Details of Metabolite

General Information of MET (ID: META00530)
Name N6-Methyladenosine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2R,3S,4R,5R)-2-Hydroxymethyl-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3,4-diol; 6-Methyladenosine; 6-Methylamino-9-beta-D-ribofuranosyl-purine; 6-Methylamino-9-beta-delta-ribofuranosyl-purine; 6-Methylaminopurine D-riboside; 6-Methylaminopurine ribonucleoside; 6-Methylaminopurine riboside; 6-Methylaminopurinosine; N(6)-Methyladenosine; N(6)-Monomethyladenosine; N(6)MAdo; N-Methyladenosine; N6-Methyladenosine; m6a
Source Endogenous;Food;Carcinogenic Potency
Structure Type   Purine nucleosides  (Click to Show/Hide the Complete Structure Type Hierarchy)
Nucleosides, nucleotides, and analogues
Purine nucleosides
PubChem CID
102175
HMDB ID
HMDB0004044
Formula
C11H15N5O4
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
21891
FooDB ID
FDB023288
ChemSpider ID
92307
Physicochemical Properties Molecular Weight 281.27 Topological Polar Surface Area 126
XlogP -0.4 Complexity 349
Heavy Atom Count 20 Rotatable Bond Count 3
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 8
Function
N6-Methyladenosine is a methylated adenine residue. N6-Methyladenosine is an endogenous urinary nucleoside product of the degradation of transfer ribonucleic acid (tRNA); urinary nucleosides are biological markers for patients with colorectal cancer. tRNA has been shown to be excreted in abnormal amounts in the urine of cancer patients. tRNA from neoplastic tissue had a much more rapid turnover rate than the tRNA from the corresponding normal tissue. Evidence indicates that methylation of tRNA occurs only after synthesis of the intact macromolecule. Because there are no specific enzyme systems to incorporate the modified nucleosides into the macromolecular nucleic acid, these nucleosides once released in the process of tRNA turnover cannot be reutilized, nor are they further degraded, but are excreted in urine.
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 N6-Methyladenosine concentration: increase (FC = 17.37 / 17.67)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the increase of N6-methyladenosine 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 N6-Methyladenosine concentration: increase (Log2 FC=1.98)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the increase of N6-methyladenosine 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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