Metabolic Modeling Tutorial
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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
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Homo sapiens 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 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

Reactions known to consume the compound:

(S)-reticuline biosynthesis :
S-norlaudanosoline + 3 S-adenosyl-L-methionine → (S)-reticuline + 3 S-adenosyl-L-homocysteine + 3 H+

7-(3-amino-3-carboxypropyl)-wyosine biosynthesis :
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+
N1-methylguanine37 in tRNAPhe + pyruvate + S-adenosyl-L-methionine → 4-demethylwyosine37 in tRNAPhe + L-methionine + 5'-deoxyadenosine + CO2 + H2O
guanine37 in tRNAPhe + S-adenosyl-L-methionineN1-methylguanine37 in tRNAPhe + S-adenosyl-L-homocysteine + H+

arsenate detoxification I (glutaredoxin) :
arsenite + S-adenosyl-L-methionine → methylarsonate + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + methylarsonite → S-adenosyl-L-homocysteine + cacodylate + 2 H+

catecholamine biosynthesis :
S-adenosyl-L-methionine + (R)-noradrenaline → S-adenosyl-L-homocysteine + (R)-adrenaline + H+

creatine biosynthesis :
guanidinoacetate + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + creatine + H+

diphthamide biosynthesis :
an L-histidine-[translation elongation factor 2] + S-adenosyl-L-methionine → a 2-[(3S)-3-amino-3-carboxypropyl]-L-histidine-[translation elongation factor 2] + S-methyl-5'-thioadenosine + H+
a 2-[(3S)-3-carboxy-3-(dimethylammonio)propyl]-L-histidine-[translation elongation factor 2] + S-adenosyl-L-methionine → a diphthine-[translation elongation factor 2] + S-adenosyl-L-homocysteine + H+
a 2-[(3S)-3-carboxy-3-(methylammonio)propyl]-L-histidine-[translation elongation factor 2] + S-adenosyl-L-methionine → a 2-[(3S)-3-carboxy-3-(dimethylammonio)propyl]-L-histidine-[translation elongation factor 2] + S-adenosyl-L-homocysteine + H+
a 2-[(3S)-3-amino-3-carboxypropyl]-L-histidine-[translation elongation factor 2] + S-adenosyl-L-methionine → a 2-[(3S)-3-carboxy-3-(methylammonio)propyl]-L-histidine-[translation elongation factor 2] + S-adenosyl-L-homocysteine + H+

dopamine degradation :
S-adenosyl-L-methionine + dopamine → S-adenosyl-L-homocysteine + 3-methoxytyramine + H+
3,4-dihydroxyphenylacetate + S-adenosyl-L-methionine → homovanillate + S-adenosyl-L-homocysteine + H+

histamine degradation :
histamine + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + Nτ-methylhistamine + H+

L-dopa degradation :
L-dopa + S-adenosyl-L-methionine → 3-O-methyldopa + S-adenosyl-L-homocysteine + H+

lipoate biosynthesis and incorporation :
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]

methionine degradation :
S-adenosyl-L-methionine + a demethylated methyl acceptor → S-adenosyl-L-homocysteine + a methylated methyl acceptor + H+

mRNA capping :
S-adenosyl-L-methionine + a 5'-(N7-methyl 5'-triphosphoguanosine)-(2'-O-methyl-purine-ribonucleotide)-[mRNA] → S-adenosyl-L-homocysteine + a 5'-(N7-methyl 5'-triphosphoguanosine)-(2'-O-methyl-purine-ribonucleotide)-(2'-O-methyl-nucleotide)-[mRNA] + H+
S-adenosyl-L-methionine + a 5'-(N7-methyl 5'-triphosphoguanosine)-(purine-ribonucleotide)-[mRNA] → a 5'-(N7-methyl 5'-triphosphoguanosine)-(2'-O-methyl-purine-ribonucleotide)-[mRNA] + S-adenosyl-L-homocysteine + H+
a 5'-(5'-triphosphoguanosine)-purine-[mRNA] + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + a 5'-(N7-methyl 5'-triphosphoguanosine)-(purine-ribonucleotide)-[mRNA] + H+

nicotine degradation IV :
(S)-nicotine + S-adenosyl-L-methionine → nicotine isomethonium ion + S-adenosyl-L-homocysteine

noradrenaline and adrenaline degradation :
(R)-adrenaline + S-adenosyl-L-methionine → metanephrine + S-adenosyl-L-homocysteine + H+
3,4-dihydroxymandelate + S-adenosyl-L-methionine → vanillyl mandelate + S-adenosyl-L-homocysteine + H+
3,4-dihydroxyphenylglycol + S-adenosyl-L-methionine → 3-methoxy-4-hydroxyphenylglycol + S-adenosyl-L-homocysteine + H+
(R)-noradrenaline + S-adenosyl-L-methionine → normetanephrine + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + (R)-noradrenaline → S-adenosyl-L-homocysteine + (R)-adrenaline + H+

serotonin and melatonin biosynthesis :
N-acetyl-serotonin + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + melatonin + H+

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

ubiquinol-10 biosynthesis :
3-demethylubiquinol-10 + S-adenosyl-L-methionine → ubiquinol-10 + S-adenosyl-L-homocysteine + H+
2-methoxy-6-all trans-decaprenyl-2-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine → 6-methoxy-3-methyl-2-all-trans-decaprenyl-1,4-benzoquinol + S-adenosyl-L-homocysteine + H+
3,4-dihydroxy-5-all-trans-decaprenylbenzoate + S-adenosyl-L-methionine → 3-methoxy-4-hydroxy-5-all-trans-decaprenylbenzoate + S-adenosyl-L-homocysteine + H+

wybutosine biosynthesis :
7-[(3S)-4-methoxy-(3-amino-3-carboxypropyl)]-wyosine37 in tRNAPhe + CO2 + S-adenosyl-L-methionine → wybutosine37 in tRNAPhe + S-adenosyl-L-homocysteine + 2 H+
7-[(3S)-(3-amino-3-carboxypropyl)]-wyosine37 in tRNAPhe + S-adenosyl-L-methionine → 7-[(3S)-4-methoxy-(3-amino-3-carboxypropyl)]-wyosine37 in tRNAPhe + S-adenosyl-L-homocysteine

Not in pathways:
2 a [methionine synthase]-methylcob(I)alamin + 2 S-adenosyl-L-homocysteine + NADP+ ← 2 a [methionine synthase]-cob(II)alamin + 2 S-adenosyl-L-methionine + NADPH + 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+
3-(all-trans-heptaprenyl)benzene-1,2-diol + S-adenosyl-L-methionine → 2-methoxy-6-(all-trans-heptaprenyl)phenol + S-adenosyl-L-homocysteine + H+
3-(all-trans-decaprenyl)benzene-1,2-diol + S-adenosyl-L-methionine → 2-methoxy-6-(all-trans-decaprenyl)phenol + S-adenosyl-L-homocysteine + H+
3-(all-trans-nonaprenyl)benzene-1,2-diol + S-adenosyl-L-methionine → 2-methoxy-6-(all-trans-nonaprenyl)phenol + S-adenosyl-L-homocysteine + H+
a 3-(all-trans-polyrenyl)benzene-1,2-diol + S-adenosyl-L-methionine → a 2-methoxy-6-(all-trans-polyprenyl)phenol + S-adenosyl-L-homocysteine + H+
a uracil54 in tRNA + S-adenosyl-L-methionine → a 5-methyluracil54 in tRNA + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + a [phosphatase 2A protein] C-terminal L-leucine → S-adenosyl-L-homocysteine + a [phosphatase 2A protein] C-terminal L-leucine methyl ester
S-adenosyl-L-methionine + an N-terminal-(A/S)PK-[protein] → S-adenosyl-L-homocysteine + an N terminal N-methyl-(A/S)PK-[protein] + H+
S-adenosyl-L-methionine + [histone]-L-arginine → S-adenosyl-L-homocysteine + [histone]-Nω-methyl-arginine + 2 H+
S-adenosyl-L-methionine + an N terminal N,N-dimethyl-(A/S)PK-[protein] → S-adenosyl-L-homocysteine + an N terminal N,N,N-trimethyl-(A/S)PK-[protein] + H+
a [histone]-L-lysine + S-adenosyl-L-methionine → a [histone] N6-methyl-L-lysine + 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
a uridine44 in tRNAser + S-adenosyl-L-methionine → a 2'-O-methyluridine44 in tRNAser + S-adenosyl-L-homocysteine + H+
orcinol + S-adenosyl-L-methionine → 3-methoxy-5-hydroxytoluene + S-adenosyl-L-homocysteine + H+
a guanine10 in tRNA + 2 S-adenosyl-L-methionineN2-dimethylguanine10 in tRNA + 2 S-adenosyl-L-homocysteine + 2 H+
a guanine10 in tRNA + S-adenosyl-L-methionine → an N2-methylguanine10 in tRNA + S-adenosyl-L-homocysteine + H+
an N2-methylguanine10 in tRNA + S-adenosyl-L-methionineN2-dimethylguanine10 in tRNA + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + glycine → S-adenosyl-L-homocysteine + sarcosine + H+
guanine37 in tRNA + S-adenosyl-L-methionineN1-methylguanine37 in tRNA + S-adenosyl-L-homocysteine + H+
adenine1518/adenine1519 in 16S rRNA + 4 S-adenosyl-L-methionine → N6-dimethyladenine1518/N6-dimethyladenine1519in 16S rRNA + 4 S-adenosyl-L-homocysteine + 4 H+
an 18S rRNA adenine1779/adenine1780 + 4 S-adenosyl-L-methionine → an 18S rRNA N6-dimethyladenine1779/N6-dimethyladenine1780 + 4 S-adenosyl-L-homocysteine + 4 H+
an adenine58 in tRNA + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + an N1-methyladenine58 in tRNA + H+
guanine9 in tRNA + S-adenosyl-L-methionineN1-methylguanine9 in tRNA + S-adenosyl-L-homocysteine + H+
a guanine26 in tRNA + 2 S-adenosyl-L-methionine → an N2dimethylguanine26 in tRNA + 2 S-adenosyl-L-homocysteine + 2 H+
a guanine26 in tRNA + S-adenosyl-L-methionine → an N2-methylguanine26 in tRNA + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + an N2-methylguanine26 in tRNA → S-adenosyl-L-homocysteine + an N2dimethylguanine26 in tRNA + H+
S-adenosyl-L-methionine + an N-terminal-PPK-[protein] → S-adenosyl-L-homocysteine + an N terminal N-methyl-PPK-[protein] + H+
S-adenosyl-L-methionine + an N terminal N-methyl-PPK-[protein] → S-adenosyl-L-homocysteine + an N terminal N,N-dimethyl-PPK-[protein] + H+
2 S-adenosyl-L-methionine + an N-terminal-PPK-[protein] → 2 S-adenosyl-L-homocysteine + an N terminal N,N-dimethyl-PPK-[protein] + 2 H+
S-adenosyl-L-methionine + an N terminal N-methyl-(A/S)PK-[protein] → S-adenosyl-L-homocysteine + an N terminal N,N-dimethyl-(A/S)PK-[protein] + H+
3 S-adenosyl-L-methionine + an N-terminal-(A/S)PK-[protein] → 3 S-adenosyl-L-homocysteine + an N terminal N,N,N-trimethyl-(A/S)PK-[protein] + 3 H+
S-adenosyl-L-methionine + a cytosine34 in tRNA precursor → S-adenosyl-L-homocysteine + a 5 methylcytosine34 in tRNA precursor
a cytosine38 in tRNA + S-adenosyl-L-methionine → a 5-methylcytosine38 in tRNA + S-adenosyl-L-homocysteine + H+
a catechol + S-adenosyl-L-methionine → a guaiacol + S-adenosyl-L-homocysteine + H+
guanine46 in tRNA + S-adenosyl-L-methionineN7-methylguanine46 in tRNA + S-adenosyl-L-homocysteine
a cytosine in DNA + S-adenosyl-L-methionine → a DNA 5-methylcytosine + S-adenosyl-L-homocysteine + H+
m7G(5')pppAm + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + m7G(5')pppm6Am + H+
an amine + S-adenosyl-L-methionine → a methylated amine + S-adenosyl-L-homocysteine
S-adenosyl-L-methionine + [myelin basic protein]-L-arginine → S-adenosyl-L-homocysteine + [myelin basic protein]-Nω-methyl-arginine + H+
a thiopurine + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + a thiopurine S-methylether + H+
a [protein] c-terminal S-farnesyl-L-cysteine + S-adenosyl-L-methionine → a protein c-terminal s-farnesyl-l-cysteine methyl ester + S-adenosyl-L-homocysteine
phenylethanolamine + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + N-methylphenylethanolamine + H+
an L-1-phosphatidyl-ethanolamine + S-adenosyl-L-methionine → a phosphatidyl-N-methylethanolamine + S-adenosyl-L-homocysteine + H+
nicotinamide + S-adenosyl-L-methionine → 1-methylnicotinamide + S-adenosyl-L-homocysteine

Reactions known to produce the compound:

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

Not in pathways:
a protein + H2O → a protein + an α amino acid

In Reactions of unknown directionality:

Not in pathways:
a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: nicotine N-methyltransferase


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of HumanCyc: Genome Biology 6(1):1-17 2004
Page generated by SRI International Pathway Tools version 18.5 on Mon Nov 24, 2014, BIOCYC13A.