S-Adenosyl methionine

S-Adenosyl methionine
Names
	Systematic IUPAC name (2S)-2-Amino-4-[(S)-{[(2S,3S,4R,5R)-5-(4-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}methylsulfaniumyl]butanoate
	Other names S-Adenosyl-L-methionine; SAM-e; SAMe, AdoMet, Heparab (India), ademethionine
Identifiers
CAS Number	29908-03-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1088977 ;
ChemSpider	8041295 ;
ECHA InfoCard	100.045.391
KEGG	C00019 ;
MeSH	S-Adenosylmethionine
PubChem CID	9865604;
UNII	7LP2MPO46S ;
CompTox Dashboard (EPA)	DTXSID6032019 ;
	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?/m1/s1 Key: MEFKEPWMEQBLKI-YDBXVIPQSA-O ; InChI=1/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?/m1/s1 Key: MEFKEPWMEQBLKI-NNGIMXIKBF;
	SMILES O=C(O)C(N)CC[S+](C)C[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3O;
Properties
Chemical formula	C15H22N6O5S
Molar mass	398.44 g·mol−1
Pharmacology
ATC code	A16AA02 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

S-Adenosyl methionine (SAM), also known under the commercial names of SAMe, SAM-e, or AdoMet, is a common cosubstrate involved in methyl group transfers, transsulfuration, and aminopropylation. Although these anabolic reactions occur throughout the body, most SAM is produced and consumed in the liver.^[1] More than 40 methyl transfers from SAM are known, to various substrates such as nucleic acids, proteins, lipids and secondary metabolites. It is made from adenosine triphosphate (ATP) and methionine by methionine adenosyltransferase. SAM was first discovered by Giulio Cantoni in 1952.^[1]

In bacteria, SAM is bound by the SAM riboswitch, which regulates genes involved in methionine or cysteine biosynthesis. In eukaryotic cells, SAM serves as a regulator of a variety of processes including DNA, tRNA, and rRNA methylation; immune response;^[2] amino acid metabolism; transsulfuration; and more. In plants, SAM is crucial to the biosynthesis of ethylene, an important plant hormone and signaling molecule.^[3]

^ ^a ^b Cantoni, GL (1952). "The Nature of the Active Methyl Donor Formed Enzymatically from L-Methionine and Adenosinetriphosphate". J Am Chem Soc. 74 (11): 2942–3. doi:10.1021/ja01131a519.
^ Ding, Wei; Smulan, Lorissa J.; Hou, Nicole S.; Taubert, Stefan; Watts, Jennifer L.; Walker, Amy K. (2015-10-06). "S-Adenosylmethionine Levels Govern Innate Immunity through Distinct Methylation-Dependent Pathways". Cell Metabolism. 22 (4): 633–645. doi:10.1016/j.cmet.2015.07.013. PMC 4598287. PMID 26321661.
^ Wang, X.; Oh, M. W.; Komatsu, S. (2016-06-01). "Characterization of S-adenosylmethionine synthetases in soybean under flooding and drought stresses". Biologia Plantarum. 60 (2): 269–278. doi:10.1007/s10535-016-0586-6. ISSN 0006-3134. S2CID 15567646.