Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 14:35:05 -0600 |
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Update Date | 2015-06-03 17:19:37 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | 8-Hydroxydeoxyguanosine 5'-triphosphate |
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Description | 8-hydroxydeoxyguanosine 5'-triphosphate (8-hydroxy-dGTP) is a member of the chemical class known as Purine 2'-deoxyribonucleoside Triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking an hydroxyl group at position 2. Hydroxylated nucleotides can appear in DNA that has been oxidatively damaged. Escherichia coli Orf135 protein is thought to be an enzyme that efficiently hydrolyzes oxidatively damaged nucleotides such as 2-hydroxy-dATP, 8-hydroxy-dGTP and 5-hydroxy-CTP, in addition to 5-methyl-dCTP, dCTP and CTP, thus preventing mutations in cells caused by unfavorable base pairing. [PMID:21553121] |
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Structure | |
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Synonyms: | - 8-Hydroxydeoxyguanosine 5'-triphosphoric acid
- 8-HYDROXYDEOXYGUANOSINE-5-TRIPHOSPHAT
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Chemical Formula: | C10H12N5O14P3 |
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Weight: | Average: 519.1487 Monoisotopic: 518.959359653 |
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InChI Key: | BUZOGVVQWCXXDP-UHFFFAOYSA-J |
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InChI: | InChI=1S/C10H16N5O14P3/c11-9-13-7-6(8(17)14-9)12-10(18)15(7)5-1-3(16)4(27-5)2-26-31(22,23)29-32(24,25)28-30(19,20)21/h3-5,16H,1-2H2,(H,12,18)(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,17)/p-4 |
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CAS number: | Not Available |
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IUPAC Name: | 9-[4-hydroxy-5-({[hydroxy({[hydroxy(phosphonatooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-2-yl]-2-imino-3,9-dihydro-2H-purine-6,8-bis(olate) |
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Traditional IUPAC Name: | 9-{4-hydroxy-5-[({hydroxy[hydroxy(phosphonatooxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-2-yl}-2-imino-3H-purine-6,8-bis(olate) |
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SMILES: | OC1CC(OC1COP(O)(=O)OP(O)(=O)OP([O-])([O-])=O)N1C([O-])=NC2=C1NC(=N)N=C2[O-] |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Purine nucleotides |
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Sub Class | Purine deoxyribonucleotides |
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Direct Parent | Purine 2'-deoxyribonucleoside triphosphates |
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Alternative Parents | |
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Substituents | - Purine 2'-deoxyribonucleoside triphosphate
- 6-oxopurine
- Hypoxanthine
- Purinone
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Pyrimidone
- N-substituted imidazole
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Pyrimidine
- Alkyl phosphate
- Heteroaromatic compound
- Azole
- Imidazole
- Vinylogous amide
- Tetrahydrofuran
- Secondary alcohol
- Urea
- Azacycle
- Oxacycle
- Organoheterocyclic compound
- Alcohol
- Organopnictogen compound
- Organonitrogen compound
- Organooxygen compound
- Primary amine
- Organic nitrogen compound
- Amine
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic anion
- 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: | Not Available |
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Charge: | -3 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | Not Available |
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | |
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References |
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References: | - Kawasaki, K., Yoneyama, M., Murata-Kamiya, N., Harashima, H., Kojima, C., Ito, Y., Kamiya, H., Mishima, M. (2012). "(1)H, (1)(3)C and (1)(5)N NMR assignments of the Escherichia coli Orf135 protein." Biomol NMR Assign 6:1-4. Pubmed: 21553121
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
- van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | |
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