Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 14:04:04 -0600 |
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Update Date | 2015-06-03 15:54:42 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | 2'-Deoxyinosine triphosphate |
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Description | 2'-Deoxyinosine triphosphate (dITP) is a deoxyribonucleotide that may be generated from dATP by slow, non-enzymatic hydrolysis or by reduction of ITP. Normally, the cellular dITP concentration is very low. The inability to demonstrate the synthesis of dITP in cellular preparations has been attributed to the presence in the cytoplasm of an inosine triphosphatase pyrophosphatase (ITPase, EC 3.6.1.19), an enzyme that does not permit accumulation of these nucleotides. dITP can be incorporated into DNA by polymerases. The deoxyribonucleotide dITP behaves as a dGTP analogue and is incorporated opposite cytosine with about 50% efficiency. Both isolated nuclei and purified DNA polymerases rapidly incorporated dITP into DNA. In the presence of ATP, dITP is stabilized in extracts of nuclei. dITP exist in all cells and is potentially mutagenic, and the levels of these nucleotides are controlled by ITPase. The function of this ubiquitous protein family is proposed to be the elimination of minor potentially mutagenic or clastogenic purine nucleoside triphosphates from the cell. (PMID: 11278832) |
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Structure | |
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Synonyms: | - 2'-Deoxy-Inosine 5'-(tetrahydrogen triphosphate)
- 2'-Deoxy-inosine 5'-(tetrahydrogen triphosphoric acid)
- 2'-Deoxyinosine triphosphoric acid
- 2'-Deoxyinosine-5'-triphosphate
- 2'-Deoxyinosine-5'-triphosphoric acid
- 2'-Ditp
- Deoxyinosine 5'-triphosphate
- Deoxyinosine 5'-triphosphoric acid
- Deoxyinosine triphosphate
- Deoxyinosine triphosphoric acid
- DITP
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Chemical Formula: | C10H15N4O13P3 |
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Weight: | Average: 492.1664 Monoisotopic: 491.984846122 |
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InChI Key: | UFJPAQSLHAGEBL-RRKCRQDMSA-N |
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InChI: | InChI=1S/C10H15N4O13P3/c15-5-1-7(14-4-13-8-9(14)11-3-12-10(8)16)25-6(5)2-24-29(20,21)27-30(22,23)26-28(17,18)19/h3-7,15H,1-2H2,(H,20,21)(H,22,23)(H,11,12,16)(H2,17,18,19)/t5-,6+,7+/m0/s1 |
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CAS number: | 16595-02-1 |
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IUPAC Name: | {[hydroxy({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphoryl]oxy}phosphonic acid |
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Traditional IUPAC Name: | [hydroxy({hydroxy[(2R,3S,5R)-3-hydroxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methoxyphosphoryl}oxy)phosphoryl]oxyphosphonic acid |
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SMILES: | O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=NC2=C1NC=NC2=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
- Imidazopyrimidine
- Purine
- Pyrimidone
- Monoalkyl phosphate
- N-substituted imidazole
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Pyrimidine
- Alkyl phosphate
- Tetrahydrofuran
- Heteroaromatic compound
- Azole
- Vinylogous amide
- Imidazole
- Secondary alcohol
- Azacycle
- Organoheterocyclic compound
- Oxacycle
- Hydrocarbon derivative
- Alcohol
- Organic nitrogen compound
- Organopnictogen compound
- Organonitrogen compound
- Organic oxygen compound
- Organooxygen compound
- Organic oxide
- 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: | -4 |
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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: | |
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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: | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0c2a-9783500000-aa0125a217188c7947c6 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0002-9461120000-3124f5b05f1627f4eec9 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0220900000-05764a0399ea663bda0a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-002r-7940100000-7be6289aa2147474bbc8 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-056r-9710000000-4a8af53537c11f3268fe | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0001900000-782c2e9109d8585c1eec | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004l-7613900000-af9cb037c1346339427b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9101000000-04cea8b7d7b629572e4b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0901200000-094550daf6257cf48e86 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-7da6dbb92e894a102ada | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1910000000-297ae75d9d85a395a019 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-b2e36fb98660834d7d24 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-b2e36fb98660834d7d24 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-0921000000-baeff84496f2b6c02a0a | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- 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
- Lin, S., McLennan, A. G., Ying, K., Wang, Z., Gu, S., Jin, H., Wu, C., Liu, W., Yuan, Y., Tang, R., Xie, Y., Mao, Y. (2001). "Cloning, expression, and characterization of a human inosine triphosphate pyrophosphatase encoded by the itpa gene." J Biol Chem 276:18695-18701. Pubmed: 11278832
- 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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