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
Synthesis of DNA fragments containing 5,6-dihydrothymine, a major product of thymine gamma radiolysis.	1988 Jan 11	3340528
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
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
Rapid gas chromatographic-mass spectrometric diagnosis of dihydropyrimidine dehydrogenase deficiency and dihydropyrimidinase deficiency.	2003 Jul 15	12829003
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
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
Vibrational spectra and structure of 5,6-diamino uracil and 5,6-dihydro-5-methyl uracil by density functional theory calculations.	2007 Feb	16920007
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
Metal-triggered changes in the stability and secondary structure of a tetrameric dihydropyrimidinase: a biophysical characterization.	2009 Jan	19008030
Saccharomyces cerevisiae-based system for studying clustered DNA damages.	2010 Aug	20552213
Photoinduced ring opening reactions and subsequent thermal ring closure reactions in the thymine-ammonia system and related systems.	2010 Sep 24	20714675

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:41:31 GMT 2023` Edited by `admin` on `Sat Dec 16 09:41:31 GMT 2023`
Record UNII	Z51MHT1W75
Record Status	`Validated (UNII)`
Record Version

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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