<?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 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. 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.</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">2026-04-02T23:54:27Z</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>CC1CNC(=O)NC1=O</moldb-smiles>
  <moldb-formula>C5H8N2O2</moldb-formula>
  <moldb-inchi>InChI=1S/C5H8N2O2/c1-3-2-6-5(9)7-4(3)8/h3H,2H2,1H3,(H2,6,7,8,9)</moldb-inchi>
  <moldb-inchikey>NBAKTGXDIBVZOO-UHFFFAOYSA-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"/>
  <chemdb-id>CHEM003292</chemdb-id>
  <dsstox-id>DTXSID30862375</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id nil="true"/>
  <iupac nil="true"/>
  <moldb-polar-surface-area>58.2</moldb-polar-surface-area>
  <moldb-refractivity>30.320000000000004</moldb-refractivity>
  <moldb-polarizability>12.032355612950356</moldb-polarizability>
  <moldb-rotatable-bond-count>0</moldb-rotatable-bond-count>
  <moldb-acceptor-count>2</moldb-acceptor-count>
  <moldb-donor-count>2</moldb-donor-count>
  <moldb-pka-strongest-acidic>11.699408342323004</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-7.380677679727569</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>1</moldb-number-of-rings>
  <moldb-alogps-logp>-0.80</moldb-alogps-logp>
  <moldb-alogps-logs>-0.84</moldb-alogps-logs>
  <moldb-alogps-solubility>1.87e+01 g/l</moldb-alogps-solubility>
</compound>
