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
Structure-activity relationship of ligands of uracil phosphoribosyltransferase from Toxoplasma gondii.	1994 Aug 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 Jul 22	8034633
Identification and characterization of a novel human DNA glycosylase for repair of cytosine-derived lesions.	2002 Aug 23	12097317
Alternative nucleotide incision repair pathway for oxidative DNA damage.	2002 Jan 10	11805838
Determination of active site residues in Escherichia coli endonuclease VIII.	2002 Jan 25	11711552
Biological consequences of free radical-damaged DNA bases.	2002 Jul 1	12086677
A back-up glycosylase in Nth1 knock-out mice is a functional Nei (endonuclease VIII) homologue.	2002 Nov 1	12200441
Repair of deaminated bases in DNA.	2002 Oct 1	12361800
Identification and characterization of mammalian 5-formyluracil-DNA glycosylase.	2003	14510466
Repair of oxidized bases in DNA bubble structures by human DNA glycosylases NEIL1 and NEIL2.	2003 Dec 12	14522990
Oxidative DNA base modifications and polycyclic aromatic hydrocarbon DNA adducts in squamous cell carcinoma of larynx.	2003 Mar	12688418
Mammalian 5-formyluracil-DNA glycosylase. 1. Identification and characterization of a novel activity that releases 5-formyluracil from DNA.	2003 May 6	12718542
Detection of p53 mutations in precancerous gastric tissue.	2003 Oct 6	14520466
Compromised incision of oxidized pyrimidines in liver mitochondria of mice deficient in NTH1 and OGG1 glycosylases.	2003 Sep 5	12819227
Oxidation of 5-hydroxy-2'-deoxyuridine into isodialuric acid, dialuric acid, and hydantoin products.	2004 Jun 2	15161271
Identification of a zinc finger domain in the human NEIL2 (Nei-like-2) protein.	2004 Nov 5	15339932
Reaction of substituted pyrimidines with photochemically generated t-BuO* radicals.	2005 Dec	16955740
5-hydroxyuracil can form stable base pairs with all four bases in a DNA duplex.	2005 Jan 21	15645051
NEIL2-initiated, APE-independent repair of oxidized bases in DNA: Evidence for a repair complex in human cells.	2006 Dec 9	16982218
Differential modulation of base excision repair activities during brain ontogeny: implications for repair of transcribed DNA.	2006 Jan	16257035
Physical and functional interactions between Escherichia coli MutY and endonuclease VIII.	2006 Jan 1	16201966
Ab initio base-pairing energies of uracil and 5-hydroxyuracil with standard DNA bases at the BSSE-free DFT and MP2 theory levels.	2006 May 7	16633566
RNA polymerase II bypass of oxidative DNA damage is regulated by transcription elongation factors.	2006 Nov 29	17110932
DNA oxidation in Alzheimer's disease.	2006 Nov-Dec	17034348
DNA polymerase delta-dependent repair of DNA single strand breaks containing 3'-end proximal lesions.	2007	17264132
Radiosensitization by nitric oxide at low radiation doses.	2007 Apr	17388699
Uracil in DNA--general mutagen, but normal intermediate in acquired immunity.	2007 Apr 1	17116429
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 Apr 14	17101234
NEIL1 is the major DNA glycosylase that processes 5-hydroxyuracil in the proximity of a DNA single-strand break.	2007 Apr 3	17348689
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 May 21	17571183
Base-pairing properties of the oxidized cytosine derivative, 5-hydroxy uracil.	2008 Feb 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 Feb 8	18032376
Examination of hypochlorous acid-induced damage to cytosine residues in a CpG dinucleotide in DNA.	2008 Jun	18826175
Base excision repair activities in organotypic hippocampal slice cultures exposed to oxygen and glucose deprivation.	2008 Jun 1	18406215
Physical and functional interaction between human oxidized base-specific DNA glycosylase NEIL1 and flap endonuclease 1.	2008 Oct 3	18662981
Base excision repair of oxidative DNA damage and association with cancer and aging.	2009 Jan	18978338
Characterization of the major formamidopyrimidine-DNA glycosylase homolog in Mycobacterium tuberculosis and its linkage to variable tandem repeats.	2009 Jul	19496823
Catalytically impaired hMYH and NEIL1 mutant proteins identified in patients with primary sclerosing cholangitis and cholangiocarcinoma.	2009 Jul	19443904
Insights into the role of Val45 and Gln182 of Escherichia coli MutY in DNA substrate binding and specificity.	2009 Jun 12	19523222
Raltegravir, elvitegravir, and metoogravir: the birth of "me-too" HIV-1 integrase inhibitors.	2009 Mar 5	19265512
The Base Excision Repair system of Salmonella enterica serovar typhimurium counteracts DNA damage by host nitric oxide.	2009 May	19478870
Modulation of DNA glycosylase activities in mesenchymal stem cells.	2009 Sep 10	19477173
Substrate specific stimulation of NEIL1 by WRN but not the other human RecQ helicases.	2010 Jun 4	20346739
Specific Inhibition of NEIL-initiated repair of oxidized base damage in human genome by copper and iron: potential etiological linkage to neurodegenerative diseases.	2010 Sep 10	20622253

Substance Class	Chemical Created by `admin` on `Sat Dec 16 00:42:07 GMT 2023` Edited by `admin` on `Sat Dec 16 00:42:07 GMT 2023`
Record UNII	438WJI1S49
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOBARBITURIC ACID

Common Name

English

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

Systematic Name

English

FLUOROURACIL RELATED COMPOUND B [USP IMPURITY]

Common 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