2.0 2012-05-31 13:02:20 -0600 2015-09-13 12:56:09 -0600 ECMDB00939 M2MDB000205 S-Adenosylhomocysteine S-Adenosylhomocysteine (AdoHcy) is the immediate precursor of homocysteine. The reaction is catalyzed by S-adenosylhomocysteine hydrolase and is reversible with the equilibrium favoring formation of AdoHcy. In vivo, the reaction is driven in the direction of homocysteine formation by the action of the enzyme adenosine deaminase, which converts the second product of the S-adenosylhomocysteine hydrolase reaction, adenosine, to inosine. Except for methyl transfer from betaine and from methylcobalamin in the methionine synthase reaction, AdoHcy is the product of all methylation reactions that involve S-adenosylmethionine (AdoMet) as the methyl donor. (S)-5'-(S)-(3-Amino-3-carboxypropyl)-5'-thioadenosine 2-<i>S</i>-adenosyl-L-homocysteine 2-S-Adenosyl-L-homocysteine 5'-Deoxy-S-adenosyl-L-homocysteine 5'-S-(3-Amino-3-carboxypropyl)-5'-thio-L-Adenosine <i>S</i>-adenosyl-homocysteine <i>S</i>-adenosylhomocysteine Adenosyl-homo-CYS Adenosyl-L-homocysteine Adenosylhomo-CYS Adenosylhomocysteine Adohcy Formycinylhomocysteine L-5'-S-(3-Amino-3-carboxypropyl)-5'-thior-Adenosine L-S-Adenosyl-Homocysteine L-S-Adenosylhomocysteine S-(5'-Adenosyl)-L-homocysteine S-(5'-Deoxyadenosin-5'-yl)-L-homocysteine S-(5'-Deoxyadenosine-5')-L-homocysteine S-Adenosyl-homocysteine S-Adenosyl-L-homocysteine S-adenosylhomocysteine SAH SAHC C14H20N6O5S 384.411 384.12158847 (2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid S-adenosyl-L-homocysteine 979-92-0 N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12)C(O)=O InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1 ZJUKTBDSGOFHSH-WFMPWKQPSA-N Solid Cytosol logp -2.37 ALOGPS logs -1.97 ALOGPS solubility 4.08e+00 g/l ALOGPS melting_point 209-211 oC logp -4 ChemAxon pka_strongest_acidic 1.81 ChemAxon pka_strongest_basic 9.5 ChemAxon iupac (2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid ChemAxon average_mass 384.411 ChemAxon mono_mass 384.12158847 ChemAxon smiles N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12)C(O)=O ChemAxon formula C14H20N6O5S ChemAxon inchi InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1 ChemAxon inchikey ZJUKTBDSGOFHSH-WFMPWKQPSA-N ChemAxon polar_surface_area 182.63 ChemAxon refractivity 92.72 ChemAxon polarizability 38.41 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 10 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Cysteine and methionine metabolism ec00270 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 Ubiquinone and other terpenoid-quinone biosynthesis ec00130 Two-component system ec02020 Mismatch repair eco03430 Metabolic pathways eco01100 Menaquinol biosythesis Menaquinol biosynthesis starts with chorismate being metabolized into isochorismate through a isochorismate synthase. Isochorismate then interacts with 2-oxoglutare and a hydrogen ion through a 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase resulting in the release of a carbon dioxide and a 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate. The latter compound then interacts with (1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase resulting in the release of a pyruvate and a (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate. This compound is the dehydrated through a o-succinylbenzoate synthase resulting in the release of a water molecule and a 2-succinylbenzoate. This compound then interacts with a coenzyme A and an ATP through a o-succinylbenzoate CoA ligase resulting in the release of a diphosphate, a AMP and a succinylbenzoyl-CoA. The latter compound interacts with a hydrogen ion through a 1,4-dihydroxy-2-naphthoyl-CoA synthase resulting in the release of a water molecule or a 1,4-dihydroxy-2-naphthoyl-CoA. This compound then interacts with water through a 1,4-dihydroxy-2-naphthoyl-CoA thioesterase resulting in the release of a coenzyme A, a hydrogen ion and a 1,4-dihydroxy-2-naphthoate. The 1,4-dihydroxy-2-naphthoate can interact with either farnesylfarnesylgeranyl-PP or octaprenyl diphosphate and a hydrogen ion through a 1,4-dihydroxy-2-naphthoate octaprenyltransferase resulting in a release of a carbon dioxide, a pyrophosphate and a demethylmenaquinol-8. This compound then interacts with SAM through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a hydrogen ion, a s-adenosyl-L-homocysteine and a menaquinol. PW001897 Metabolic Porphyrin metabolism The metabolism of porphyrin begins with with glutamic acid being processed by an ATP-driven glutamyl-tRNA synthetase by interacting with hydrogen ion and tRNA(Glu), resulting in amo, pyrophosphate and L-glutamyl-tRNA(Glu) Glutamic acid. Glutamic acid can be obtained as a result of L-glutamate metabolism pathway, glutamate / aspartate : H+ symporter GltP, glutamate:sodium symporter or a glutamate / aspartate ABC transporter . L-glutamyl-tRNA(Glu) Glutamic acid interacts with a NADPH glutamyl-tRNA reductase resulting in a NADP, a tRNA(Glu) and a (S)-4-amino-5-oxopentanoate. This compound interacts with a glutamate-1-semialdehyde aminotransferase resulting a 5-aminolevulinic acid. This compound interacts with a porphobilinogen synthase resulting in a hydrogen ion, water and porphobilinogen. The latter compound interacts with water resulting in hydroxymethylbilane synthase resulting in ammonium, and hydroxymethylbilane. Hydroxymethylbilane can either be dehydrated to produce uroporphyrinogen I or interact with a uroporphyrinogen III synthase resulting in a water molecule and a uroporphyrinogen III. Uroporphyrinogen I interacts with hydrogen ion through a uroporphyrinogen decarboxylase resulting in a carbon dioxide and a coproporphyrinogen I Uroporphyrinogen III can be metabolized into precorrin by interacting with a S-adenosylmethionine through a siroheme synthase resulting in hydrogen ion, an s-adenosylhomocysteine and a precorrin-1. On the other hand, Uroporphyrinogen III interacts with hydrogen ion through a uroporphyrinogen decarboxylase resulting in a carbon dioxide and a Coproporphyrinogen III. Precorrin-1 reacts with a S-adenosylmethionine through a siroheme synthase resulting in a S-adenosylhomocysteine and a Precorrin-2. The latter compound is processed by a NAD dependent uroporphyrin III C-methyltransferase [multifunctional] resulting in a NADH and a sirohydrochlorin. This compound then interacts with Fe 2+ uroporphyrin III C-methyltransferase [multifunctional] resulting in a hydrogen ion and a siroheme. The siroheme is then processed in sulfur metabolism pathway. Uroporphyrinogen III can be processed in anaerobic or aerobic condition. Anaerobic: Uroporphyrinogen III interacts with an oxygen molecule, a hydrogen ion through a coproporphyrinogen III oxidase resulting in water, carbon dioxide and protoporphyrinogen IX. The latter compound then interacts with an 3 oxygen molecule through a protoporphyrinogen oxidase resulting in 3 hydrogen peroxide and a Protoporphyrin IX Aerobic: Uroporphyrinogen III reacts with S-adenosylmethionine through a coproporphyrinogen III dehydrogenase resulting in carbon dioxide, 5-deoxyadenosine, L-methionine and protoporphyrinogen IX. The latter compound interacts with a meanquinone through a protoporphyrinogen oxidase resulting in protoporphyrin IX. The protoporphyrin IX interacts with Fe 2+ through a ferrochelatase resulting in a hydrogen ion and a ferroheme b. The ferroheme b can either be incorporated into the oxidative phosphorylation as a cofactor of the enzymes involved in that pathway or it can interact with hydrogen peroxide through a catalase HPII resulting in a heme D. Heme D can then be incorporated into the oxidative phosphyrlation pathway as a cofactor of the enzymes involved in that pathway. Ferroheme b can also interact with water and a farnesyl pyrophosphate through a heme O synthase resulting in a release of pyrophosphate and heme O. Heme O is then incorporated into the Oxidative phosphorylation pathway. PW000936 Metabolic Quorum Sensing Bacterial Autoinducer 2 (AI-2) mediates the quorum sensing 2 system. AI-2 is catalyzed by the luxS enzyme. This enzyme is found in E.coli and S.typhimurium. In E. coli and most pathogenic bacteria that form AI-2 are spontaneous transformations that include cyclization to (2R,4S)-2-methyl-2,4-dihydroxydihydrofuran-3-one and hydration to the final autoinducer (2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran. This product is released from the cell through the AI-2 transporter (tqsA). As the level of AI-2 increases, other cells detect it and import it through the autoinducer-2 ABC transporter (lsrACDB). AI-2 is then degraded in the cells by phosphorylating the AI-2 which is then isomerized to P-HPD which follows by the transfer of and acetyl group to coenzyme A and releases dihydroxyacetone phosphate PW000836 Signaling Secondary Metabolites: Ubiquinol biosynthesis The biosynthesis of ubiquinol starts the interaction of 4-hydroxybenzoic acid interacting with an octaprenyl diphosphate. The former compound comes from the chorismate interacting with a chorismate lyase resulting in the release of a pyruvic acid and a 4-hydroxybenzoic acid. On the other hand, the latter compound, octaprenyl diphosphate is the result of a farnesyl pyrophosphate interacting with an isopentenyl pyrophosphate through an octaprenyl diphosphate synthase resulting in the release of a pyrophosphate and an octaprenyl diphosphate. The 4-hydroxybenzoic acid interacts with octaprenyl diphosphate through a 4-hydroxybenzoate octaprenyltransferase resulting in the release of a pyrophosphate and a 3-octaprenyl-4-hydroxybenzoate. The latter compound then interacts with a hydrogen ion through a 3-octaprenyl-4-hydroxybenzoate carboxy-lyase resulting in the release of a carbon dioxide and a 2-octaprenylphenol. The latter compound interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenylphenol hydroxylase resulting in a NADP, a water molecule and a 2-octaprenyl-6-hydroxyphenol. The 2-octaprenyl-6-hydroxyphenol interacts with an S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in the release of a hydrogen ion, an s-adenosylhomocysteine and a 2-methoxy-6-(all-trans-octaprenyl)phenol. The latter compound then interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenyl-6-methoxyphenol hydroxylase resulting in a NADP, a water molecule and a 2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol. The latter compound interacts with a S-adenosylmethionine through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a s-adenosylhomocysteine, a hydrogen ion and a 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. The 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. interacts with a reduced acceptor, an oxygen molecule through a 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase resulting in the release of a water molecule, an oxidized electron acceptor and a 3-demethylubiquinol-8. The latter compound then interacts with a S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in a hydrogen ion, a S-adenosylhomocysteine and a ubiquinol 8. PW000981 Metabolic Secondary Metabolites: Ubiquinol biosynthesis 2 The biosynthesis of ubiquinol starts the interaction of 4-hydroxybenzoic acid interacting with an octaprenyl diphosphate. The former compound comes from the chorismate interacting with a chorismate lyase resulting in the release of a pyruvic acid and a 4-hydroxybenzoic acid. On the other hand, the latter compound, octaprenyl diphosphate is the result of a farnesyl pyrophosphate interacting with an isopentenyl pyrophosphate through an octaprenyl diphosphate synthase resulting in the release of a pyrophosphate and an octaprenyl diphosphate. The 4-hydroxybenzoic acid interacts with octaprenyl diphosphate through a 4-hydroxybenzoate octaprenyltransferase resulting in the release of a pyrophosphate and a 3-octaprenyl-4-hydroxybenzoate. The latter compound then interacts with a hydrogen ion through a 3-octaprenyl-4-hydroxybenzoate carboxy-lyase resulting in the release of a carbon dioxide and a 2-octaprenylphenol. The latter compound interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenylphenol hydroxylase resulting in a NADP, a water molecule and a 2-octaprenyl-6-hydroxyphenol. The 2-octaprenyl-6-hydroxyphenol interacts with an S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in the release of a hydrogen ion, an s-adenosylhomocysteine and a 2-methoxy-6-(all-trans-octaprenyl)phenol. The latter compound then interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenyl-6-methoxyphenol hydroxylase resulting in a NADP, a water molecule and a 2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol. The latter compound interacts with a S-adenosylmethionine through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a s-adenosylhomocysteine, a hydrogen ion and a 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. The 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. interacts with a reduced acceptor, an oxygen molecule through a 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase resulting in the release of a water molecule, an oxidized electron acceptor and a 3-demethylubiquinol-8. The latter compound then interacts with a S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in a hydrogen ion, a S-adenosylhomocysteine and a ubiquinol 8. PW002036 Metabolic Cyclopropane Fatty Acid (CFA) Biosynthesis Cyclopropane fatty acyl phospholipid synthase catalyzes the modification of acyl chains of phospholipid bilayers through methylenation (using S-adenosyl-L-methionine) of an unsaturated bond to their cyclopropane derivatives. It is one of the few enzymes known to act on the nonpolar portion of phospholipids dispersed in a vesicle. The enzyme acts on the double bond of a phospholipid unsaturated fatty acid residue, which must be nine to eleven carbon atoms removed from the glycerol backbone of the molecule. S-adenosyl-L-methionine is the methyl donor for formation of the methylene moiety. CFA synthase exhibits activity toward phosphatidylglycerol, phosphatidylethanolamine, cardiolipin, and also toward phosphatidylcholine. (EcoCyc) PW002109 Metabolic S-adenosyl-L-methionine cycle The S-adenosyl-L-methionine cycle starts with S-adenosyl-L-methionine reacting with (a demethylated methyl donor ) dimethylglycine resulting in the release of a hydrogen ion, a betain (a methylated methyl donor) and a S-adenosyl-L-homocysteine. The s-adenosyl-L-homocysteine reacts with a water molecule through a S-adenosylhomocysteine nucleosidase resulting in the release of a adenine and a ribosyl-L-homocysteine. This compound in turn reacts with a s-ribosylhomocysteine lyase resulting in the release of a l-homocysteine and a autoinducer 2. The L-homocysteine reacts with a N5-methyl-tetrahydropteroyl tri-L-glutamate through a methionine synthase resulting in the release of a tetrahydropteroyl tri-L-glutamate and a methione. The methionine in turn reacts with a water molecule and ATP molecule through a methionine adenosyltransferase resulting in the release of a diphosphate, a phosphate and a s-adenosyl-L-methionine. PW002080 Metabolic <i>S</i>-adenosyl-L-methionine cycle I PWY-6151 autoinducer AI-2 biosynthesis I PWY-6153 7-keto-8-aminopelargonate biosynthesis I PWY-6519 ubiquinol-8 biosynthesis (prokaryotic) PWY-6708 siroheme biosynthesis PWY-5194 cyclopropane fatty acid (CFA) biosynthesis PWY0-541 menaquinol-8 biosynthesis MENAQUINONESYN-PWY Specdb::CMs 23475 Specdb::CMs 37852 Specdb::CMs 135712 Specdb::CMs 143446 Specdb::CMs 1081911 Specdb::CMs 1081913 Specdb::CMs 1081914 Specdb::CMs 1081916 Specdb::CMs 1081918 Specdb::CMs 1081920 Specdb::CMs 1081922 Specdb::CMs 1081924 Specdb::CMs 1081926 Specdb::CMs 1081928 Specdb::CMs 1081930 Specdb::CMs 1081932 Specdb::CMs 1081933 Specdb::CMs 1081935 Specdb::CMs 1081937 Specdb::CMs 1081939 Specdb::CMs 1081941 Specdb::CMs 1081943 Specdb::CMs 1081945 Specdb::CMs 1081947 Specdb::CMs 1081949 Specdb::NmrOneD 1613 Specdb::NmrOneD 4788 Specdb::NmrOneD 4789 Specdb::NmrOneD 8022 Specdb::NmrOneD 8023 Specdb::NmrOneD 8024 Specdb::NmrOneD 8025 Specdb::NmrOneD 8026 Specdb::NmrOneD 8027 Specdb::NmrOneD 8028 Specdb::NmrOneD 8029 Specdb::NmrOneD 8030 Specdb::NmrOneD 8031 Specdb::NmrOneD 8032 Specdb::NmrOneD 8033 Specdb::NmrOneD 8034 Specdb::NmrOneD 8035 Specdb::NmrOneD 8036 Specdb::NmrOneD 8037 Specdb::NmrOneD 8038 Specdb::NmrOneD 8039 Specdb::NmrOneD 8040 Specdb::NmrOneD 8041 Specdb::MsMs 6252 Specdb::MsMs 6253 Specdb::MsMs 6254 Specdb::MsMs 6255 Specdb::MsMs 6256 Specdb::MsMs 6257 Specdb::MsMs 6258 Specdb::MsMs 6259 Specdb::MsMs 6260 Specdb::MsMs 6261 Specdb::MsMs 6262 Specdb::MsMs 6263 Specdb::MsMs 6264 Specdb::MsMs 6265 Specdb::MsMs 6266 Specdb::MsMs 6267 Specdb::MsMs 6268 Specdb::MsMs 6269 Specdb::MsMs 178686 Specdb::MsMs 178687 Specdb::MsMs 178688 Specdb::MsMs 181005 Specdb::MsMs 181006 Specdb::MsMs 181007 Specdb::MsMs 438820 Specdb::NmrTwoD 1049 Specdb::NmrTwoD 1554 HMDB00939 439155 388301 C00021 16680 ADENOSYL-HOMO-CYS SAH SAH 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 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. 19212411 Hershfield MS, Kredich NM, Koller CA, Mitchell BS, Kurtzberg J, Kinney TR, Falletta JM: S-adenosylhomocysteine catabolism and basis for acquired resistance during treatment of T-cell acute lymphoblastic leukemia with 2'-deoxycoformycin alone and in combination with 9-beta-D-arabinofuranosyladenine. Cancer Res. 1983 Jul;43(7):3451-8. 6601986 Augoustides-Savvopoulou P, Luka Z, Karyda S, Stabler SP, Allen RH, Patsiaoura K, Wagner C, Mudd SH: Glycine N -methyltransferase deficiency: a new patient with a novel mutation. J Inherit Metab Dis. 2003;26(8):745-59. 14739680 Miller AL: The methionine-homocysteine cycle and its effects on cognitive diseases. Altern Med Rev. 2003 Feb;8(1):7-19. 12611557 Struys EA, Jansen EE, de Meer K, Jakobs C: Determination of S-adenosylmethionine and S-adenosylhomocysteine in plasma and cerebrospinal fluid by stable-isotope dilution tandem mass spectrometry. Clin Chem. 2000 Oct;46(10):1650-6. 11017945 Wang J, Dudman NP, Wilcken DE: Effects of homocysteine and related compounds on prostacyclin production by cultured human vascular endothelial cells. Thromb Haemost. 1993 Dec 20;70(6):1047-52. 8165599 Palella TD, Schatz RA, Wilens TE, Fox IH: S-Adenosylhomocysteine accumulation and selective cytotoxicity in cultured J Lab Clin Med. 1982 Aug;100(2):269-78. 6980250 van Guldener C, Stehouwer CD: Homocysteine and methionine metabolism in renal failure. Semin Vasc Med. 2005 May;5(2):201-8. 16047272 Muskiet FA: The importance of (early) folate status to primary and secondary coronary artery disease prevention. Reprod Toxicol. 2005 Sep-Oct;20(3):403-10. 15964170 Fowler B: Homocysteine: overview of biochemistry, molecular biology, and role in disease processes. Semin Vasc Med. 2005 May;5(2):77-86. 16047261 Gordon RK, Ginalski K, Rudnicki WR, Rychlewski L, Pankaskie MC, Bujnicki JM, Chiang PK: Anti-HIV-1 activity of 3-deaza-adenosine analogs. Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners. Eur J Biochem. 2003 Sep;270(17):3507-17. 12919315 Metz J: Cobalamin deficiency and the pathogenesis of nervous system disease. Annu Rev Nutr. 1992;12:59-79. 1354465 Mulder C, Schoonenboom NS, Jansen EE, Verhoeven NM, van Kamp GJ, Jakobs C, Scheltens P: The transmethylation cycle in the brain of Alzheimer patients. Neurosci Lett. 2005 Sep 30;386(2):69-71. 16040194 Delabar U, Kloor D, Luippold G, Muhlbauer B: Simultaneous determination of adenosine, S-adenosylhomocysteine and S-adenosylmethionine in biological samples using solid-phase extraction and high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1999 Mar 19;724(2):231-8. 10219663 Hermes M, von Hippel S, Osswald H, Kloor D: S-adenosylhomocysteine metabolism in different cell lines: effect of hypoxia and cell density. Cell Physiol Biochem. 2005;15(5):233-44. 15956786 Weir DG, Molloy AM, Keating JN, Young PB, Kennedy S, Kennedy DG, Scott JM: Correlation of the ratio of S-adenosyl-L-methionine to S-adenosyl-L-homocysteine in the brain and cerebrospinal fluid of the pig: implications for the determination of this methylation ratio in human brain. Clin Sci (Lond). 1992 Jan;82(1):93-7. 1310924 Wagner C, Koury MJ: S-Adenosylhomocysteine: a better indicator of vascular disease than homocysteine? Am J Clin Nutr. 2007 Dec;86(6):1581-5. 18065573 Herrmann W, Obeid R: Biomarkers of folate and vitamin B(12) status in cerebrospinal fluid. Clin Chem Lab Med. 2007;45(12):1614-20. 17892439 Holy, Antonin; Rosenberg, Ivan. Studies on S-adenosyl-L-homocysteine hydrolase. Part XV. An improved synthesis of S-adenosyl-L-homocysteine and related compounds. Collection of Czechoslovak Chemical Communications (1985), 50(7), 1514-18. http://hmdb.ca/system/metabolites/msds/000/000/845/original/HMDB00939.pdf?1358462988 Chemotaxis protein methyltransferase P07364 CHER_ECOLI cheR http://ecmdb.ca/proteins/P07364.xml Type I restriction enzyme EcoKI M protein P08957 T1MK_ECOLI hsdM http://ecmdb.ca/proteins/P08957.xml 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 tRNA (guanine-N(1)-)-methyltransferase P0A873 TRMD_ECOLI trmD http://ecmdb.ca/proteins/P0A873.xml tRNA (guanine-N(7)-)-methyltransferase P0A8I5 TRMB_ECOLI trmB http://ecmdb.ca/proteins/P0A8I5.xml Cyclopropane-fatty-acyl-phospholipid synthase P0A9H7 CFA_ECOLI cfa http://ecmdb.ca/proteins/P0A9H7.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 DNA adenine methylase P0AEE8 DMA_ECOLI dam http://ecmdb.ca/proteins/P0AEE8.xml 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI mtnN http://ecmdb.ca/proteins/P0AF12.xml tRNA guanosine-2'-O-methyltransferase P0AGJ2 TRMH_ECOLI trmH http://ecmdb.ca/proteins/P0AGJ2.xml 3-demethylubiquinone-9 3-methyltransferase P17993 UBIG_ECOLI ubiG http://ecmdb.ca/proteins/P17993.xml tRNA (uracil-5-)-methyltransferase P23003 TRMA_ECOLI trmA http://ecmdb.ca/proteins/P23003.xml Uncharacterized adenine-specific methylase yhdJ P28638 YHDJ_ECOLI yhdJ http://ecmdb.ca/proteins/P28638.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 Ribosomal RNA large subunit methyltransferase F P75782 RLMF_ECOLI rlmF http://ecmdb.ca/proteins/P75782.xml Trans-aconitate 2-methyltransferase P76145 TAM_ECOLI tam http://ecmdb.ca/proteins/P76145.xml tRNA 5-methylaminomethyl-2-thiouridine biosynthesis bifunctional protein mnmC P77182 MNMC_ECOLI mnmC http://ecmdb.ca/proteins/P77182.xml Homocysteine S-methyltransferase Q47690 MMUM_ECOLI mmuM http://ecmdb.ca/proteins/Q47690.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 23S rRNA (guanosine-2'-O-)-methyltransferase rlmB P63177 RLMB_ECOLI rlmB http://ecmdb.ca/proteins/P63177.xml 23S rRNA (uracil-5-)-methyltransferase rumB P75817 RUMB_ECOLI rumB http://ecmdb.ca/proteins/P75817.xml 23S rRNA (uracil-5-)-methyltransferase rumA P55135 RUMA_ECOLI rumA http://ecmdb.ca/proteins/P55135.xml Ribosomal RNA large subunit methyltransferase E P0C0R7 RLME_ECOLI rlmE http://ecmdb.ca/proteins/P0C0R7.xml Ribosomal RNA large subunit methyltransferase H P0A8I8 RLMH_ECOLI rlmH http://ecmdb.ca/proteins/P0A8I8.xml Ribosomal RNA large subunit methyltransferase I P75876 RLMI_ECOLI rlmI http://ecmdb.ca/proteins/P75876.xml Ribosomal RNA large subunit methyltransferase M P0ADR6 RLMM_ECOLI rlmM http://ecmdb.ca/proteins/P0ADR6.xml Ribosomal RNA large subunit methyltransferase N P36979 RLMN_ECOLI rlmN http://ecmdb.ca/proteins/P36979.xml Ribosomal RNA small subunit methyltransferase A P06992 RSMA_ECOLI rsmA http://ecmdb.ca/proteins/P06992.xml Ribosomal RNA small subunit methyltransferase B P36929 RSMB_ECOLI rsmB http://ecmdb.ca/proteins/P36929.xml Ribosomal RNA small subunit methyltransferase E P0AGL7 RSME_ECOLI rsmE http://ecmdb.ca/proteins/P0AGL7.xml Ribosomal RNA small subunit methyltransferase F P76273 RSMF_ECOLI rsmF http://ecmdb.ca/proteins/P76273.xml Ribosomal RNA small subunit methyltransferase G P0A6U5 RSMG_ECOLI rsmG http://ecmdb.ca/proteins/P0A6U5.xml Ribosomal RNA small subunit methyltransferase H P60390 RSMH_ECOLI rsmH http://ecmdb.ca/proteins/P60390.xml Ribosomal RNA small subunit methyltransferase I P67087 RSMI_ECOLI rsmI http://ecmdb.ca/proteins/P67087.xml UPF0341 protein yhiQ P68567 YHIQ_ECOLI yhiQ http://ecmdb.ca/proteins/P68567.xml tRNA (cytidine/uridine-2'-O-)-methyltransferase trmJ P0AE01 TRMJ_ECOLI trmJ http://ecmdb.ca/proteins/P0AE01.xml Uncharacterized tRNA/rRNA methyltransferase yibK P0AGJ7 YIBK_ECOLI yibK http://ecmdb.ca/proteins/P0AGJ7.xml tRNA (adenine-N(6)-)-methyltransferase P31825 TRMN6_ECOLI yfiC http://ecmdb.ca/proteins/P31825.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-Adenosylhomocysteine + Water <> Adenine + S-Ribosyl-L-homocysteine R00194 ADENOSYLHOMOCYSTEINE-NUCLEOSIDASE-RXN S-Adenosylmethionine + L-Homocysteine + S-Methylmethionine <> S-Adenosylhomocysteine + Hydrogen ion + L-Methionine R00650 HOMOCYSTEINE-S-METHYLTRANSFERASE-RXN 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 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 S-Adenosylmethionine + L-Homocysteine <> S-Adenosylhomocysteine + L-Methionine R00650 HOMOCYSTEINE-S-METHYLTRANSFERASE-RXN 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 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 S-Adenosylmethionine + Uroporphyrinogen III <> S-Adenosylhomocysteine + precorrin-1 + Hydrogen ion UROPORIIIMETHYLTRANSA-RXN S-Adenosylmethionine + a [protein]-L-&beta;-isoaspartate > S-Adenosylhomocysteine + a protein L-&beta;-isoaspartate &alpha;-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-Ribosyl-L-homocysteine + Adenine < S-Adenosylhomocysteine + Water R00194 ADENOSYLHOMOCYSTEINE-NUCLEOSIDASE-RXN 2-octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine > Hydrogen ion + Ubiquinol-8 + S-Adenosylhomocysteine DHHB-METHYLTRANSFER-RXN L-Homocysteine + S-Adenosylmethionine Hydrogen ion + L-Methionine + S-Adenosylhomocysteine HOMOCYSTEINE-S-METHYLTRANSFERASE-RXN S-Adenosylmethionine + a demethylated methyl acceptor > S-Adenosylhomocysteine + a methylated methyl acceptor RXN-7605 N-6-isopentyl adenosine-37 tRNA + S-Adenosylmethionine + <i>S</i>-sulfanyl-[acceptor] 2-methylthio-N-6-isopentyl adenosine-37 tRNA + S-Adenosylhomocysteine + L-Methionine + 5'-Deoxyadenosine + an unsulfurated sulfur acceptor + Hydrogen ion RXN0-5063 a guanine¹⁵¹⁶ in 16S rRNA + S-Adenosylmethionine > an <i>N</i>²-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 S-adenosyl-L-methionine + Malonyl-CoA > S-Adenosylhomocysteine + malonyl-CoA methyl ester S-adenosyl-L-methionine + phospholipid olefinic fatty acid > S-Adenosylhomocysteine + phospholipid cyclopropane fatty acid S-adenosyl-L-methionine + protein L-glutamate > S-Adenosylhomocysteine + protein L-glutamate methyl ester S-adenosyl-L-methionine + Uroporphyrinogen III > S-Adenosylhomocysteine + Precorrin-1 S-adenosyl-L-methionine + Precorrin-1 > S-Adenosylhomocysteine + Precorrin-2 S-adenosyl-L-methionine + DNA > S-Adenosylhomocysteine + DNA containing 5-methylcytosine S-adenosyl-L-methionine + DNA adenine > S-Adenosylhomocysteine + DNA 6-methylaminopurine S-adenosyl-L-methionine + tRNA > S-Adenosylhomocysteine + tRNA containing 5-methylaminomethyl-2-thiouridylate S-Adenosylhomocysteine + Water > S-Ribosyl-L-homocysteine + Adenine S-adenosyl-L-methionine + protein L-isoaspartate > S-Adenosylhomocysteine + protein L-isoaspartate alpha-methyl ester S-adenosyl-L-methionine + glutamine in ribosomal protein L3 > S-Adenosylhomocysteine + N5-methylglutamine in ribosomal protein L3 S-adenosyl-L-methionine + glutamine in release factor > S-Adenosylhomocysteine + N5-methylglutamine in release factor S-adenosyl-L-methionine + guanine(745) in 23S rRNA > S-Adenosylhomocysteine + N(1)-methylguanine(745) in 23S rRNA S-adenosyl-L-methionine + guanosine(2251) in 23S rRNA > S-Adenosylhomocysteine + 2'-O-methylguanosine(2251) in 23S rRNA S-adenosyl-L-methionine + uracil(747) in 23S rRNA > S-Adenosylhomocysteine + 5-methyluracil(747) in 23S rRNA S-adenosyl-L-methionine + uracil(1939) in 23S rRNA > S-Adenosylhomocysteine + 5-methyluracil(1939) in 23S rRNA S-adenosyl-L-methionine + uridine(2552) in 23S rRNA > S-Adenosylhomocysteine + 2'-O-methyluridine(2552) in 23S rRNA S-adenosyl-L-methionine + adenine(1618) in 23S rRNA > S-Adenosylhomocysteine + rRNA containing N(6)-methyladenine(1618) in 23S rRNA S-adenosyl-L-methionine + guanine(1835) in 23S rRNA > S-Adenosylhomocysteine + N(2)-methylguanine(1835) in 23S rRNA S-adenosyl-L-methionine + rRNA > S-Adenosylhomocysteine + rRNA containing N3-methylpseudouridine S-adenosyl-L-methionine + pseudouridine(1915) in 23S rRNA > S-Adenosylhomocysteine + N(3)-methylpseudouridine(1915) in 23S rRNA S-adenosyl-L-methionine + cytosine(1962) in 23S rRNA > S-Adenosylhomocysteine + 5-methylcytosine(1962) in 23S rRNA S-adenosyl-L-methionine + guanine(2445) in 23S rRNA > S-Adenosylhomocysteine + N(2)-methylguanine(2445) in 23S rRNA S-adenosyl-L-methionine + cytidine(2498) in 23S rRNA > S-Adenosylhomocysteine + 2'-O-methylcytidine(2498) in 23S rRNA 2 S-adenosyl-L-methionine + adenine(2503) in 23S rRNA > S-Adenosylhomocysteine + L-Methionine + 5'-Deoxyadenosine + 2-methyladenine(2503) in 23S rRNA 4 S-adenosyl-L-methionine + adenine(1518)/adenine(1519) in 16S rRNA >4 S-Adenosylhomocysteine + N(6)-dimethyladenine(1518)/N(6)-dimethyladenine(1519) in 16S rRNA S-adenosyl-L-methionine + cytosine(967) in 16S rRNA > S-Adenosylhomocysteine + 5-methylcytosine(967) in 16S rRNA S-adenosyl-L-methionine + guanine(1207) in 16S rRNA > S-Adenosylhomocysteine + N(2)-methylguanine(1207) in 16S rRNA S-adenosyl-L-methionine + guanine(966) in 16S rRNA > S-Adenosylhomocysteine + N(2)-methylguanine(966) in 16S rRNA S-adenosyl-L-methionine + uracil(1498) in 16S rRNA > S-Adenosylhomocysteine + N(3)-methyluracil(1498) in 16S rRNA S-adenosyl-L-methionine + cytosine(1407) in 16S rRNA > S-Adenosylhomocysteine + 5-methylcytosine(1407) in 16S rRNA S-adenosyl-L-methionine + guanine(527) in 16S rRNA > S-Adenosylhomocysteine + N(7)-methylguanine(527) in 16S rRNA S-adenosyl-L-methionine + cytosine(1402) in 16S rRNA > S-Adenosylhomocysteine + N(4)-methylcytosine(1402) in 16S rRNA S-adenosyl-L-methionine + cytidine(1402) in 16S rRNA > S-Adenosylhomocysteine + 2'-O-methylcytidine(1402) in 16S rRNA S-adenosyl-L-methionine + guanine(1516) in 16S rRNA > S-Adenosylhomocysteine + N(2)-methylguanine(1516) in 16S rRNA S-adenosyl-L-methionine + trans-Aconitic acid > S-Adenosylhomocysteine + (E)-3-(Methoxycarbonyl)pent-2-enedioate S-adenosyl-L-methionine + uridine(54) in tRNA > S-Adenosylhomocysteine + 5-methyluridine(54) in tRNA S-adenosyl-L-methionine + guanine(46) in tRNA > S-Adenosylhomocysteine + N(7)-methylguanine(46) in tRNA S-adenosyl-L-methionine + guanine(37) in tRNA > S-Adenosylhomocysteine + N(1)-methylguanine(37) in tRNA S-adenosyl-L-methionine + guanosine(18) in tRNA > S-Adenosylhomocysteine + 2'-O-methylguanosine(18) in tRNA S-adenosyl-L-methionine + cytidine(32) in tRNA > S-Adenosylhomocysteine + 2'-O-methylcytidine(32) in tRNA S-adenosyl-L-methionine + uridine(32) in tRNA > S-Adenosylhomocysteine + 2'-O-methyluridine(32) in tRNA S-adenosyl-L-methionine + cytidine(34) in tRNA > S-Adenosylhomocysteine + 2'-O-methylcytidine(34) in tRNA S-adenosyl-L-methionine + 5-carboxymethylaminomethyluridine(34) in tRNA(Leu) > S-Adenosylhomocysteine + 5-carboxymethylaminomethyl-2'-O-methyluridine(34) in tRNA(Leu) S-adenosyl-L-methionine + adenine(37) in tRNA(1)(Val) > S-Adenosylhomocysteine + N(6)-methyladenine(37) in tRNA(1)(Val) A demethylmenaquinone + S-adenosyl-L-methionine > Menaquinol 6 + S-Adenosylhomocysteine S-adenosyl-L-methionine + 2-methoxy-6-all-trans-polyprenyl-1,4-benzoquinol > S-Adenosylhomocysteine + 6-methoxy-3-methyl-2-all-trans-polyprenyl-1,4-benzoquinol S-adenosyl-L-methionine + 3-demethylubiquinone-n > S-Adenosylhomocysteine + ubiquinone-n S-adenosyl-L-methionine + 3-(all-trans-polyprenyl)benzene-1,2-diol > S-Adenosylhomocysteine + 2-methoxy-6-(all-trans-polyprenyl)phenol 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 S-Adenosylmethionine + tRNA <> S-Adenosylhomocysteine + tRNA containing N6-methyladenine R00599 S-Adenosylhomocysteine + Water > Adenine + S-ribosyl-L-homocysteine + S-ribosyl-L-homocysteine PW_R003067 a malonyl-[acp] + S-adenosyl-L-methionine > S-Adenosylhomocysteine + a malonyl-[acp] methyl ester PW_R002455 Uroporphyrinogen III + S-adenosyl-L-methionine > Hydrogen ion + S-Adenosylhomocysteine + Precorrin-1 PW_R003489 2-Octaprenyl-6-hydroxyphenol + S-adenosyl-L-methionine + 2-Octaprenyl-6-hydroxyphenol > Hydrogen ion + S-Adenosylhomocysteine + 2-methoxy-6-(all-trans-octaprenyl)phenol PW_R003719 3-demethylubiquinol-8 + S-adenosyl-L-methionine > Hydrogen ion + S-Adenosylhomocysteine + Ubiquinol 8 + Ubiquinol-8 PW_R003723 2-Octaprenyl-6-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine > S-Adenosylhomocysteine + Hydrogen ion + 6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol PW_R003721 2-Demethylmenaquinol 8 + S-adenosyl-L-methionine > Hydrogen ion + S-Adenosylhomocysteine + Menaquinol 8 PW_R005240 S-Adenosylhomocysteine + Water > Adenine PW_R006077 2-octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + S-adenosyl-L-methionine > S-Adenosylhomocysteine + Ubiquinol-8 + Hydrogen ion PW_R005948 2-Octaprenyl-6-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine > 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol + S-Adenosylhomocysteine + Hydrogen ion PW_R005949 a [phospholipid] olefinic fatty acid + S-adenosyl-L-methionine > a [phospholipid] cyclopropane fatty acid + S-Adenosylhomocysteine + Hydrogen ion PW_R006143 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 + 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 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 + 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 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