2.02012-05-31 10:23:28 -06002015-09-13 12:56:06 -0600ECMDB00192M2MDB000081L-CystineCystine is an oxidized dimeric form of cysteine. It is formed by linking two cysteine residues via a disulfide bond (cys-S-S-cys) between the -SH groups. The L-cysteine transporter, YdeD, is required for the tolerance of E. coli cells to hydrogen peroxide. L-cystine, a product from the oxidation of L-cysteine by hydrogen peroxide, is imported back into the cytoplasm in a manner dependent on the periplasmic L-cystine-binding protein (FliY). This protein is involved in the recycling of the oxidized L-cysteine and is important for the hydrogen peroxide resistance of E. coli. In E. coli the L-cysteine/L-cystine shuttle system plays an important role in oxidative stress tolerance through providing a reducing equivalent to the periplasm in E. coli.(-)-Cystine(R-(R*,R*))-3,3'-Dithiobis2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoate2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic acid2-Amino-3-(2-amino-2-carboxy-ethyl)disulphanyl-propanoate2-Amino-3-(2-amino-2-carboxy-ethyl)disulphanyl-propanoic acid2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoate2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acid3,3'-Dithiobis3,3'-Dithiobis-L-Alanine3,3'-Dithiobis[2-amino-[R-(R*,R*)]-Propanoate3,3'-Dithiobis[2-amino-[R-(R*,R*)]-Propanoic acid3,3'-DithiodialanineB,b'-Diamino-b,b'-dicarboxydiethyl disulfideb,B'-diamino-b,b'-dicarboxydiethyl disulphideB,b'-Dithiodialanineb,Beta'-diamino-b,b'-dicarboxydiethyl disulfideb,Beta'-diamino-b,b'-dicarboxydiethyl disulphideb,Beta'-dithiobisalanineb,Beta'-dithiodialanineBeta,beta'-Diamino-b,b'-dicarboxydiethyl disulfideBeta,beta'-Diamino-b,b'-dicarboxydiethyl disulphideBeta,beta'-DithiobisalanineBeta,beta'-DithiodialanineBis(b-amino-b-carboxyethyl) disulfideBis(b-amino-b-carboxyethyl) disulphideBis(b-amino-beta-carboxyethyl) disulfideBis(b-amino-beta-carboxyethyl) disulphideBis(b-amino-β-carboxyethyl) disulfideBis(b-amino-β-carboxyethyl) disulphideCysteine disulfideCysteine disulphideCystinCystineCystine acidD(+)-3,3'-Dithiobis(2-aminopropanoateD(+)-3,3'-Dithiobis(2-aminopropanoate)D(+)-3,3'-Dithiobis(2-aminopropanoic acidD(+)-3,3'-Dithiobis(2-aminopropanoic acid)DicysteineGelucystineL-(-)-CystineL-Cysteine disulfideL-Cysteine disulphideL-CystinL-CystineOxidized L-cysteine[R-(R*,R*)]-3,3'-Dithiobisβ,Beta'-diamino-b,b'-dicarboxydiethyl disulfideβ,Beta'-diamino-b,b'-dicarboxydiethyl disulphideβ,Beta'-dithiobisalanineβ,Beta'-dithiodialanineC6H12N2O4S2240.3240.023848262(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acidL-cystine56-89-3N[C@@H](CSSC[C@H](N)C(O)=O)C(O)=OInChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1LEVWYRKDKASIDU-IMJSIDKUSA-NSolidCytoplasmPeriplasmlogp-3.16logs-1.16solubility1.68e+01 g/lmelting_point260.5 oClogp-5.9pka_strongest_acidic1.56pka_strongest_basic9.34iupac(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acidaverage_mass240.3mono_mass240.023848262smilesN[C@@H](CSSC[C@H](N)C(O)=O)C(O)=OformulaC6H12N2O4S2inchiInChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1inchikeyLEVWYRKDKASIDU-IMJSIDKUSA-Npolar_surface_area126.64refractivity54.87polarizability22.77rotatable_bond_count7acceptor_count6donor_count4physiological_charge0formal_charge0Cysteine and methionine metabolismec00270ABC transportersec02010Specdb::CMs441Specdb::CMs442Specdb::CMs443Specdb::CMs1955Specdb::CMs3266Specdb::CMs30366Specdb::CMs30789Specdb::CMs31061Specdb::CMs31775Specdb::CMs31959Specdb::CMs37348Specdb::CMs154243Specdb::CMs1053872Specdb::CMs1053874Specdb::CMs1053876Specdb::CMs1053878Specdb::CMs1053879Specdb::CMs1053881Specdb::CMs1053883Specdb::CMs1053885Specdb::CMs1053887Specdb::CMs1053888Specdb::CMs1053890Specdb::CMs1053892Specdb::CMs1053894Specdb::EiMs1720Specdb::NmrOneD1167Specdb::NmrOneD4182Specdb::NmrOneD4987Specdb::NmrOneD4988Specdb::NmrOneD4989Specdb::NmrOneD4990Specdb::MsMs307Specdb::MsMs308Specdb::MsMs309Specdb::MsMs179796Specdb::MsMs179797Specdb::MsMs179798Specdb::MsMs182130Specdb::MsMs182131Specdb::MsMs182132Specdb::MsMs1471165Specdb::MsMs1471937Specdb::MsMs1471938Specdb::MsMs1471939Specdb::MsMs1471940Specdb::MsMs1471941Specdb::MsMs1471942Specdb::MsMs1471943Specdb::MsMs1471944Specdb::MsMs1471945Specdb::MsMs1471946Specdb::MsMs1471947Specdb::MsMs1471948Specdb::MsMs1471949Specdb::MsMs1471950Specdb::MsMs1471951Specdb::NmrTwoD991Specdb::NmrTwoD1197HMDB001926767860997C0049116283CYSTINECystineKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510Winder, 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." 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Journal of Organic Chemistry (2002), 67(24), 8625-8630.http://hmdb.ca/system/metabolites/msds/000/000/135/original/HMDB00192.pdf?1358894670Cystathionine beta-lyase metCP06721METC_ECOLImetChttp://ecmdb.ca/proteins/P06721.xmlProtein malYP23256MALY_ECOLImalYhttp://ecmdb.ca/proteins/P23256.xmlL-Cystine + Water <> Pyruvic acid + Ammonia + ThiocysteineR02408