2.0 2012-05-31 13:03:03 -0600 2015-09-13 12:56:09 -0600 ECMDB00996 M2MDB000218 3-Sulfinoalanine 3-Sulfinoalanine or cysteinesulfinic acid is a N-methyl-D-aspartate agonist. It is a prodcut of cysteine dioxygenase or CDO [EC 1.13.11.20]. 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. 3-Sulfino- Alanine 3-Sulfino-L-alanine 3-Sulphino- Alanine 3-Sulphino-L-alanine 3-Sulphinoalanine Alanine 3-sulfinate Alanine 3-sulfinic acid Alanine 3-sulphinate Alanine 3-sulphinic acid Cysteine hydrogen sulfite ester Cysteine hydrogen sulphite ester Cysteine sulfinate Cysteine sulfinic acid Cysteine sulphinate Cysteine sulphinic acid Cysteine-sulfinate Cysteine-sulfinic acid Cysteine-sulphinate Cysteine-sulphinic acid L-Cysteine sulfinate L-Cysteine sulfinic acid L-Cysteine sulphinate L-Cysteine sulphinic acid L-Cysteinesulfinate L-Cysteinesulfinic acid L-Cysteinesulphinate L-Cysteinesulphinic acid C3H7NO4S 153.157 153.009578407 [({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid udp-α-D-glucose 1115-65-7 N[C@@H](CS(=O)=O)C(O)=O InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2,9H,1,4H2,(H,5,6)/t2-/m0/s1 WVMUCBHSEHBMKA-REOHCLBHSA-N Solid Cytosol logp -1.43 ALOGPS logs -1.58 ALOGPS solubility 1.50e+01 g/l ALOGPS logp -5 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac [({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid ChemAxon average_mass 153.157 ChemAxon mono_mass 153.009578407 ChemAxon smiles N[C@@H](CS(=O)=O)C(O)=O ChemAxon formula C3H7NO4S ChemAxon inchi InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2,9H,1,4H2,(H,5,6)/t2-/m0/s1 ChemAxon inchikey WVMUCBHSEHBMKA-REOHCLBHSA-N ChemAxon polar_surface_area 291.54 ChemAxon refractivity 106.46 ChemAxon polarizability 45.39 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 14 ChemAxon donor_count 9 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Cysteine and methionine metabolism ec00270 Taurine and hypotaurine metabolism ec00430 Specdb::CMs 36799 Specdb::CMs 48056 Specdb::CMs 282129 Specdb::CMs 359703 Specdb::CMs 359704 Specdb::CMs 359705 Specdb::CMs 359706 Specdb::CMs 359707 Specdb::CMs 359708 Specdb::CMs 359709 Specdb::CMs 359710 Specdb::CMs 359711 Specdb::CMs 359712 Specdb::CMs 359713 Specdb::CMs 359714 Specdb::CMs 359715 Specdb::CMs 359716 Specdb::CMs 359717 Specdb::CMs 359718 Specdb::CMs 359719 Specdb::CMs 359720 Specdb::CMs 359721 Specdb::CMs 359722 Specdb::CMs 359723 Specdb::CMs 359724 Specdb::NmrOneD 5217 Specdb::NmrOneD 5218 Specdb::NmrOneD 6422 Specdb::NmrOneD 6423 Specdb::NmrOneD 6424 Specdb::NmrOneD 6425 Specdb::NmrOneD 6426 Specdb::NmrOneD 6427 Specdb::NmrOneD 6428 Specdb::NmrOneD 6429 Specdb::NmrOneD 6430 Specdb::NmrOneD 6431 Specdb::NmrOneD 6432 Specdb::NmrOneD 6433 Specdb::NmrOneD 6434 Specdb::NmrOneD 6435 Specdb::NmrOneD 6436 Specdb::NmrOneD 6437 Specdb::NmrOneD 6438 Specdb::NmrOneD 6439 Specdb::NmrOneD 6440 Specdb::NmrOneD 6441 Specdb::MsMs 105438 Specdb::MsMs 105439 Specdb::MsMs 105440 Specdb::MsMs 171927 Specdb::MsMs 171928 Specdb::MsMs 171929 Specdb::MsMs 1448446 Specdb::MsMs 1448447 Specdb::MsMs 1448448 Specdb::MsMs 2227236 Specdb::MsMs 2227489 Specdb::MsMs 2229639 Specdb::MsMs 2229829 Specdb::MsMs 2232087 Specdb::MsMs 2232122 Specdb::MsMs 2407733 Specdb::MsMs 2407734 Specdb::MsMs 2407735 Specdb::MsMs 2531259 Specdb::MsMs 2531260 Specdb::MsMs 2531261 Specdb::NmrTwoD 2043 HMDB00996 109 16743745 C00606 16345 3-SULFINOALANINE CSW Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Lin SY, Nui DM, Tu CP, Cheng YD, Lin HL: Evidence of L-cysteinesulfinic acid in PKU neonatal hair roots, with disappearance after dietary control. Ultrastruct Pathol. 2000 Sep-Oct;24(5):351-2. 11071575 Hoeltzli SD, Kelley LK, Moe AJ, Smith CH: Anionic amino acid transport systems in isolated basal plasma membrane of human placenta. Am J Physiol. 1990 Jul;259(1 Pt 1):C47-55. 1973601 Kissman, Henry M.; Baker, B. R. Preparation of various amides of p-methoxy-L-phenylalanine. Journal of Medicinal & Pharmaceutical Chemistry (1960), 2 415-23. http://hmdb.ca/system/metabolites/msds/000/000/895/original/HMDB00996.pdf?1358462681 Aspartate aminotransferase P00509 AAT_ECOLI aspC http://ecmdb.ca/proteins/P00509.xml Glutamate decarboxylase alpha P69908 DCEA_ECOLI gadA http://ecmdb.ca/proteins/P69908.xml Glutamate decarboxylase beta P69910 DCEB_ECOLI gadB http://ecmdb.ca/proteins/P69910.xml Cysteine sulfinate desulfinase Q46925 CSDA_ECOLI csdA http://ecmdb.ca/proteins/Q46925.xml 3-Sulfinoalanine + 2 Hydrogen ion > L-Alanine + Sulfur dioxide 3-Sulfinoalanine <> Hypotaurine + Carbon dioxide R02466 3-Sulfinoalanine + alpha-Ketoglutarate <> 3-Sulfinylpyruvic acid + L-Glutamate R02619 3-Sulfinoalanine + Water Hydrogen ion + L-Alanine + Sulfite RXN0-279 3-Sulfinoalanine > Hypotaurine + Carbon dioxide + Hypotaurine PW_R002554