General Information of MET (ID: META00770)
Name Dihydrothymine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(-)-(S)-5,6-Dihydrothymine; (5S)-5-Methyl-1,3-diazinane-2,4-dione; 5,6-Dihydro-5-methyluracil; 5,6-Dihydrothymine; 5-Methyl-5,6-dihydrouracil; 5-Methyldihydropyrimidine-2,4(1H,3H)-dione; Dihydro-5-methyl-2,4(1H,3H)-pyrimidinedione; Dihydrothymine
Source Endogenous;Escherichia Coli Metabolite;Food;Toxins/Pollutant;Microbial
Structure Type   Pyrimidines and pyrimidine derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organoheterocyclic compounds
Diazines
Pyrimidines and pyrimidine derivatives
PubChem CID
676414
HMDB ID
HMDB0000079
Formula
C5H8N2O2
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
C00906
FooDB ID
FDB021892
ChemSpider ID
589127
Physicochemical Properties Molecular Weight 128.13 Topological Polar Surface Area 58.2
XlogP -0.6 Complexity 155
Heavy Atom Count 9 Rotatable Bond Count N.A.
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Function
Dihydrothymine (CAS: 696-04-8) is an intermediate breakdown product of thymine. Dihydropyrimidine dehydrogenase catalyzes the reduction of thymine into 5,6-dihydrothymine; then dihydropyrimidinase hydrolyzes 5,6-dihydrothymine into N-carbamyl-beta-alanine. Finally, beta-ureidopropionase catalyzes the conversion of N-carbamyl-beta-alanine into beta-alanine. When present at abnormally high levels, dihydrothymine can be toxic, although the mechanism of toxicity is not clear. In particular, patients with dihydropyrimidinase deficiency exhibit highly increased concentrations of 5,6-dihydrouracil and 5,6-dihydrothymine; and moderately increased concentrations of uracil and thymine can be detected in urine. Dihydropyrimidinase deficiency is a disorder that can cause neurological and gastrointestinal problems in some affected individuals. The most common neurological abnormalities that occur are intellectual disability, seizures, weak muscle tone (hypotonia), abnormally small head size (microcephaly), and autistic behaviours that affect communication and social interaction. Gastrointestinal problems that occur in dihydropyrimidinase deficiency include the backflow of acidic stomach contents into the esophagus (gastroesophageal reflux) and recurrent episodes of vomiting.
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 Dihydrothymine concentration: decrease (Log2 FC=0.61)
                      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 dihydrothymine 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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