1.0 2016-09-30 22:26:32 UTC 2020-06-04 21:10:52 UTC BMDB0000192 BMDB00192 L-Cystine Cystine, also known as L-dicysteine or E921, belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated. Cystine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Cystine exists in all living species, ranging from bacteria to humans. Cystine has been found to be associated with several diseases known as molybdenum cofactor deficiency, schizophrenia, parkinson's disease, and colorectal cancer; also cystine has been linked to the inborn metabolic disorders including fumarase deficiency. (R,R)-3,3'-Dithiobis(2-aminopropanoic acid) (R-(R*,r*))-3,3'-dithiobis(2-aminopropanoic acid) 3,3'-Dithiobis-L-alanine beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulfide beta,Beta'-dithiodialanine Bis(beta-amino-beta-carboxyethyl) disulfide e921 L-alpha-Diamino-beta-dithiolactic acid L-Dicysteine Oxidized L-cysteine (R,R)-3,3'-Dithiobis(2-aminopropanoate) (R-(R*,r*))-3,3'-dithiobis(2-aminopropanoate) b,Beta'-diamino-b,beta'-dicarboxydiethyl disulfide b,Beta'-diamino-b,beta'-dicarboxydiethyl disulphide beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulphide Β,beta'-diamino-β,beta'-dicarboxydiethyl disulfide Β,beta'-diamino-β,beta'-dicarboxydiethyl disulphide b,Beta'-dithiodialanine Β,beta'-dithiodialanine Bis(b-amino-b-carboxyethyl) disulfide Bis(b-amino-b-carboxyethyl) disulphide Bis(beta-amino-beta-carboxyethyl) disulphide Bis(β-amino-β-carboxyethyl) disulfide Bis(β-amino-β-carboxyethyl) disulphide L-a-Diamino-b-dithiolactate L-a-Diamino-b-dithiolactic acid L-alpha-Diamino-beta-dithiolactate L-Α-diamino-β-dithiolactate L-Α-diamino-β-dithiolactic acid (-)-Cystine (R-(R*,r*))-3,3'-dithiobis 2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoate 2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic acid 2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoate 2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acid 3,3'-Dithiobis 3,3'-Dithiobis[2-amino-[R-(r*,r*)]-propanoate 3,3'-Dithiobis[2-amino-[R-(r*,r*)]-propanoic acid 3,3'-Dithiodialanine b,B'-diamino-b,b'-dicarboxydiethyl disulfide b,B'-dithiodialanine beta,Beta'-dithiobisalanine Bis(b-amino-beta-carboxyethyl) disulfide Cysteine disulfide Cystin Cystine Cystine acid D(+)-3,3'-Dithiobis(2-aminopropanoate D(+)-3,3'-Dithiobis(2-aminopropanoic acid Dicysteine Gelucystine L-(-)-Cystine L-Cysteine disulfide L-Cystin [R-(R*,r*)]-3,3'-dithiobis L Cystine Copper cystinate L-Cystine C6H12N2O4S2 240.3 240.023848262 (2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid L-cystine 56-89-3 N[C@@H](CSSC[C@H](N)C(O)=O)C(O)=O InChI=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/s1 LEVWYRKDKASIDU-IMJSIDKUSA-N belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues L-cysteine-S-conjugates Amino acids Carbonyl compounds Carboxylic acids Dialkyldisulfides Dicarboxylic acids and derivatives Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines Organic oxides Organopnictogen compounds Sulfenyl compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Carbonyl group Carboxylic acid Dialkyldisulfide Dicarboxylic acid or derivatives Hydrocarbon derivative L-alpha-amino acid L-cysteine-s-conjugate Organic disulfide Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Primary aliphatic amine Primary amine Sulfenyl compound Aliphatic acyclic compounds L-cysteine derivative cystine non-proteinogenic L-alpha-amino acid Solid melting_point 260.5 °C water_solubility 0.19 mg/mL logp -5.08 CHMELIK,J ET AL. (1991) logp -3.16 ALOGPS logs -1.16 ALOGPS logp -5.9 ChemAxon pka_strongest_acidic 1.56 ChemAxon pka_strongest_basic 9.34 ChemAxon iupac (2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid ChemAxon average_mass 240.3 ChemAxon mono_mass 240.023848262 ChemAxon smiles N[C@@H](CSSC[C@H](N)C(O)=O)C(O)=O ChemAxon formula C6H12N2O4S2 ChemAxon inchi InChI=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/s1 ChemAxon inchikey LEVWYRKDKASIDU-IMJSIDKUSA-N ChemAxon polar_surface_area 126.64 ChemAxon refractivity 54.87 ChemAxon polarizability 22.77 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::EiMs 1720 Specdb::NmrTwoD 991 Specdb::NmrTwoD 1197 Specdb::NmrOneD 1167 Specdb::NmrOneD 4182 Specdb::NmrOneD 4987 Specdb::NmrOneD 4988 Specdb::NmrOneD 4989 Specdb::NmrOneD 4990 Specdb::CMs 441 Specdb::CMs 442 Specdb::CMs 443 Specdb::CMs 1955 Specdb::CMs 3266 Specdb::CMs 30366 Specdb::CMs 30789 Specdb::CMs 31061 Specdb::CMs 31775 Specdb::CMs 31959 Specdb::CMs 37348 Specdb::CMs 154243 Specdb::CMs 1053872 Specdb::CMs 1053874 Specdb::CMs 1053876 Specdb::CMs 1053878 Specdb::CMs 1053879 Specdb::CMs 1053881 Specdb::CMs 1053883 Specdb::CMs 1053885 Specdb::CMs 1053887 Specdb::CMs 1053888 Specdb::CMs 1053890 Specdb::CMs 1053892 Specdb::CMs 1053894 Specdb::MsMs 307 Specdb::MsMs 308 Specdb::MsMs 309 Specdb::MsMs 179796 Specdb::MsMs 179797 Specdb::MsMs 179798 Specdb::MsMs 182130 Specdb::MsMs 182131 Specdb::MsMs 182132 Specdb::MsMs 1471165 Specdb::MsMs 1471937 Specdb::MsMs 1471938 Specdb::MsMs 1471939 Specdb::MsMs 1471940 Specdb::MsMs 1471941 Specdb::MsMs 1471942 Specdb::MsMs 1471943 Specdb::MsMs 1471944 Specdb::MsMs 1471945 Specdb::MsMs 1471946 Specdb::MsMs 1471947 Specdb::MsMs 1471948 Specdb::MsMs 1471949 Specdb::MsMs 1471950 Specdb::MsMs 1471951 All Tissues Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk Milk from Friesuan Holstein cows (n=1035) Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 Milk 1123.596 uM Milk, partly skim, conventional (not organic), 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 1123.596 uM Milk, partly skim, organic, 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 1123.596 uM Skim milk Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 1123.596 uM Milk, skim, organic Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 1081.981 uM Milk, whole, 3.5, (UHT), % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 1081.981 uM Milk, whole, conventional (not organic), 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 1081.981 uM Milk, whole, organic, 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Semen From 5 bulls Sexton TJ, Amann RP, Flipse RJ: Free amino acids and protein in rete testis fluid, vas deferens plasma, accessory sex gland fluid, and seminal plasma of the conscious bull. J Dairy Sci. 1971 Mar;54(3):412-6. doi: 10.3168/jds.s0022-0302(71)85854-x. 5096119 Testis From 5 bulls Sexton TJ, Amann RP, Flipse RJ: Free amino acids and protein in rete testis fluid, vas deferens plasma, accessory sex gland fluid, and seminal plasma of the conscious bull. J Dairy Sci. 1971 Mar;54(3):412-6. doi: 10.3168/jds.s0022-0302(71)85854-x. 5096119 C00491 FDB012672 DB00138 67678 60997 16283 C00001352 Cystine 35134 5207 Grossi, Loris; Montevecchi, Pier Carlo. S-Nitrosocysteine and Cystine from Reaction of Cysteine with Nitrous Acid. A Kinetic Investigation. Journal of Organic Chemistry (2002), 67(24), 8625-8630. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241 Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. 29291809 Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en