ISOBARBITURIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C4H4N2O3
Molecular Weight	128.0862
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1NCC(=O)C(=O)N1

InChI

InChIKey=FQXOOGHQVPKHPG-UHFFFAOYSA-N

InChI=1S/C4H4N2O3/c7-2-1-5-4(9)6-3(2)8/h1H2,(H2,5,6,8,9)

HIDE SMILES / InChI

Molecular Formula	C4H4N2O3
Molecular Weight	128.0862
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Molecular mechanisms of ultraviolet radiation-induced DNA damage and repair.	2010-12-16	21209706
Base-promoted reaction of 5-hydroxyuracil derivatives with peroxyl radicals.	2010-09-17	20795653
Early Steps in the DNA Base Excision Repair Pathway of a Fission Yeast Schizosaccharomyces pombe.	2010-09-16	20936170
Specific Inhibition of NEIL-initiated repair of oxidized base damage in human genome by copper and iron: potential etiological linkage to neurodegenerative diseases.	2010-09-10	20622253
Stimulation of DNA Glycosylase Activities by XPC Protein Complex: Roles of Protein-Protein Interactions.	2010-07-25	20798892
Cockayne syndrome group B protein promotes mitochondrial DNA stability by supporting the DNA repair association with the mitochondrial membrane.	2010-07	20181933
Substrate specific stimulation of NEIL1 by WRN but not the other human RecQ helicases.	2010-06-04	20346739
RPA physically interacts with the human DNA glycosylase NEIL1 to regulate excision of oxidative DNA base damage in primer-template structures.	2010-06-04	20338831
The oxidative DNA glycosylases of Mycobacterium tuberculosis exhibit different substrate preferences from their Escherichia coli counterparts.	2010-02-04	20031487
Sources of extracellular, oxidatively-modified DNA lesions: implications for their measurement in urine.	2009-11	19902015
Modulation of DNA glycosylase activities in mesenchymal stem cells.	2009-09-10	19477173
Characterization of the major formamidopyrimidine-DNA glycosylase homolog in Mycobacterium tuberculosis and its linkage to variable tandem repeats.	2009-07	19496823
Catalytically impaired hMYH and NEIL1 mutant proteins identified in patients with primary sclerosing cholangitis and cholangiocarcinoma.	2009-07	19443904
Insights into the role of Val45 and Gln182 of Escherichia coli MutY in DNA substrate binding and specificity.	2009-06-12	19523222
The Base Excision Repair system of Salmonella enterica serovar typhimurium counteracts DNA damage by host nitric oxide.	2009-05	19478870
Raltegravir, elvitegravir, and metoogravir: the birth of "me-too" HIV-1 integrase inhibitors.	2009-03-05	19265512
Base excision repair of oxidative DNA damage and association with cancer and aging.	2009-01	18978338
Physical and functional interaction between human oxidized base-specific DNA glycosylase NEIL1 and flap endonuclease 1.	2008-10-03	18662981
Base excision repair activities in organotypic hippocampal slice cultures exposed to oxygen and glucose deprivation.	2008-06-01	18406215
Examination of hypochlorous acid-induced damage to cytosine residues in a CpG dinucleotide in DNA.	2008-06	18826175
Base-pairing properties of the oxidized cytosine derivative, 5-hydroxy uracil.	2008-02-15	18078807
Interaction of the human DNA glycosylase NEIL1 with proliferating cell nuclear antigen. The potential for replication-associated repair of oxidized bases in mammalian genomes.	2008-02-08	18032376
Base excision repair and the role of MUTYH.	2007-12-15	19725997
Ab initio base-pairing energies of an oxidized thymine product, 5-formyluracil, with standard DNA bases at the BSSE-free DFT and MP2 theory levels.	2007-05-21	17571183
Different organization of base excision repair of uracil in DNA in nuclei and mitochondria and selective upregulation of mitochondrial uracil-DNA glycosylase after oxidative stress.	2007-04-14	17101234
NEIL1 is the major DNA glycosylase that processes 5-hydroxyuracil in the proximity of a DNA single-strand break.	2007-04-03	17348689
Uracil in DNA--general mutagen, but normal intermediate in acquired immunity.	2007-04-01	17116429
Radiosensitization by nitric oxide at low radiation doses.	2007-04	17388699
DNA polymerase delta-dependent repair of DNA single strand breaks containing 3'-end proximal lesions.	2007	17264132
NEIL2-initiated, APE-independent repair of oxidized bases in DNA: Evidence for a repair complex in human cells.	2006-12-09	16982218
RNA polymerase II bypass of oxidative DNA damage is regulated by transcription elongation factors.	2006-11-29	17110932
DNA oxidation in Alzheimer's disease.	2006-10-13	17034348
Ab initio base-pairing energies of uracil and 5-hydroxyuracil with standard DNA bases at the BSSE-free DFT and MP2 theory levels.	2006-05-07	16633566
Physical and functional interactions between Escherichia coli MutY and endonuclease VIII.	2006-01-01	16201966
Differential modulation of base excision repair activities during brain ontogeny: implications for repair of transcribed DNA.	2006-01	16257035
Reaction of substituted pyrimidines with photochemically generated t-BuO* radicals.	2005-12	16955740
5-hydroxyuracil can form stable base pairs with all four bases in a DNA duplex.	2005-01-21	15645051
Identification of a zinc finger domain in the human NEIL2 (Nei-like-2) protein.	2004-11-05	15339932
Oxidation of 5-hydroxy-2'-deoxyuridine into isodialuric acid, dialuric acid, and hydantoin products.	2004-06-02	15161271
Repair of oxidized bases in DNA bubble structures by human DNA glycosylases NEIL1 and NEIL2.	2003-12-12	14522990
Detection of p53 mutations in precancerous gastric tissue.	2003-10-06	14520466
Compromised incision of oxidized pyrimidines in liver mitochondria of mice deficient in NTH1 and OGG1 glycosylases.	2003-09-05	12819227
Mammalian 5-formyluracil-DNA glycosylase. 1. Identification and characterization of a novel activity that releases 5-formyluracil from DNA.	2003-05-06	12718542
Oxidative DNA base modifications and polycyclic aromatic hydrocarbon DNA adducts in squamous cell carcinoma of larynx.	2003-03	12688418
Identification and characterization of mammalian 5-formyluracil-DNA glycosylase.	2003	14510466
A back-up glycosylase in Nth1 knock-out mice is a functional Nei (endonuclease VIII) homologue.	2002-11-01	12200441
Repair of deaminated bases in DNA.	2002-10-01	12361800
Identification and characterization of a novel human DNA glycosylase for repair of cytosine-derived lesions.	2002-08-23	12097317
Structure-activity relationship of ligands of uracil phosphoribosyltransferase from Toxoplasma gondii.	1994-08-17	8080452
New substrates for old enzymes. 5-Hydroxy-2'-deoxycytidine and 5-hydroxy-2'-deoxyuridine are substrates for Escherichia coli endonuclease III and formamidopyrimidine DNA N-glycosylase, while 5-hydroxy-2'-deoxyuridine is a substrate for uracil DNA N-glycosylase.	1994-07-22	8034633

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:39:23 GMT 2025` Edited by `admin` on `Mon Mar 31 20:39:23 GMT 2025`
Record UNII	438WJI1S49
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLUOROURACIL RELATED COMPOUND B [USP IMPURITY]

Preferred Name

English

ISOBARBITURIC ACID

Common Name

English

5-HYDROXY-2,4(1H,3H)-PYRIMIDINEDIONE

Systematic Name

English

DIHYDROPYRIMIDINE-2,4,5(3H)-TRIONE

Systematic Name

English

NSC-90431

Code

English

2,4(1H,3H)-PYRIMIDINEDIONE, 5-HYDROXY-

Systematic Name

English

2,4,5(3H)-PYRIMIDINETRIONE, DIHYDRO-

Systematic Name

English

5-HYDROXYURACIL

Systematic Name

English

FLUOROURACIL RELATED COMPOUND B [USP-RS]

Common Name

English

FLUOROURACIL IMPURITY B [EP IMPURITY]

Common Name

English

NSC-95958

Code

English

Code System Code Type Description

EPA CompTox

DTXSID30174667