1.0 2016-09-30 22:34:23 UTC 2020-05-11 20:37:29 UTC BMDB0000656 BMDB00656 Cysteineglutathione disulfide Cysteineglutathione disulphide CYSSG Cysteine-glutathione disulfide Cysteine-glutathione mixed disulfide Nereithione (2S)-2-Amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulfanyl]-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoate (2S)-2-Amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulphanyl]-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoate (2S)-2-Amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulphanyl]-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid Cysteine glutathione disulphide C13H22N4O8S2 426.466 426.08790508 (2S)-2-amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid (2S)-2-amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulfanyl]-1-(carboxymethylcarbamoyl)ethyl]carbamoyl}butanoic acid 13081-14-6 N[C@@H](CCC(=O)N[C@@H](CSSCC(N)C(O)=O)C(=O)NCC(O)=O)C(O)=O InChI=1S/C13H22N4O8S2/c14-6(12(22)23)1-2-9(18)17-8(11(21)16-3-10(19)20)5-27-26-4-7(15)13(24)25/h6-8H,1-5,14-15H2,(H,16,21)(H,17,18)(H,19,20)(H,22,23)(H,24,25)/t6-,7?,8-/m0/s1 BNRXZEPOHPEEAS-PPSBICQBSA-N belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Oligopeptides Alpha amino acid amides Amino acids Carbonyl compounds Carboxylic acids Cysteine and derivatives Dialkyldisulfides Gamma-glutamyl peptides Glutamine and derivatives Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines N-acyl amines N-acyl-alpha amino acids Organic oxides Organopnictogen compounds Secondary carboxylic acid amides Sulfenyl compounds Tricarboxylic acids and derivatives Aliphatic acyclic compound Alpha-amino acid Alpha-amino acid amide Alpha-amino acid or derivatives Alpha-oligopeptide Amine Amino acid Amino acid or derivatives Carbonyl group Carboxamide group Carboxylic acid Cysteine or derivatives Dialkyldisulfide Fatty acyl Fatty amide Gamma-glutamyl alpha peptide Glutamine or derivatives Hydrocarbon derivative L-alpha-amino acid N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-amine N-substituted-alpha-amino acid Organic disulfide Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Primary aliphatic amine Primary amine Secondary carboxylic acid amide Sulfenyl compound Tricarboxylic acid or derivatives Aliphatic acyclic compounds Solid melting_point 234 °C logp -3.86 ALOGPS logs -2.46 ALOGPS logp -8 ChemAxon pka_strongest_acidic 1.39 ChemAxon pka_strongest_basic 9.5 ChemAxon iupac (2S)-2-amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid ChemAxon average_mass 426.466 ChemAxon mono_mass 426.08790508 ChemAxon smiles N[C@@H](CCC(=O)N[C@@H](CSSCC(N)C(O)=O)C(=O)NCC(O)=O)C(O)=O ChemAxon formula C13H22N4O8S2 ChemAxon inchi InChI=1S/C13H22N4O8S2/c14-6(12(22)23)1-2-9(18)17-8(11(21)16-3-10(19)20)5-27-26-4-7(15)13(24)25/h6-8H,1-5,14-15H2,(H,16,21)(H,17,18)(H,19,20)(H,22,23)(H,24,25)/t6-,7?,8-/m0/s1 ChemAxon inchikey BNRXZEPOHPEEAS-PPSBICQBSA-N ChemAxon polar_surface_area 222.14 ChemAxon refractivity 95.76 ChemAxon polarizability 40.45 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 10 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::NmrTwoD 1403 Specdb::CMs 12506 Specdb::CMs 37676 Specdb::CMs 162365 Specdb::CMs 1071622 Specdb::CMs 1071624 Specdb::CMs 1071626 Specdb::CMs 1071628 Specdb::CMs 1071629 Specdb::CMs 1071631 Specdb::CMs 1071633 Specdb::CMs 1071635 Specdb::CMs 1071637 Specdb::CMs 1071639 Specdb::CMs 1071641 Specdb::CMs 1071643 Specdb::CMs 1071645 Specdb::CMs 1071647 Specdb::CMs 1071649 Specdb::CMs 1071651 Specdb::CMs 1071653 Specdb::CMs 1071655 Specdb::CMs 1071657 Specdb::CMs 1071658 Specdb::CMs 1071660 Specdb::CMs 1071662 Specdb::MsMs 894 Specdb::MsMs 895 Specdb::MsMs 896 Specdb::MsMs 293536 Specdb::MsMs 293537 Specdb::MsMs 293538 Specdb::MsMs 334024 Specdb::MsMs 334025 Specdb::MsMs 334026 Specdb::MsMs 2266152 Specdb::MsMs 2266153 Specdb::MsMs 2266154 Specdb::MsMs 3075441 Specdb::MsMs 3075442 Specdb::MsMs 3075443 Specdb::NmrOneD 1458 Specdb::NmrOneD 144730 Specdb::NmrOneD 144731 Specdb::NmrOneD 144732 Specdb::NmrOneD 144733 Specdb::NmrOneD 144734 Specdb::NmrOneD 144735 Specdb::NmrOneD 144736 Specdb::NmrOneD 144737 Specdb::NmrOneD 144738 Specdb::NmrOneD 144739 Specdb::NmrOneD 144740 Specdb::NmrOneD 144741 Specdb::NmrOneD 144742 Specdb::NmrOneD 144743 Specdb::NmrOneD 144744 Specdb::NmrOneD 144745 Specdb::NmrOneD 144746 Specdb::NmrOneD 144747 Specdb::NmrOneD 144748 Specdb::NmrOneD 144749 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 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 FDB022166 53477713 35013023 143243 5628 Eriksson, Bengt; Eriksson, Stellan A. Synthesis and characterization of the L-cysteine-glutathione mixed disulfide. Acta Chemica Scandinavica (1947-1973) (1967), 21(5), 1304-12.