1.0 2016-09-30 22:40:22 UTC 2020-05-21 16:28:25 UTC BMDB0001049 BMDB01049 Gamma-Glutamylcysteine 5-L-Glutamyl-L-cysteine gamma-Glu-cys gamma-L-Glutamyl-L-cysteine L-gamma-Glutamylcysteine g-Glu-cys Γ-glu-cys g-L-Glutamyl-L-cysteine Γ-L-glutamyl-L-cysteine L-g-Glutamylcysteine L-Γ-glutamylcysteine g-Glutamylcysteine Γ-glutamylcysteine Γ-L-glu-L-cys L-Γ-glutamyl-L-cysteine N-Γ-glutamylcysteine N-L-Γ-glutamylcysteine N-L-Γ-glutamyl-L-cysteine gamma-L-Glu-L-cys L-gamma-Glutamyl-L-cysteine N-gamma-Glutamylcysteine N-L-gamma-Glutamylcysteine N-L-gamma-Glutamyl-L-cysteine 5-L-Glutamylcysteine H-gamma-Glu-cys-OH L-g-Glutamyl-L-cysteine N-Γ-L-glutamyl-L-cysteine gamma-Glutamylcysteine C8H14N2O5S 250.272 250.062342258 (2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid gamma-glutamylcysteine 636-58-8 N[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1 RITKHVBHSGLULN-WHFBIAKZSA-N belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues N-acyl-alpha amino acids Alkylthiols Amino acids Carbonyl compounds Carboximidic acids Carboxylic acids Cysteine and derivatives Dicarboxylic acids and derivatives Fatty acids and conjugates Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines Organic oxides Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Aliphatic acyclic compound Alkylthiol Alpha-amino acid Amine Amino acid Carbonyl group Carboximidic acid Carboximidic acid derivative Carboxylic acid Cysteine or derivatives Dicarboxylic acid or derivatives Fatty acid Hydrocarbon derivative L-alpha-amino acid N-acyl-alpha-amino acid Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Primary aliphatic amine Primary amine Propargyl-type 1,3-dipolar organic compound Aliphatic acyclic compounds gamma-glutamylcysteine Solid logp -2.53 ALOGPS logs -1.98 ALOGPS logp -3.8 ChemAxon pka_strongest_acidic 1.91 ChemAxon pka_strongest_basic 9.24 ChemAxon iupac (2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid ChemAxon average_mass 250.272 ChemAxon mono_mass 250.062342258 ChemAxon smiles N[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O ChemAxon formula C8H14N2O5S ChemAxon inchi InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1 ChemAxon inchikey RITKHVBHSGLULN-WHFBIAKZSA-N ChemAxon polar_surface_area 129.72 ChemAxon refractivity 56.31 ChemAxon polarizability 23.36 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge -1 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 Specdb::CMs 698 Specdb::CMs 3015 Specdb::CMs 30722 Specdb::CMs 37904 Specdb::CMs 172234 Specdb::NmrTwoD 1577 Specdb::NmrOneD 1636 Specdb::NmrOneD 8382 Specdb::NmrOneD 8383 Specdb::NmrOneD 8384 Specdb::NmrOneD 8385 Specdb::NmrOneD 8386 Specdb::NmrOneD 8387 Specdb::NmrOneD 8388 Specdb::NmrOneD 8389 Specdb::NmrOneD 8390 Specdb::NmrOneD 8391 Specdb::NmrOneD 8392 Specdb::NmrOneD 8393 Specdb::NmrOneD 8394 Specdb::NmrOneD 8395 Specdb::NmrOneD 8396 Specdb::NmrOneD 8397 Specdb::NmrOneD 8398 Specdb::NmrOneD 8399 Specdb::NmrOneD 8400 Specdb::NmrOneD 8401 Specdb::MsMs 1400 Specdb::MsMs 1401 Specdb::MsMs 1402 Specdb::MsMs 5038 Specdb::MsMs 179316 Specdb::MsMs 179317 Specdb::MsMs 179318 Specdb::MsMs 181641 Specdb::MsMs 181642 Specdb::MsMs 181643 Specdb::MsMs 448145 Specdb::MsMs 2252663 Specdb::MsMs 2253828 Specdb::MsMs 2254673 Specdb::MsMs 2255888 Specdb::MsMs 2378503 Specdb::MsMs 2378504 Specdb::MsMs 2378505 Specdb::MsMs 2557701 Specdb::MsMs 2557702 Specdb::MsMs 2557703 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 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 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 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 C00669 110467 DB03408 FDB003603 123938 17515 L-GAMMA-GLUTAMYLCYSTEINE C00007507 35655 Gamma-Glutamylcysteine 5966 Bridge, Wallace John; Zarka, Martin Hani. Enzymic production of g-glutamylcysteine. PCT Int. Appl. (2006), 76pp. BMDBP00197 Glutathione synthetase Q5EAC2 GSS Enzyme BMDBP01217 Glutamate-cysteine ligase catalytic subunit Q32S38 GCLC Enzyme BMDBP01242 Gamma-glutamylcyclotransferase Q32LE4 GGCT Enzyme BMDBP02852 Glutamate--cysteine ligase regulatory subunit Q2T9Y6 GCLM Enzyme