General Information of MET (ID: META00777)
Name 2-Hydroxyadenine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
2-Hydroxy-6-aminopurine; 2-Hydroxyadenine; 2-OH-Ade; 2-Oxoadenine; 2-Oxyadenine; 6-Amino-1,3-dihydro-2H-purin-2-one; 6-Amino-2-hydroxypurine; 6-Amino-3,7(9)-dihydro-purin-2-one; 6-Amino-3,7-dihydro-purin-2-one; 6-Amino-3,9-dihydro-2H-purin-2-one; 6-Amino-7H-purin-2-ol; 6-Amino-9H-purin-2-ol; Crotonoside; Isoguanine
Source Endogenous;Food;TCM Ingredients
Structure Type   Purines and purine derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organoheterocyclic compounds
Imidazopyrimidines
Purines and purine derivatives
PubChem CID
76900
HMDB ID
HMDB0000403
Formula
C5H5N5O
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
62462
FooDB ID
FDB022019
ChemSpider ID
69351
METLIN ID
5392
Physicochemical Properties Molecular Weight 151.13 Topological Polar Surface Area 91.9
XlogP -1.7 Complexity 313
Heavy Atom Count 11 Rotatable Bond Count N.A.
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 2
Function
2-Hydroxyadenine (2-OH-Ade) is formed by hydroxyl radical attack on DNA bases and shows a genotoxicity in human, being the source of the mutations induced by reactive oxygen species. 2-OH-Ade in DNA is miscoding and elicits various mutations, and is a mutagenic in bacterial and mammalian cells. (Recent Research Developments in Biochemistry (2000)2:41-50).
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      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 [1]
                      Introduced Variation Knockout of TP53
                      Induced Change 2-Hydroxyadenine concentration: increase (Log2 FC=7.58)
                      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 2-hydroxyadenine levels compared with control group.
References
1 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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