2.0 2012-05-31 14:54:20 -0600 2015-06-03 17:20:25 -0600 ECMDB21010 M2MDB001428 Selenohomocysteine Selenohomocysteine is the precursor of selenocysteine, which is synthesized by catalysis of cystathionine beta-synthase (EC 4.2.1.22) and cystathionine gamma-lyase (EC 4.4.1.1). Selenohomocysteine (lactone) has been found to be a competitive and irreversible inhibitor of lysyl oxidase. L-selenohomocysteine also can serve as a substituent donor in the beta-replacement reaction to yield selenocystathionine. (PMID: 10609891, 9405445, 6456763, 3338973) 2-Amino-4-selanyl-butanoate 2-Amino-4-selanyl-butanoic acid Se-selenocysteine C4H9NO2Se 182.08 182.979850365 2-amino-4-selanylbutanoic acid 2-amino-4-selanylbutanoic acid 29412-93-9 NC(CC[SeH])C(O)=O InChI=1S/C4H9NO2Se/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7) RCWCGLALNCIQNM-UHFFFAOYSA-N Solid Cytoplasm Periplasm logp -3.07 ALOGPS logs 0.06 ALOGPS solubility 2.10e+02 g/l ALOGPS logp -3.9 ChemAxon pka_strongest_acidic 1.41 ChemAxon pka_strongest_basic 9.5 ChemAxon iupac 2-amino-4-selanylbutanoic acid ChemAxon average_mass 182.08 ChemAxon mono_mass 182.979850365 ChemAxon smiles NC(CC[SeH])C(O)=O ChemAxon formula C4H9NO2Se ChemAxon inchi InChI=1S/C4H9NO2Se/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7) ChemAxon inchikey RCWCGLALNCIQNM-UHFFFAOYSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 38.16 ChemAxon polarizability 12.78 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Selenoamino acid metabolism ec00450 Specdb::CMs 3209 Specdb::CMs 38718 Specdb::NmrOneD 248468 Specdb::NmrOneD 248469 Specdb::NmrOneD 248470 Specdb::NmrOneD 248471 Specdb::NmrOneD 248472 Specdb::NmrOneD 248473 Specdb::NmrOneD 248474 Specdb::NmrOneD 248475 Specdb::NmrOneD 248476 Specdb::NmrOneD 248477 Specdb::NmrOneD 248478 Specdb::NmrOneD 248479 Specdb::NmrOneD 248480 Specdb::NmrOneD 248481 Specdb::NmrOneD 248482 Specdb::NmrOneD 248483 Specdb::NmrOneD 248484 Specdb::NmrOneD 248485 Specdb::NmrOneD 248486 Specdb::NmrOneD 248487 Specdb::MsMs 26756 Specdb::MsMs 26757 Specdb::MsMs 26758 Specdb::MsMs 33314 Specdb::MsMs 33315 Specdb::MsMs 33316 HMDB04119 6326973 389632 C05698 SELENOHOMOCYSTEINE 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 Soda, K., Oikawa, T., Esaki, N. (1999). "Vitamin B6 enzymes participating in selenium amino acid metabolism." Biofactors 10:257-262. 10609891 Esaki N, Nakamura T, Tanaka H, Suzuki T, Morino Y, Soda K: Enzymatic synthesis of selenocysteine in rat liver. Biochemistry. 1981 Jul 21;20(15):4492-6. 6456763 Liu G, Nellaiappan K, Kagan HM: Irreversible inhibition of lysyl oxidase by homocysteine thiolactone and its selenium and oxygen analogues. Implications for homocystinuria. J Biol Chem. 1997 Dec 19;272(51):32370-7. 9405445 Esaki N, Seraneeprakarn V, Tanaka H, Soda K: Purification and characterization of Clostridium sticklandii D-selenocystine alpha, beta-lyase. J Bacteriol. 1988 Feb;170(2):751-6. 3338973 Cystathionine beta-lyase metC P06721 METC_ECOLI metC http://ecmdb.ca/proteins/P06721.xml Methionine synthase P13009 METH_ECOLI metH http://ecmdb.ca/proteins/P13009.xml Protein malY P23256 MALY_ECOLI malY http://ecmdb.ca/proteins/P23256.xml 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase P25665 METE_ECOLI metE http://ecmdb.ca/proteins/P25665.xml Selenocystathionine + Water <> Selenohomocysteine + Ammonia + Pyruvic acid R04941 Selenohomocysteine + 5-Methyltetrahydropteroyltri-L-glutamic acid <> Selenomethionine + Tetrahydropteroyltri-L-glutamic acid R09365