Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 18:26:24 UTC |
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Updated at | 2021-08-12 19:51:48 UTC |
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NP-MRD ID | NP0002665 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | dADP |
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Provided By | BMRB |
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Description | DADP, also known as 2'-dADP, belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside diphosphates. These are purine nucleotides with diphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. DADP exists in all living organisms, ranging from bacteria to humans. In humans, dADP is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. DADP is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. dADP is found in Apis cerana and Daphnia pulex. It was first documented in 1969 (PMID: 11947151). Based on a literature review a significant number of articles have been published on dADP (PMID: 17984079) (PMID: 1545776) (PMID: 23721485) (PMID: 5316336). |
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Structure | NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O1 InChI=1S/C10H15N5O9P2/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(23-7)2-22-26(20,21)24-25(17,18)19/h3-7,16H,1-2H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1 |
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Synonyms | Value | Source |
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2'-Deoxyadenosine 5'-diphosphate | ChEBI | 2'-DEOXYADENOSINE-5'-diphosphATE | ChEBI | Deoxyadenosine diphosphate | ChEBI | 2'-Deoxyadenosine 5'-diphosphoric acid | Generator | 2'-DEOXYADENOSINE-5'-diphosphoric acid | Generator | Deoxyadenosine diphosphoric acid | Generator | 2'-Deoxyadenosine 5'-(trihydrogen diphosphate) | HMDB | 2'-Deoxyadenosine 5'-pyrophosphate | HMDB | 2'-Deoxyadenosine diphosphate | HMDB | 2'-dADP | HMDB | 2’-deoxyadenosine 5’-(trihydrogen diphosphate) | HMDB | 2’-deoxyadenosine 5’-diphosphate | HMDB | 2’-deoxyadenosine 5’-pyrophosphate | HMDB | 2’-deoxyadenosine diphosphate | HMDB | 2’-dADP | HMDB | Deoxyadenosine 5'-diphosphate | HMDB | Deoxyadenosine 5’-diphosphate | HMDB | 2’-deoxyadenosine-5’-diphosphate | HMDB | 2’-deoxyadenosine-5’-diphosphoric acid | HMDB | dADP | HMDB |
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Chemical Formula | C10H15N5O9P2 |
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Average Mass | 411.2017 Da |
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Monoisotopic Mass | 411.03450 Da |
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IUPAC Name | [({[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid |
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Traditional Name | dADP |
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CAS Registry Number | Not Available |
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SMILES | NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O1 |
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InChI Identifier | InChI=1S/C10H15N5O9P2/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(23-7)2-22-26(20,21)24-25(17,18)19/h3-7,16H,1-2H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1 |
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InChI Key | DAEAPNUQQAICNR-RRKCRQDMSA-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 | 13C NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, 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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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside diphosphates. These are purine nucleotides with diphosphate 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 diphosphates |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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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 | - Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Kaufmann G, Littauer UZ: Deoxyadenosine diphosphate as substrate for polynucleotide phosphorylase from Escherichia coli. FEBS Lett. 1969 Jul;4(2):79-83. doi: 10.1016/0014-5793(69)80201-2. [PubMed:11947151 ]
- Schwanstecher C, Dickel C, Panten U: Cytosolic nucleotides enhance the tolbutamide sensitivity of the ATP-dependent K+ channel in mouse pancreatic B cells by their combined actions at inhibitory and stimulatory receptors. Mol Pharmacol. 1992 Mar;41(3):480-6. [PubMed:1545776 ]
- Das U, Wang LK, Smith P, Shuman S: Structural and biochemical analysis of the phosphate donor specificity of the polynucleotide kinase component of the bacterial pnkp*hen1 RNA repair system. Biochemistry. 2013 Jul 9;52(27):4734-43. doi: 10.1021/bi400412x. Epub 2013 Jun 26. [PubMed:23721485 ]
- Chou JY, Singer MF: Deoxyadenosine diphosphate as a substrate and inhibitor of polynucleotide phosphorylase of Micrococcus luteus. I. Deoxyadenosine diphosphate as a substrate for polymerization and the exchange reaction with inorganic 32 P. J Biol Chem. 1971 Dec 25;246(24):7486-96. [PubMed:5316336 ]
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