Chemical Formula: C5H5N5O
Chemical Formula C5H5N5O
Found 26 metabolite its formula value is C5H5N5O
Guanine
Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA. Guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with conjugated double bonds. Being unsaturated, the bicyclic molecule is planar. The guanine nucleoside is called guanosine. The first isolation of guanine was reported in 1844 from the excreta of sea birds, known as guano, which was used as a source of fertilizer. High affinity binding of guanine nucleotides and the ability to hydrolyze bound GTP to GDP are characteristics of an extended family of intracellular proteins. Guanine nucleotide-binding regulatory proteins may be involved in the activation of phospholipases C and A2 by hormones and other ligands. The binding of hormones to receptors that activate phospholipase C is decreased by guanine nucleotides and these hormones also stimulate a high-affinity GTPase activity in cell membranes. Effects of hormones on phospholipase C activity in cell-free preparations are dependent on the presence of guanine nucleotides. Hypoxanthine-guanine phosphoribosyltransferase (HPRT, EC 2.4.2.8) is a purine salvage enzyme that catalyses the conversion of hypoxanthine and guanine to their respective mononucleotides. Partial deficiency of this enzyme can result in the overproduction of uric acid leading to a severe form of gout, whilst a virtual absence of HPRT activity causes the Lesch-Nyhan syndrome, an inborn error of metabolism, which is characterised by hyperuricaemia, mental retardation, choreoathetosis and compulsive self-mutilation. Peroxynitrite induces DNA base damage predominantly at guanine (G) and 8-oxoguanine (8-oxoG) nucleobases via oxidation reactions. G and 8-oxoG are the most reactive bases toward Peroxynitrite and possibly the major contributors to peroxynitrite-derived genotoxic and mutagenic lesions. The neutral G radical, reacts with NO2 to yield 8-nitroguanine and 5-nitro-4-guanidinohydantoin (PMID: 16352449, 2435586, 2838362, 1487231). Guanine is a 2-aminopurine carrying a 6-oxo substituent. It has a role as a human metabolite, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purine nucleobase, an oxopurine and a member of 2-aminopurines. It derives from a hydride of a 9H-purine. Guanine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Guanine is a natural product found in Fritillaria thunbergii, Isatis tinctoria, and other organisms with data available. Guanine is a purine base that is a constituent of nucleotides occurring in nucleic acids. Guanine is a mineral with formula of C5H3(NH2)N4O. The corresponding IMA (International Mineralogical Association) number is IMA1973-056. The IMA symbol is Gni. Guanine is a metabolite found in or produced by Saccharomyces cerevisiae. Occurs widely in animals and plants. Component of nucleic acids (CCD) A 2-aminopurine carrying a 6-oxo substituent. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS [Spectral] Guanine (exact mass = 151.04941) and 3,4-Dihydroxy-L-phenylalanine (exact mass = 197.06881) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Guanine (exact mass = 151.04941) and D-Gluconic acid (exact mass = 196.0583) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Guanine (exact mass = 151.04941) and L-Valine (exact mass = 117.07898) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 54 CONFIDENCE standard compound; ML_ID 43
2-Hydroxyadenine
2-Hydroxyadenine (2-OH-Ade) is formed by hydroxyl radical attack on DNA bases and shows a genotoxicity in human, being the source of the mutations induced by reactive oxygen species. 2-OH-Ade in DNA is miscoding and elicits various mutations, and is a mutagenic in bacterial and mammalian cells. (Recent Research Developments in Biochemistry (2000)2:41-50) [HMDB] 2-Hydroxyadenine (2-OH-Ade) is formed by hydroxyl radical attack on DNA bases and shows a genotoxicity in human, being the source of the mutations induced by reactive oxygen species. 2-OH-Ade in DNA is miscoding and elicits various mutations, and is a mutagenic in bacterial and mammalian cells. (Recent Research Developments in Biochemistry (2000)2:41-50). Isoguanine is an oxopurine that is 3,7-dihydro-purin-2-one in which the hydrogen at position 6 is substituted by an amino group.
8-Hydroxyadenine
8-hydroxyadenine is an intermediate in the oxidation of adenine to 2,8-dihydroxyadenine by xanthine oxidase (EC 1.1.3.22). A controversy exists as to whether or not this metabolite is a marker of DNA damage. Several papers have reported an artifactual formation of a number of modified bases from intact DNA bases during derivatization of DNA hydrolysates to be analyzed by gas chromatography-mass spectrometry (GC/MS). These reports dealt with 8-hydroxyadenine (8-OH). It needs to be emphasized that the procedures for hydrolysis of DNA and derivatization of DNA hydrolysates used in these papers substantially differed from the established procedures previously described. Furthermore, a large number of relevant papers reporting the levels of these modified bases in DNA of various sources have been ignored. Interestingly, the levels of modified bases reported in the literature were not as high as those reported prior to prepurification. Levels of 8-OH-Ade were quite close to, or even the same as, or smaller than the level reported after prepurification. All these facts raise the question of the validity of the claims about the measurement of these modified DNA bases by GC/MS. Oxidative damage to DNA may play an important role in aging and neurodegenerative diseases such as Alzheimers disease (AD). Attack on DNA by reactive oxygen species, particularly hydroxyl radicals, can lead to strand breaks, DNA-DNA and DNA-protein cross-linking, sister chromatid exchange and translocation, and formation of at least 20 oxidized base adducts. Modification of DNA bases can lead to mutation and altered protein synthesis. In late-stage AD brain, several studies have shown an elevation of the base adducts 8-hydroxyadenine (8-OHA). Several studies have shown a decline in repair of 8-OHG in AD. Most recently studies have shown elevated 8-OHA in nuclear and mitochondrial DNA in mild cognitive impairment, the earliest detectable form of AD, suggesting that oxidative damage to DNA is an early event in AD and not a secondary phenomenon. (PMID: 10098459, 17034348) [HMDB] 8-hydroxyadenine is an intermediate in the oxidation of adenine to 2,8-dihydroxyadenine by xanthine oxidase (EC 1.1.3.22). A controversy exists as to whether or not this metabolite is a marker of DNA damage. Several papers have reported an artifactual formation of a number of modified bases from intact DNA bases during derivatization of DNA hydrolysates to be analyzed by gas chromatography-mass spectrometry (GC/MS). These reports dealt with 8-hydroxyadenine (8-OH). It needs to be emphasized that the procedures for hydrolysis of DNA and derivatization of DNA hydrolysates used in these papers substantially differed from the established procedures previously described. Furthermore, a large number of relevant papers reporting the levels of these modified bases in DNA of various sources have been ignored. Interestingly, the levels of modified bases reported in the literature were not as high as those reported prior to prepurification. Levels of 8-OH-Ade were quite close to, or even the same as, or smaller than the level reported after prepurification. All these facts raise the question of the validity of the claims about the measurement of these modified DNA bases by GC/MS. Oxidative damage to DNA may play an important role in aging and neurodegenerative diseases such as Alzheimers disease (AD). Attack on DNA by reactive oxygen species, particularly hydroxyl radicals, can lead to strand breaks, DNA-DNA and DNA-protein cross-linking, sister chromatid exchange and translocation, and formation of at least 20 oxidized base adducts. Modification of DNA bases can lead to mutation and altered protein synthesis. In late-stage AD brain, several studies have shown an elevation of the base adducts 8-hydroxyadenine (8-OHA). Several studies have shown a decline in repair of 8-OHG in AD. Most recently studies have shown elevated 8-OHA in nuclear and mitochondrial DNA in mild cognitive impairment, the earliest detectable form of AD, suggesting that oxidative damage to DNA is an early event in AD and not a secondary phenomenon. (PMID: 10098459, 17034348).
Guanine
MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; UYTPUPDQBNUYGX_STSL_0161_Guanine_0125fmol_180430_S2_LC02_MS02_179; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I.
8-Hydroxyadenine
A nucleobase analogue that is adenine bearing a single hydroxy substituent at position 8.
Pyrimido[5,4-e]-1,2,4-triazin-5-ol, 1,5-dihydro- (9CI)
Cyanamide, (6-amino-1,4-dihydro-4-oxo-2-pyrimidinyl)-
6H-Pyrazolo[3,4-d]pyrimidin-6-one,4-amino-1,7-dihydro-
6-METHYL[1,2,4]TRIAZOLO[4,3-B][1,2,4]TRIAZIN-7(8H)-ONE
(2-Amino-6-oxo-1,6-dihydropyrimidin-4-yl)cyanamide
[1,2,4]Triazolo[1,5-a]pyrimidin-5(1H)-one,7-amino-
8-Oxoadenine
An oxopurine that is adenine bearing a single oxo substituent at position 8.