2.02012-05-31 14:53:00 -06002015-06-03 17:20:22 -0600ECMDB20604M2MDB001404S-Carboxymethyl-D-cysteineS-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-cysteineC5H8NO4S178.186178.0174034392-[(2-amino-2-carboxyethyl)sulfanyl]acetate2-[(2-amino-2-carboxyethyl)sulfanyl]acetateNC(CSCC([O-])=O)C(O)=OInChI=1S/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-1GBFLZEXEOZUWRN-UHFFFAOYSA-MCytoplasmPeriplasmlogp-2.87logs-0.60solubility4.91e+01 g/llogp-3.3pka_strongest_acidic1.84pka_strongest_basic9.14iupac2-[(2-amino-2-carboxyethyl)sulfanyl]acetateaverage_mass178.186mono_mass178.017403439smilesNC(CSCC([O-])=O)C(O)=OformulaC5H8NO4SinchiInChI=1S/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-1inchikeyGBFLZEXEOZUWRN-UHFFFAOYSA-Mpolar_surface_area103.45refractivity49.94polarizability16.23rotatable_bond_count5acceptor_count5donor_count2physiological_charge-1formal_charge-1Specdb::NmrOneD276018Specdb::NmrOneD276019Specdb::NmrOneD276020Specdb::NmrOneD276021Specdb::NmrOneD276022Specdb::NmrOneD276023Specdb::NmrOneD276024Specdb::NmrOneD276025Specdb::NmrOneD276026Specdb::NmrOneD276027Specdb::NmrOneD276028Specdb::NmrOneD276029Specdb::NmrOneD276030Specdb::NmrOneD276031Specdb::NmrOneD276032Specdb::NmrOneD276033Specdb::NmrOneD276034Specdb::NmrOneD276035Specdb::NmrOneD276036Specdb::NmrOneD276037Specdb::MsMs25475Specdb::MsMs25476Specdb::MsMs25477Specdb::MsMs32033Specdb::MsMs32034Specdb::MsMs320352520375114489359S-CARBOXYMETHYL-D-CYSTEINEKeseler, 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-D590.21097882van 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 370:17-25.17765195D-cysteine desulfhydraseP76316DCYD_ECOLIdcyDhttp://ecmdb.ca/proteins/P76316.xml3-chloro-D-alanine + thioglycolate <> Hydrogen ion + S-Carboxymethyl-D-cysteine + ChlorideALADEHYDCHLORO-RXN