Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:06:08 UTC |
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Update date | 2020-09-17 15:38:21 UTC |
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Primary ID | FDB004222 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Guanine |
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Description | Guanine, also known as G or mearlmaid aa, 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. Guanine is a moderately basic compound (based on its pKa). Guanine exists in all living species, ranging from bacteria to humans. Within humans, guanine participates in a number of enzymatic reactions. In particular, guanine and phosphoribosyl pyrophosphate can be biosynthesized from guanosine monophosphate through its interaction with the enzyme adenine phosphoribosyltransferase. In addition, guanine and ribose 1-phosphate can be biosynthesized from guanosine; which is catalyzed by the enzyme purine nucleoside phosphorylase. In humans, guanine is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. Outside of the human body, Guanine is found, on average, in the highest concentration within beers and milk (cow). Guanine has also been detected, but not quantified in, several different foods, such as kombus, black radish, chinese cabbages, dills, and devilfish. This could make guanine a potential biomarker for the consumption of these foods. Guanine, with regard to humans, has been found to be associated with several diseases such as lewy body disease, frontotemporal dementia, colorectal cancer, and alzheimer's disease; guanine has also been linked to the inborn metabolic disorder lesch-nyhan syndrome. A 2-aminopurine carrying a 6-oxo substituent. |
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CAS Number | 73-40-5 |
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Structure | |
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Synonyms | Synonym | Source |
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2-Amino-6-hydroxypurine | ChEBI | 2-Amino-6-oxopurine | ChEBI | G | ChEBI | Gua | ChEBI | 2-Amino-1,7-dihydro-6H-purin-6-one | HMDB | 2-Amino-1,9-dihydro-6H-purin-6-one | HMDB | 2-Amino-1,9-dihydro-purin-6-one | HMDB | 2-Amino-3,7-dihydro-6H-purin-6-one | HMDB | 2-Amino-6-hydroxy-1H-purine | HMDB | 2-Amino-6-purinol | HMDB | 2-Amino-hypoxanthine | HMDB | 2-Aminohypoxanthine | HMDB | 6-Hydroxy-2-aminopurine | HMDB | C.I. natural white 1 | HMDB | CI natural white 1 | HMDB | Dew pearl | HMDB | Guanin | HMDB | Guanine enol | HMDB | GUN | HMDB | Mearlmaid | HMDB | Mearlmaid aa | HMDB | Natural pearl essence | HMDB | Natural white 1 | HMDB | Naturon | HMDB | Pathocidin | HMDB | Pearl essence | HMDB | Stella polaris | HMDB | 2-Amino-1,7-dihydro-6H-Purin-6-one | biospider | 2-amino-6-Oxopurine | ChEBI | 2-Amino-9H-purin-6-ol | biospider | 2-Amino-Hypoxanthine | biospider | 2(1H)-pyrimidinone, 4-amino- | biospider | 6H-Purin-6-one, 2-amino-1,7-dihydro- (9CI) | biospider | 6H-Purin-6-one, 2-amino-1,9-dihydro- | biospider | 6H-purin-6-one, 2-amino-3,7-dihydro- | biospider | Hypoxanthine, 2-amino- | biospider |
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Predicted Properties | |
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Chemical Formula | C5H5N5O |
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IUPAC name | 2-amino-6,7-dihydro-3H-purin-6-one |
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InChI Identifier | InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11) |
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InChI Key | UYTPUPDQBNUYGX-UHFFFAOYSA-N |
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Isomeric SMILES | NC1=NC(=O)C2=C(N1)N=CN2 |
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Average Molecular Weight | 151.1261 |
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Monoisotopic Molecular Weight | 151.049409807 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Imidazopyrimidines |
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Sub Class | Purines and purine derivatives |
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Direct Parent | Purines and purine derivatives |
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Alternative Parents | |
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Substituents | - Purine
- Hydroxypyrimidine
- Pyrimidine
- Heteroaromatic compound
- Imidazole
- Azole
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Cryst. | CCD |
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Mass Composition | C 39.74%; H 3.33%; N 46.34%; O 10.59% | CCD |
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Melting Point | Mp 300° | CCD |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 2.08 mg/mL at 37 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | -0.91 | HANSCH,C ET AL. (1995) |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0udi-8900000000-699c510cfaf838ab1922 | 2015-03-01 | View Spectrum | GC-MS | Guanine, non-derivatized, GC-MS Spectrum | splash10-0udi-1938000000-e15e09f2007f35659bb9 | Spectrum | GC-MS | Guanine, 3 TMS, GC-MS Spectrum | splash10-0udi-3739000000-66a080b08ba9b9f82e20 | Spectrum | GC-MS | Guanine, non-derivatized, GC-MS Spectrum | splash10-0udi-5900000000-0a63148e3a8dc8d026df | Spectrum | GC-MS | Guanine, non-derivatized, GC-MS Spectrum | splash10-0udi-1938000000-e15e09f2007f35659bb9 | Spectrum | GC-MS | Guanine, non-derivatized, GC-MS Spectrum | splash10-0udi-3739000000-66a080b08ba9b9f82e20 | Spectrum | GC-MS | Guanine, non-derivatized, GC-MS Spectrum | splash10-0udi-2928000000-073bf70794fe99ce737f | Spectrum | GC-MS | Guanine, non-derivatized, GC-MS Spectrum | splash10-000t-2790000000-77e6b5b71c9ff6ad2b23 | Spectrum | Predicted GC-MS | Guanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0ff0-5900000000-f103c75addeafe7ac6f0 | Spectrum | Predicted GC-MS | Guanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0udi-0901000000-2864e73c83444d566e9a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0a4i-2900000000-4229d3d01623054b4ceb | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-0900000000-d5ae84fefadd84f988b4 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0900000000-7d48b2e8db6967e98407 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0uxr-0900000000-67a7784963ec75cecaa0 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-9000000000-4569516f23d8a712b434 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0900000000-d928cac1226f19b8edc3 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0udi-0900000000-34059351f2cbd94a8acc | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0udj-0903100000-deb9c022884d7c98782e | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0900000000-45d9db80ce4657ef1773 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004i-1900000000-86b7ee5755cbb8236f5b | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0udi-0900000000-ba534850b64f39d81fa0 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-0900000000-422f992621ab9626d1b2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0f89-0900000000-64e388178db73f06cb20 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0udi-0900000000-f0a95c55947ca990359c | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-001i-0900000000-45d9db80ce4657ef1773 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0udi-0900000000-ba534850b64f39d81fa0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0f89-0900000000-64e388178db73f06cb20 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-0udi-0900000000-c2e1c1e8841cc741dac1 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0900000000-e74c005384d71f4787e5 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-de4a4c4479ea93d742b5 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a5i-9800000000-da506476184e5c2313a4 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-03d17084c3cb072c0237 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-2900000000-c372e3ba919cba4f561f | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kf-9200000000-8ac435f998deda6437e1 | 2015-05-27 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 744 |
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ChEMBL ID | CHEMBL219568 |
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KEGG Compound ID | C00242 |
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Pubchem Compound ID | 764 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 16235 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB02377 |
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HMDB ID | HMDB00132 |
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CRC / DFC (Dictionary of Food Compounds) ID | HHS79-J:HHS79-J |
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EAFUS ID | Not Available |
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Dr. Duke ID | GUANINE |
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BIGG ID | 34363 |
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KNApSAcK ID | Not Available |
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HET ID | GUN |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Guanine |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Name | Gene Name | UniProt ID |
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Purine nucleoside phosphorylase | PNP | P00491 | Adenine phosphoribosyltransferase | APRT | P07741 | Guanine nucleotide-binding protein G(s) subunit alpha isoforms short | GNAS | P63092 | Guanine nucleotide-binding protein G(q) subunit alpha | GNAQ | P50148 | Queuine tRNA-ribosyltransferase subunit QTRTD1 | QTRTD1 | Q9H974 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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