DIHYDROTHYMINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C5H8N2O2
Molecular Weight	128.1292
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1CNC(=O)NC1=O

InChI

InChIKey=NBAKTGXDIBVZOO-UHFFFAOYSA-N

InChI=1S/C5H8N2O2/c1-3-2-6-5(9)7-4(3)8/h3H,2H2,1H3,(H2,6,7,8,9)

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Synthesis of DNA fragments containing 5,6-dihydrothymine, a major product of thymine gamma radiolysis.	1988 Jan 11	3340528
Processing of DNA base damage by DNA polymerases. Dihydrothymine and beta-ureidoisobutyric acid as models for instructive and noninstructive lesions.	1991 Jan 25	1988431
Identification and tissue-specific expression of a NADH-dependent activity of dihydropyrimidine dehydrogenase in man.	1996 Jan-Feb	8615641
Dihydropyrimidinase deficiency and congenital microvillous atrophy: coincidence or genetic relation?	1997 Sep	9323563
Porcine recombinant dihydropyrimidine dehydrogenase: comparison of the spectroscopic and catalytic properties of the wild-type and C671A mutant enzymes.	1998 Dec 15	9860876
[A case of gastric cancer with decreased dihydropyrimidine dehydrogenase activity].	1998 Jul	9679586
Population and family studies of dihydropyrimidinuria: prevalence, inheritance mode, and risk of fluorouracil toxicity.	1998 Jul 24	9714435
Possible prediction of adverse reactions to fluorouracil by the measurement of urinary dihydrothymine and thymine.	1998 Oct	9857238
Defects in pyrimidine degradation identified by HPLC-electrospray tandem mass spectrometry of urine specimens or urine-soaked filter paper strips.	2000 Dec	11106323
DNA substrates containing defined oxidative base lesions and their application to study substrate specificities of base excision repair enzymes.	2001	11554298
Simple gas chromatographic-mass spectrometric procedure for diagnosing pyrimidine degradation defects for prevention of severe anticancer side effects.	2001 Jul 5	11482736
Recognition and kinetics for excision of a base lesion within clustered DNA damage by the Escherichia coli proteins Fpg and Nth.	2001 May 15	11341839
Efficiency of excision of 8-oxo-guanine within DNA clustered damage by XRS5 nuclear extracts and purified human OGG1 protein.	2001 Oct 2	11570881
Repair of oxidized purines and damaged pyrimidines by E. coli Fpg protein: different roles of proline 2 and lysine 57 residues.	2002	11813291
Development and characterization of a monoclonal antibody with cross-reactivity towards uracil and thymine, and its potential use in screening patients treated with 5-fluorouracil for possible risks.	2002 Aug	12104082
Alternative nucleotide incision repair pathway for oxidative DNA damage.	2002 Jan 10	11805838
Efficiency of incision of an AP site within clustered DNA damage by the major human AP endonuclease.	2002 Jan 15	11781104
Screening and diagnosis of beta-ureidopropionase deficiency by gas chromatographic/mass spectrometric analysis of urine.	2002 Sep	12271438
Acyclic nucleoside analogues as novel inhibitors of human mitochondrial thymidine kinase.	2002 Sep 12	12213066
Identification and characterization of an intermediate in the alkali degradation of (6-4) photoproduct-containing DNA.	2003 Dec 19	14534315
Rapid gas chromatographic-mass spectrometric diagnosis of dihydropyrimidine dehydrogenase deficiency and dihydropyrimidinase deficiency.	2003 Jul 15	12829003
Sensitive method for the quantification of urinary pyrimidine metabolites in healthy adults by gas chromatography-tandem mass spectrometry.	2003 Jul 5	12798197
Qualitative and quantitative analyses of the decomposition products that arise from the exposure of thymine to monochromatic ultrasoft X rays and 60Co gamma rays in the solid state.	2004 Apr	15038767
Gamma-radiolysis DNA products: synthesis of 6-(alpha-thyminyl)-5,6-dihydro-4-thiothymine derivatives.	2004 Jul 9	15230605
Dihydrothymine lesion in X-irradiated DNA: characterization at the molecular level and detection in cells.	2004 May	15223768
Crystallization and X-ray diffraction analysis of dihydropyrimidinase from Saccharomyces kluyveri.	2005 Apr 1	16511040
XRCC1 interactions with multiple DNA glycosylases: a model for its recruitment to base excision repair.	2005 Jul 12	15927541
The roles of specific glycosylases in determining the mutagenic consequences of clustered DNA base damage.	2006	16893955
Crystallization and preliminary crystallographic studies of the recombinant dihydropyrimidinase from Sinorhizobium meliloti CECT4114.	2006 Dec 1	17142902
Purification, crystallization and X-ray diffraction analysis of dihydropyrimidinase from Dictyostelium discoideum.	2006 Jan 1	16511257
Contributions of an endonuclease IV homologue to DNA repair in the African swine fever virus.	2006 Mar 7	16503634
Study of interaction of XRCC1 with DNA and proteins of base excision repair by photoaffinity labeling technique.	2007 Aug	17922646
Vibrational spectra and structure of 5,6-diamino uracil and 5,6-dihydro-5-methyl uracil by density functional theory calculations.	2007 Feb	16920007
Clinical, biochemical and genetic findings in two siblings with a dihydropyrimidinase deficiency.	2007 Jun	17383919
HPLC-electrospray tandem mass spectrometry for rapid determination of dihydropyrimidine dehydrogenase activity.	2007 Mar	17272486
Use of damaged DNA and dNTP substrates by the error-prone DNA polymerase X from African swine fever virus.	2007 Mar 27	17335287
Interconversion of the cis-5R,6S- and trans-5R,6R-thymine glycol lesions in duplex DNA.	2008 Sep 3	18681438
Fluorescence detection of the endonuclease III reaction using modified oligonucleotides.	2009	19749336
A functional analysis of the pyrimidine catabolic pathway in Arabidopsis.	2009	19413687
Metal-triggered changes in the stability and secondary structure of a tetrameric dihydropyrimidinase: a biophysical characterization.	2009 Jan	19008030
Processing of thymine glycol in a clustered DNA damage site: mutagenic or cytotoxic.	2009 Jul	19468043
Catalytically impaired hMYH and NEIL1 mutant proteins identified in patients with primary sclerosing cholangitis and cholangiocarcinoma.	2009 Jul	19443904
5,6-Dihydrothymine impairs the base excision repair pathway of a closely opposed AP site or single-strand break.	2009 Nov	19883221
Biological consequences of potential repair intermediates of clustered base damage site in Escherichia coli.	2009 Oct 2	19540248
Saccharomyces cerevisiae-based system for studying clustered DNA damages.	2010 Aug	20552213
Molecular mechanisms of ultraviolet radiation-induced DNA damage and repair.	2010 Dec 16	21209706
DNA repair by photolyase: a novel substrate with low background absorption around 265 nm for transient absorption studies in the UV.	2010 Jan 19	20000331
Dihydropyrimidinase deficiency: Phenotype, genotype and structural consequences in 17 patients.	2010 Jul-Aug	20362666
Sequence dependence of excess electron transfer in DNA.	2010 Nov 18	20509700
Photoinduced ring opening reactions and subsequent thermal ring closure reactions in the thymine-ammonia system and related systems.	2010 Sep 24	20714675

Name

Type

Language

DIHYDROTHYMINE

Systematic Name

English

NSC-44131

Code

English

2,4(1H,3H)-PYRIMIDINEDIONE, DIHYDRO-5-METHYL-

Systematic Name

English

5,6-DIHYDROTHYMINE

Systematic Name

English

HYDROURACIL, 5-METHYL-

Systematic Name

English

5-METHYLDIHYDROPYRIMIDINE-2,4(1H,3H)-DIONE

Systematic Name

English

5-METHYL-5,6-DIHYDROURACIL

Systematic Name

English

5,6-DIHYDRO-5-METHYLURACIL

Systematic Name

English

Classification Tree Code System Code

LOINC

79651-6