<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4386</id>
  <title>T3D4332</title>
  <common-name>Dihydrothymine</common-name>
  <description>Dihydrothymine 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 to 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 backflow of acidic stomach contents into the esophagus (gastroesophageal reflux) and recurrent episodes of vomiting.</description>
  <cas>696-04-8</cas>
  <pubchem-id>93556</pubchem-id>
  <chemical-formula>C5H8N2O2</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity>Dihydropyrimidine dehydrogenase catalyzes the reduction of thymine to 5, 6-dihydrothymine then dihydropyrimidinase hydrolyzes 5, 6-dihydrothymine to N-carbamyl-b-alanine. Finally, beta-ureidopropionase catalyzes the conversion of N-carbamyl-b-alanine to beta-alanine. Accumulation of dihydrothymine in the body has been shown to be toxic.</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T06:28:37Z</created-at>
  <updated-at type="dateTime">2018-03-21T17:46:23Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C00906</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>27468</chebi-id>
  <biocyc-id>DIHYDRO-THYMINE</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CC1CN=C(O)N=C1O</moldb-smiles>
  <moldb-formula>C5H8N2O2</moldb-formula>
  <moldb-inchi>InChI=1/C5H8N2O2/c1-3-2-6-5(9)7-4(3)8/h3H,2H2,1H3,(H2,6,7,8,9)</moldb-inchi>
  <moldb-inchikey>InChIKey=NBAKTGXDIBVZOO-UHFFFAOYNA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">128.1292</moldb-average-mass>
  <moldb-mono-mass type="decimal">128.05857751</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB00079</hmdb-id>
  <chembl-id nil="true"/>
  <chemspider-id>84456</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>Yamane, Tetsuo; Wyluda, Benjamin J.; Shulman, Robert G.  Dihydrothymine from ultraviolet-irradiated DNA.    Proceedings of the National Academy of Sciences of the United States of America  (1967),  58(2),  439-42. </synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
