2.0 2012-05-31 13:02:56 -0600 2015-06-03 15:53:38 -0600 ECMDB00988 M2MDB000216 S-Adenosylmethioninamine S-Adenosylmethioninamine is a biological sulfonium compound known as the major biological methyl donor. It is also a donor of methylene groups, amino groups, ribosyl groups and aminopropyl groups (PMID 15130560). S-Adenosylmethioninamine is a prodcut of enzyme adenosylmethionine decarboxylase [EC 4.1.1.50] in methionine metabolism pathway (KEGG). (5-deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium salt (5-deoxy-5-adenosyl)(3-aminopropyl) methylsulphonium salt 3-amino-propyl-<i>S</i>-adenosine 3-Amino-propyl-S-adenosine <i>S</i>-adenosylmethioninamine <i>S</i>-methyl-<i>S</i>-adenosyl homocysteamine DAdoMet DcSAM Decarboxylated AdoMet Decarboxylated S-adenosylmethionine Decarboxylated SAM S-Adenosyl-(5')-3-methylthiopropylamine S-Adenosyl-L-methioninamine S-Adenosylmethioninamine S-Methyl-S-adenosyl homocysteamine C14H23N6O3S 355.436 355.155234322 {[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-aminopropyl)methylsulfanium decarboxylated sam 22365-13-5 C[S+](CCCN)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N InChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/t8-,10-,11-,14-,24?/m1/s1 ZUNBITIXDCPNSD-LSRJEVITSA-N Solid Cytosol logp 0.28 ALOGPS logs -2.49 ALOGPS solubility 1.27e+00 g/l ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 12.45 ChemAxon pka_strongest_basic 10.09 ChemAxon iupac {[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-aminopropyl)methylsulfanium ChemAxon average_mass 355.436 ChemAxon mono_mass 355.155234322 ChemAxon smiles C[S+](CCCN)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N ChemAxon formula C14H23N6O3S ChemAxon inchi InChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/t8-,10-,11-,14-,24?/m1/s1 ChemAxon inchikey ZUNBITIXDCPNSD-LSRJEVITSA-N ChemAxon polar_surface_area 145.33 ChemAxon refractivity 90.4 ChemAxon polarizability 36.97 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge 2 ChemAxon formal_charge 1 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 S-adenosyl-L-methionine biosynthesis S-adenosyl-L-methionine biosynthesis(SAM) is synthesized in the cytosol of the cell from L-methionine and ATP. This reaction is catalyzed by methionine adenosyltransferase. L methione is taken up from the environment through a complex reaction coupled transport and then proceeds too synthesize the s adenosylmethionine through a adenosylmethionine synthase. The S-adenosylmethionine then interacts with a hydrogen ion through a adenosylmethionine decarboxylase resulting in a carbon dioxide and a S-adenosyl 3-methioninamine.This compound interacts with a putrescine through a spermidine synthase resulting in a spermidine, a hydrogen ion and a S-methyl-5'-thioadenosine. The latter compound is degraded by interacting with a water molecule through a 5' methylthioadenosine nucleosidase resulting in a adenine and a S-methylthioribose which is then release into the environment PW000837 Metabolic Spermidine biosynthesis and metabolism Spermidine metabolism starts with S-adenosyl-L-methionine reacting with a hydrogen ion through a adenosylmethionine decarboxylase resulting in the release of a carbon dioxide and a S-adenosyl 3-(methylthio)propylamine. The later compound in turn reacts with putrescine resulting in the release of a hydrogen ion, a spermidine and a S-methyl-5'-thioadenosine. S-methyl-5'-thioadenosine in turn reacts with a water molecule through a 5-methylthioadenosine nucleosidase resulting in the release of a adenine and a S-methyl-5-thio-D-ribose which in in turn is released into the environment. PW002085 Metabolic aminopropylcadaverine biosynthesis PWY0-1303 spermidine biosynthesis I BSUBPOLYAMSYN-PWY Specdb::CMs 23282 Specdb::CMs 37878 Specdb::CMs 175206 Specdb::CMs 1083099 Specdb::CMs 1083100 Specdb::CMs 1083101 Specdb::CMs 1083102 Specdb::CMs 1083103 Specdb::CMs 1083104 Specdb::CMs 1083105 Specdb::CMs 1083106 Specdb::CMs 1083107 Specdb::CMs 1083108 Specdb::CMs 1083109 Specdb::CMs 1083110 Specdb::CMs 1083111 Specdb::CMs 1083112 Specdb::CMs 1083113 Specdb::CMs 1083114 Specdb::CMs 1083115 Specdb::CMs 1083116 Specdb::CMs 1083117 Specdb::CMs 1083118 Specdb::CMs 1083119 Specdb::CMs 1083120 Specdb::NmrOneD 8162 Specdb::NmrOneD 8163 Specdb::NmrOneD 8164 Specdb::NmrOneD 8165 Specdb::NmrOneD 8166 Specdb::NmrOneD 8167 Specdb::NmrOneD 8168 Specdb::NmrOneD 8169 Specdb::NmrOneD 8170 Specdb::NmrOneD 8171 Specdb::NmrOneD 8172 Specdb::NmrOneD 8173 Specdb::NmrOneD 8174 Specdb::NmrOneD 8175 Specdb::NmrOneD 8176 Specdb::NmrOneD 8177 Specdb::NmrOneD 8178 Specdb::NmrOneD 8179 Specdb::NmrOneD 8180 Specdb::NmrOneD 8181 Specdb::MsMs 317656 Specdb::MsMs 317657 Specdb::MsMs 317658 Specdb::MsMs 3099943 Specdb::MsMs 3099944 Specdb::MsMs 3099945 HMDB00988 1078 388529 C01137 15625 S-ADENOSYLMETHIONINAMINE 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 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 Fontecave, M., Atta, M., Mulliez, E. (2004). "S-adenosylmethionine: nothing goes to waste." Trends Biochem Sci 29:243-249. 15130560 Pegg, Anthony E. Assay of aminopropyltransferases. Methods in Enzymology (1983), 94(Polyamines), 260-5. Spermidine synthase P09158 SPEE_ECOLI speE http://ecmdb.ca/proteins/P09158.xml S-adenosylmethionine decarboxylase proenzyme P0A7F6 SPED_ECOLI speD http://ecmdb.ca/proteins/P0A7F6.xml S-Adenosylmethionine + Hydrogen ion <> S-Adenosylmethioninamine + Carbon dioxide R00178 SAMDECARB-RXN S-Adenosylmethioninamine + Putrescine + Ethylenediamine <> 5'-Methylthioadenosine + Hydrogen ion + Spermidine R01920 SPERMIDINESYN-RXN Cadaverine + S-Adenosylmethioninamine > 5'-Methylthioadenosine + Hydrogen ion + Aminopropylcadaverine R08359 RXN0-5217 S-Adenosylmethioninamine + Putrescine <> 5'-Methylthioadenosine + Spermidine R01920 SPERMIDINESYN-RXN S-Adenosylmethioninamine + Spermidine <> 5'-Methylthioadenosine + Spermine R02869 S-Adenosylmethioninamine + Cadaverine <> 5'-Methylthioadenosine + Aminopropylcadaverine R08359 Hydrogen ion + S-Adenosylmethionine > Carbon dioxide + S-Adenosylmethioninamine SAMDECARB-RXN Putrescine + S-Adenosylmethioninamine > Hydrogen ion + Spermidine + 5'-Methylthioadenosine SPERMIDINESYN-RXN S-Adenosylmethioninamine + Putrescine > 5'-Methylthioadenosine + Spermidine S-adenosyl-L-methionine + Hydrogen ion > Carbon dioxide + S-Adenosylmethioninamine PW_R005165 Putrescine + S-Adenosylmethioninamine > Spermidine + Hydrogen ion + 5'-S-methyl-5'-thioadenosine PW_R005166 S-Adenosylmethionine + Hydrogen ion <> S-Adenosylmethioninamine + Carbon dioxide S-Adenosylmethioninamine + Putrescine + Ethylenediamine <>5 5'-Methylthioadenosine + Hydrogen ion + Spermidine Cadaverine + S-Adenosylmethioninamine >5 5'-Methylthioadenosine + Hydrogen ion + Aminopropylcadaverine S-Adenosylmethionine + Hydrogen ion <> S-Adenosylmethioninamine + Carbon dioxide S-Adenosylmethioninamine + Putrescine + Ethylenediamine <>5 5'-Methylthioadenosine + Hydrogen ion + Spermidine