2.0 2012-05-31 13:47:10 -0600 2015-10-15 16:13:52 -0600 ECMDB01185 M2MDB000289 S-Adenosylmethionine S-Adenosylmethionine is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It is made from adenosine triphosphate (ATP) and methionine by methionine adenosyltransferase (EC 2.5.1.6). Transmethylation, transsulfuration, and aminopropylation are the metabolic pathways that use S-Adenosylmethionine. In bacteria, SAM is bound by the SAM riboswitch, which regulates genes involved in methionine or cysteine biosynthesis. (Wikipedia) (3S)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine (3S)-5'-[(3-amino-3-carboxypropyl)methylsulphonio]-5'-deoxyadenosine 2-S-adenosyl-L-methionine 2-S-Adenosyl-L-methionine 5'-Deoxyadenosine-5'-L-methionine disulfate ditosylate 5'-Deoxyadenosine-5'-L-methionine disulfuric acid ditosylic acid 5'-Deoxyadenosine-5'-L-methionine disulphate ditosylate 5'-Deoxyadenosine-5'-L-methionine disulphuric acid ditosylic acid S-adenosyl-methionine S-adenosylmethionine Active methionine Ademetionine Adenosylmethionine AdoMet Donamet L-S-Adenosylmethionine S-(5'-Adenosyl)-L-methionine S-(5'-Deoxyadenosin-5'-yl)-L-methionine S-Adenosyl methionine S-Adenosyl-L-methionine S-Adenosyl-L-Methionine Disulfate Tosylate S-Adenosyl-L-methionine disulfuric acid tosylic acid S-Adenosyl-L-methionine disulphate tosylate S-Adenosyl-L-methionine disulphuric acid tosylic acid S-Adenosyl-methionine S-Adenosylmethionine SAM C15H23N6O5S 399.445 399.145063566 [(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium SAMe 29908-03-0 C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12 InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1 MEFKEPWMEQBLKI-AIRLBKTGSA-O Solid Cytosol logp -1.99 ALOGPS logs -2.56 ALOGPS solubility 1.19e+00 g/l ALOGPS logp -5.3 ChemAxon pka_strongest_acidic 1.7 ChemAxon pka_strongest_basic 9.41 ChemAxon iupac [(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium ChemAxon average_mass 399.445 ChemAxon mono_mass 399.145063566 ChemAxon smiles C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12 ChemAxon formula C15H23N6O5S ChemAxon inchi InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1 ChemAxon inchikey MEFKEPWMEQBLKI-AIRLBKTGSA-O ChemAxon polar_surface_area 182.63 ChemAxon refractivity 96.23 ChemAxon polarizability 40.37 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 10 ChemAxon donor_count 5 ChemAxon physiological_charge 1 ChemAxon formal_charge 1 ChemAxon Arginine and proline metabolism ec00330 Cysteine and methionine metabolism ec00270 Selenoamino acid metabolism ec00450 Porphyrin and chlorophyll metabolism ec00860 Biotin metabolism Biotin (vitamin H or vitamin B7) is the essential cofactor of biotin-dependent carboxylases, such as pyruvate carboxylase and acetyl-CoA carboxylase.In E. coli and many organisms, pimelate thioester is derived from malonyl-ACP. The pathway starts with a malonyl-[acp] interacting with S-adenosylmethionine through a biotin synthesis protein BioC resulting in a S-adenosylhomocysteine and a malonyl-[acp] methyl ester. The latter compound is then involved in the synthesis of a 3-ketoglutaryl-[acp] methyl ester through a 3-oxoacyl-[acyl-carrier-protein] synthase. The compound 3-ketoglutaryl-[acp] methyl ester is reduced by a NADPH mediated 3-oxoacyl-[acyl-carrier-protein] reductase resulting in a 3R-hydroxyglutaryl-[acp] methyl ester. This compound is then dehydrated through ad (3R)-hydroxymyristoyl-[acp] dehydratase producing a enoylglutaryl-[acp] methyl ester. This compound is then reduced through a NADPH mediated enoyl-acp-reductase [NADH] resulting in a glutaryl-[acp] methyl ester. This compound interacts with a malonyl-[acp] through a 3-oxoacyl-[acp] synthase 2 resulting in a 3-ketopimeloyl [acp] methyl ester. This compound is then reduced through a NADPH 3-oxoacyl [acp] reductase producing a 3-hydroxypimeloyl-[acp] methyl ester and then dehydrated by (3R)-hydroxymyristoyl-[acp] dehydratase to produce a enoylpimeloyl-[acp] methyl ester. This compound is then reduced by a NADPH dependent enoyl-[acp]reductase resulting in a pimeloyl-[acp] methyl ester. This compound then reacts with water through a carboxylesterase resulting in a pimeloyl-[acp] and a methanol. The pimeloyl-acp reacts with L-alanine through a 8-amino-7-oxononanoate synthase resulting in 8-amino-7-oxononanoate which in turn reacts with S-adenosylmethionine through a 7,8 diaminonanoate transaminase resulting in a S-adenosyl-4-methylthio-2-oxobutanoate and 7,8 diaminononanoate. The latter compound is then dephosphorylated through a dethiobiotin synthetase resulting in a dethiobiotin. This compound interacts with a sulfurated[sulfur carrier), a hydrogen ion and a S-adenosylmethionine through a biotin synthase to produce Biotin and releasing l-methionine and a 5-deoxyadenosine. Biotin is then metabolized by a bifunctional protein resulting in pyrophosphate and Biotinyl-5-AMP which in turn reacts with the same protein (bifunctional protein birA resulting ina biotin caroxyl carrying protein.This product then enters the fatty acid biosynthesis. PW000762 ec00780 Metabolic Thiamine metabolism ec00730 Ubiquinone and other terpenoid-quinone biosynthesis ec00130 Lipoic acid metabolism Lipoic acid metabolism starts with caprylic acid being introduced into the cytoplasm however no transporter has been identified yet. Once caprylic acid is in the cytoplasm, it can either reacts with a holo-acp, through an ATP driven 2-acylglycerophosphoethanolamine acyltransferase / acyl-ACP synthetase resulting in pyrophosphate, AMP and octanoyl-[acp]. The latter compound can also be obtained from palmitate biosynthesis. Octanoyl-acp interacts with a lipoyl-carrier protein L-lysine through a Octanoyltransferase resulting in a hydrogen ion, a holo-acyl-acp, and a protein N6-0octanoyl) lysine. The latter compound reacts with an S-adenosylmethionine, a sulfurated[sulfur carrier] and a reduced ferredoxin through a lipoate-protein ligase A, resulting in a 5-deoxyadenosine, a L-methionine, an unsulfurated [sulfur carrier], oxidized ferredoxin, and a Protein N6-(lipoyl) lysine. Caprylic acid can also interact with ATP and a lipoyl-carrier protein-L-lysine through a lipoate-protein ligase A resulting in a amp, pyrophosphate, hydrogen ion, protein N6-(octanoyl)lysine. The latter compound reacts with an S-adenosylmethionine, a sulfurated[sulfur carrier] and a reduced ferredoxin through a lipoate-protein ligase A, resulting in a 5-deoxyadenosine, a L-methionine, an unsulfurated [sulfur carrier], oxidized ferredoxin, and a Protein N6-(lipoyl) lysine. R-lipoic acid can be absorbed from the environment, as seen in studies by Morris TW. In this pathway the lipoyl-protein ligase LplA utilizes pre-existing lipoate that has been imported from outside the cell, and thus catalyzes a salvage pathway. Lipoic acid interacts with ATP and hydrogen ion through a lipoyl-protein ligase A, resulting in a pyrophosphate and a Lipoyl-AMP (lipoyl-adenylate). This compound then interacts with a lipoyl-carrier protein-L-lysine through a lipoate-protein ligase A resulting a AMP, a hydrogen ion and a Protein N6-(lipoyl) lysine. It has been suggested that the conversion of octanoylated-domains to lipoylated ones described in this pathway may be a type of a repair pathway, activated only if the other lipoate biosynthetic pathways are malfunctioning . PW000770 ec00785 Metabolic Two-component system ec02020 Sulfur relay system ec04122 Mismatch repair eco03430 Metabolic pathways eco01100 biotin biosynthesis from 7-keto-8-aminopelargonate PWY0-1507 methylphosphonate degradation PWY0-1533 queuosine biosynthesis PWY-6700 S-adenosyl-L-methionine cycle I PWY-6151 autoinducer AI-2 biosynthesis I PWY-6153 thiazole biosynthesis I (E. coli) PWY-6892 lipoate biosynthesis and incorporation II PWY0-1275 preQ0 biosynthesis PWY-6703 4-amino-2-methyl-5-diphosphomethylpyrimidine biosynthesis PWY-6890 7-keto-8-aminopelargonate biosynthesis I PWY-6519 ubiquinol-8 biosynthesis (prokaryotic) PWY-6708 heme biosynthesis from uroporphyrinogen-III II HEMESYN2-PWY superpathway of S-adenosyl-L-methionine biosynthesis SAM-PWY lipoate biosynthesis and incorporation I PWY0-501 siroheme biosynthesis PWY-5194 cyclopropane fatty acid (CFA) biosynthesis PWY0-541 menaquinol-8 biosynthesis MENAQUINONESYN-PWY spermidine biosynthesis I BSUBPOLYAMSYN-PWY Specdb::CMs 17861 Specdb::CMs 37964 Specdb::CMs 148643 Specdb::NmrOneD 146690 Specdb::NmrOneD 146691 Specdb::NmrOneD 146692 Specdb::NmrOneD 146693 Specdb::NmrOneD 146694 Specdb::NmrOneD 146695 Specdb::NmrOneD 146696 Specdb::NmrOneD 146697 Specdb::NmrOneD 146698 Specdb::NmrOneD 146699 Specdb::NmrOneD 146700 Specdb::NmrOneD 146701 Specdb::NmrOneD 146702 Specdb::NmrOneD 146703 Specdb::NmrOneD 146704 Specdb::NmrOneD 146705 Specdb::NmrOneD 146706 Specdb::NmrOneD 146707 Specdb::NmrOneD 146708 Specdb::NmrOneD 146709 Specdb::MsMs 305554 Specdb::MsMs 305555 Specdb::MsMs 305556 Specdb::MsMs 445541 Specdb::MsMs 445542 Specdb::MsMs 445543 Specdb::MsMs 445544 Specdb::MsMs 445545 Specdb::MsMs 447191 Specdb::MsMs 2973573 Specdb::MsMs 2973574 Specdb::MsMs 2973575 HMDB01185 1079 21169292 C00019 15414 S-ADENOSYLMETHIONINE S-Adenosylmethionine 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 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776 Lin, Jian-Ping; Tian, Jun; You, Jian-Feng; Jin, Zhi-Hua; Xu, Zhi-Nan; Cen, Pei-Lin. An effective strategy for the co-production of S-adenosyl-L-methionine and glutathione by fed-batch fermentation. Biochemical Engineering Journal (2004), 21(1), 19-25. http://hmdb.ca/system/metabolites/msds/000/001/063/original/S-Adenosylmethionine_MSDS.pdf?1368651702 Putative uroporphyrinogen-III C-methyltransferase P09127 HEMX_ECOLI hemX http://ecmdb.ca/proteins/P09127.xml Protein-L-isoaspartate O-methyltransferase P0A7A5 PIMT_ECOLI pcm http://ecmdb.ca/proteins/P0A7A5.xml S-adenosylmethionine decarboxylase proenzyme P0A7F6 SPED_ECOLI speD http://ecmdb.ca/proteins/P0A7F6.xml S-adenosylmethionine synthase P0A817 METK_ECOLI metK http://ecmdb.ca/proteins/P0A817.xml tRNA (guanine-N(1)-)-methyltransferase P0A873 TRMD_ECOLI trmD http://ecmdb.ca/proteins/P0A873.xml Cyclopropane-fatty-acyl-phospholipid synthase P0A9H7 CFA_ECOLI cfa http://ecmdb.ca/proteins/P0A9H7.xml Pyruvate formate-lyase 1-activating enzyme P0A9N4 PFLA_ECOLI pflA http://ecmdb.ca/proteins/P0A9N4.xml Anaerobic ribonucleoside-triphosphate reductase-activating protein P0A9N8 NRDG_ECOLI nrdG http://ecmdb.ca/proteins/P0A9N8.xml Ribosomal RNA small subunit methyltransferase D P0ADX9 RSMD_ECOLI rsmD http://ecmdb.ca/proteins/P0ADX9.xml Siroheme synthase P0AEA8 CYSG_ECOLI cysG http://ecmdb.ca/proteins/P0AEA8.xml DNA-cytosine methyltransferase P0AED9 DCM_ECOLI dcm http://ecmdb.ca/proteins/P0AED9.xml Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI bioA http://ecmdb.ca/proteins/P12995.xml Biotin synthase P12996 BIOB_ECOLI bioB http://ecmdb.ca/proteins/P12996.xml 3-demethylubiquinone-9 3-methyltransferase P17993 UBIG_ECOLI ubiG http://ecmdb.ca/proteins/P17993.xml Oxygen-independent coproporphyrinogen-III oxidase P32131 HEMN_ECOLI hemN http://ecmdb.ca/proteins/P32131.xml Pyruvate formate-lyase 2-activating enzyme P32675 PFLC_ECOLI pflC http://ecmdb.ca/proteins/P32675.xml Ribosomal RNA large subunit methyltransferase A P36999 RLMA_ECOLI rlmA http://ecmdb.ca/proteins/P36999.xml Uncharacterized adenine-specific methylase yfcB P39199 YFCB_ECOLI yfcB http://ecmdb.ca/proteins/P39199.xml Ribosomal RNA small subunit methyltransferase C P39406 RSMC_ECOLI rsmC http://ecmdb.ca/proteins/P39406.xml Ribosomal RNA large subunit methyltransferase G P42596 RLMG_ECOLI rlmG http://ecmdb.ca/proteins/P42596.xml Oxygen-independent coproporphyrinogen-III oxidase-like protein yggW P52062 YGGW_ECOLI yggW http://ecmdb.ca/proteins/P52062.xml Lipoyl synthase P60716 LIPA_ECOLI lipA http://ecmdb.ca/proteins/P60716.xml Ribosomal RNA large subunit methyltransferase F P75782 RLMF_ECOLI rlmF http://ecmdb.ca/proteins/P75782.xml Putative pyruvate formate-lyase 3-activating enzyme P75794 PFLE_ECOLI ybiY http://ecmdb.ca/proteins/P75794.xml Trans-aconitate 2-methyltransferase P76145 TAM_ECOLI tam http://ecmdb.ca/proteins/P76145.xml Homocysteine S-methyltransferase Q47690 MMUM_ECOLI mmuM http://ecmdb.ca/proteins/Q47690.xml Thiazole synthase P30139 THIG_ECOLI thiG http://ecmdb.ca/proteins/P30139.xml Dehydroglycine synthase P30140 THIH_ECOLI thiH http://ecmdb.ca/proteins/P30140.xml Phosphomethylpyrimidine synthase P30136 THIC_ECOLI thiC http://ecmdb.ca/proteins/P30136.xml Ubiquinone/menaquinone biosynthesis methyltransferase ubiE P0A887 UBIE_ECOLI ubiE http://ecmdb.ca/proteins/P0A887.xml Biotin synthesis protein BioC P12999 BIOC_ECOLI bioC http://ecmdb.ca/proteins/P12999.xml 23S rRNA mG2445 methyltransferase, SAM-dependent P75864 rlmL http://ecmdb.ca/proteins/P75864.xml Protein methyltransferase hemK P0ACC1 HEMK_ECOLI hemK http://ecmdb.ca/proteins/P0ACC1.xml Ribosomal RNA small subunit methyltransferase A P06992 RSMA_ECOLI rsmA http://ecmdb.ca/proteins/P06992.xml tRNA-2-methylthio-N(6)-dimethylallyladenosine synthase P0AEI1 MIAB_ECOLI miaB http://ecmdb.ca/proteins/P0AEI1.xml Ribosomal protein S12 methylthiotransferase RimO P0AEI4 RIMO_ECOLI rimO http://ecmdb.ca/proteins/P0AEI4.xml 2 S-Adenosylmethionine + Uroporphyrinogen III >2 S-Adenosylhomocysteine + Precorrin 2 + Hydrogen ion R03194 S-Adenosylmethionine + Hydrogen ion <> S-Adenosylmethioninamine + Carbon dioxide R00178 SAMDECARB-RXN S-Adenosylmethionine + L-Homocysteine + S-Methylmethionine <> S-Adenosylhomocysteine + Hydrogen ion + L-Methionine R00650 HOMOCYSTEINE-S-METHYLTRANSFERASE-RXN [4Fe-4S] iron-sulfur cluster + 2 S-Adenosylmethionine + Hydrogen ion + NAD + octanoate (protein bound) > [2Fe-2S] iron-sulfur cluster +2 5'-Deoxyadenosine +2 Iron + lipoate (protein bound) +2 L-Methionine + NADH 8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate R03231 DAPASYN-RXN [2Fe-2S] iron-sulfur cluster + S-Adenosylmethionine + Dethiobiotin > [2Fe-1S] desulfurated iron-sulfur cluster + Biotin + 5'-Deoxyadenosine + Hydrogen ion + L-Methionine S-Adenosylmethionine + Malonyl-CoA > S-Adenosylhomocysteine + malonyl-CoA methyl ester RXN-11475 trans-Aconitic acid + S-Adenosylmethionine > E-3-Carboxy-2-pentenedioate 6-methyl ester + S-Adenosylhomocysteine RXN0-2441 2 S-Adenosylmethionine + PE(14:0/14:0) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylethanolamine (dihexadec-9,10-cyclo-anoyl, N-C16:0 cyclo) +2 Hydrogen ion 2 S-Adenosylmethionine + PE(14:0/14:0) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylethanolamine (dioctadec-11,12-cyclo-anoyl, N-C18:0 cyclo) +2 Hydrogen ion 2 S-Adenosylmethionine + PG(16:1(9Z)/16:1(9Z)) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylglycerol (dihexadec-9,10-cyclo-anoyl, N-C16:0 cyclo) +2 Hydrogen ion 2 S-Adenosylmethionine + PG(18:1(11Z)/18:1(11Z)) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylglycerol (dioctadec-11,12-cyclo-anoyl, N-C18:0 cyclo) +2 Hydrogen ion 2-Octaprenyl-6-hydroxyphenol + S-Adenosylmethionine > 2-Octaprenyl-6-methoxyphenol + S-Adenosylhomocysteine + Hydrogen ion R04988 2-OCTAPRENYL-6-OHPHENOL-METHY-RXN 2-Octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol + S-Adenosylmethionine > S-Adenosylhomocysteine + Hydrogen ion + Ubiquinol-8 Adenosine triphosphate + Water + L-Methionine <> S-Adenosylmethionine + Phosphate + Pyrophosphate R00177 S-ADENMETSYN-RXN 2-Demethylmenaquinol 8 + S-Adenosylmethionine > S-Adenosylhomocysteine + Hydrogen ion + Menaquinol 8 ADOMET-DMK-METHYLTRANSFER-RXN 2-Octaprenyl-6-methoxy-1,4-benzoquinol + S-Adenosylmethionine > 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol + S-Adenosylhomocysteine + Hydrogen ion 2-OCTAPRENYL-METHOXY-BENZOQ-METH-RXN 2 S-Adenosylmethionine + Coproporphyrin III <>2 Carbon dioxide +2 5'-Deoxyadenosine +2 L-Methionine + Protoporphyrinogen IX R06895 S-Adenosylmethionine + NADPH + L-Tyrosine > p-Cresol + 5'-Deoxyadenosine + Dehydroglycine + Hydrogen ion + L-Methionine + NADP Phosphate + Pyrophosphate + S-Adenosylmethionine <> Adenosine triphosphate + L-Methionine + Water R00177 S-Adenosylmethionine + L-Homocysteine <> S-Adenosylhomocysteine + L-Methionine R00650 HOMOCYSTEINE-S-METHYLTRANSFERASE-RXN Dethiobiotin + Sulfur donor + 2 S-Adenosylmethionine + 2 e- + 2 Hydrogen ion <> Biotin +2 L-Methionine +2 5'-Deoxyadenosine R01078 2 S-Adenosylmethionine + Uroporphyrinogen III <>2 S-Adenosylhomocysteine + Precorrin 2 R03194 S-Adenosylmethionine + DNA cytosine <> S-Adenosylhomocysteine + DNA 5-methylcytosine R04858 2-Octaprenyl-6-hydroxyphenol + S-Adenosylmethionine <> 2-Octaprenyl-6-methoxyphenol + S-Adenosylhomocysteine R04988 2-octaprenyl-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine <> 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone + S-Adenosylhomocysteine R04990 2-Demethylmenaquinone 8 + S-Adenosylmethionine <> Menaquinone + S-Adenosylhomocysteine R04993 2-octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine <> Ubiquinone-8 + S-Adenosylhomocysteine R05614 2-Phytyl-1,4-naphthoquinone + S-Adenosylmethionine <> Phylloquinone + S-Adenosylhomocysteine R06859 S-Adenosylmethionine + rRNA <> S-Adenosylhomocysteine + rRNA containing N6-methyladenine R07232 S-Adenosylmethionine + rRNA <> S-Adenosylhomocysteine + rRNA containing N1-methylguanine R07233 S-Adenosylmethionine + rRNA <> S-Adenosylhomocysteine + rRNA containing N2-methylguanine R07234 Protein N6-(octanoyl)lysine + 2 Sulfur donor + 2 S-Adenosylmethionine + Protein N6-(octanoyl)lysine <> Protein N6-(lipoyl)lysine +2 L-Methionine +2 5'-Deoxyadenosine + Protein N6-(lipoyl)lysine R07767 Octanoyl-[acp] + 2 Sulfur donor + 2 S-Adenosylmethionine <> Lipoyl-[acp] +2 L-Methionine +2 5'-Deoxyadenosine R07768 2-Polyprenyl-6-hydroxyphenol + S-Adenosylmethionine <> 2-Polyprenyl-6-methoxyphenol + S-Adenosylhomocysteine R08769 2-Polyprenyl-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine <> 2-Polyprenyl-3-methyl-6-methoxy-1,4-benzoquinone + S-Adenosylhomocysteine R08774 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine <> Ubiquinone-1 + S-Adenosylhomocysteine R08781 Demethylmenaquinol + S-Adenosylmethionine + Demethylmenaquinol <> Menaquinol 6 + S-Adenosylhomocysteine R09736 S-Adenosylmethionine + precorrin-1 > S-Adenosylhomocysteine + Precorrin 2 RXN-8675 S-Adenosylmethionine + a [protein]-L-glutamine > Hydrogen ion + S-Adenosylhomocysteine + a [protein]-N5-methyl-L-glutamine RXN0-1241 tellurite + S-Adenosylmethionine methylated tellurite + S-Adenosylhomocysteine RXN0-6576 Hydrogen ion + α-D-ribose-1-methylphosphonate-5-phosphate + S-Adenosylmethionine > α-D-ribose-1,2-cyclic-phosphate-5-phosphate + methane + 5'-Deoxyadenosine + L-Methionine RXN0-6734 S-Adenosylmethionine + Uroporphyrinogen III <> S-Adenosylhomocysteine + precorrin-1 + Hydrogen ion UROPORIIIMETHYLTRANSA-RXN S-Adenosylmethionine + a [protein]-L-β-isoaspartate > S-Adenosylhomocysteine + a protein L-β-isoaspartate α-methyl ester + Hydrogen ion 2.1.1.77-RXN a phospholipid olefinic fatty acid + S-Adenosylmethionine > a phospholipid cyclopropane fatty acid + S-Adenosylhomocysteine + Hydrogen ion 2.1.1.79-RXN S-sulfanyl-[acceptor] + Dethiobiotin + S-Adenosylmethionine > an unsulfurated sulfur acceptor + Biotin + 5'-Deoxyadenosine + L-Methionine + Hydrogen ion 2.8.1.6-RXN S-Adenosylmethionine + 8-Amino-7-oxononanoate > S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate DAPASYN-RXN 2-octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine > Hydrogen ion + Ubiquinol-8 + S-Adenosylhomocysteine DHHB-METHYLTRANSFER-RXN Coproporphyrinogen III + S-Adenosylmethionine > Protoporphyrinogen IX + Carbon dioxide + L-Methionine + 5'-Deoxyadenosine HEMN-RXN L-Homocysteine + S-Adenosylmethionine Hydrogen ion + L-Methionine + S-Adenosylhomocysteine HOMOCYSTEINE-S-METHYLTRANSFERASE-RXN 5-Aminoimidazole ribonucleotide + S-Adenosylmethionine 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + carbon monoxide + Hydrogen ion PYRIMSYN1-RXN S-Adenosylmethionine + Ribonuc-tri-P-reductases-inactive <> 5'-Deoxyadenosine + L-Methionine + Ribonuc-tri-P-reductases-active RNTRACTIV-RXN L-Tyrosine + S-Adenosylmethionine + a reduced electron acceptor > Dehydroglycine + p-Cresol + 5'-Deoxyadenosine + L-Methionine + an oxidized electron acceptor + Hydrogen ion RXN-11319 S-Adenosylmethionine + a demethylated methyl acceptor > S-Adenosylhomocysteine + a methylated methyl acceptor RXN-7605 N-6-isopentyl adenosine-37 tRNA + S-Adenosylmethionine + S-sulfanyl-[acceptor] 2-methylthio-N-6-isopentyl adenosine-37 tRNA + S-Adenosylhomocysteine + L-Methionine + 5'-Deoxyadenosine + an unsulfurated sulfur acceptor + Hydrogen ion RXN0-5063 6-Carboxy-5,6,7,8-tetrahydropterin + S-Adenosylmethionine + Hydrogen ion > 7-carboxy-7-deazaguanine + 5'-Deoxyadenosine + L-Methionine + Ammonia RXN0-6575 a guanine1516 in 16S rRNA + S-Adenosylmethionine > an N2-methylguanine1516 in 16S rRNA + S-Adenosylhomocysteine + Hydrogen ion RXN0-6731 guanine2069 in 23S rRNA + S-Adenosylmethionine > N7-methylguanine2069 in 23S rRNA + S-Adenosylhomocysteine RXN0-6950 Adenosine triphosphate + L-Methionine + Water > Phosphate + Pyrophosphate + S-Adenosylmethionine S-ADENMETSYN-RXN Hydrogen ion + S-Adenosylmethionine > Carbon dioxide + S-Adenosylmethioninamine SAMDECARB-RXN S-Adenosylmethionine <> S-Adenosylhomocysteine R02917 S-Adenosylmethionine + trans-Aconitic acid <> S-Adenosylhomocysteine + E-3-Carboxy-2-pentenedioate 6-methyl ester R05763 S-Adenosylmethionine + Phospholipid olefinic fatty acid <> S-Adenosylhomocysteine + Phospholipid cyclopropane fatty acid R03411 S-Adenosylmethionine + tRNA containing 5-aminomethyl-2-thiouridine <> S-Adenosylhomocysteine + tRNA containing 5-methylaminomethyl-2-thiouridylate R00601 S-Adenosylmethionine + DNA adenine <> S-Adenosylhomocysteine + DNA 6-methylaminopurine R02961 2 S-Adenosylmethionine + Uroporphyrinogen III + Precorrin-1 <>2 S-Adenosylhomocysteine + Precorrin 2 R03194 2 S-Adenosylmethionine <> S-Adenosylhomocysteine +2 L-Methionine + 5'-Deoxyadenosine R10645 2 S-Adenosylmethionine + Reduced acceptor <> S-Adenosylhomocysteine +2 L-Methionine + 5'-Deoxyadenosine R10652 S-Adenosylmethionine + Protein glutamate <> S-Adenosylhomocysteine + Protein glutamate methyl ester R02623 S-Adenosylmethionine <> S-Adenosylhomocysteine + DNA 5-methylcytosine R00380 S-Adenosylmethionine + Protein L-isoaspartate <> S-Adenosylhomocysteine + Protein L-isoaspartate methyl ester R04190 L-Tyrosine + S-Adenosylmethionine + NADPH <> 2-iminoacetate + p-Cresol + 5'-Deoxyadenosine + L-Methionine + NADP + Hydrogen ion R10246 4-Amino-5-hydroxymethyl-2-methylpyrimidine + S-Adenosylmethionine <> 5-Aminoimidazole ribonucleotide + 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + CO R03472 S-Adenosylmethionine + tRNA <> S-Adenosylhomocysteine + tRNA containing N6-methyladenine R00599 S-Adenosylmethionine + Protein glutamate <> S-Adenosylhomocysteine + Protein glutamate methyl ester S-Adenosylmethionine + rRNA <> S-Adenosylhomocysteine + rRNA containing N2-methylguanine S-Adenosylmethionine <> S-Adenosylhomocysteine 2 S-Adenosylmethionine + Coproporphyrin III <>2 Carbon dioxide +2 5'-Deoxyadenosine +2 L-Methionine + Protoporphyrinogen IX 8 8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate +7 7,8-Diaminononanoate Dethiobiotin + Sulfur donor + 2 S-Adenosylmethionine + 2 e- + 2 Hydrogen ion <> Biotin +2 L-Methionine +2 5'-Deoxyadenosine Adenosine triphosphate + Water + L-Methionine <> S-Adenosylmethionine + Phosphate + Pyrophosphate S-Adenosylmethionine + Hydrogen ion <> S-Adenosylmethioninamine + Carbon dioxide 2 S-Adenosylmethionine + Reduced acceptor <> S-Adenosylhomocysteine +2 L-Methionine +5 5'-Deoxyadenosine S-Adenosylmethionine + DNA adenine <> S-Adenosylhomocysteine + DNA 6-methylaminopurine 2 S-Adenosylmethionine + Uroporphyrinogen III >2 S-Adenosylhomocysteine + Precorrin 2 + Hydrogen ion 2 2-Octaprenyl-6-hydroxyphenol + S-Adenosylmethionine >2 2-Octaprenyl-6-methoxyphenol + S-Adenosylhomocysteine + Hydrogen ion S-Adenosylmethionine + Protein L-isoaspartate <> S-Adenosylhomocysteine + Protein L-isoaspartate methyl ester S-Adenosylmethionine + rRNA <> S-Adenosylhomocysteine + rRNA containing N6-methyladenine 2 S-Adenosylmethionine <> S-Adenosylhomocysteine +2 L-Methionine +5 5'-Deoxyadenosine 4 4-Amino-5-hydroxymethyl-2-methylpyrimidine + S-Adenosylmethionine <>5 5-Aminoimidazole ribonucleotide +4 4-Amino-2-methyl-5-phosphomethylpyrimidine +5 5'-Deoxyadenosine + L-Methionine + Formic acid + CO 2 2-Demethylmenaquinone 8 + S-Adenosylmethionine <> Menaquinone + S-Adenosylhomocysteine 2 2-Phytyl-1,4-naphthoquinone + S-Adenosylmethionine <> Phylloquinone + S-Adenosylhomocysteine S-Adenosylmethionine + Protein glutamate <> S-Adenosylhomocysteine + Protein glutamate methyl ester 2 S-Adenosylmethionine + Coproporphyrin III <>2 Carbon dioxide +2 5'-Deoxyadenosine +2 L-Methionine + Protoporphyrinogen IX 8 8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate +7 7,8-Diaminononanoate Dethiobiotin + Sulfur donor + 2 S-Adenosylmethionine + 2 e- + 2 Hydrogen ion <> Biotin +2 L-Methionine +2 5'-Deoxyadenosine S-Adenosylmethionine + Hydrogen ion <> S-Adenosylmethioninamine + Carbon dioxide 2 S-Adenosylmethionine + Reduced acceptor <> S-Adenosylhomocysteine +2 L-Methionine +5 5'-Deoxyadenosine 2 S-Adenosylmethionine + Coproporphyrin III <>2 Carbon dioxide +2 5'-Deoxyadenosine +2 L-Methionine + Protoporphyrinogen IX S-Adenosylmethionine + DNA adenine <> S-Adenosylhomocysteine + DNA 6-methylaminopurine 2 S-Adenosylmethionine + Uroporphyrinogen III >2 S-Adenosylhomocysteine + Precorrin 2 + Hydrogen ion Protein N6-(octanoyl)lysine + 2 Sulfur donor + 2 S-Adenosylmethionine <> Protein N6-(lipoyl)lysine +2 L-Methionine +2 5'-Deoxyadenosine S-Adenosylmethionine + Protein L-isoaspartate <> S-Adenosylhomocysteine + Protein L-isoaspartate methyl ester S-Adenosylmethionine <> S-Adenosylhomocysteine S-Adenosylmethionine + rRNA <> S-Adenosylhomocysteine + rRNA containing N6-methyladenine 4 4-Amino-5-hydroxymethyl-2-methylpyrimidine + S-Adenosylmethionine <>5 5-Aminoimidazole ribonucleotide +4 4-Amino-2-methyl-5-phosphomethylpyrimidine +5 5'-Deoxyadenosine + L-Methionine + Formic acid + CO Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 184.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 736000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Shake flask and filter culture 1100.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 4400000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Shake flask and filter culture 388.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 1552000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 44.2 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 176800 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776