2.0 2012-05-31 13:46:47 -0600 2015-09-13 12:56:10 -0600 ECMDB01173 M2MDB000282 5'-Methylthioadenosine 5-Methylthioadenosine is a normal metabolite in Cysteine and methionine metabolism. Spermidine synthase (putrescine aminopropyltransferase)(EC:2.5.1.16) catalyzes the its formation and it is then converted to 5-Methylthio-D-ribose via S-adenosylhomocysteine/5'-methylthioadenosine nucleosidase [EC:3.2.2.9]. (KEGG) 1-(6-amino-9H-Purin-9-yl)-1-deoxy-5-S-methyl-5-thio-b-D-ribofuranose 1-(6-amino-9H-Purin-9-yl)-1-deoxy-5-S-methyl-5-thio-b-delta-ribofuranose 1-(6-amino-9H-Purin-9-yl)-1-deoxy-5-S-methyl-5-thio-b-δ-ribofuranose 1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-D-Ribofuranose 1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-delta-Ribofuranose 1-(6-amino-9H-Purin-9-yl)-1-deoxy-5-S-methyl-5-thio-β-D-ribofuranose 1-(6-amino-9H-Purin-9-yl)-1-deoxy-5-S-methyl-5-thio-β-δ-ribofuranose 5'-(Methylthio)-5'-deoxyadenosine 5'-(Methylthio)adenosine 5'-<i>S</i>-methyl-5'-thioadenosine 5'-Deoxy-5'-(methylthio)adenosine 5'-Methylthioadenosine 5'-S-Methyl-5'-thio-Adenosine 5'-S-Methyl-5'-thioadenosine 5-Methylthioadenosine <i>S</i>-methyl-adenosine Methylthioadenosine MTA S-Methyl-5'-thioadenosine S-Methyl-5-thioadenosine S-Methyl-adenosine Thiomethyladenosine C11H15N5O3S 297.334 297.089560061 (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol methylthioadenosine 2457-80-9 CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1 WUUGFSXJNOTRMR-IOSLPCCCSA-N Solid Cytosol logp -0.14 ALOGPS logs -1.66 ALOGPS solubility 6.50e+00 g/l ALOGPS logp -0.61 ChemAxon pka_strongest_acidic 12.47 ChemAxon pka_strongest_basic 3.92 ChemAxon iupac (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol ChemAxon average_mass 297.334 ChemAxon mono_mass 297.089560061 ChemAxon smiles CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N ChemAxon formula C11H15N5O3S ChemAxon inchi InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1 ChemAxon inchikey WUUGFSXJNOTRMR-IOSLPCCCSA-N ChemAxon polar_surface_area 119.31 ChemAxon refractivity 74.03 ChemAxon polarizability 29.26 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 7 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Glutathione metabolism The biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione. This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione. PW000833 ec00480 Metabolic Arginine and proline metabolism ec00330 Cysteine and methionine metabolism ec00270 beta-Alanine metabolism The Beta-Alanine Metabolism starts with a product of Aspartate metabolism. Aspartate is decarboxylated by aspartate 1-decarboxylase, releasing carbon dioxide and Beta-alanine. Beta alanine is then metabolized through a pantothenate synthetase resulting in Pantothenic acid undergoes phosphorylation through a ATP driven pantothenate kinase, resulting in D-4-phosphopantothenate. Pantothenate (vitamin B5) is the universal precursor for the synthesis of the 4'-phosphopantetheine moiety of coenzyme A and acyl carrier protein. Only plants and microorganismscan synthesize pantothenate de novo - animals require a dietary supplement. The enzymes of this pathway are therefore considered to be antimicrobial drug targets. PW000896 ec00410 Metabolic Metabolic pathways eco01100 Spermidine Biosynthesis I Spermidine is formed by the addition of a propylamine moiety to putrescine, catalyzed by an aminopropyltransferase termed spermidine synthase, the the product of gene speE. The source of the propylamine group is decarboxylated S-adenosyl-L-methionine (S-adenosyl-L-methioninamine) which is produced by the action of the pyruvoyl-containing enzyme adenosylmethionine decarboxylase. The other product of the aminopropyltransferase reaction is S-methyl-5'-thioadenosine (MTA), which can be recycled back to L-methionine in many organisms, but not in E. coli. Inhibition of E. coli adenosylmethionine decarboxylase by spermidine appears to be the most significant regulator of polyamine biosynthesis, probably limiting it when the intracellular spermidine concentration becomes excessive. In E. coli most intracellular spermidine is bound to nucleic acids and phospholipids. (EcoCyc) PW002040 Metabolic aminopropylcadaverine biosynthesis Polyamines are important for cell growth and are believed to be involved in many processes including DNA, RNA, and protein synthesis, as well as membrane integrity and resistance to stress, to name a few. Cadaverine and aminopropylcadaverine are alternative polyamines that can at least partially substitute for purtrescine and spermidine, the primary polyamines found in E. coli. Lysine is decarboxylated to form cadaverine which is then converted to aminopropylcadaverine by the aminopropyltransferase, SpeE. (EcoCyc) PW002039 Metabolic <i>S</i>-methyl-5'-thioadenosine degradation IV PWY0-1391 aminopropylcadaverine biosynthesis PWY0-1303 spermidine biosynthesis I BSUBPOLYAMSYN-PWY Specdb::CMs 707 Specdb::CMs 9449 Specdb::CMs 30466 Specdb::CMs 31809 Specdb::CMs 31810 Specdb::CMs 37957 Specdb::CMs 137611 Specdb::CMs 145345 Specdb::NmrOneD 1655 Specdb::NmrOneD 21382 Specdb::NmrOneD 21383 Specdb::NmrOneD 21384 Specdb::NmrOneD 21385 Specdb::NmrOneD 21386 Specdb::NmrOneD 21387 Specdb::NmrOneD 21388 Specdb::NmrOneD 21389 Specdb::NmrOneD 21390 Specdb::NmrOneD 21391 Specdb::NmrOneD 21392 Specdb::NmrOneD 21393 Specdb::NmrOneD 21394 Specdb::NmrOneD 21395 Specdb::NmrOneD 21396 Specdb::NmrOneD 21397 Specdb::NmrOneD 21398 Specdb::NmrOneD 21399 Specdb::NmrOneD 21400 Specdb::NmrOneD 21401 Specdb::MsMs 1448 Specdb::MsMs 1449 Specdb::MsMs 1450 Specdb::MsMs 5062 Specdb::MsMs 5063 Specdb::MsMs 5064 Specdb::MsMs 5065 Specdb::MsMs 5066 Specdb::MsMs 5067 Specdb::MsMs 5068 Specdb::MsMs 5070 Specdb::MsMs 5071 Specdb::MsMs 178995 Specdb::MsMs 178996 Specdb::MsMs 178997 Specdb::MsMs 181320 Specdb::MsMs 181321 Specdb::MsMs 181322 Specdb::MsMs 439184 Specdb::MsMs 446024 Specdb::MsMs 446025 Specdb::MsMs 446026 Specdb::MsMs 446027 Specdb::MsMs 446028 Specdb::MsMs 447222 Specdb::NmrTwoD 1596 HMDB01173 149 388321 C00170 17509 5-METHYLTHIOADENOSINE MTA Keseler, I. 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Journal of Medicinal Chemistry (1989), 32(5), 997-1001. http://hmdb.ca/system/metabolites/msds/000/001/051/original/HMDB01173.pdf?1358461858 Spermidine synthase P09158 SPEE_ECOLI speE http://ecmdb.ca/proteins/P09158.xml 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI mtnN http://ecmdb.ca/proteins/P0AF12.xml S-Adenosylmethioninamine + Putrescine + Ethylenediamine <> 5'-Methylthioadenosine + Hydrogen ion + Spermidine R01920 SPERMIDINESYN-RXN Cadaverine + S-Adenosylmethioninamine > 5'-Methylthioadenosine + Hydrogen ion + Aminopropylcadaverine R08359 RXN0-5217 5'-Methylthioadenosine + Water > 5-Methylthioribose + Adenine R01401 METHYLTHIOADENOSINE-NUCLEOSIDASE-RXN 5'-Methylthioadenosine + Water <> Adenine + 5-Methylthioribose R01401 S-Adenosylmethioninamine + Putrescine <> 5'-Methylthioadenosine + Spermidine R01920 SPERMIDINESYN-RXN S-Adenosylmethioninamine + Spermidine <> 5'-Methylthioadenosine + Spermine R02869 S-Adenosylmethioninamine + Cadaverine <> 5'-Methylthioadenosine + Aminopropylcadaverine R08359 Putrescine + S-Adenosylmethioninamine > Hydrogen ion + Spermidine + 5'-Methylthioadenosine SPERMIDINESYN-RXN 5'-Methylthioadenosine + Water > S-methyl-5-thio-D-ribose + Adenine S-Adenosylmethioninamine + Putrescine > 5'-Methylthioadenosine + Spermidine Cadaverine + Decarboxy-SAM > Aminopropylcadaverine + 5'-Methylthioadenosine + Hydrogen ion PW_R005959 Decarboxy-SAM + Putrescine > 5'-Methylthioadenosine + Spermidine + Hydrogen ion PW_R005961 S-Adenosylmethioninamine + Putrescine + Ethylenediamine <>5 5'-Methylthioadenosine + Hydrogen ion + Spermidine Cadaverine + S-Adenosylmethioninamine >5 5'-Methylthioadenosine + Hydrogen ion + Aminopropylcadaverine S-Adenosylmethioninamine + Putrescine + Ethylenediamine <>5 5'-Methylthioadenosine + Hydrogen ion + Spermidine