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

Molecular Formula	C5H8N2O2
Molecular Weight	128.1292
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Approval Year

PubMed

Title	Date	PubMed
Molecular mechanisms of ultraviolet radiation-induced DNA damage and repair.	2010-12-16	21209706
Sequence dependence of excess electron transfer in DNA.	2010-11-18	20509700
Photoinduced ring opening reactions and subsequent thermal ring closure reactions in the thymine-ammonia system and related systems.	2010-09-24	20714675
Saccharomyces cerevisiae-based system for studying clustered DNA damages.	2010-08	20552213
Dihydropyrimidinase deficiency: Phenotype, genotype and structural consequences in 17 patients.	2010-02-01	20362666
DNA repair by photolyase: a novel substrate with low background absorption around 265 nm for transient absorption studies in the UV.	2010-01-19	20000331
5,6-Dihydrothymine impairs the base excision repair pathway of a closely opposed AP site or single-strand break.	2009-11	19883221
Biological consequences of potential repair intermediates of clustered base damage site in Escherichia coli.	2009-10-02	19540248
Processing of thymine glycol in a clustered DNA damage site: mutagenic or cytotoxic.	2009-07	19468043
Catalytically impaired hMYH and NEIL1 mutant proteins identified in patients with primary sclerosing cholangitis and cholangiocarcinoma.	2009-07	19443904
Metal-triggered changes in the stability and secondary structure of a tetrameric dihydropyrimidinase: a biophysical characterization.	2009-01	19008030
Fluorescence detection of the endonuclease III reaction using modified oligonucleotides.	2009	19749336
A functional analysis of the pyrimidine catabolic pathway in Arabidopsis.	2009	19413687
Interconversion of the cis-5R,6S- and trans-5R,6R-thymine glycol lesions in duplex DNA.	2008-09-03	18681438
Study of interaction of XRCC1 with DNA and proteins of base excision repair by photoaffinity labeling technique.	2007-08	17922646
Clinical, biochemical and genetic findings in two siblings with a dihydropyrimidinase deficiency.	2007-06	17383919
Use of damaged DNA and dNTP substrates by the error-prone DNA polymerase X from African swine fever virus.	2007-03-27	17335287
HPLC-electrospray tandem mass spectrometry for rapid determination of dihydropyrimidine dehydrogenase activity.	2007-03	17272486
Vibrational spectra and structure of 5,6-diamino uracil and 5,6-dihydro-5-methyl uracil by density functional theory calculations.	2007-02	16920007
Crystallization and preliminary crystallographic studies of the recombinant dihydropyrimidinase from Sinorhizobium meliloti CECT4114.	2006-12-01	17142902
Contributions of an endonuclease IV homologue to DNA repair in the African swine fever virus.	2006-03-07	16503634
Purification, crystallization and X-ray diffraction analysis of dihydropyrimidinase from Dictyostelium discoideum.	2006-01-01	16511257
The roles of specific glycosylases in determining the mutagenic consequences of clustered DNA base damage.	2006	16893955
XRCC1 interactions with multiple DNA glycosylases: a model for its recruitment to base excision repair.	2005-07-12	15927541
Crystallization and X-ray diffraction analysis of dihydropyrimidinase from Saccharomyces kluyveri.	2005-04-01	16511040
Gamma-radiolysis DNA products: synthesis of 6-(alpha-thyminyl)-5,6-dihydro-4-thiothymine derivatives.	2004-07-09	15230605
Dihydrothymine lesion in X-irradiated DNA: characterization at the molecular level and detection in cells.	2004-05	15223768
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.	2004-04	15038767
Identification and characterization of an intermediate in the alkali degradation of (6-4) photoproduct-containing DNA.	2003-12-19	14534315
Rapid gas chromatographic-mass spectrometric diagnosis of dihydropyrimidine dehydrogenase deficiency and dihydropyrimidinase deficiency.	2003-07-15	12829003
Sensitive method for the quantification of urinary pyrimidine metabolites in healthy adults by gas chromatography-tandem mass spectrometry.	2003-07-05	12798197
Acyclic nucleoside analogues as novel inhibitors of human mitochondrial thymidine kinase.	2002-09-12	12213066
Screening and diagnosis of beta-ureidopropionase deficiency by gas chromatographic/mass spectrometric analysis of urine.	2002-09	12271438
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.	2002-08	12104082
Efficiency of incision of an AP site within clustered DNA damage by the major human AP endonuclease.	2002-01-15	11781104
Alternative nucleotide incision repair pathway for oxidative DNA damage.	2002-01-10	11805838
Repair of oxidized purines and damaged pyrimidines by E. coli Fpg protein: different roles of proline 2 and lysine 57 residues.	2002	11813291
Efficiency of excision of 8-oxo-guanine within DNA clustered damage by XRS5 nuclear extracts and purified human OGG1 protein.	2001-10-02	11570881
Simple gas chromatographic-mass spectrometric procedure for diagnosing pyrimidine degradation defects for prevention of severe anticancer side effects.	2001-07-05	11482736
Recognition and kinetics for excision of a base lesion within clustered DNA damage by the Escherichia coli proteins Fpg and Nth.	2001-05-15	11341839
DNA substrates containing defined oxidative base lesions and their application to study substrate specificities of base excision repair enzymes.	2001	11554298
Defects in pyrimidine degradation identified by HPLC-electrospray tandem mass spectrometry of urine specimens or urine-soaked filter paper strips.	2000-12	11106323
Porcine recombinant dihydropyrimidine dehydrogenase: comparison of the spectroscopic and catalytic properties of the wild-type and C671A mutant enzymes.	1998-12-15	9860876
Possible prediction of adverse reactions to fluorouracil by the measurement of urinary dihydrothymine and thymine.	1998-10	9857238
Population and family studies of dihydropyrimidinuria: prevalence, inheritance mode, and risk of fluorouracil toxicity.	1998-07-24	9714435
[A case of gastric cancer with decreased dihydropyrimidine dehydrogenase activity].	1998-07	9679586
Dihydropyrimidinase deficiency and congenital microvillous atrophy: coincidence or genetic relation?	1997-09	9323563
Identification and tissue-specific expression of a NADH-dependent activity of dihydropyrimidine dehydrogenase in man.	1996-01-01	8615641
Processing of DNA base damage by DNA polymerases. Dihydrothymine and beta-ureidoisobutyric acid as models for instructive and noninstructive lesions.	1991-01-25	1988431
Synthesis of DNA fragments containing 5,6-dihydrothymine, a major product of thymine gamma radiolysis.	1988-01-11	3340528

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:47:39 GMT 2025` Edited by `admin` on `Mon Mar 31 22:47:39 GMT 2025`
Record UNII	Z51MHT1W75
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-44131

Preferred Name

English

DIHYDROTHYMINE

Systematic Name

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