1.0 2011-09-21 00:26:16 UTC 2015-07-21 06:57:35 UTC FDB023203 Thiocysteine The reactive species in the phosphofructokinase modulation system could be considered thiocysteine (R-S-S-) or cystine trisulfide (R-S-S-S-R) produced from cystine in the presence of gamma-Cystathionase (CST, EC 4.4.1.1). The desulfuration reaction of cystine in vivo produces thiocysteine containing a bound sulfur atom. Persulfide generated from L-cysteine inactivates tyrosine aminotransferase. Thiocysteine is the reactive (unstable) intermediate of thiocystine which functions as a persulfide in transferring its sulfane sulfur to thiophilic acceptors. Thiocystine conversion to unstable thiocysteine is accelerated by sulfhydryl compounds, or reagents that cleave sulfur-sulfur bonds to yield sulfhydryl groups. Thiocystine is proposed as the storage form of sulfane sulfur in biological systems. Liver cytosols contain factors that produce an inhibitor of tyrosine aminotransferase in 3 steps: initial oxidation of cysteine to form cystine; desulfurization of cystine catalyzed by cystathionase to form the persulfide, thiocysteine; and reaction of thiocysteine (or products of its decomposition) with proteins to form protein-bound sulfane. (PMID: 2903161, 454618, 7287665) [HMDB] 3-(thiosulfeno)-Alanine 3-Disulfanyl-L-alanine C3H7NO2S2 153.223 152.991819853 (2S)-2-amino-3-disulfanylpropanoic acid (2S)-2-amino-3-disulfanylpropanoic acid 5652-32-4 N[C@H](CSS)C(O)=O InChI=1S/C3H7NO2S2/c4-2(1-8-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m1/s1 XBKONSCREBSMCS-UWTATZPHSA-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. Cysteine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboxylic acids D-alpha-amino acids Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Sulfenyl compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Carbonyl group Carboxylic acid Cysteine or derivatives D-alpha-amino acid Hydrocarbon derivative 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 Sulfenyl compound Solid logp -2.04 ALOGPS logs -1.03 ALOGPS solubility 1.43e+01 g/l ALOGPS logp -2.4 ChemAxon pka_strongest_acidic 2.04 ChemAxon pka_strongest_basic 8.9 ChemAxon iupac (2S)-2-amino-3-disulfanylpropanoic acid ChemAxon average_mass 153.223 ChemAxon mono_mass 152.991819853 ChemAxon smiles N[C@H](CSS)C(O)=O ChemAxon formula C3H7NO2S2 ChemAxon inchi InChI=1S/C3H7NO2S2/c4-2(1-8-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m1/s1 ChemAxon inchikey XBKONSCREBSMCS-UWTATZPHSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 33.99 ChemAxon polarizability 14.19 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 2013 Specdb::MsIr 2014 Specdb::MsIr 2015 Specdb::CMs 11726 Specdb::CMs 38636 Specdb::CMs 152131 Specdb::MsMs 291892 Specdb::MsMs 291893 Specdb::MsMs 291894 Specdb::MsMs 331918 Specdb::MsMs 331919 Specdb::MsMs 331920 Specdb::MsMs 2677860 Specdb::MsMs 2677861 Specdb::MsMs 2677862 Specdb::MsMs 3031193 Specdb::MsMs 3031194 Specdb::MsMs 3031195 Specdb::NmrOneD 28382 Specdb::NmrOneD 28383 Specdb::NmrOneD 28384 Specdb::NmrOneD 28385 Specdb::NmrOneD 28386 Specdb::NmrOneD 28387 Specdb::NmrOneD 28388 Specdb::NmrOneD 28389 Specdb::NmrOneD 28390 Specdb::NmrOneD 28391 Specdb::NmrOneD 28392 Specdb::NmrOneD 28393 Specdb::NmrOneD 28394 Specdb::NmrOneD 28395 Specdb::NmrOneD 28396 Specdb::NmrOneD 28397 Specdb::NmrOneD 28398 Specdb::NmrOneD 28399 Specdb::NmrOneD 28400 Specdb::NmrOneD 28401 HMDB03585 28839 #<Reference:0x000055ce33056548> #<Reference:0x000055ce330562c8> #<Reference:0x000055ce330560e8> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Cystathionine gamma-lyase P32929 CTH