Details of Metabolite

General Information of MET (ID: META00875)
Name 2-Hydroxypyridine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1-Hydroxy-2-pyridine; 1H-Pyridin-2-one; 2(1H)-Pyridinone; 2(1H)-Pyridone; 2-Hydroxypyridine; 2-Hydroxypyridine sodium salt; 2-Oxopyridine; 2-Pyridinol; 2-Pyridinol (acd/name 4.0); 2-Pyridinone; 2-Pyridol; 2-Pyridone; Pyridin-2-ol; Pyridone-2; alpha -Pyridone; alpha-Pyridone
Source Endogenous;Endogenous
Structure Type   Hydropyridines  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organoheterocyclic compounds
Pyridines and derivatives
Hydropyridines
PubChem CID
8871
HMDB ID
HMDB0013751
Formula
C5H5NO
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
C02502
ChEBI ID
16540
ChemSpider ID
8537
Physicochemical Properties Molecular Weight 95.1 Topological Polar Surface Area 29.1
XlogP -0.6 Complexity 135
Heavy Atom Count 7 Rotatable Bond Count N.A.
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Function
This colourless crystalline solid is used in peptide synthesis. It is well known to form hydrogen bonded structures somewhat related to the base-pairing mechanism found in RNA and DNA. It is also a classic case of a molecule that exists as tautomers. Some publications only focus one of the two possible patterns, and neglect the influence of the other. For example, to calculation of the energy difference of the two tautomers in a non-polar solution will lead to a wrong result if a large quantity of the substance is on the side of the dimer in an equilibrium. The direct tautomerisation is not energetically favoured, but a dimerisation followed by a double proton transfer and dissociation of the dimer is a self catalytic path from one tautomer to the other. Protic solvents also mediate the proton transfer during the tautomerisation.
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-Hydroxypyridine concentration: decrease (Log2 FC=0.54)
                      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 2-hydroxypyridine 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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