2.0 2012-05-31 14:53:00 -0600 2015-06-03 17:20:22 -0600 ECMDB20604 M2MDB001404 S-Carboxymethyl-D-cysteine S-carboxymethyl-D-cysteine is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). S-carboxymethyl-D-cysteine is a product of the reaction of D-cysteine desulfhydraase with chloro-D-alanine, which is part of the chloro-alanine degradation process. D-Cysteine desulfhydrase also catalyzes the beta-replacement reaction of the chlorine of 3-chloro-D-alanine with thioglycolic acid to yield S-carboxymethyl-D-cysteine [PMID:3908101] Carboxymethyl-D-cysteine C5H8NO4S 178.186 178.017403439 2-[(2-amino-2-carboxyethyl)sulfanyl]acetate 2-[(2-amino-2-carboxyethyl)sulfanyl]acetate NC(CSCC([O-])=O)C(O)=O InChI=1S/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-1 GBFLZEXEOZUWRN-UHFFFAOYSA-M Cytoplasm Periplasm logp -2.87 ALOGPS logs -0.60 ALOGPS solubility 4.91e+01 g/l ALOGPS logp -3.3 ChemAxon pka_strongest_acidic 1.84 ChemAxon pka_strongest_basic 9.14 ChemAxon iupac 2-[(2-amino-2-carboxyethyl)sulfanyl]acetate ChemAxon average_mass 178.186 ChemAxon mono_mass 178.017403439 ChemAxon smiles NC(CSCC([O-])=O)C(O)=O ChemAxon formula C5H8NO4S ChemAxon inchi InChI=1S/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-1 ChemAxon inchikey GBFLZEXEOZUWRN-UHFFFAOYSA-M ChemAxon polar_surface_area 103.45 ChemAxon refractivity 49.94 ChemAxon polarizability 16.23 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon Specdb::NmrOneD 276018 Specdb::NmrOneD 276019 Specdb::NmrOneD 276020 Specdb::NmrOneD 276021 Specdb::NmrOneD 276022 Specdb::NmrOneD 276023 Specdb::NmrOneD 276024 Specdb::NmrOneD 276025 Specdb::NmrOneD 276026 Specdb::NmrOneD 276027 Specdb::NmrOneD 276028 Specdb::NmrOneD 276029 Specdb::NmrOneD 276030 Specdb::NmrOneD 276031 Specdb::NmrOneD 276032 Specdb::NmrOneD 276033 Specdb::NmrOneD 276034 Specdb::NmrOneD 276035 Specdb::NmrOneD 276036 Specdb::NmrOneD 276037 Specdb::MsMs 25475 Specdb::MsMs 25476 Specdb::MsMs 25477 Specdb::MsMs 32033 Specdb::MsMs 32034 Specdb::MsMs 32035 25203751 14489359 S-CARBOXYMETHYL-D-CYSTEINE 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 D-cysteine desulfhydrase P76316 DCYD_ECOLI dcyD http://ecmdb.ca/proteins/P76316.xml 3-chloro-D-alanine + thioglycolate <> Hydrogen ion + S-Carboxymethyl-D-cysteine + Chloride ALADEHYDCHLORO-RXN