Guanine (ECMDB00132) (M2MDB000051)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 10:21:39 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:06 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Guanine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | 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. High affinity binding of guanine nucleotides and the ability to hydrolyze bound GTP to GDP are characteristics of an extended family of intracellular proteins. 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. 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) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C5H5N5O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 151.1261 Monoisotopic: 151.049409807 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | UYTPUPDQBNUYGX-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 73-40-5 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | 2-amino-6,7-dihydro-3H-purin-6-one | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | 2-aminohypoxanthine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | NC1=NC(=O)C2=C(N1)N=CN2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organoheterocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Imidazopyrimidines | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Purines and purine derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Purines and purine derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 360 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Guanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + Pyrophosphate Deoxyguanosine + Phosphate <> Deoxyribose 1-phosphate + Guanine Guanosine + Phosphate <> Guanine + Ribose-1-phosphate Guanine + Hydrogen ion + Water > Ammonium + Xanthine Guanosine monophosphate + Pyrophosphate <> Guanine + Phosphoribosyl pyrophosphate Guanine + Water <> Xanthine + Ammonia Guanosine + Water <> Guanine + Ribose Guanosine + Phosphate <> Guanine + alpha-D-Ribose 1-phosphate Deoxyguanosine + Phosphate <> deoxyribose-1-phosphate + Guanine Water + Guanine > Ammonia + Xanthine Guanine(34) in tRNA + Queuine > queuosine(34) in tRNA + Guanine Guanine(34) in tRNA + 7-Aminomethyl-7-carbaguanine > 7-aminomethyl-7-carbaguanine(34) in tRNA + Guanine Queuine + 7-Aminomethyl-7-carbaguanine <> Guanine 7-Aminomethyl-7-carbaguanine + tRNA guanine > 7-aminomethyl-7-deazaguanosine34 in tRNA + Guanine Guanosine + Phosphate > Ribose-1-phosphate + Guanine Guanine + Phosphoribosyl pyrophosphate > Pyrophosphate + Guanosine monophosphate Guanine + Water <> Xanthine + Ammonia Guanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + Pyrophosphate Queuine + 7 7-Aminomethyl-7-carbaguanine <> Guanine Guanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + Pyrophosphate Queuine + 7 7-Aminomethyl-7-carbaguanine <> Guanine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Xiao, Xuhua; Ma, Weiyong. One-pot synthesis of guanine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in queuine tRNA-ribosyltransferase activity
- Specific function:
- Exchanges the guanine residue with 7-aminomethyl-7- deazaguanine in tRNAs with GU(N) anticodons (tRNA-Asp, -Asn, -His and -Tyr). After this exchange, a cyclopentendiol moiety is attached to the 7-aminomethyl group of 7-deazaguanine, resulting in the hypermodified nucleoside queuosine (Q) (7-(((4,5-cis- dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanosine)
- Gene Name:
- tgt
- Uniprot ID:
- P0A847
- Molecular weight:
- 42593
Reactions
[tRNA]-guanine + queuine = [tRNA]-queuine + guanine. |
[tRNA]-guanine + 7-aminomethyl-7-carbaguanine = [tRNA]-7-aminomethyl-7-carbaguanine + guanine. |
- General function:
- Involved in hypoxanthine phosphoribosyltransferase activity
- Specific function:
- This enzyme acts exclusively on hypoxanthine; it does not act on guanine
- Gene Name:
- hpt
- Uniprot ID:
- P0A9M2
- Molecular weight:
- 20115
Reactions
IMP + diphosphate = hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate. |
- General function:
- Involved in nucleoside metabolic process
- Specific function:
- Acts on guanine, xanthine and to a lesser extent hypoxanthine
- Gene Name:
- gpt
- Uniprot ID:
- P0A9M5
- Molecular weight:
- 16971
Reactions
XMP + diphosphate = 5-phospho-alpha-D-ribose 1-diphosphate + xanthine. |
- General function:
- Involved in purine-nucleoside phosphorylase activity
- Specific function:
- Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules
- Gene Name:
- deoD
- Uniprot ID:
- P0ABP8
- Molecular weight:
- 25950
Reactions
Purine nucleoside + phosphate = purine + alpha-D-ribose 1-phosphate. |
- General function:
- Involved in hydrolase activity, hydrolyzing N-glycosyl compounds
- Specific function:
- Hydrolyzes cytidine or uridine to ribose and cytosine or uracil, respectively. Has a clear preference for cytidine over uridine. Strictly specific for ribonucleosides. Has a low but significant activity for the purine nucleoside xanthosine
- Gene Name:
- rihB
- Uniprot ID:
- P33022
- Molecular weight:
- 33748
Reactions
A pyrimidine nucleoside + H(2)O = D-ribose + a pyrimidine base. |
- General function:
- Involved in adenine phosphoribosyltransferase activity
- Specific function:
- Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis
- Gene Name:
- apt
- Uniprot ID:
- P69503
- Molecular weight:
- 19859
Reactions
AMP + diphosphate = adenine + 5-phospho-alpha-D-ribose 1-diphosphate. |
- General function:
- Involved in hydrolase activity
- Specific function:
- Catalyzes the hydrolytic deamination of guanine, producing xanthine and ammonia
- Gene Name:
- guaD
- Uniprot ID:
- P76641
- Molecular weight:
- 50244
Reactions
Guanine + H(2)O = xanthine + NH(3). |
- General function:
- Involved in purine-nucleoside phosphorylase activity
- Specific function:
- The nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the nucleoside molecule, with the formation of the corresponding free bases and pentose-1-phosphate. This protein can degrade all purine nucleosides except adenosine and deoxyadenosine
- Gene Name:
- xapA
- Uniprot ID:
- P45563
- Molecular weight:
- 29834
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Specific, proton motive force-dependent high-affinity transporter for xanthine
- Gene Name:
- xanP
- Uniprot ID:
- P0AGM9
- Molecular weight:
- 48868
- General function:
- Involved in nucleoside transmembrane transporter activity
- Specific function:
- Constitutes the receptor for colicin K and phage T6, and functions as substrate-specific channel for nucleosides and deoxynucleosides
- Gene Name:
- tsx
- Uniprot ID:
- P0A927
- Molecular weight:
- 33589