SAM

S-ADENOSYLMETHIONINE


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Chemical Component Summary

NameS-ADENOSYLMETHIONINE
Identifiers(2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methyl-methyl-sulfonio]butanoate
FormulaC15 H22 N6 O5 S
Molecular Weight398.437
TypeNON-POLYMER
Isomeric SMILESC[S@@+](CC[C@@H](C(=O)[O-])N)C[C@@H]1[C@H]([C@H]([C@@H](O1)n2cnc3c2ncnc3N)O)O
InChIInChI=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)/t7-,8+,10+,11+,14+,27-/m0/s1
InChIKeyMEFKEPWMEQBLKI-FCKMPRQPSA-N

Chemical Details

Formal Charge0
Atom Count49
Chiral Atom Count6
Bond Count51
Aromatic Bond Count10

Drug Info: DrugBank

DrugBank IDDB00118 
NameAdemetionine
Groups
  • approved
  • investigational
  • nutraceutical
DescriptionPhysiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in treatment of chronic liver disease. (From Merck, 11th ed)
Synonyms
  • Ademetionine disulfate ditosylate
  • Ademetionine
  • L-S-Adenosylmethionine
  • SAM-e
  • SAMe
IndicationS-Adenosylmethionine (SAMe) is used as a drug in Europe for the treatment of depression, liver disorders, fibromyalgia, and osteoarthritis. It has also been introduced into the United States market as a dietary supplement for the support of bone and joint health, as well as mood and emotional well being.
Categories
  • Alimentary Tract and Metabolism
  • Amino Acids
  • Amino Acids and Derivatives
  • Amino Acids, Peptides, and Proteins
  • Amino Acids, Sulfur
ATC-CodeA16AA02
CAS number29908-03-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Catechol O-methyltransferaseMPEAPPLLLAAVLLGLVLLVVLLLLLRHWGWGLCLIGWNEFILQPIHNLL...unknowncofactor
Cap-specific mRNA (nucleoside-2'-O-)-methyltransferase 1MKRRTDPECTAPIKKQKKRVAELALSLSSTSDDEPPSSVSHGAKASTTSL...unknown
Arsenite methyltransferaseMAALRDAEIQKDVQTYYGQVLKRSADLQTNGCVTTARPVPKHIREALQNV...unknown
Glycine N-methyltransferaseMVDSVYRTRSLGVAAEGLPDQYADGEAARVWQLYIGDTRSRTAEYKAWLL...unknowncofactor
S-adenosylmethionine decarboxylase proenzymeMEAAHFFEGTEKLLEVWFSRQQPDANQGSGDLRTIPRSEWDILLKDVQCS...unknowncofactor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682