Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
twitter

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 acidall carboxy acidsa carboxylatean amino acidan alpha amino acida non-standard alpha amino acid
an amino acid or its derivativean amino acidan alpha amino acida 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: 400.1528886021 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

Not in pathways:
an L-1-phosphatidyl-inositol + H2O → a 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an acylcholine + H2O → choline + a carboxylate + H+
a 2-acyl 1-lyso-phosphatidylcholine + H2O → a carboxylate + sn-glycero-3-phosphocholine + H+
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

In Reactions of unknown directionality:

Not in pathways:
S-adenosyl-L-methionine + [protein]-ω-NG-methyl-L-arginine = S-adenosyl-L-homocysteine + [protein]-ω-NG,N'G-dimethyl-L-arginine + H+
S-adenosyl-L-methionine + a [protein]-L-arginine = S-adenosyl-L-homocysteine + [protein]-ω-NG-methyl-L-arginine + H+
S-adenosyl-L-methionine + [protein]-ω-NG-methyl-L-arginine = S-adenosyl-L-homocysteine + [protein]-ω-NG,NG-dimethyl-L-arginine + H+
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

Not in pathways:
an aldehyde + NAD+ + H2O = a carboxylate + NADH + 2 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an aldehyde + FAD + H2O = a carboxylate + FADH2
a nitrile + 2 H2O = a carboxylate + ammonium
an aldehyde + NADP+ + H2O = a carboxylate + NADPH + 2 H+
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a triacyl-sn-glycerol + H2O = a carboxylate + a 1,2-diacyl-sn-glycerol + H+
an acyl phosphate + H2O = a carboxylate + phosphate + H+

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 Pathway Tools version 19.5 (software by SRI International) on Tue May 3, 2016, biocyc13.