6-AZAURACIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C3H3N3O2
Molecular Weight	113.0748
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1NN=CC(=O)N1

InChI

InChIKey=SSPYSWLZOPCOLO-UHFFFAOYSA-N

InChI=1S/C3H3N3O2/c7-2-1-4-6-3(8)5-2/h1H,(H2,5,6,7,8)

HIDE SMILES / InChI

Molecular Formula	C3H3N3O2
Molecular Weight	113.0748
Charge	0
Count

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Pseudococcidae 1 Target ID: CHEMBL2367092 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8672580	Inhibitor 8504

PubMed

Title	Date	PubMed
Overruling the energy gap law: fast triplet formation in 6-azauracil.	2010-12-28	20680213
The SWR1 histone replacement complex causes genetic instability and genome-wide transcription misregulation in the absence of H2A.Z.	2010-08-12	20711347
Roles for H2A.Z and its acetylation in GAL1 transcription and gene induction, but not GAL1-transcriptional memory.	2010-06-22	20582323
Overexpression of SNG1 causes 6-azauracil resistance in Saccharomyces cerevisiae.	2010-06	20424846
Histone H3 serine 57 and lysine 56 interplay in transcription elongation and recovery from S-phase stress.	2010-05-26	20520775
A chemical genetic screen for modulators of asymmetrical 2,2'-dimeric naphthoquinones cytotoxicity in yeast.	2010-05-26	20520766
Triplet formation of 6-azauridine and singlet oxygen sensitization with UV light irradiation.	2010-05-21	20445916
Evidence that transcript cleavage is essential for RNA polymerase II transcription and cell viability.	2010-04-23	20417599
A nucleosome surface formed by histone H4, H2A, and H3 residues is needed for proper histone H3 Lys36 methylation, histone acetylation, and repression of cryptic transcription.	2010-04-09	20139424
Improving binding specificity of pharmacological chaperones that target mutant superoxide dismutase-1 linked to familial amyotrophic lateral sclerosis using computational methods.	2010-04-08	20232802
The YEATS domain of Taf14 in Saccharomyces cerevisiae has a negative impact on cell growth.	2010-04	20179968
The Snf2 homolog Fun30 acts as a homodimeric ATP-dependent chromatin-remodeling enzyme.	2010-03-26	20075079
Functional characterization and virulence study of ADE8 and GUA1 genes involved in the de novo purine biosynthesis in Candida albicans.	2010-03	20082641
A Bre1-associated protein, large 1 (Lge1), promotes H2B ubiquitylation during the early stages of transcription elongation.	2010-01-22	19923226
The SNF2-family member Fun30 promotes gene silencing in heterochromatic loci.	2009-12-01	19956593
Intersystem crossing to excited triplet state of aza analogues of nucleic acid bases in acetonitrile.	2009-11-05	19795828
Global analysis of mutual interaction surfaces of nucleosomes with comprehensive point mutants.	2009-11	19903202
Yeast genetic analysis reveals the involvement of chromatin reassembly factors in repressing HIV-1 basal transcription.	2009-01	19148280
Excited state characteristics of 6-azauracil in acetonitrile: drastically different relaxation mechanism from uracil.	2008-12-25	19053223
Spt2p defines a new transcription-dependent gross chromosomal rearrangement pathway.	2008-12	19057669
H3K9 methylation regulates growth and development in Aspergillus fumigatus.	2008-12	18849468
Histone H3 K36 methylation is mediated by a trans-histone methylation pathway involving an interaction between Set2 and histone H4.	2008-10-15	18923077
Neo-clinicians, clinical trials, and the reorganization of medical research in Paris hospitals after the Second World War: the trajectory of Jean Bernard.	2008-10	18958252
Mutations of RNA polymerase II activate key genes of the nucleoside triphosphate biosynthetic pathways.	2008-09-17	18716630
Identification and characterization of two trypanosome TFIIS proteins exhibiting particular domain architectures and differential nuclear localizations.	2008-09	18627464
Chemogenetic fingerprinting by analysis of cellular growth dynamics.	2008-08-22	18721464
Comprehensive structural studies of 2',3'-difluorinated nucleosides: comparison of theory, solution, and solid state.	2008-07-16	18558684
Genomewide recruitment analysis of Rpb4, a subunit of polymerase II in Saccharomyces cerevisiae, reveals its involvement in transcription elongation.	2008-06	18441121
Reversal of RNA polymerase II ubiquitylation by the ubiquitin protease Ubp3.	2008-05-23	18498751
The tumor suppressor p53 associates with gene coding regions and co-traverses with elongating RNA polymerase II in an in vivo model.	2008-04-24	18026140
Cell-to-cell stochastic variation in gene expression is a complex genetic trait.	2008-04-11	18404214
[Lectins from Sambucus nigra L inflorescences: isolation and investigation of biological activity using procaryotic test-systems].	2008-03-25	18357788
6-Azauracil or 8-aza-7-deazaadenine nucleosides and oligonucleotides: the effect of 2'-fluoro substituents and nucleobase nitrogens on conformation and base pairing.	2008-02-07	18219432
Recruitment of P-TEFb (Cdk9-Pch1) to chromatin by the cap-methyl transferase Pcm1 in fission yeast.	2007-03-21	17332744
Identification and Characterization of a Schizosaccharomyces pombe RNA Polymerase II Elongation Factor with Similarity to the Metazoan Transcription Factor ELL.	2007-02-23	17150956
Global analysis of functional surfaces of core histones with comprehensive point mutants.	2007-01	17212652
6-azauracil sensitivity assay for yeast.	2006-12-01	22484669
Combined use of two transcriptional reporters improves signalling assays for G protein-coupled receptors in fission yeast.	2006-09	17001618
[The synthesis of arginine derivatives of chromone and azauracil].	2006-07-01	16808173
Mutations in the Saccharomyces cerevisiae RPB1 gene conferring hypersensitivity to 6-azauracil.	2006-04	16510790
Folding free energies of 5'-UTRs impact post-transcriptional regulation on a genomic scale in yeast.	2005-12	16355254
Altered nucleosome occupancy and histone H3K4 methylation in response to 'transcriptional stress'.	2005-07-06	15944735
A novel domain in Set2 mediates RNA polymerase II interaction and couples histone H3 K36 methylation with transcript elongation.	2005-04	15798214
Distinction and relationship between elongation rate and processivity of RNA polymerase II in vivo.	2005-03-18	15780939
Synthesis and biological activity of some unsaturated 6-azauracil acyclonucleosides.	2005	15892255
The uses of genome-wide yeast mutant collections.	2004	15239820
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.	1996-12	9039272
Structure-activity relationship of ligands of uracil phosphoribosyltransferase from Toxoplasma gondii.	1994-08-17	8080452
2,4-Bis(arylamino)-5-methylpyrimidines as antimicrobial agents.	1967-09	4963369
2,4-Bis(arylamino)pyrimidines as antimicrobial agents.	1966-05	5960924

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:39:50 GMT 2025` Edited by `admin` on `Mon Mar 31 19:39:50 GMT 2025`
Record UNII	I14TWN70LR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

6-AZAURACIL

Systematic Name

English

NSC-3425

Preferred Name

English

1,2,4-TRIAZINE-3,5-DIONE

Systematic Name

English

3,5-DIHYDROXY-1,2,4-TRIAZINE

Systematic Name

English

Code System Code Type Description

MESH

C100248