Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000289
Identification
Name: S-Adenosylmethionine
Description:S-Adenosylmethionine is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It is made from adenosine triphosphate (ATP) and methionine by methionine adenosyltransferase (EC 2.5.1.6). Transmethylation, transsulfuration, and aminopropylation are the metabolic pathways that use S-Adenosylmethionine. In bacteria, SAM is bound by the SAM riboswitch, which regulates genes involved in methionine or cysteine biosynthesis. (Wikipedia)
Structure
Thumb
Synonyms:
  • (3S)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine
  • (3S)-5'-[(3-amino-3-carboxypropyl)methylsulphonio]-5'-deoxyadenosine
  • 2-S-adenosyl-L-methionine
  • 2-S-Adenosyl-L-methionine
  • 5'-Deoxyadenosine-5'-L-methionine disulfate ditosylate
  • 5'-Deoxyadenosine-5'-L-methionine disulfuric acid ditosylic acid
  • 5'-Deoxyadenosine-5'-L-methionine disulphate ditosylate
  • 5'-Deoxyadenosine-5'-L-methionine disulphuric acid ditosylic acid
  • S-adenosyl-methionine
  • S-adenosylmethionine
  • Active methionine
  • Ademetionine
  • Adenosylmethionine
  • AdoMet
  • Donamet
  • L-S-Adenosylmethionine
  • S-(5'-Adenosyl)-L-methionine
  • S-(5'-Deoxyadenosin-5'-yl)-L-methionine
  • S-Adenosyl methionine
  • S-Adenosyl-L-methionine
  • S-Adenosyl-L-Methionine Disulfate Tosylate
  • S-Adenosyl-L-methionine disulfuric acid tosylic acid
  • S-Adenosyl-L-methionine disulphate tosylate
  • S-Adenosyl-L-methionine disulphuric acid tosylic acid
  • S-Adenosyl-methionine
  • S-Adenosylmethionine
  • SAM
Chemical Formula: C15H23N6O5S
Average Molecular Weight: 399.445
Monoisotopic Molecular Weight: 399.145063566
InChI Key: MEFKEPWMEQBLKI-AIRLBKTGSA-O
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
CAS number: 29908-03-0
IUPAC Name:[(3R)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium
Traditional IUPAC Name: [(3R)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium
SMILES:C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an?amine?with a?beta-N-glycosidic bond?to a carbohydrate, thus forming a cyclic?hemiaminal ether?bond (alpha-amino ether).
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct Parent Glycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • D-alpha-amino acid
  • Methionine or derivatives
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Thia fatty acid
  • Aminopyrimidine
  • Amino fatty acid
  • Fatty acyl
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.19 mg/mLALOGPS
logP-2ALOGPS
logP-5.3ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)1.71ChemAxon
pKa (Strongest Basic)9.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area182.63 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity96.23 m3·mol-1ChemAxon
Polarizability39.84 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
2 S-Adenosylmethionine + Uroporphyrinogen III >2 S-Adenosylhomocysteine + Precorrin 2 + Hydrogen ion
S-Adenosylmethionine + Hydrogen ion <> S-Adenosylmethioninamine + Carbon dioxide
S-Adenosylmethionine + L-Homocysteine + S-Methylmethionine <> S-Adenosylhomocysteine + Hydrogen ion + L-Methionine
[4Fe-4S] iron-sulfur cluster + 2 S-Adenosylmethionine + Hydrogen ion + NAD + octanoate (protein bound) > [2Fe-2S] iron-sulfur cluster +2 5'-Deoxyadenosine +2 Iron + lipoate (protein bound) +2 L-Methionine + NADH
8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate
[2Fe-2S] iron-sulfur cluster + S-Adenosylmethionine + Dethiobiotin > [2Fe-1S] desulfurated iron-sulfur cluster + Biotin + 5'-Deoxyadenosine + Hydrogen ion + L-Methionine
S-Adenosylmethionine + Malonyl-CoA > S-Adenosylhomocysteine + malonyl-CoA methyl ester
trans-Aconitic acid + S-Adenosylmethionine > E-3-Carboxy-2-pentenedioate 6-methyl ester + S-Adenosylhomocysteine
2 S-Adenosylmethionine + PE(14:0/14:0) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylethanolamine (dihexadec-9,10-cyclo-anoyl, N-C16:0 cyclo) +2 Hydrogen ion
2 S-Adenosylmethionine + PE(14:0/14:0) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylethanolamine (dioctadec-11,12-cyclo-anoyl, N-C18:0 cyclo) +2 Hydrogen ion
2 S-Adenosylmethionine + PG(16:1(9Z)/16:1(9Z)) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylglycerol (dihexadec-9,10-cyclo-anoyl, N-C16:0 cyclo) +2 Hydrogen ion
2 S-Adenosylmethionine + PG(18:1(11Z)/18:1(11Z)) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylglycerol (dioctadec-11,12-cyclo-anoyl, N-C18:0 cyclo) +2 Hydrogen ion
2-Octaprenyl-6-hydroxyphenol + S-Adenosylmethionine > 2-Octaprenyl-6-methoxyphenol + S-Adenosylhomocysteine + Hydrogen ion
2-Octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol + S-Adenosylmethionine > S-Adenosylhomocysteine + Hydrogen ion + Ubiquinol-8
Adenosine triphosphate + Water + L-Methionine <> S-Adenosylmethionine + Phosphate + Pyrophosphate
2-Demethylmenaquinol 8 + S-Adenosylmethionine > S-Adenosylhomocysteine + Hydrogen ion + Menaquinol 8
2-Octaprenyl-6-methoxy-1,4-benzoquinol + S-Adenosylmethionine > 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol + S-Adenosylhomocysteine + Hydrogen ion
2 S-Adenosylmethionine + Coproporphyrin III <>2 Carbon dioxide +2 5'-Deoxyadenosine +2 L-Methionine + Protoporphyrinogen IX
S-Adenosylmethionine + NADPH + L-Tyrosine > p-Cresol + 5'-Deoxyadenosine + Dehydroglycine + Hydrogen ion + L-Methionine + NADP
S-Adenosylmethionine + L-Homocysteine <> S-Adenosylhomocysteine + L-Methionine
Dethiobiotin + Sulfur donor + 2 S-Adenosylmethionine + 2 e- + 2 Hydrogen ion <> Biotin +2 L-Methionine +2 5'-Deoxyadenosine
2 S-Adenosylmethionine + Uroporphyrinogen III <>2 S-Adenosylhomocysteine + Precorrin 2
4-Amino-5-hydroxymethyl-2-methylpyrimidine + S-Adenosylmethionine <> 5-Aminoimidazole ribonucleotide + 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + CO
S-Adenosylmethionine + DNA cytosine <> S-Adenosylhomocysteine + DNA 5-methylcytosine
2-Octaprenyl-6-hydroxyphenol + S-Adenosylmethionine <> 2-Octaprenyl-6-methoxyphenol + S-Adenosylhomocysteine
2-Demethylmenaquinone 8 + S-Adenosylmethionine <> Menaquinone + S-Adenosylhomocysteine
2-Phytyl-1,4-naphthoquinone + S-Adenosylmethionine <> Phylloquinone + S-Adenosylhomocysteine
S-Adenosylmethionine + rRNA <> S-Adenosylhomocysteine + rRNA containing N6-methyladenine
S-Adenosylmethionine + rRNA <> S-Adenosylhomocysteine + rRNA containing N1-methylguanine
S-Adenosylmethionine + rRNA <> S-Adenosylhomocysteine + rRNA containing N2-methylguanine
Protein N6-(octanoyl)lysine + 2 Sulfur donor + 2 S-Adenosylmethionine + Protein N6-(octanoyl)lysine <> Protein N6-(lipoyl)lysine +2 L-Methionine +2 5'-Deoxyadenosine + Protein N6-(lipoyl)lysine
Octanoyl-[acp] + 2 Sulfur donor + 2 S-Adenosylmethionine <> Lipoyl-[acp] +2 L-Methionine +2 5'-Deoxyadenosine
2-Polyprenyl-6-hydroxyphenol + S-Adenosylmethionine <> 2-Polyprenyl-6-methoxyphenol + S-Adenosylhomocysteine
2-Polyprenyl-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine <> 2-Polyprenyl-3-methyl-6-methoxy-1,4-benzoquinone + S-Adenosylhomocysteine
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine <> Ubiquinone-1 + S-Adenosylhomocysteine
Demethylmenaquinol + S-Adenosylmethionine + Demethylmenaquinol <> Menaquinol 6 + S-Adenosylhomocysteine
S-Adenosylmethionine + precorrin-1 > S-Adenosylhomocysteine + Precorrin 2
S-Adenosylmethionine + a [protein]-L-glutamine > Hydrogen ion + S-Adenosylhomocysteine + a [protein]-N<sup>5</sup>-methyl-L-glutamine
tellurite + S-Adenosylmethionine methylated tellurite + S-Adenosylhomocysteine
Hydrogen ion + &alpha;-D-ribose-1-methylphosphonate-5-phosphate + S-Adenosylmethionine > &alpha;-D-ribose-1,2-cyclic-phosphate-5-phosphate + methane + 5'-Deoxyadenosine + L-Methionine
S-Adenosylmethionine + Uroporphyrinogen III <> S-Adenosylhomocysteine + precorrin-1 + Hydrogen ion
S-Adenosylmethionine + a [protein]-L-&beta;-isoaspartate > S-Adenosylhomocysteine + a protein L-&beta;-isoaspartate &alpha;-methyl ester + Hydrogen ion
a phospholipid olefinic fatty acid + S-Adenosylmethionine > a phospholipid cyclopropane fatty acid + S-Adenosylhomocysteine + Hydrogen ion
<i>S</i>-sulfanyl-[acceptor] + Dethiobiotin + S-Adenosylmethionine > an unsulfurated sulfur acceptor + Biotin + 5'-Deoxyadenosine + L-Methionine + Hydrogen ion
Coproporphyrinogen III + S-Adenosylmethionine > Protoporphyrinogen IX + Carbon dioxide + L-Methionine + 5'-Deoxyadenosine
L-Homocysteine + S-Adenosylmethionine Hydrogen ion + L-Methionine + S-Adenosylhomocysteine
5-Aminoimidazole ribonucleotide + S-Adenosylmethionine 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + carbon monoxide + Hydrogen ion
S-Adenosylmethionine + Ribonuc-tri-P-reductases-inactive <> 5'-Deoxyadenosine + L-Methionine + Ribonuc-tri-P-reductases-active
L-Tyrosine + S-Adenosylmethionine + a reduced electron acceptor > Dehydroglycine + p-Cresol + 5'-Deoxyadenosine + L-Methionine + an oxidized electron acceptor + Hydrogen ion
S-Adenosylmethionine + a demethylated methyl acceptor > S-Adenosylhomocysteine + a methylated methyl acceptor
N-6-isopentyl adenosine-37 tRNA + S-Adenosylmethionine + <i>S</i>-sulfanyl-[acceptor] 2-methylthio-N-6-isopentyl adenosine-37 tRNA + S-Adenosylhomocysteine + L-Methionine + 5'-Deoxyadenosine + an unsulfurated sulfur acceptor + Hydrogen ion
6-Carboxy-5,6,7,8-tetrahydropterin + S-Adenosylmethionine + Hydrogen ion > 7-carboxy-7-deazaguanine + 5'-Deoxyadenosine + L-Methionine + Ammonia
a guanine<sup>1516</sup> in 16S rRNA + S-Adenosylmethionine > an <i>N</i><sup>2</sup>-methylguanine<sup>1516</sup> in 16S rRNA + S-Adenosylhomocysteine + Hydrogen ion
guanine<sup>2069</sup> in 23S rRNA + S-Adenosylmethionine > N<sup>7</sup>-methylguanine<sup>2069</sup> in 23S rRNA + S-Adenosylhomocysteine
S-Adenosylmethionine <> S-Adenosylhomocysteine
S-Adenosylmethionine + Phospholipid olefinic fatty acid <> S-Adenosylhomocysteine + Phospholipid cyclopropane fatty acid
S-Adenosylmethionine + tRNA containing 5-aminomethyl-2-thiouridine <> S-Adenosylhomocysteine + tRNA containing 5-methylaminomethyl-2-thiouridylate
S-Adenosylmethionine + DNA adenine <> S-Adenosylhomocysteine + DNA 6-methylaminopurine
2 S-Adenosylmethionine + Uroporphyrinogen III + Precorrin-1 <>2 S-Adenosylhomocysteine + Precorrin 2
2 S-Adenosylmethionine <> S-Adenosylhomocysteine +2 L-Methionine + 5'-Deoxyadenosine
2 S-Adenosylmethionine + Reduced acceptor <> S-Adenosylhomocysteine +2 L-Methionine + 5'-Deoxyadenosine
S-Adenosylmethionine + Protein glutamate <> S-Adenosylhomocysteine + Protein glutamate methyl ester
S-Adenosylmethionine <> S-Adenosylhomocysteine + DNA 5-methylcytosine
S-Adenosylmethionine + Protein L-isoaspartate <> S-Adenosylhomocysteine + Protein L-isoaspartate methyl ester
L-Tyrosine + S-Adenosylmethionine + NADPH <> 2-iminoacetate + p-Cresol + 5'-Deoxyadenosine + L-Methionine + NADP + Hydrogen ion
S-Adenosylmethionine + tRNA <> S-Adenosylhomocysteine + tRNA containing N6-methyladenine
More...

Pathways:
Spectra
Spectra:
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Lin, Jian-Ping; Tian, Jun; You, Jian-Feng; Jin, Zhi-Hua; Xu, Zhi-Nan; Cen, Pei-Lin. An effective strategy for the co-production of S-adenosyl-L-methionine and glutathione by fed-batch fermentation. Biochemical Engineering Journal (2004), 21(1), 19-25.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID15414
HMDB IDHMDB01185
Pubchem Compound ID1079
Kegg IDC00019
ChemSpider ID21169292
WikipediaS-Adenosylmethionine
BioCyc IDS-ADENOSYLMETHIONINE
EcoCyc IDS-ADENOSYLMETHIONINE