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Record Information |
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| Version |
1.0 |
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| Update Date |
1/22/2018 11:54:54 AM |
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Metabolite ID | PAMDB110474 |
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Identification |
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| Name: |
isoguanine |
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| Description: | An oxopurine that is 3,7-dihydro-purin-2-one in which the hydrogen at position 6 is substituted by an amino group. |
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Structure |
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| Synonyms: | -
2-oxoadenine
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2-hydroxyadenine
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Chemical Formula: |
C5H5N5O
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| Average Molecular Weight: |
151.0494098086 |
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| Monoisotopic Molecular
Weight: |
151.0494098086 |
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| InChI Key: |
DRAVOWXCEBXPTN-UHFFFAOYSA-N |
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| InChI: |
InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1H,(H4,6,7,8,9,10,11) |
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| CAS
number: |
3373-53-3 |
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| IUPAC Name: | 6-amino-3,7-dihydro-2H-purin-2-one |
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Traditional IUPAC Name: |
2-hydroxy-6-aminopurine |
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| SMILES: | C2(=NC1(=C(NC(N=C(N)1)=O)N2)) |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of chemical entities known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. |
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Kingdom |
Chemical entities |
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| Super Class | Organic compounds |
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Class |
Organoheterocyclic compounds |
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| Sub Class | Imidazopyrimidines |
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Direct Parent |
6-aminopurines |
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| Alternative Parents |
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| Substituents |
- 6-aminopurine
- Aminopyrimidine
- Hydroxypyrimidine
- Primary aromatic amine
- Pyrimidine
- Imidolactam
- Azole
- Imidazole
- Heteroaromatic compound
- Azacycle
- Organopnictogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Amine
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework |
Aromatic heteropolycyclic compounds |
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| External Descriptors |
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Physical Properties |
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| State: |
Solid |
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| Charge: | 0 |
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Melting point: |
> 360 °C |
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| Experimental Properties: |
| Property | Value | Reference |
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| Melting Point | > 360 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.0625 mg/mL | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties |
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Biological Properties |
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| Cellular Locations: |
Not Available |
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| Reactions: | |
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Pathways: |
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Spectra |
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| Spectra: |
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References |
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| References: |
- Kamiya H, Kasai H (1995)2-Hydroxyadenine (isoguanine) as oxidative DNA damage: its formation and mutation inducibility. Nucleic acids symposium series233-234 [PubMed:8841637][show Abstract]In our experiments we found that hydroxylation occurs at the C-2 position of adenine by oxygen radical treatment (Fe(2+)-EDTA) of dA, dATP, and single- and double-stranded DNA. This oxidatively damaged base, 2-hydroxyadenine (also known as isoguanine), was produced more efficiently in monomers than in polynucleotides. 2-Hydroxydeoxyadenosine triphosphate was incorporated opposite T and C in a DNA template by DNA polymerase alpha and only opposite T by the Klenow fragment. The Klenow fragment, DNA polymerases alpha and beta incorporated dTMP and other nucleotides opposite 2-OH-Ade in DNA templates in vitro in a sequence-dependent manner. These results suggest that the formation of 2-OH-Ade in DNA will induce mutations in cells.
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| Rogstad KN, Jang YH, Sowers LC, Goddard WA (2003)First principles calculations of the pKa values and tautomers of isoguanine and xanthine. Chemical research in toxicology 16, Pubmed: 14615972 Blas JR, Luque FJ, Orozco M (2004)Unique tautomeric properties of isoguanine. Journal of the American Chemical Society 126, Pubmed: 14709079 Yang XL, Sugiyama H, Ikeda S, Saito I, Wang AH (1998)Structural studies of a stable parallel-stranded DNA duplex incorporating isoguanine:cytosine and isocytosine:guanine basepairs by nuclear magnetic resonance spectroscopy. Biophysical journal 75, Pubmed: 9726918 Pettit GR, Ode RH, Coomes RM, Ode SL (1976)Antineoplastic agents. 42. The butterfly, Prioneris thestylis. Lloydia 39, Pubmed: 1018622 |
| Synthesis Reference: |
Hayashi, Taketo; Tamato, Toyomochi. Preparation of isoguanine. Jpn. Kokai Tokkyo Koho (1994), 3 pp. |
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| Material Safety Data Sheet (MSDS) |
Download (PDF) |
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Links |
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| External Links: |
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