Details of Metabolite

General Information of MET (ID: META00385)
Name S-Adenosylmethionine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(3S)-5'-[(3-Amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine, inner salt, '[1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfonium; ASTA medica brand OF ademetionine tosilate disulfate; Acylcarnitine; Ademetionine; Ademetionine europharma brand; Adenosylmethionine; AdoMet', S-(5'-Deoxyadenosin-5'-yl)-L-methionine, 'SAM; Amet, S; Donamet; Europharma brand OF ademetionine; Gumbaral; Knoll brand OF brand OF ademetionine tosilate disulfate; L-S-Adenosylmethionine', S-(5'-Adenosyl)-L-methionine, 'S-Adenosyl methionine; S Adenosyl L methionine; S Adenosylmethionine; S Adenosylmethionine sulfate tosylate; S Amet; S-Adenosyl-L-methionine; S-Adenosyl-L-methionine disulfate tosylate; S-Adenosyl-L-methionine disulphate tosylate; S-Adenosyl-methionine; S-Adenosylmethionine sulfate tosylate; SAM-e; SAMe', (3S)-5'-[(3-Amino-3-carboxypropyl)methylsulphonio]-5'-deoxyadenosine, inner salt, '[1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfonium; Samyr; Sulfate tosylate, S-adenosylmethionine; Tosylate, S-adenosylmethionine sulfate; [1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulphonium
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;Drug
Structure Type   5'-deoxy-5'-thionucleosides  (Click to Show/Hide the Complete Structure Type Hierarchy)
Nucleosides, nucleotides, and analogues
5'-deoxyribonucleosides
5'-deoxy-5'-thionucleosides
PubChem CID
34756
HMDB ID
HMDB0001185
Formula
C15H23N6O5S
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00019
ChEBI ID
15414
FooDB ID
FDB031152
ChemSpider ID
21169292
METLIN ID
6064
Physicochemical Properties Molecular Weight 399.4 Topological Polar Surface Area 184
XlogP -3.5 Complexity 533
Heavy Atom Count 27 Rotatable Bond Count 7
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 10
Function
S-Adenosylmethionine (CAS: 29908-03-0), also known as SAM or AdoMet, is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in the treatment of chronic liver disease (From Merck, 11th ed). S-Adenosylmethionine is a natural substance present in the cells of the body. It plays a crucial biochemical role by donating a one-carbon methyl group in a process called transmethylation. S-Adenosylmethionine, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine, and other molecules.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Leukotriene-C4 hydrolase (GGT1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockdown (siRNA) of GGT1
                      Induced Change S-Adenosylmethionine concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Renal cell carcinoma [ICD-11: 2C90]
                      Details It is reported that knockdown of GGT1 leads to the increase of s-adenosylmethionine levels compared with control group.
      Oxidoreductases (EC 1)
            Glutamate-cysteine ligase modifier (GCLM) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockout of Gclm
                      Induced Change S-Adenosylmethionine concentration: decrease (FC = 0.75)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Metabolic liver disease [ICD-11: 5C90]
                      Details It is reported that knockout of Gclm leads to the decrease of s-adenosylmethionine levels compared with control group.
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Knockout of TP53
                      Induced Change S-Adenosylmethionine concentration: decrease (Log2 FC=0.8)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the decrease of s-adenosylmethionine levels compared with control group.
      Transferases (EC 2)
            Pyridoxal kinase (PDXK) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [4]
                      Introduced Variation Knockout (CRISPR/Cas9 sgRNA) of Pdxk
                      Induced Change S-Adenosylmethionine concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Acute myeloid leukaemia [ICD-11: 2A60]
                      Details It is reported that knockout of Pdxk leads to the decrease of s-adenosylmethionine levels compared with control group.
References
1 Impairment of gamma-glutamyl transferase 1 activity in the metabolic pathogenesis of chromophobe renal cell carcinoma. Proc Natl Acad Sci U S A. 2018 Jul 3;115(27):E6274-E6282.
2 Hepatic metabolic adaptation in a murine model of glutathione deficiency. Chem Biol Interact. 2019 Apr 25;303:1-6.
3 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.
4 Vitamin B6 Addiction in Acute Myeloid Leukemia. Cancer Cell. 2020 Jan 13;37(1):71-84.e7.

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