Details of Metabolite

General Information of MET (ID: META00382)
Name 5'-Methylthioadenosine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-D-ribofuranose; 1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-delta-ribofuranose', 5'-(Methylthio)-5'-deoxyadenosine, 5'-(Methylthio)adenosine, 5'-S-Methyl-5'-thio-adenosine, 5'-S-Methyl-5'-thioadenosine, 'S-Methyl-5-thioadenosine', Adenine(5'-deoxy-5'-methylthio)9-beta-D-furanoriboside, '5-MTDA', 5'-Methylthio-5'-deoxyadenosine, 5'-Deoxy-5'-methylthioadenosine, 5'-Methylthioadenosine, methyl-(14)C-labeled, 5'-Methylthioadenosine; 5'-Deoxy-5'-(methylthio)adenosine, '5-Methylthioadenosine; 9-(5-S-Methyl-5-thio-beta-D-ribofuranosyl)-9H-purin-6-amine; MTA', S-Methyl-5'-thioadenosine, 'Thiomethyladenosine; Methylthioadenosine
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;Cosmetic;TCM Ingredients;Microbial
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
439176
HMDB ID
HMDB0001173
Formula
C11H15N5O3S
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
C00170
DrugBank ID
DB02282
ChEBI ID
17509
FooDB ID
FDB031156
ChemSpider ID
388321
METLIN ID
3425
Physicochemical Properties Molecular Weight 297.34 Topological Polar Surface Area 145
XlogP -0.3 Complexity 352
Heavy Atom Count 20 Rotatable Bond Count 3
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 8
Function
5'-Methylthioadenosine (MTA) is a naturally occurring sulfur-containing nucleoside present in all mammalian tissues. It is produced from S-adenosylmethionine mainly through the polyamine biosynthetic pathway, where it behaves as a powerful inhibitory product. MTA is metabolized solely by MTA-phosphorylase, to yield 5-methylthioribose-1-phosphate and adenine, a crucial step in the methionine and purine salvage pathways, respectively. Evidence suggests that MTA can affect cellular processes in many ways. For instance, MTA has been shown to influence the regulation of gene expression, proliferation, differentiation, and apoptosis. 5-Methylthioadenosine can be found in human urine. Elevated excretion appears in children with severe combined immunodeficiency syndrome (SCID).
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Sulfatase sulf-1 (SULF1) 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 (shRNA) of SULF1
                      Induced Change 5'-Methylthioadenosine concentration: decrease (FC = 0.71)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the decrease of 5'-methylthioadenosine 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 [2]
                      Introduced Variation Knockout of TP53
                      Induced Change 5'-Methylthioadenosine concentration: decrease (Log2 FC=0.72)
                      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 5'-methylthioadenosine levels compared with control group.
References
1 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
2 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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