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
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

Escherichia coli K-12 substr. MG1655 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

Component of: MetJ-S-adenosylmethionine

Summary from MetaCyc:
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): -111.889

Reactions known to consume the compound:

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

8-amino-7-oxononanoate biosynthesis I :
a malonyl-[acp] + S-adenosyl-L-methionine → a malonyl-[acp] methyl ester + S-adenosyl-L-homocysteine

autoinducer AI-2 biosynthesis I , S-adenosyl-L-methionine cycle I :
S-adenosyl-L-methionine + a demethylated methyl acceptor → S-adenosyl-L-homocysteine + a methylated methyl acceptor + H+

biotin biosynthesis from 8-amino-7-oxononanoate I :
a sulfurated [sulfur carrier] + dethiobiotin + 2 S-adenosyl-L-methionine → an unsulfurated [sulfur carrier] + biotin + 2 5'-deoxyadenosine + 2 L-methionine

cyclopropane fatty acid (CFA) biosynthesis :
a phospholipid olefinic fatty acid + S-adenosyl-L-methionine → a phospholipid cyclopropane fatty acid + S-adenosyl-L-homocysteine + H+

heme biosynthesis II (anaerobic) :
coproporphyrinogen III + 2 S-adenosyl-L-methionine → protoporphyrinogen IX + 2 CO2 + 2 L-methionine + 2 5'-deoxyadenosine

lipoate biosynthesis and incorporation I , lipoate biosynthesis and incorporation II :
a [lipoyl-carrier protein] N6-octanoyl-L-lysine + 2 S-adenosyl-L-methionine + 2 a sulfurated [sulfur carrier] → a [lipoyl-carrier protein] N6-lipoyl-L-lysine + 2 5'-deoxyadenosine + 2 L-methionine + 2 an unsulfurated [sulfur carrier]

menaquinol-8 biosynthesis :
S-adenosyl-L-methionine + demethylmenaquinol-8 → S-adenosyl-L-homocysteine + menaquinol-8 + H+

queuosine biosynthesis :
a 7-aminomethyl-7-deazaguanosine34 in tRNA + S-adenosyl-L-methionine → an epoxyqueuosine34 in tRNA + adenine + L-methionine + 2 H+

siroheme biosynthesis :
S-adenosyl-L-methionine + precorrin-1 → S-adenosyl-L-homocysteine + precorrin-2
S-adenosyl-L-methionine + uroporphyrinogen-III → S-adenosyl-L-homocysteine + precorrin-1 + H+

spermidine biosynthesis I :
S-adenosyl-L-methionine + H+ → CO2 + S-adenosyl 3-(methylthio)propylamine

thiazole biosynthesis I (E. coli) :
L-tyrosine + S-adenosyl-L-methionine + NADPH → 2-iminoacetate + 4-methylphenol + 5'-deoxyadenosine + L-methionine + NADP+ + H+

ubiquinol-8 biosynthesis (prokaryotic) :
2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine → 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol + S-adenosyl-L-homocysteine + H+
3-(all-trans-octaprenyl)benzene-1,2-diol + S-adenosyl-L-methionine → 2-methoxy-6-(all-trans-octaprenyl)phenol + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + 3-demethylubiquinol-8S-adenosyl-L-homocysteine + ubiquinol-8 + H+

Not in pathways:
N6-L-threonylcarbamoyladenine37 in tRNA + S-adenosyl-L-methionineN6-methyl-threonylcarbamoyladenosine 37 in tRNA + S-adenosyl-L-homocysteine + H+
rRNA + S-adenosyl-L-methionine → rRNA containing N6,N6-dimethyladenine + S-adenosyl-L-homocysteine
a [ribosomal protein L3]-L-glutamine + S-adenosyl-L-methionine → a [ribosomal protein L3]-N5-methyl-L-glutamine + S-adenosyl-L-homocysteine + H+
a [release factor]-L-glutamine + S-adenosyl-L-methionine → a [release factor]-N5-methyl-L-glutamine + S-adenosyl-L-homocysteine + H+
a uracil54 in tRNA + S-adenosyl-L-methionine → a 5-methyluracil54 in tRNA + S-adenosyl-L-homocysteine + H+
a [ribosomal protein S12] L-aspartate89 + 2 S-adenosyl-L-methionine + a sulfurated [sulfur carrier] → a [ribosomal protein S12] 3-methylthio-L-aspartate89 + S-adenosyl-L-homocysteine + an unsulfurated [sulfur carrier] + L-methionine + 5'-deoxyadenosine + H+
2-thio-N6-dimethylallyladenosine37 in tRNA + S-adenosyl-L-methionine → 2-methylthio-N6-dimethylallyladenosine37 in tRNA + S-adenosyl-L-homocysteine + H+
N6-dimethylallyladenosine37 in tRNA + 2 S-adenosyl-L-methionine + a sulfurated [sulfur carrier] → 2-methylthio-N6-dimethylallyladenosine37 in tRNA + S-adenosyl-L-homocysteine + L-methionine + 5'-deoxyadenosine + an unsulfurated [sulfur carrier] + H+
a [protein]-α-L-glutamate + S-adenosyl-L-methionine → a [protein]-L-glutamate-O5-methyl-ester + S-adenosyl-L-homocysteine
a tRNA containing 5-aminomethyl-2-thiouridine + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + a 5-methylaminomethyl-2-thiouridine in tRNA + 2 H+
2 S-adenosyl-L-methionine + an adenine37 in tRNA → S-adenosyl-L-homocysteine + L-methionine + 5'-deoxyadenosine + a 2-methyladenine37 in tRNA
adenine2030 in 23S rRNA + S-adenosyl-L-methionineN6-methyladenine2030 in 23S rRNA + S-adenosyl-L-homocysteine + H+
2 S-adenosyl-L-methionine + adenine2503 in 23S rRNA → S-adenosyl-L-homocysteine + L-methionine + 5'-deoxyadenosine + 2-methyladenine2503 in 23S rRNA
guanine2069 in 23S rRNA + S-adenosyl-L-methionine → N7-methylguanine2069 in 23S rRNA + S-adenosyl-L-homocysteine
a guanine1516 in 16S rRNA + S-adenosyl-L-methionine → an N2-methylguanine1516 in 16S rRNA + S-adenosyl-L-homocysteine + H+
a guanosine18 in tRNA + S-adenosyl-L-methionine → a 2'-O-methylguanosine18 in tRNA + S-adenosyl-L-homocysteine + H+
guanine46 in tRNA + S-adenosyl-L-methionineN7-methylguanine46 in tRNA + S-adenosyl-L-homocysteine
S-adenosyl-L-methionine + adenine37 in tRNA1valS-adenosyl-L-homocysteine + N6-methyladenine37 in tRNA1val + H+
guanine37 in tRNA + S-adenosyl-L-methionineN1-methylguanine37 in tRNA + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + a [protein]-L-β-isoaspartate → S-adenosyl-L-homocysteine + a protein L-β-isoaspartate α-methyl ester
S-adenosyl-L-methionine + cytidine1402 in 16S rRNA → S-adenosyl-L-homocysteine + 2'-O-methylcytidine1402 in 16S rRNA + H+
S-adenosyl-L-methionine + cytidine1402 in 16S rRNA → S-adenosyl-L-homocysteine + N4-methylcytidine1402 in 16S rRNA + H+
tellurite + S-adenosyl-L-methionine → methanetelluronate + S-adenosyl-L-homocysteine
an rRNA + S-adenosyl-L-methionine → rRNA containing 2-methyladenine + S-adenosyl-L-homocysteine
a cytosine in DNA + S-adenosyl-L-methionine → a DNA 5-methylcytosine + S-adenosyl-L-homocysteine + H+
a uridine32 in tRNA + S-adenosyl-L-methionine → a 2'-O-methyluridine32 in tRNA + S-adenosyl-L-homocysteine + H+
a cytidine 32 in tRNA + S-adenosyl-L-methionine → a 2'-O-methylcytidine32 in tRNA + S-adenosyl-L-homocysteine + H+
a 5-carboxymethylaminomethyluridine34 in tRNALeu + S-adenosyl-L-methionine → a 5-carboxymethylaminomethyl-2'-O-methyluridine34 in tRNALeu + S-adenosyl-L-homocysteine + H+
a cytidine34 in tRNA + S-adenosyl-L-methionine → a 2'-O-methylcytidine34 in tRNA + S-adenosyl-L-homocysteine + H+
uridine2552 in 23S rRNA + S-adenosyl-L-methionine → 2-O-methyluridine2552 in 23S rRNA + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + guanine1835 in 23S rRNA → S-adenosyl-L-homocysteine + N2-methylguanine1835 in 23S rRNA + H+
adenine1518/adenine1519 in 16S rRNA + 4 S-adenosyl-L-methionine → N6-dimethyladenine1518/N6-dimethyladenine1519in 16S rRNA + 4 S-adenosyl-L-homocysteine + 4 H+
cytosine1962 in 23S rRNA + S-adenosyl-L-methionine → 5-methylcytosine1962 in 23S rRNA + S-adenosyl-L-homocysteine + H+
a uracil1939 in 23S rRNA + S-adenosyl-L-methionine → a 5-methyluracil1939 in 23S rRNA + S-adenosyl-L-homocysteine + H+
a uracil747 in 23S rRNA + S-adenosyl-L-methionine → a 5-methyluracil747 in 23S rRNA + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + uracil1498 in 16S rRNA → S-adenosyl-L-homocysteine + N3-methyluracil1498 in 16S rRNA + H+
adenine1618 in 23S rRNA + S-adenosyl-L-methionine → N6-methyladenine1618 in 23S rRNA + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + cytosine1407 in 16S rRNA → S-adenosyl-L-homocysteine + 5-methylcytosine1407 in 16S rRNA + H+
S-adenosyl-L-methionine + a pseudouridine1915 in 23S rRNA → S-adenosyl-L-homocysteine + an N3-methylpseudouridine1915 in 23S rRNA + H+
cytosine967 in 16S rRNA + S-adenosyl-L-methionine → 5-methylcytosine967 in 16S rRNA + S-adenosyl-L-homocysteine + H+
cytidine2498 in 23S rRNA + S-adenosyl-L-methionine → 2-O-methylcytidine2498 in 23S rRNA + S-adenosyl-L-homocysteine + H+
guanosine2251 in 23S rRNA + S-adenosyl-L-methionine → 2-O-methylguanosine2251 in 23S rRNA + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + guanine527 in 16S rRNA → S-adenosyl-L-homocysteine + N7-methylguanine527 in 16S rRNA
S-adenosyl-L-methionine + guanine966 in 16S rRNA → S-adenosyl-L-homocysteine + N2-methylguanine966 in 16S rRNA + H+
S-adenosyl-L-methionine + guanine1207 in 16S rRNA → S-adenosyl-L-homocysteine + N2-methylguanine1207 in 16S rRNA + H+
S-adenosyl-L-methionine + guanine2445 in 23S rRNA → S-adenosyl-L-homocysteine + N2-methylguanine2445 in 23S rRNA + H+
guanine745 in 23S rRNA + S-adenosyl-L-methionine → N1-methylguanine745 in 23S rRNA + S-adenosyl-L-homocysteine + H+
a non-methylated ribosomal protein L11 + S-adenosyl-L-methionine → a methylated ribosomal protein L11 + S-adenosyl-L-homocysteine
trans-aconitate + S-adenosyl-L-methionine → (E)-3-(methoxycarbonyl)pent-2-enedioate + S-adenosyl-L-homocysteine
2-ketobutyrate formate-lyase/pyruvate formate-lyase 4, inactive + a reduced flavodoxin + S-adenosyl-L-methionine → 5'-deoxyadenosine + 2-ketobutyrate formate-lyase / pyruvate formate-lyase 4 + an oxidized flavodoxin
L-homocysteine + S-adenosyl-L-methionine → L-methionine + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + TsrgluS-adenosyl-L-homocysteine + Tsrglu-Me
S-adenosyl-L-methionine + TrggluS-adenosyl-L-homocysteine + Trgglu-Me
S-adenosyl-L-methionine + TargluS-adenosyl-L-homocysteine + Targlu-Me
S-adenosyl-L-methionine + TapgluS-adenosyl-L-homocysteine + Tapglu-Me
a DNA adenine + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + a DNA 6-methylaminopurine + H+
pyruvate formate-lyase (inactive) + a reduced flavodoxin + S-adenosyl-L-methionine → 5'-deoxyadenosine + L-methionine + pyruvate formate-lyase / 2-ketobutyrate formate-lyase + an oxidized flavodoxin

Reactions known to produce the compound:

S-adenosyl-L-methionine biosynthesis :
ATP + L-methionine + H2O → S-adenosyl-L-methionine + phosphate + diphosphate

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

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

In Reactions of unknown directionality:

Not in pathways:
MetJ + S-adenosyl-L-methionine = MetJ-S-adenosylmethionine
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
S-adenosyl-L-methionine + a protein = a methylated protein


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

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

Inhibitor (Competitive) of: methionine adenosyltransferase [Markham80]

Inhibitor (Allosteric) of: homoserine O-succinyltransferase [Comment 1]

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: lysine 2,3-aminomutase , HMP-P synthase

Regulated Transcription Units (1 total): ?

Notes:


References

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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 28, 2014, BIOCYC13A.