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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

<i>S</i>-adenosyl-L-methionine compound structure

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 :
dehypoxanthine futalosine + S-adenosyl-L-methionine → cyclic dehypoxanthine futalosine + L-methionine + 5'-deoxyadenosine + H+
3-[(1-carboxyvinyl)oxy]benzoate + S-adenosyl-L-methionine + H2O → 6-amino-6-deoxyfutalosine + L-methionine + hydrogen carbonate + H+

1,4-dihydroxy-6-naphthoate biosynthesis II :
dehypoxanthine futalosine + S-adenosyl-L-methionine → cyclic dehypoxanthine futalosine + L-methionine + 5'-deoxyadenosine + H+
3-[(1-carboxyvinyl)oxy]benzoate + S-adenosyl-L-methionine + H2O → 6-amino-6-deoxyfutalosine + L-methionine + hydrogen carbonate + H+

2'-deoxymugineic acid phytosiderophore biosynthesis , L-nicotianamine biosynthesis :
3 S-adenosyl-L-methionine → L-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+

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 :
5-guanidino-2-oxo-pentanoate + 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+

Reactions known to produce the compound:

2'-deoxymugineic acid phytosiderophore biosynthesis , ethylene biosynthesis I (plants) , L-methionine degradation I (to L-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:
a (4E)-4-sphinga-4,8-dienine ceramide + S-adenosyl-L-methionine = a 9-methyl-sphinga-4,8-dienine ceramide + S-adenosyl-L-homocysteine + H+
N6-dimethylallyladenosine37 in tRNA + a sulfurated [sulfur carrier] + S-adenosyl-L-methionine + an unknown reduced electron acceptor = 2-thio-N6-dimethylallyladenosine37 in tRNA + an unsulfurated [sulfur carrier] + 5'-deoxyadenosine + L-methionine + an unknown oxidized electron acceptor + H+
S-adenosyl-L-methionine + 7-demethylmitomycin A = S-adenosyl-L-homocysteine + mitomycin A
S-adenosyl-L-methionine + 7-demethylmitomycin B = S-adenosyl-L-homocysteine + mitomycin B
a uridine47 in tRNAPhe + S-adenosyl-L-methionine = a 3-[(3S)-3-amino-3-carboxypropyl]-uridine47 in tRNAPhe + S-methyl-5'-thioadenosine + H+
cytosyl-β-D-glucuronate + 2 S-adenosyl-L-methionine + 2 a reduced flavodoxin = cytosyl-α-L-arabinopyranose + CO2 + 2 5'-deoxyadenosine + 2 L-methionine + 2 an oxidized flavodoxin + H+
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
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 (3R)-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-1-2 + H+
a butyryl-[acp] + S-adenosyl-L-methionine = a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + PAI-1-2 + 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-1 + 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

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

This compound has been characterized as an alternative substrate of the following enzymes: homocysteine S-methyltransferase


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
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