2.0 2012-05-31 13:58:57 -0600 2015-09-13 12:56:13 -0600 ECMDB03417 M2MDB000498 D-Cysteine Cysteine is a naturally occurring, sulfur-containing amino acid that is a building block to most proteins. Cysteine is unique among the twenty common amino acids because it contains a thiol group. Thiol groups can undergo oxidation of a pair of cysteine residues is oxidised produces cystine, a disulfide-containing derivative. This reaction is reversible. The disulphide bonds of cystine are crucial to defining the structures of many proteins. Related to its redox behavoir, cysteine is incorporated into many proteins that are redox-active, such as the antioxidant glutathione. Cysteine is named after cystine, which comes from the Greek word kustis meaning bladder & D-Amino-3-mercaptopropionate D-Amino-3-mercaptopropionic acid D-Cys C3H7NO2S 121.158 121.019749163 (2S)-2-amino-3-sulfanylpropanoic acid L cysteine 921-01-7 N[C@H](CS)C(O)=O InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m1/s1 XUJNEKJLAYXESH-UWTATZPHSA-N Solid Cytosol Extra-organism Periplasm logp -2.57 ALOGPS logs -0.72 ALOGPS solubility 2.31e+01 g/l ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 2.35 ChemAxon pka_strongest_basic 9.05 ChemAxon iupac (2S)-2-amino-3-sulfanylpropanoic acid ChemAxon average_mass 121.158 ChemAxon mono_mass 121.019749163 ChemAxon smiles N[C@H](CS)C(O)=O ChemAxon formula C3H7NO2S ChemAxon inchi InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m1/s1 ChemAxon inchikey XUJNEKJLAYXESH-UWTATZPHSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 28.22 ChemAxon polarizability 11.4 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Cysteine and methionine metabolism ec00270 Specdb::CMs 3463 Specdb::CMs 38595 Specdb::CMs 136050 Specdb::CMs 143784 Specdb::NmrOneD 1966 Specdb::NmrOneD 21762 Specdb::NmrOneD 21763 Specdb::NmrOneD 21764 Specdb::NmrOneD 21765 Specdb::NmrOneD 21766 Specdb::NmrOneD 21767 Specdb::NmrOneD 21768 Specdb::NmrOneD 21769 Specdb::NmrOneD 21770 Specdb::NmrOneD 21771 Specdb::NmrOneD 21772 Specdb::NmrOneD 21773 Specdb::NmrOneD 21774 Specdb::NmrOneD 21775 Specdb::NmrOneD 21776 Specdb::NmrOneD 21777 Specdb::NmrOneD 21778 Specdb::NmrOneD 21779 Specdb::NmrOneD 21780 Specdb::NmrOneD 21781 Specdb::NmrOneD 166357 Specdb::NmrOneD 166561 Specdb::MsMs 2295 Specdb::MsMs 2296 Specdb::MsMs 2297 Specdb::MsMs 180222 Specdb::MsMs 180223 Specdb::MsMs 180224 Specdb::MsMs 182556 Specdb::MsMs 182557 Specdb::MsMs 182558 Specdb::MsMs 3054320 Specdb::MsMs 3054321 Specdb::MsMs 3054322 Specdb::MsMs 3115507 Specdb::MsMs 3115508 Specdb::MsMs 3115509 Specdb::NmrTwoD 1901 HMDB03417 92851 83819 C00793 16375 D-CYSTEINE DCY 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Tsukamoto S, Kanegae T, Nagoya T, Shimamura M, Mieda Y, Nomura M, Hojo K, Okubo H: Effects of amino acids on acute alcohol intoxication in mice--concentrations of ethanol, acetaldehyde, acetate and acetone in blood and tissues. Arukoru Kenkyuto Yakubutsu Ison. 1990 Oct;25(5):429-40. 2275637 Riemenschneider A, Wegele R, Schmidt A, Papenbrock J: Isolation and characterization of a D-cysteine desulfhydrase protein from Arabidopsis thaliana. FEBS J. 2005 Mar;272(5):1291-304. 15720402 http://hmdb.ca/system/metabolites/msds/000/002/998/original/HMDB03417.pdf?1358462517 D-cysteine desulfhydrase P76316 DCYD_ECOLI dcyD http://ecmdb.ca/proteins/P76316.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 Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml D-Cysteine + Water > Hydrogen sulfide + Ammonium + Pyruvic acid D-Cysteine + Water <> Hydrogen sulfide + Ammonia + Pyruvic acid R01874 D-Cysteine + Water <> Pyruvic acid + Hydrogen sulfide + Ammonia + Hydrogen ion R01874 DCYSDESULF-RXN D-Cysteine + Water > Hydrogen sulfide + Ammonia + Pyruvic acid