2.0 2012-05-31 13:00:52 -0600 2015-09-13 12:56:09 -0600 ECMDB00731 M2MDB000180 Cysteine-S-sulfate Cysteine-S-sulfate (SSC) is produced by reaction of inorganic sulfite and cystine by a yet unknown pathway and is a very potent NMDA-receptor agonist. Electrophysiological studies have shown that SSC displays depolarizing properties similar to glutamate. It is an intermediate of cysteine and methionine metabolism. Alaninethiosulfate Alaninethiosulfurate Alaninethiosulfuric acid Alaninethiosulphate Alaninethiosulphurate Alaninethiosulphuric acid Cysteine-S-sulfate Cysteine-S-sulfonate Cysteine-S-sulfonic acid Cysteine-S-sulfuric acid Cysteine-S-sulphate Cysteine-S-sulphonate Cysteine-S-sulphonic acid Cysteine-S-sulphuric acid Cysteinyl-S-sulfonate Cysteinyl-S-sulfonic acid Cysteinyl-S-sulphonate Cysteinyl-S-sulphonic acid L-Cysteine hydrogen sulfate (ester) L-Cysteine hydrogen sulfuric acid (ester) L-Cysteine hydrogen sulphate (ester) L-Cysteine hydrogen sulphuric acid (ester) L-Cysteine S-sulfate L-Cysteine S-sulfuric acid L-Cysteine S-sulphate L-Cysteine S-sulphuric acid L-Cysteine-S-sulfonate L-Cysteine-S-sulfonic acid L-Cysteine-S-sulphonate L-Cysteine-S-sulphonic acid L-Cysteinesulfonate L-Cysteinesulfonic acid L-Cysteinesulphonate L-Cysteinesulphonic acid S-Cysteinesulfonate S-Cysteinesulfonic acid S-Cysteinesulphonate S-Cysteinesulphonic acid S-Sulfo-L-cysteine S-Sulfocysteine S-Sulpho-L-cysteine S-Sulphocysteine C3H7NO5S2 201.221 200.976563719 (2R)-2-amino-3-(sulfosulfanyl)propanoic acid S-sulphocysteine 1637-71-4 N[C@@H](CSS(O)(=O)=O)C(O)=O InChI=1S/C3H7NO5S2/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1 NOKPBJYHPHHWAN-REOHCLBHSA-N Solid Cytoplasm Periplasm logp -2.33 ALOGPS logs -0.57 ALOGPS solubility 5.38e+01 g/l ALOGPS melting_point 170-171 oC logp -2.3 ChemAxon pka_strongest_acidic -1.9 ChemAxon pka_strongest_basic 8.99 ChemAxon iupac (2R)-2-amino-3-(sulfosulfanyl)propanoic acid ChemAxon average_mass 201.221 ChemAxon mono_mass 200.976563719 ChemAxon smiles N[C@@H](CSS(O)(=O)=O)C(O)=O ChemAxon formula C3H7NO5S2 ChemAxon inchi InChI=1S/C3H7NO5S2/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1 ChemAxon inchikey NOKPBJYHPHHWAN-REOHCLBHSA-N ChemAxon polar_surface_area 117.69 ChemAxon refractivity 38.64 ChemAxon polarizability 16.76 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Cysteine and methionine metabolism ec00270 cysteine biosynthesis The pathway of cysteine biosynthesis is a two-step conversion starting from L-serine and yielding L-cysteine. L-serine biosynthesis is shown for context. L-cysteine can also be synthesized from sulfate derivatives. The process through L-serine involves a serine acetyltransferase that produces a O-acetylserine which reacts together with hydrogen sulfide through a cysteine synthase complex in order to produce L-cysteine and acetic acid. Hydrogen sulfide is produced from a sulfate. Sulfate reacts with sulfate adenylyltransferase to produce adenosine phosphosulfate. This compound in turn is phosphorylated through a adenylyl-sulfate kinase into a phosphoadenosine phosphosulfate which in turn reacts with a phosphoadenosine phosphosulfate reductase to produce a sulfite. The sulfite reacts with a sulfite reductase to produce the hydrogen sulfide. This pathway is regulated at the genetic level in its second step, wtih both cysteine synthase isozymes being under the positive control of the cysteine-responsive transcription factor CysB. It is also subject to very strong feedback inhibition of its first step by the final pathway product, cysteine. Although two cysteine synthase isozymes exist, only cysteine synthase A (CysK) forms a complex with serine acetyltransferase. CysK is also the only one of the two cysteine synthases that is required for cell viability on cysteine-free medium. Both steps in this pathway are reversible. Based on genetic and proteomic data, it appears that the cysteine synthases may actually act as a sulfur scavenging system during sulfur starvation, stripping sulfur off of L-cysteine, generating any number of variant amino acids in the process. PW000800 Metabolic Specdb::CMs 8354 Specdb::CMs 37728 Specdb::CMs 162855 Specdb::CMs 1072951 Specdb::CMs 1072953 Specdb::CMs 1072955 Specdb::CMs 1072957 Specdb::CMs 1072959 Specdb::NmrOneD 1505 Specdb::NmrOneD 7542 Specdb::NmrOneD 7543 Specdb::NmrOneD 7544 Specdb::NmrOneD 7545 Specdb::NmrOneD 7546 Specdb::NmrOneD 7547 Specdb::NmrOneD 7548 Specdb::NmrOneD 7549 Specdb::NmrOneD 7550 Specdb::NmrOneD 7551 Specdb::NmrOneD 7552 Specdb::NmrOneD 7553 Specdb::NmrOneD 7554 Specdb::NmrOneD 7555 Specdb::NmrOneD 7556 Specdb::NmrOneD 7557 Specdb::NmrOneD 7558 Specdb::NmrOneD 7559 Specdb::NmrOneD 7560 Specdb::NmrOneD 7561 Specdb::NmrOneD 166362 Specdb::NmrOneD 166415 Specdb::NmrOneD 166559 Specdb::MsMs 1029 Specdb::MsMs 1030 Specdb::MsMs 1031 Specdb::MsMs 4560 Specdb::MsMs 4561 Specdb::MsMs 4562 Specdb::MsMs 4563 Specdb::MsMs 4564 Specdb::MsMs 4565 Specdb::MsMs 4566 Specdb::MsMs 4567 Specdb::MsMs 4568 Specdb::MsMs 4569 Specdb::MsMs 4570 Specdb::MsMs 4571 Specdb::MsMs 4572 Specdb::MsMs 4573 Specdb::MsMs 4574 Specdb::MsMs 259266 Specdb::MsMs 259267 Specdb::MsMs 259268 Specdb::MsMs 279204 Specdb::MsMs 279205 Specdb::MsMs 279206 Specdb::MsMs 437490 Specdb::NmrTwoD 1451 HMDB00731 115015 102939 C05824 CSU 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 Graf WD, Oleinik OE, Jack RM, Weiss AH, Johnson JL: Ahomocysteinemia in molybdenum cofactor deficiency. Neurology. 1998 Sep;51(3):860-2. 9748040 Arnold GL, Greene CL, Stout JP, Goodman SI: Molybdenum cofactor deficiency. J Pediatr. 1993 Oct;123(4):595-8. 8410516 Duran M, Aarsen G, Fokkens RH, Nibbering NM, Cats BP, de Bree PK, Wadman SK: 2-Mercaptoethanesulfonate-cysteine disulfide excretion following the administration of 2-mercaptoethanesulfonate--a pitfall in the diagnosis of sulfite oxidase deficiency. Clin Chim Acta. 1981 Mar 19;111(1):47-53. 6784974 Beemer FA, Duran M, Wadman SK, Cats BP: Absence of hepatic molybdenum cofactor. An inborn error of metabolism associated with lens dislocation. 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Analytical biochemist http://hmdb.ca/system/metabolites/msds/000/000/650/original/HMDB00731.pdf?1358462019 Cystathionine gamma-synthase P00935 METB_ECOLI metB http://ecmdb.ca/proteins/P00935.xml Cysteine synthase B P16703 CYSM_ECOLI cysM http://ecmdb.ca/proteins/P16703.xml Putative aliphatic sulfonates transport permease protein ssuC P75851 SSUC_ECOLI ssuC http://ecmdb.ca/proteins/P75851.xml Putative aliphatic sulfonates-binding protein P75853 SSUA_ECOLI ssuA http://ecmdb.ca/proteins/P75853.xml Aliphatic sulfonates import ATP-binding protein SsuB P0AAI1 SSUB_ECOLI ssuB http://ecmdb.ca/proteins/P0AAI1.xml Putative aliphatic sulfonates transport permease protein ssuC P75851 SSUC_ECOLI ssuC http://ecmdb.ca/proteins/P75851.xml Putative aliphatic sulfonates-binding protein P75853 SSUA_ECOLI ssuA http://ecmdb.ca/proteins/P75853.xml Aliphatic sulfonates import ATP-binding protein SsuB P0AAI1 SSUB_ECOLI ssuB http://ecmdb.ca/proteins/P0AAI1.xml O-Acetylserine + Thiosulfate <> Cysteine-S-sulfate + Acetic acid R03132 O-Acetylserine + Thiosulfate + Thiosulfate > Cysteine-S-sulfate + Acetic acid PW_R005147 Cysteine-S-sulfate + Adenosine triphosphate + Water > Cysteine-S-sulfate + Adenosine diphosphate + Phosphate + Hydrogen ion + ADP PW_RCT000167 Cysteine-S-sulfate + Adenosine triphosphate + Water > Cysteine-S-sulfate + Adenosine diphosphate + Phosphate + Hydrogen ion + ADP PW_RCT000167