1.0 2011-09-21 00:12:42 UTC 2019-11-26 03:21:02 UTC FDB022358 3-Sulfinoalanine 3-Sulfinoalanine or cysteinesulfinic acid is a N-methyl-D-aspartate agonist. It is a product of cysteine dioxygenase or CDO [EC 1.13.11.20]. In humans cysteine catabolism is tightly regulated via regulation of cysteine dioxygenase (CDO) levels in the liver, with the turnover of CDO protein being dramatically decreased when intracellular cysteine levels increase. This occurs in response to changes in the intracellular cysteine concentration via changes in the rate of CDO ubiquitination and degradation. Expressed at high levels in the liver with lower levels in the kidney, brain, and lung, cysteine dioxygenase catalyzes the addition of molecular oxygen to the sulfhydryl group of cysteine, yielding cysteinesulfinic acid. The oxidative catabolism of cysteine to cysteinesulfinate by CDO represents an irreversible loss of cysteine from the free amino acid pool. Once generated, cysteinesulfinate is shuttled into several pathways including hypotaurine/taurine synthesis, sulfite/sulfate production, and the generation of pyruvate. [HMDB] 2-amino-3-Sulfino-propionate 2-amino-3-Sulfino-propionic acid 2-amino-3-Sulphino-propionate 2-amino-3-Sulphino-propionic acid 3-sulfino- Alanine 3-Sulfino-L-alanine 3-Sulphino-L-alanine Alanine 3-sulfinic acid Cysteine hydrogen sulfite ester Cysteine sulfinate Cysteine sulfinic acid Cysteine-S-dioxide Cysteine-S,S-dioxide L-cysteine sulfinic acid L-Cysteine-S,S-dioxide L-cysteinesulfinic acid C3H6NO4S 152.149 152.001753375 [(2R)-2-amino-2-carboxyethanesulfinyl]oxidanyl [(2R)-2-amino-2-carboxyethanesulfinyl]oxidanyl 1115-65-7 N[C@@H](C[S](=O)=O)C(O)=O InChI=1S/C3H6NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)/t2-/m0/s1 GEAMCHVNTOUKJC-REOHCLBHSA-N belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-alpha-amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Organosulfur compounds Aliphatic acyclic compound Amine Amino acid Carbonyl group Carboxylic acid 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 Solid logp -2.06 ALOGPS logs -0.70 ALOGPS solubility 3.02e+01 g/l ALOGPS logp -4.3 ChemAxon pka_strongest_acidic 1.09 ChemAxon pka_strongest_basic 7.99 ChemAxon iupac [(2R)-2-amino-2-carboxyethanesulfinyl]oxidanyl ChemAxon average_mass 152.149 ChemAxon mono_mass 152.001753375 ChemAxon smiles N[C@@H](C[S](=O)=O)C(O)=O ChemAxon formula C3H6NO4S ChemAxon inchi InChI=1S/C3H6NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)/t2-/m0/s1 ChemAxon inchikey GEAMCHVNTOUKJC-REOHCLBHSA-N ChemAxon polar_surface_area 80.39 ChemAxon refractivity 27.87 ChemAxon polarizability 12.56 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Cysteine Metabolism SMP00013 map00270 Taurine and Hypotaurine Metabolism SMP00021 map00430 HMDB00996 16345 CSW #<Reference:0x000055ce32ada970> #<Reference:0x000055ce32ada6a0> 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 Milk (Cow) Type 2 specific 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 Aspartate aminotransferase, cytoplasmic P17174 GOT1 Aspartate aminotransferase, mitochondrial P00505 GOT2 Cysteine dioxygenase Q16857 CDO-1 Cysteine sulfinic acid decarboxylase Q9Y600 CSAD Glutamate decarboxylase 1 Q99259 GAD1 Glutamate decarboxylase 2 Q05329 GAD2