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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

<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

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] + 2 a reduced [2Fe-2S] ferredoxin → a [lipoyl-carrier protein] N6-lipoyl-L-lysine + 2 5'-deoxyadenosine + 2 L-methionine + 2 an unsulfurated [sulfur carrier] + 2 an oxidized [2Fe-2S] ferredoxin

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

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 CpG site + S-adenosyl-L-methionine = a 5-methyl-CpG site + S-adenosyl-L-homocysteine + H+

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


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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 19.0 on Sat Mar 28, 2015, BIOCYC13B.