1.0 2016-09-30 22:33:02 UTC 2020-05-21 16:29:27 UTC BMDB0000574 BMDB00574 L-Cysteine L-Cysteine, also known as C or e 920, belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Cysteine is a drug which is used for the prevention of liver damage and kidney damage associated with overdoses of acetaminophen. L-Cysteine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Cysteine exists in all living species, ranging from bacteria to humans. L-Cysteine participates in a number of enzymatic reactions, within cattle. In particular, L-Cysteine can be converted into 3-sulfinoalanine through its interaction with the enzyme cysteine dioxygenase type 1. In addition, L-Cysteine can be converted into hydrogen sulfide and pyruvic acid through its interaction with the enzyme cystathionine gamma-lyase. In cattle, L-cysteine is involved in the metabolic pathway called the cysteine metabolism pathway. L-Cysteine is a potentially toxic compound. (2R)-2-Amino-3-mercaptopropanoic acid (2R)-2-Amino-3-sulfanylpropanoic acid (R)-2-Amino-3-mercaptopropanoic acid C Cys CYSTEINE e 920 e-920 e920 FREE cysteine L-2-Amino-3-mercaptopropionic acid L-Cystein L-Zystein Ecolan (2R)-2-Amino-3-mercaptopropanoate (2R)-2-Amino-3-sulfanylpropanoate (2R)-2-Amino-3-sulphanylpropanoate (2R)-2-Amino-3-sulphanylpropanoic acid (R)-2-Amino-3-mercaptopropanoate L-2-Amino-3-mercaptopropionate (+)-2-Amino-3-mercaptopropionic acid (R)-(+)-Cysteine (R)-2-Amino-3-mercapto-propanoate (R)-2-Amino-3-mercapto-propanoic acid (R)-Cysteine 2-Amino-3-mercaptopropanoate 2-Amino-3-mercaptopropanoic acid 2-Amino-3-mercaptopropionate 2-Amino-3-mercaptopropionic acid 3-Mercapto-L-alanine Acetylcysteine alpha-Amino-beta-thiolpropionic acid b-Mercaptoalanine beta-Mercaptoalanine Carbocysteine Cisteina Cisteinum Cystein Cysteinum Half-cystine L Cysteine L-(+)-Cysteine L-2-Amino-3-mercaptopropanoate L-2-Amino-3-mercaptopropanoic acid Polycysteine Thioserine Cysteine hydrochloride Zinc cysteinate Half cystine C3H7NO2S 121.158 121.019749163 (2R)-2-amino-3-sulfanylpropanoic acid L-cysteine 52-90-4 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-/m0/s1 XUJNEKJLAYXESH-REOHCLBHSA-N belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Cysteine and derivatives Alkylthiols Amino acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Aliphatic acyclic compound Alkylthiol Alpha-amino acid Amine Amino acid Carbonyl group Carboxylic acid Cysteine or derivatives Hydrocarbon derivative L-alpha-amino acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Primary aliphatic amine Primary amine Aliphatic acyclic compounds Common amino acids L-alpha-amino acid cysteine proteinogenic amino acid serine family amino acid Solid melting_point 220 °C water_solubility 277 mg/mL at 25 °C BEILSTEIN logp -2.49 HANSCH,C ET AL. (1995) logp -2.57 ALOGPS logs -0.72 ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 2.35 ChemAxon pka_strongest_basic 9.05 ChemAxon iupac (2R)-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-/m0/s1 ChemAxon inchikey XUJNEKJLAYXESH-REOHCLBHSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 28.22 ChemAxon polarizability 11.41 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 3 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 Cysteine Metabolism SMP0087189 Glutamate Metabolism SMP0087169 Glutathione Metabolism SMP0087167 Glycine and Serine Metabolism SMP0087245 Homocysteine Degradation SMP0087201 Kidney Function SMP0119376 Methionine Metabolism SMP0087249 Pantothenate and CoA Biosynthesis SMP0087207 Protein Synthesis: Cysteine SMP0119388 Taurine and Hypotaurine Metabolism SMP0087214 Specdb::CMs 572 Specdb::CMs 573 Specdb::CMs 574 Specdb::CMs 575 Specdb::CMs 576 Specdb::CMs 3282 Specdb::CMs 30101 Specdb::CMs 30201 Specdb::CMs 30306 Specdb::CMs 30307 Specdb::CMs 30592 Specdb::CMs 30734 Specdb::CMs 30756 Specdb::CMs 31774 Specdb::CMs 37632 Specdb::CMs 146278 Specdb::CMs 1066885 Specdb::CMs 1066887 Specdb::CMs 1066889 Specdb::CMs 1066890 Specdb::CMs 1066892 Specdb::MsIr 649 Specdb::MsIr 650 Specdb::MsIr 651 Specdb::NmrTwoD 1024 Specdb::NmrTwoD 1371 Specdb::NmrOneD 1241 Specdb::NmrOneD 1426 Specdb::NmrOneD 4743 Specdb::NmrOneD 144450 Specdb::NmrOneD 144451 Specdb::NmrOneD 144452 Specdb::NmrOneD 144453 Specdb::NmrOneD 144454 Specdb::NmrOneD 144455 Specdb::NmrOneD 144456 Specdb::NmrOneD 144457 Specdb::NmrOneD 144458 Specdb::NmrOneD 144459 Specdb::NmrOneD 144460 Specdb::NmrOneD 144461 Specdb::NmrOneD 144462 Specdb::NmrOneD 144463 Specdb::NmrOneD 144464 Specdb::NmrOneD 144465 Specdb::NmrOneD 144466 Specdb::NmrOneD 144467 Specdb::NmrOneD 144468 Specdb::NmrOneD 144469 Specdb::NmrOneD 166443 Specdb::MsMs 800 Specdb::MsMs 801 Specdb::MsMs 802 Specdb::MsMs 4204 Specdb::MsMs 4205 Specdb::MsMs 4206 Specdb::MsMs 4207 Specdb::MsMs 4208 Specdb::MsMs 4209 Specdb::MsMs 4210 Specdb::MsMs 4211 Specdb::MsMs 4217 Specdb::MsMs 179826 Specdb::MsMs 179827 Specdb::MsMs 179828 Specdb::MsMs 182160 Specdb::MsMs 182161 Specdb::MsMs 182162 Specdb::MsMs 447649 Specdb::MsMs 447738 Specdb::MsMs 1471148 Specdb::MsMs 2226479 Specdb::MsMs 2228252 Specdb::MsMs 2228881 Specdb::MsMs 2230541 Adrenal Cortex 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 Epidermis 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 Fibroblasts 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 Intestine 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 Kidney 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 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 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 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 By UPLC-Q-TOF Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. 29565828 Neuron 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 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 Platelet 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 Prostate Tissue 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 Skeletal Muscle 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 Spleen 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 Testis 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 Thyroid Gland 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 FDB012678 C00097 5653 5862 17561 DB00151 CYS C00001351 33843 Cysteine 5556 Kumagai, Hidehiko; Tanaka, Hideyuki; Sejima, Shunsuke; Yamada, Hideaki. Elimination and replacement reactions of b-chloro-L-alanine by cysteine desulfhydrase from Aerobacter aerogenes. Agricultural and Biological Chemistry (1977), 41(10), 2071-5. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. 29565828 BMDBP00233 Disintegrin and metalloproteinase domain-containing protein 10 Q10741 ADAM10 Enzyme BMDBP00567 Aspartate aminotransferase, cytoplasmic P33097 GOT1 Enzyme BMDBP00683 Cysteine dioxygenase type 1 Q3SZU4 CDO1 Enzyme BMDBP00811 Interstitial collagenase P28053 MMP1 Enzyme BMDBP00812 Cysteine--tRNA ligase, mitochondrial Q2KIF8 CARS2 Enzyme BMDBP00813 Matrix metalloproteinase-9 P52176 MMP9 Enzyme BMDBP00814 Matrix metalloproteinase-14 Q9GLE4 MMP14 Enzyme BMDBP00815 Collagenase 3 O77656 MMP13 Enzyme BMDBP00816 Matrix metalloproteinase-20 O18767 MMP20 Enzyme BMDBP00817 Methylated-DNA--protein-cysteine methyltransferase P29177 MGMT Enzyme BMDBP00818 Cystathionine gamma-lyase Q58DW2 CTH Enzyme BMDBP00819 72 kDa type IV collagenase Q9GLE5 MMP2 Enzyme BMDBP00820 A disintegrin and metalloproteinase with thrombospondin motifs 4 Q9TT93 ADAMTS4 Enzyme BMDBP01217 Glutamate-cysteine ligase catalytic subunit Q32S38 GCLC Enzyme BMDBP01242 Gamma-glutamylcyclotransferase Q32LE4 GGCT Enzyme BMDBP02004 Calpastatin P20811 CAST Enzyme BMDBP02852 Glutamate--cysteine ligase regulatory subunit Q2T9Y6 GCLM Enzyme BMDBP03009 CARS protein A4FUC8 CARS1 Enzyme