Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2021-06-29 00:47:04 UTC |
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NP-MRD ID | NP0000794 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | dGTP |
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Description | Deoxyguanosine triphosphate (dGTP) is a nucleoside triphosphate, and a nucleotide precursor used in cells for DNA synthesis. DGTP is used in the polymerase chain reaction technique, in sequencing, and in cloning. It is also the competitor of inhibition onset by acyclovir in the treatment of HSV virus. Under normal physiologic conditions, deoxyguanosine (dGuo) undergoes phosphorolysis by purine nucleoside phosphorylase (PNP, EC 2.4.2.1, An enzyme involved in the recycling of nucleosides and deoxynucleosides in cellular remodeling). However, when PNP is inhibited, deoxycytidine kinase (dCK, EC 2.7.1.74) Shunts unmetabolized dGuo into deoxyguanosine triphosphate (dGTP), which accumulates and blocks DNA synthesis. Deficiency of purine nucleoside phosphorylase results in defective T-cell immunity. A correlation between the degree of T cell inhibition and the level of dCK activity has been observed. (PMID: 11287638 , 402573 ). |
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Structure | NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)N1 InChI=1S/C10H16N5O13P3/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(26-6)2-25-30(21,22)28-31(23,24)27-29(18,19)20/h3-6,16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1 |
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Synonyms | Value | Source |
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2'-Deoxy-GTP | ChEBI | 2'-Deoxyguanosine 5'-triphosphate | ChEBI | 2'-Deoxyguanosine triphosphate | ChEBI | Deoxy-GTP | ChEBI | Deoxyguanosine 5'-triphosphate | ChEBI | Deoxyguanosine triphosphate | ChEBI | 2'-Deoxyguanosine 5'-triphosphoric acid | Generator | 2'-Deoxyguanosine triphosphoric acid | Generator | Deoxyguanosine 5'-triphosphoric acid | Generator | Deoxyguanosine triphosphoric acid | Generator | Deoxyguanosine triphosphate, 3H-labeled | HMDB |
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Chemical Formula | C10H16N5O13P3 |
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Average Mass | 507.1810 Da |
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Monoisotopic Mass | 506.99575 Da |
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IUPAC Name | ({[({[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid |
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Traditional Name | dGTP |
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CAS Registry Number | 2564-35-4 |
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SMILES | NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)N1 |
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InChI Identifier | InChI=1S/C10H16N5O13P3/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(26-6)2-25-30(21,22)28-31(23,24)27-29(18,19)20/h3-6,16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1 |
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InChI Key | HAAZLUGHYHWQIW-KVQBGUIXSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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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
- Imidazopyrimidine
- Purine
- Hydroxypyrimidine
- Monoalkyl phosphate
- N-substituted imidazole
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Pyrimidine
- Azole
- Imidazole
- Heteroaromatic compound
- Tetrahydrofuran
- Secondary alcohol
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Alcohol
- 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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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Kicska GA, Long L, Horig H, Fairchild C, Tyler PC, Furneaux RH, Schramm VL, Kaufman HL: Immucillin H, a powerful transition-state analog inhibitor of purine nucleoside phosphorylase, selectively inhibits human T lymphocytes. Proc Natl Acad Sci U S A. 2001 Apr 10;98(8):4593-8. Epub 2001 Apr 3. [PubMed:11287638 ]
- Hardy CD, Schultz CS, Collins K: Requirements for the dGTP-dependent repeat addition processivity of recombinant Tetrahymena telomerase. J Biol Chem. 2001 Feb 16;276(7):4863-71. doi: 10.1074/jbc.M005158200. Epub 2000 Nov 28. [PubMed:11096070 ]
- Torti A, Lossani A, Savi L, Focher F, Wright GE, Brown NC, Xu WC: Clostridium difficile DNA polymerase IIIC: basis for activity of antibacterial compounds. Curr Enzym Inhib. 2011 Oct;7(3):147-153. doi: 10.2174/157340811798807597. [PubMed:22844265 ]
- Muller EG: Deoxyribonucleotides are maintained at normal levels in a yeast thioredoxin mutant defective in DNA synthesis. J Biol Chem. 1994 Sep 30;269(39):24466-71. [PubMed:7929110 ]
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