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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: S-adenosyl-L-methionine

Abbrev Name: SAM

Synonyms: AdoMet, SAM, 2-S-adenosyl-L-methionine, S-adenosyl-methionine, adenosylmethionine, S-adenosylmethionine

Superclasses: an amino acid or its derivative an amino acid an alpha amino acid a non-standard alpha amino acid

Summary:
S-adenosyl-L-methionine (AdoMet) is a sulfonium compound in which each of the carbons attached to the sulfur is activated toward nucleophilic attack.

Chemical Formula: C15H23N6O5S

Molecular Weight: 399.44 Daltons

Monoisotopic Molecular Weight: 399.14506357 Daltons

SMILES: C[S+](CC3(C(O)C(O)C(N2(C1(N=CN=C(N)C=1N=C2)))O3))CCC(C([O-])=O)[N+]

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

InChIKey: InChIKey=MEFKEPWMEQBLKI-AIRLBKTGSA-O

Unification Links: CAS:29908-03-0 , ChEBI:59789 , HMDB:HMDB01185 , IAF1260:33530 , KEGG:C00019 , MetaboLights:MTBLC59789 , PubChem:44229224

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 124.03472 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

(S)-reticuline biosynthesis I : (S)-coclaurine + S-adenosyl-L-methionine → (S)-N-methylcoclaurine + S-adenosyl-L-homocysteine + H+ 3'-hydroxy-N-methyl-(S)-coclaurine + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + (S)-reticuline + H+ (S)-norcoclaurine + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + (S)-coclaurine + H+ (S)-reticuline biosynthesis II : S-norlaudanosoline + 3 S-adenosyl-L-methionine → (S)-reticuline + 3 S-adenosyl-L-homocysteine + 3 H+ 1,3,5-trimethoxybenzene biosynthesis : 3,5-dimethoxyphenol + S-adenosyl-L-methionine → 1,3,5-trimethoxybenzene + S-adenosyl-L-homocysteine + H+ 3,5-dihydroxyanisole + S-adenosyl-L-methionine → 3,5-dimethoxyphenol + S-adenosyl-L-homocysteine + H+ phloroglucinol + S-adenosyl-L-methionine → 3,5-dihydroxyanisole + S-adenosyl-L-homocysteine + H+ 1,4-dihydroxy-6-naphthoate biosynthesis I : 3-[(1-carboxyvinyl)oxy]benzoate + S-adenosyl-L-methionine + H2O → 6-amino-6-deoxyfutalosine + L-methionine + hydrogen carbonate + H+ dehypoxanthine futalosine + S-adenosyl-L-methionine → cyclic dehypoxanthine futalosine + L-methionine + 5'-deoxyadenosyl radical + 2 H+ 1,4-dihydroxy-6-naphthoate biosynthesis II : 3-[(1-carboxyvinyl)oxy]benzoate + S-adenosyl-L-methionine + H2O → 6-amino-6-deoxyfutalosine + L-methionine + hydrogen carbonate + H+ dehypoxanthine futalosine + S-adenosyl-L-methionine → cyclic dehypoxanthine futalosine + L-methionine + 5'-deoxyadenosyl radical + 2 H+ 2'-deoxymugineic acid phytosiderophore biosynthesis , nicotianamine biosynthesis : 3 S-adenosyl-L-methionine → nicotianamine + 3 S-methyl-5'-thioadenosine + 3 H+ 2-methylisoborneol biosynthesis : S-adenosyl-L-methionine + geranyl diphosphate → S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate + H+ 26,27-dehydrozymosterol metabolism : 26,27-dehydrozymosterol + methanol + S-adenosyl-L-methionine + H+ → 24-alkyl sterol 3 + S-adenosyl-L-homocysteine + methyl-group 26,27-dehydrozymosterol + methanol + S-adenosyl-L-methionine + H+ → 24-alkyl sterol 2 + S-adenosyl-L-homocysteine + methyl-group 26,27-dehydrozymosterol + S-adenosyl-L-methionine → 24-alkyl sterol 1 + S-adenosyl-L-homocysteine 3,5-dimethoxytoluene biosynthesis : orcinol + S-adenosyl-L-methionine → 3-methoxy-5-hydroxytoluene + S-adenosyl-L-homocysteine + H+ 3-methoxy-5-hydroxytoluene + S-adenosyl-L-methionine → 3,5-dimethoxytoluene + S-adenosyl-L-homocysteine + H+ 3-methylarginine biosynthesis : 2-ketoarginine + S-adenosyl-L-methionine → 5-guanidino-3-methyl-2-oxo-pentanoate + S-adenosyl-L-homocysteine + H+ 4-amino-2-methyl-5-diphosphomethylpyrimidine biosynthesis : 5-amino-1-(5-phospho-β-D-ribosyl)imidazole + S-adenosyl-L-methionine → 4-amino-2-methyl-5-phosphomethylpyrimidine + 5'-deoxyadenosine + L-methionine + formate + carbon monoxide + 3 H+ 5-(carboxymethoxy)uridine biosynthesis : prephenate + S-adenosyl-L-methionine → 2-oxo-3-phenylpropanoate + carboxy-S-adenosyl-L-methionine + H2O 6-gingerol biosynthesis : 1-(3,4-dihydroxyphenyl)-5-hydroxy-3-decanone + S-adenosyl-L-methionine → 6-gingerol + S-adenosyl-L-homocysteine + H+ 6-methoxymellein biosynthesis : 6-hydroxymellein + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + 6-methoxymellein + H+ 7-(3-amino-3-carboxypropyl)-wyosine biosynthesis : N1-methylguanine37 in tRNAPhe + pyruvate + S-adenosyl-L-methionine → 4-demethylwyosine37 in tRNAPhe + L-methionine + 5'-deoxyadenosine + CO2 + H2O S-adenosyl-L-methionine + 7-[(3S)-3-amino-3-carboxypropyl]-4-demethylwyosine37 in tRNAPheS-adenosyl-L-homocysteine + 7-[(3S)-(3-amino-3-carboxypropyl)]-wyosine37 in tRNAPhe + H+ S-adenosyl-L-methionine + 4-demethylwyosine37 in tRNAPheS-methyl-5'-thioadenosine + 7-[(3S)-3-amino-3-carboxypropyl]-4-demethylwyosine37 in tRNAPhe + H+ guanine37 in tRNAPhe + S-adenosyl-L-methionineN1-methylguanine37 in tRNAPhe + S-adenosyl-L-homocysteine + H+ 7-dehydroporiferasterol biosynthesis : S-adenosyl-L-methionine + cycloartenol → S-adenosyl-L-homocysteine + 24-methylenecycloartanol + H+ 8-amino-7-oxononanoate biosynthesis I : a malonyl-[acp] + S-adenosyl-L-methionine → a malonyl-[acp] methyl ester + S-adenosyl-L-homocysteine acacetin biosynthesis : apigenin + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + acacetin + H+ aclacinomycin biosynthesis : S-adenosyl-L-methionine + aklanonate → S-adenosyl-L-homocysteine + methyl aklanonate acridone alkaloid biosynthesis , N-methylanthraniloyl-β-D-glucopyranose biosynthesis , superpathway avenacin A biosynthesis : anthranilate + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + N-methylanthranilate + H+ aflatoxins B1 and G1 biosynthesis : sterigmatocystin + S-adenosyl-L-methionine → 8-O-methylsterigmatocystin + S-adenosyl-L-homocysteine + H+ aflatoxins B2 and G2 biosynthesis : dihydrosterigmatocystin + S-adenosyl-L-methionine → 8-O-methyldihydrosterigmatocystin + S-adenosyl-L-homocysteine + H+ dihydrodemethylsterigmatocystin + S-adenosyl-L-methionine → dihydrosterigmatocystin + S-adenosyl-L-homocysteine + H+ ajmaline and sarpagine biosynthesis : 17-O-acetylnorajmaline + S-adenosyl-L-methionine → 17-O-acetylajmaline + S-adenosyl-L-homocysteine norajmaline + S-adenosyl-L-methionine → ajmaline + S-adenosyl-L-homocysteine + H+ arsenate detoxification I (glutaredoxin) : S-adenosyl-L-methionine + methylarsonite → S-adenosyl-L-homocysteine + cacodylate + 2 H+ arsenite + S-adenosyl-L-methionine → methylarsonate + S-adenosyl-L-homocysteine + H+ autoinducer AI-1 biosynthesis : an acyl-[acyl-carrier protein] + S-adenosyl-L-methionine → a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + an N-acyl-L-homoserine lactone + H+ autoinducer AI-2 biosynthesis I , autoinducer AI-2 biosynthesis II (Vibrio) , methionine degradation I (to homocysteine) , S-adenosyl-L-methionine cycle I , S-adenosyl-L-methionine cycle II : S-adenosyl-L-methionine + a demethylated methyl acceptor → S-adenosyl-L-homocysteine + a methylated methyl acceptor + H+ berberine biosynthesis : (S)-scoulerine + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + S-tetrahydrocolumbamine + H+ β-alanine betaine biosynthesis : N,N-dimethyl-β-alanine + S-adenosyl-L-methionine → β-alanine betaine + S-adenosyl-L-homocysteine + H+ N-methyl-β-alanine + S-adenosyl-L-methionine → N,N-dimethyl-β-alanine + S-adenosyl-L-homocysteine + H+ β-alanine + S-adenosyl-L-methionine → N-methyl-β-alanine + S-adenosyl-L-homocysteine + H+ betaxanthin biosynthesis : S-adenosyl-L-methionine + dopamine → S-adenosyl-L-homocysteine + 3-methoxytyramine + H+ biotin biosynthesis from 8-amino-7-oxononanoate I , biotin biosynthesis from 8-amino-7-oxononanoate II : a sulfurated [sulfur carrier] + dethiobiotin + 2 S-adenosyl-L-methionine → an unsulfurated [sulfur carrier] + biotin + 2 5'-deoxyadenosine + 2 L-methionine bixin biosynthesis : bixin + S-adenosyl-L-methionine → bixin dimethyl ester + S-adenosyl-L-homocysteine norbixin + S-adenosyl-L-methionine → bixin + S-adenosyl-L-homocysteine botryococcenes and methylated squalene biosynthesis : showacene + S-adenosyl-L-methionine → 3,20-dimethyl-1,2,21,22-tetradehydro-2,3,20,21-tetrahydrobotryococcene + S-adenosyl-L-homocysteine + H+ C30 botryococcene + S-adenosyl-L-methionine → showacene + S-adenosyl-L-homocysteine + H+ 3-methyl-1,2-didehydro-2,3-dihydrosqualene + S-adenosyl-L-methionine → 3,22-dimethyl-1,2,23,24-tetradehydro-2,3,22,23-tetrahydrosqualene + S-adenosyl-L-homocysteine + H+ squalene + S-adenosyl-L-methionine → 3-methyl-1,2-didehydro-2,3-dihydrosqualene + S-adenosyl-L-homocysteine + H+ 3,20-dimethyl-1,2,21,22-tetradehydro-2,3,20,21-tetrahydrobotryococcene + S-adenosyl-L-methionine → C33 botryococcene + S-adenosyl-L-homocysteine + H+ C33 botryococcene + S-adenosyl-L-methionine → a C34 botryococcenes + S-adenosyl-L-homocysteine + H+ brassicicene C biosynthesis : fusicocca-1,10(14)-diene-3,8β,16-triol + S-adenosyl-L-methionine → fusicocca-1,10(14)-diene-16-(hydroxymethyl)-3,8β-diol + S-adenosyl-L-homocysteine + H+ caffeine biosynthesis I : theobromine + S-adenosyl-L-methionine → caffeine + S-adenosyl-L-homocysteine + H+ 7-methylxanthine + S-adenosyl-L-methionine → theobromine + S-adenosyl-L-homocysteine + H+ xanthosine + S-adenosyl-L-methionine → 7-methylxanthosine + S-adenosyl-L-homocysteine + H+ caffeine biosynthesis II (via paraxanthine) : paraxanthine + S-adenosyl-L-methionine → caffeine + S-adenosyl-L-homocysteine + H+ 7-methylxanthine + S-adenosyl-L-methionine → paraxanthine + S-adenosyl-L-homocysteine + H+ xanthosine + S-adenosyl-L-methionine → 7-methylxanthosine + S-adenosyl-L-homocysteine + H+ capsaicin biosynthesis , chlorogenic acid biosynthesis I , coumarins biosynthesis (engineered) , scopoletin biosynthesis : caffeoyl-CoA + S-adenosyl-L-methionine → feruloyl-CoA + S-adenosyl-L-homocysteine + H+ catecholamine biosynthesis : S-adenosyl-L-methionine + (R)-noradrenaline → S-adenosyl-L-homocysteine + (R)-adrenaline + H+ cephamycin C biosynthesis : 7-α-hydroxy-O-carbamoyl-deacetylcephalosporin C + S-adenosyl-L-methionine → cephamycin C + S-adenosyl-L-homocysteine + H+ chanoclavine I aldehyde biosynthesis : 4-(3-methylbut-2-enyl)-L-tryptophan + S-adenosyl-L-methionine → 4-(3-methylbut-2-enyl)-L-abrine + S-adenosyl-L-homocysteine + H+ chlorophyllide a biosynthesis I (aerobic, light-dependent) , chlorophyllide a biosynthesis II (anaerobic) , chlorophyllide a biosynthesis III (aerobic, light independent) : Mg-protoporphyrin + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + magnesium-protoporphyrin IX 13-monomethyl ester choline biosynthesis I : N-dimethylethanolamine phosphate + S-adenosyl-L-methionine → phosphocholine + S-adenosyl-L-homocysteine + H+ N-methylethanolamine phosphate + S-adenosyl-L-methionine → N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine + H+ phosphoryl-ethanolamine + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + N-methylethanolamine phosphate + H+ choline biosynthesis II : N-dimethylethanolamine + S-adenosyl-L-methionine → choline + S-adenosyl-L-homocysteine + H+ N-monomethylethanolamine + S-adenosyl-L-methionineN-dimethylethanolamine + S-adenosyl-L-homocysteine + H+ ethanolamine + S-adenosyl-L-methionineN-monomethylethanolamine + S-adenosyl-L-homocysteine + H+ chrysoeriol biosynthesis : luteolin + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + chrysoeriol + H+ cob(II)yrinate a,c-diamide biosynthesis I (early cobalt insertion) : S-adenosyl-L-methionine + cobalt-precorrin-4 → S-adenosyl-L-homocysteine + cobalt-precorrin-5A + H+ cobalt-precorrin-7 + S-adenosyl-L-methionine → cobalt-precorrin-8 + S-adenosyl-L-homocysteine cobalt-precorrin-3 + S-adenosyl-L-methionine → cobalt-precorrin-4 + S-adenosyl-L-homocysteine cobalt-precorrin-5B + S-adenosyl-L-methionine → cobalt-precorrin-6A + S-adenosyl-L-homocysteine cobalt-precorrin-6B + S-adenosyl-L-methionine + H+ → cobalt-precorrin-7 + S-adenosyl-L-homocysteine + CO2 S-adenosyl-L-methionine + uroporphyrinogen-III → S-adenosyl-L-homocysteine + precorrin-1 + H+ S-adenosyl-L-methionine + precorrin-1 → S-adenosyl-L-homocysteine + precorrin-2 S-adenosyl-L-methionine + cobalt-sirohydrochlorin → S-adenosyl-L-homocysteine + cobalt-factor III + H+ cob(II)yrinate a,c-diamide biosynthesis II (late cobalt incorporation) : precorrin-6B + S-adenosyl-L-methionine + H+ → precorrin-7 + S-adenosyl-L-homocysteine + CO2 precorrin-4 + S-adenosyl-L-methionine → precorrin-5 + S-adenosyl-L-homocysteine + H+ precorrin-7 + S-adenosyl-L-methionine → precorrin-8x + S-adenosyl-L-homocysteine + 2 H+ S-adenosyl-L-methionine + uroporphyrinogen-III → S-adenosyl-L-homocysteine + precorrin-1 + H+ S-adenosyl-L-methionine + precorrin-1 → S-adenosyl-L-homocysteine + precorrin-2 precorrin-5 + S-adenosyl-L-methionine + H2O → precorrin-6A + S-adenosyl-L-homocysteine + acetate + 2 H+ precorrin-2 + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + precorrin-3A + H+ precorrin-3B + S-adenosyl-L-methionine → precorrin-4 + S-adenosyl-L-homocysteine + 2 H+ colchicine biosynthesis : (S)-isoandrocymbine + S-adenosyl-L-methionine → O-methylandrocymbine + S-adenosyl-L-homocysteine + H+ creatine biosynthesis : guanidinoacetate + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + creatine + H+ cyclopropane and cyclopropene fatty acid biosynthesis : oleate + S-adenosyl-L-methionine → dihydrosterculate + S-adenosyl-L-homocysteine + H+ cyclopropane fatty acid (CFA) biosynthesis : a phospholipid olefinic fatty acid + S-adenosyl-L-methionine → a phospholipid cyclopropane fatty acid + S-adenosyl-L-homocysteine + H+ daphnetin modification : S-adenosyl-L-methionine + daphnetin → S-adenosyl-L-homocysteine + 7-hydroxy-8-methoxycoumarin + H+ daunorubicin biosynthesis : S-adenosyl-L-methionine + aklanonate → S-adenosyl-L-homocysteine + methyl aklanonate 13-deoxycarminomycin + S-adenosyl-L-methionine → 13-deoxydaunorubicin + S-adenosyl-L-homocysteine + H+ dehydrophos biosynthesis : desmethyl dehydrophos + S-adenosyl-L-methionine → dehydrophos + S-adenosyl-L-homocysteine diacylglyceryl-N,N,N-trimethylhomoserine biosynthesis : S-adenosyl-L-methionine + a 1,2-diacyl-sn-glycerol → a diacylglycerolhomoserine + S-methyl-5'-thioadenosine + H+ a diacylglycerolhomoserine + 3 S-adenosyl-L-methionine → a diacylglyceryl-N,N,N-trimethylhomoserine + 3 S-adenosyl-L-homocysteine + 3 H+ DIMBOA-glucoside biosynthesis : TRIBOA-β-D-glucoside + S-adenosyl-L-methionine → DIMBOA-β-D-glucoside + S-adenosyl-L-homocysteine + H+

Reactions known to produce the compound:

2'-deoxymugineic acid phytosiderophore biosynthesis , ethylene biosynthesis I (plants) , methionine degradation I (to homocysteine) , S-adenosyl-L-methionine biosynthesis , S-adenosyl-L-methionine cycle II :
ATP + L-methionine + H2O → S-adenosyl-L-methionine + phosphate + diphosphate

Not in pathways:
amino acids(n) + H2O → amino acids(n-1) + an α amino acid
an α amino acid ester + H2O → an alcohol + an α amino acid + H+
a protein + H2O → a protein + an α amino acid

Reactions known to both consume and produce the compound:

biotin biosynthesis from 8-amino-7-oxononanoate I :
S-adenosyl-L-methionine + 8-amino-7-oxononanoate ↔ S-adenosyl-4-methylthio-2-oxobutanoate + 7,8-diaminopelargonate

salinosporamide A biosynthesis :
S-adenosyl-L-methionine + chloride ↔ 5'-deoxy-5'-chloroadenosine + L-methionine

Not in pathways:
an inactive ribonucleoside triphosphate reductase + S-adenosyl-L-methionine ↔ an active ribonucleoside triphosphate reductase + 5'-deoxyadenosine + L-methionine

In Reactions of unknown directionality:

Not in pathways:
mercaptohistidine + S-adenosyl-L-methionine = ovothiol + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + a uracil2634 in 25S rRNA = S-adenosyl-L-homocysteine + N3-methyluracil2634 in 25S rRNA + H+
S-adenosyl-L-methionine + a uracil2843 in 25S rRNA = S-adenosyl-L-homocysteine + N3-methyluracil2843 in 25S rRNA + H+
S-adenosyl-L-methionine + cytosine2278 in 25S rRNA = S-adenosyl-L-homocysteine + 5-methylcytosine2278 in 25S rRNA + H+
S-adenosyl-L-methionine + cytosine2870 in 25S rRNA = S-adenosyl-L-homocysteine + 5-methylcytosine2870 in 25S rRNA + H+
S-adenosyl-L-methionine + a guanine1575 in 18S tRNA = S-adenosyl-L-homocysteine + N7-methylguanine1575 in 18S rRNA
N6-dimethylallyladenosine37 in tRNA + S-adenosyl-L-methionine + a sulfurated [sulfur carrier] = 2-thio-N6-dimethylallyladenosine37 in tRNA + an unsulfurated [sulfur carrier] + L-methionine + 5'-deoxyadenosine
a CpG site + S-adenosyl-L-methionine = a 5-methyl-CpG site + S-adenosyl-L-homocysteine + H+
4-coumaryl-CoA + S-adenosyl-L-methionine = S-methyl-5'-thioadenosine + N-4-coumaryl-L-homoserine lactone + coenzyme A + H+
isovaleryl-CoA + S-adenosyl-L-methionine = S-methyl-5'-thioadenosine + N-isovaleryl-L-homoserine lactone + coenzyme A + H+
S-adenosyl-L-methionine = L-homoserine lactone + S-methyl-5'-thioadenosine
a (R)-3-hydroxybutanoyl-[acp] + S-adenosyl-L-methionine = a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + HAI-1 + H+
an octanoyl-[acp] + S-adenosyl-L-methionine = a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + VAI-2 + H+
a butyryl-[acp] + S-adenosyl-L-methionine = a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + PAI-2 + H+
a 3-oxo-dodecanoyl-[acp] + S-adenosyl-L-methionine = a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + PAI-1 + H+
a 3-oxo-hexanoyl-[acp] + S-adenosyl-L-methionine = a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + VAI-1 + H+
a 3-oxo-octanoyl-[acp] + S-adenosyl-L-methionine = a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + AAI + H+
a uridine in tRNA + S-adenosyl-L-methionine = a tRNA 3-(3-amino-3-carboxypropyl)-uridine + S-methyl-5'-thioadenosine + H+
S-adenosyl-L-methionine + a protein = a methylated protein
nocardicin E + S-adenosyl-L-methionine = isonocardicin A + S-methyl-5'-thioadenosine + H+
a [formate C acetyltransferase]-glycine + S-adenosyl-L-methionine + a reduced flavodoxin = a [formate C acetyltransferase]-glycin -2-yl radical + 5'-deoxyadenosine + L-methionine + a flavodoxin semiquinone
N6-dimethylallyladenine + S-adenosyl-L-methionine = discadenine + S-methyl-5'-thioadenosine + H+
S-adenosyl-L-methionine + H2O = L-homoserine + S-methyl-5'-thioadenosine + H+


a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

Enzymes activated by S-adenosyl-L-methionine, sorted by the type of activation, are:

Activator (Mechanism unknown) of: methionine adenosyltransferase [Comment 1]

Enzymes inhibited by S-adenosyl-L-methionine, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: methionine adenosyltransferase [Markham80]

Inhibitor (Noncompetitive) of: homoserine O-acetyltransferase [Shiio81]

Inhibitor (Allosteric) of: homoserine O-succinyltransferase [Comment 2]

Inhibitor (Mechanism unknown) of: S-methyl-L-methionine decarboxylase [Kocsis00] , methionine adenosyltransferase [Comment 3] , O-acetylhomoserine sulfhydrylase [Belfaiza98] , homoserine O-acetyltransferase [Yamagata87] , methionine adenosyltransferase [Cabrero87] , S-adenosylmethionine synthetase [Schroder97]

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: HMP-P synthase , lysine 2,3-aminomutase , 15-demethoxy-ε-rhodomycinone 10-hydroxylase , 15-demethoxyaclacinomycin T decarboxylase , 15-demethoxyaclacinomycin A decarboxylase , (2R,3R)-3-methylornithine synthase , nicotine N-methyltransferase , 2-hydroxyethylphosphonate methylase , lysine 2,3-aminomutase


References

Belfaiza98: Belfaiza J, Martel A, Margarita D, Saint Girons I (1998). "Direct sulfhydrylation for methionine biosynthesis in Leptospira meyeri." J Bacteriol 180(2);250-5. PMID: 9440513

Cabrero87: Cabrero C, Puerta J, Alemany S (1987). "Purification and comparison of two forms of S-adenosyl-L-methionine synthetase from rat liver." Eur J Biochem 170(1-2);299-304. PMID: 3121322

Chou72: Chou TC, Talalay P (1972). "The mechanism of S-adenosyl-L-methionine synthesis by purified preparations of bakers' yeast." Biochemistry 1972;11(6);1065-73. PMID: 4552214

Kocsis00: Kocsis MG, Hanson AD (2000). "Biochemical evidence for two novel enzymes in the biosynthesis of 3-dimethylsulfoniopropionate in Spartina alterniflora." Plant Physiol 123(3);1153-61. PMID: 10889264

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lee66: Lee LW, Ravel JM, Shive W (1966). "Multimetabolite control of a biosynthetic pathway by sequential metabolites." J Biol Chem 1966;241(22);5479-80. PMID: 5333667

Markham80: Markham GD, Hafner EW, Tabor CW, Tabor H (1980). "S-Adenosylmethionine synthetase from Escherichia coli." J Biol Chem 1980;255(19);9082-92. PMID: 6251075

Schroder97: Schroder G, Eichel J, Breinig S, Schroder J (1997). "Three differentially expressed S-adenosylmethionine synthetases from Catharanthus roseus: molecular and functional characterization." Plant Mol Biol 33(2);211-22. PMID: 9037140

Shiio81: Shiio I, Ozaki H (1981). "Feedback inhibition by methionine and S-adenosylmethionine, and desensitization of homoserine O-acetyltransferase in Brevibacterium flavum." J Biochem (Tokyo) 89(5);1493-500. PMID: 7275950

Yamagata87: Yamagata S (1987). "Partial purification and some properties of homoserine O-acetyltransferase of a methionine auxotroph of Saccharomyces cerevisiae." J Bacteriol 1987;169(8);3458-63. PMID: 3301801


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Tue Nov 25, 2014, biocyc13.