChemAxon iupac (2R)-2-amino-3-selanylpropanoic acid ChemAxon average_mass 168.05 ChemAxon mono_mass 168.964200301 ChemAxon smiles N[C@@H](C[SeH])C(O)=O ChemAxon formula C3H7NO2Se ChemAxon inchi InChI=1S/C3H7NO2Se/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1 ChemAxon inchikey ZKZBPNGNEQAJSX-REOHCLBHSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 33.45 ChemAxon polarizability 10.67 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Selenoamino acid metabolism ec00450 Specdb::CMs 2681 Specdb::CMs 38562 Specdb::CMs 153066 Specdb::NmrOneD 135550 Specdb::NmrOneD 135551 Specdb::NmrOneD 135552 Specdb::NmrOneD 135553 Specdb::NmrOneD 135554 Specdb::NmrOneD 135555 Specdb::NmrOneD 135556 Specdb::NmrOneD 135557 Specdb::NmrOneD 135558 Specdb::NmrOneD 135559 Specdb::NmrOneD 135560 Specdb::NmrOneD 135561 Specdb::NmrOneD 135562 Specdb::NmrOneD 135563 Specdb::NmrOneD 135564 Specdb::NmrOneD 135565 Specdb::NmrOneD 135566 Specdb::NmrOneD 135567 Specdb::NmrOneD 135568 Specdb::NmrOneD 135569 Specdb::MsMs 29324 Specdb::MsMs 29325 Specdb::MsMs 29326 Specdb::MsMs 35882 Specdb::MsMs 35883 Specdb::MsMs 35884 Specdb::MsMs 2717892 Specdb::MsMs 2717893 Specdb::MsMs 2717894 Specdb::MsMs 2963673 Specdb::MsMs 2963674 Specdb::MsMs 2963675 HMDB03288 6326983 23436 C05688 9093 L-SELENOCYSTEINE CSE Selenocysteine Zinoni, F., Birkmann, A., Stadtman, T. C., Bock, A. (1986). "Nucleotide sequence and expression of the selenocysteine-containing polypeptide of formate dehydrogenase (formate-hydrogen-lyase-linked) from Escherichia coli." Proc Natl Acad Sci U S A 83:4650-4654. 2941757 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). 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Epub 2004 Aug 4. 15294905 Rooseboom M, Vermeulen NP, Andreadou I, Commandeur JN: Evaluation of the kinetics of beta-elimination reactions of selenocysteine Se-conjugates in human renal cytosol: possible implications for the use as kidney selective prodrugs. J Pharmacol Exp Ther. 2000 Aug;294(2):762-9. 10900258 Cystathionine gamma-synthase P00935 METB_ECOLI metB http://ecmdb.ca/proteins/P00935.xml Cysteine synthase A P0ABK5 CYSK_ECOLI cysK http://ecmdb.ca/proteins/P0ABK5.xml Cysteine synthase B P16703 CYSM_ECOLI cysM http://ecmdb.ca/proteins/P16703.xml Cysteine desulfurase_ P77444 SUFS_ECOLI sufS http://ecmdb.ca/proteins/P77444.xml Uncharacterized amino-acid ABC transporter ATP-binding protein yecC P37774 YECC_ECOLI yecC http://ecmdb.ca/proteins/P37774.xml Inner membrane amino-acid ABC transporter permease protein yecS P0AFT2 YECS_ECOLI yecS http://ecmdb.ca/proteins/P0AFT2.xml Selenocysteine + Reduced acceptor <> Hydrogen selenide + L-Alanine + Acceptor R03599 O-Acetylserine + Hydrogen selenide <> Selenocysteine + Acetic acid R03601 O-Phosphorylhomoserine + Selenocysteine <> Selenocystathionine + Phosphate R04944 o-acetyl-l-homoserine + Selenocysteine <> Selenocystathionine + Acetic acid R04945 O-Succinyl-L-homoserine + Selenocysteine <> Selenocystathionine + Succinic acid R04946 a reduced electron acceptor + Selenocysteine <> L-Alanine + Selenium + an oxidized electron acceptor + Hydrogen ion SELENOCYSTEINE-LYASE-RXN Selenocysteine + reduced acceptor > Hydrogen selenide + L-Alanine + acceptor