Guanine

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H5N5O
Molecular Weight	151.1261
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC2=C(N=CN2)C(=O)N1

InChI

InChIKey=UYTPUPDQBNUYGX-UHFFFAOYSA-N

InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)

HIDE SMILES / InChI

Molecular Formula	C5H5N5O
Molecular Weight	151.1261
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
Base sequence-specific attack of stilbene estrogen metabolite(s) on the mitochondrial DNA: implications in the induction of instability in the mitochondrial genome in the kidney of Syrian hamsters.	2001-04	11254879
Reduction of BCNU toxicity to lung cells by high-level expression of O(6)-methylguanine-DNA methyltransferase.	2001-04	11238017
A-like guanine-guanine stacking in the aqueous DNA duplex of d(GGGGCCCC).	2001-03-23	11254379
Structure, folding and activity of the VS ribozyme: importance of the 2-3-6 helical junction.	2001-03-15	11250907
Affinity of mismatch-binding protein MutS for heteroduplexes containing different mismatches.	2001-03-15	11237867
Solution structure of an A-tract DNA bend.	2001-03-09	11237619
Characterization of cDNA encoding the human tRNA-guanine transglycosylase (TGT) catalytic subunit.	2001-03-07	11255023
The Drosophila S3 multifunctional DNA repair/ribosomal protein protects Fanconi anemia cells against oxidative DNA damaging agents.	2001-03-07	11182542
Comparison of the protective effect of melatonin with other antioxidants in the hamster kidney model of estradiol-induced DNA damage.	2001-03-01	11239965
Conjugative metabolism of 1,2-dibromoethane in mitochondria: disruption of oxidative phosphorylation and alkylation of mitochondrial DNA.	2001-03-01	11239503
A seminested PCR test for simultaneous detection of two common mutations (35delG and 167delT) in the connexin-26 gene.	2001-03	11257213
Ratio of 8-hydroxyguanine in intact DNA to free 8-hydroxyguanine is increased in Alzheimer disease ventricular cerebrospinal fluid.	2001-03	11255442
New biochemical markers in Alzheimer disease.	2001-03	11255437
Substrate assisted catalysis -- application to G proteins.	2001-03	11246021
Metabolic fate of AMP, IMP, GMP and XMP in the cytosol of rat brain: an experimental and theoretical analysis.	2001-03	11238714
Metabolism of the beta-oxidized intermediates of N-nitrosodi-n-propylamine: N-nitroso-beta-hydroxypropylpropylamine and N-nitroso-beta-oxopropylpropylamine.	2001-03	11238192
Patterns of p53 G-->T transversions in lung cancers reflect the primary mutagenic signature of DNA-damage by tobacco smoke.	2001-03	11238174
Cytoskeletal effects of rho-like small guanine nucleotide-binding proteins in the vascular system.	2001-03	11231907
Mechanism of guanine-specific DNA damage by oxidative stress and its role in carcinogenesis and aging.	2001-03	11223405
Inactivation of human O(6)-alkylguanine-DNA alkyltransferase by modified oligodeoxyribonucleotides containing O(6)-benzylguanine.	2001-03	11181929
Cloning and direct G-protein regulation of phospholipase D from tobacco.	2001-02-26	11239820
Characterization of the mouse liver fructose-1,6-bisphosphatase gene.	2001-02-21	11250076
Alkylating agent and chromatin structure determine sequence context-dependent formation of alkylpurines.	2001-02-16	11237592
Invasiveness of cutaneous malignant melanoma is influenced by matrix metalloproteinase 1 gene polymorphism.	2001-02-15	11245423
Specific binding of 2-amino-1,8-naphthyridine into a single guanine bulge as evidenced by photooxidation of GG doublet.	2001-02-12	11212104
Oxidation kinetics of guanine in DNA molecules adsorbed onto indium tin oxide electrodes.	2001-02-01	11217762
Miscoding and misincorporation of 8-oxo-guanine during leading and lagging strand synthesis in Escherichia coli.	2001-02	11254131
Gemcitabine and Pemetrexed disodium in treating breast cancer.	2001-02	11252887
Alanine scan mutagenesis of the switch I domain of the Caulobacter crescentus CgtA protein reveals critical amino acids required for in vivo function.	2001-02	11251813
The anti-herpesvirus activity of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)-cycloprop-1'-yl]methyl]guanine is markedly potentiated by the immunosuppressive agent mycophenolate mofetil.	2001-02	11248364
Anti-herpesvirus activity of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)-cycloprop-1'-yl]methyl] x guanine (A-5021) in vitro and in vivo.	2001-02	11248363
Genetic changes of hOGG1 and the activity of oh8Gua glycosylase in colon cancer.	2001-02	11239755
Quantification and validation of enzyme immunoassay for urinary aflatoxin B1-N7-guanine adduct for biological monitoring of aflatoxins.	2001-02	11235100
Thresholds of O6-alkylguanine-DNA alkyltransferase which confer significant resistance of human glial tumor xenografts to treatment with 1,3-bis(2-chloroethyl)-1-nitrosourea or temozolomide.	2001-02	11234899
Cisplatin-DNA cross-link retro models with a chirality-neutral carrier ligand: evidence for the importance of "second-sphere communication".	2001-01-29	11209601
The N-terminal domain of the Caulobacter crescentus CgtA protein does not function as a guanine nucleotide exchange factor.	2001-01-26	11231024
Genetic study of SOX9 in a case of campomelic dysplasia.	2001-01-15	11223854
DNA electrochemical biosensors.	2001-01-01	11210224
Topoisomerase I-mediated cytotoxicity of N-methyl-N'-nitro-N-nitrosoguanidine: trapping of topoisomerase I by the O6-methylguanine.	2001-01-01	11196197
Specific p53 mutations detected in plasma and tumors of hepatocellular carcinoma patients by electrospray ionization mass spectrometry.	2001-01-01	11196182
Enhanced loop DNA folding induced by thymine-CH3 group contact and perpendicular guanine-thymine interaction.	2001-01	11246853
Evidence of a no-effect level in silica-induced rat lung mutagenicity but not in fibrogenicity.	2001-01	11218049
Quantum chemistry predicted correlations between geometric isomerism (conformation) of -OH and =NH substituents and typical group frequencies of nucleic acid bases: cytosine.	2001-01	11209867
Reduction of wobble-position GC bases in Corynebacteria genes and enhancement of PCR and heterologous expression.	2001-01	11200224
Spreadsheet-based program for the analysis of DNA methylation.	2001-01	11196300
Guanine versus deoxyribose damage in DNA oxidation mediated by vanadium(IV) and vanadium(V) complexes.	2001-01	11191217
UAG readthrough in mammalian cells: effect of upstream and downstream stop codon contexts reveal different signals.	2001	11242562
Regulation of gene expression by GC-rich DNA cis-elements.	2001	11237405
Sequence-specific DNA damage induced by UVA radiation in the presence of endogenous and exogenous photosensitizers.	2001	11225203
Inactivation of O6-alkylguanine-DNA alkyltransferase by 8-substituted O6-benzylguanine analogs in mice.	2001	11221964

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:22:18 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:18 GMT 2025`
Record UNII	5Z93L87A1R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CI 75170

Preferred Name

English

Guanine

Official Name

English

GUANINE [EP IMPURITY]

Common Name

English

2-AMINOHYPOXANTHINE

Common Name

English

2-AMINO-1,7-DIHYDRO-6H-PURIN-6-ONE [WHO-IP]

Systematic Name

English

GANCICLOVIR IMPURITY F [EP IMPURITY]

Common Name

English

C.I. NO. 75170 (GUANINE)

Common Name

English

6H-PURIN-6-ONE, 2-AMINO-1,7-DIHYDRO-

Systematic Name

English

VALGANCICLOVIR HYDROCHLORIDE IMPURITY B [USP IMPURITY]

Common Name

English

GUANINE [USP IMPURITY]

Common Name

English

VALACICLOVIR HYDROCHLORIDE HYDRATE IMPURITY A [EP IMPURITY]

Common Name

English

ACICLOVIR IMPURITY B [EP IMPURITY]

Common Name

English

GUANINE [WHO-IP]

Common Name

English

GUANINE [USP-RS]

Common Name

English

GUANINE [HSDB]

Common Name

English

ACICLOVIR IMPURITY B [WHO-IP]

Common Name

English

GUANINE [MI]

Common Name

English

VALACICLOVIR HYDROCHLORIDE IMPURITY A [EP IMPURITY]

Common Name

English

Classification Tree Code System Code

LOINC

78695-4