Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2021-09-14 14:58:17 UTC |
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HMDB ID | HMDB0001507 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Diguanosine diphosphate |
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Description | Diguanosine diphosphate is a diguanosine polyphosphate. Diguanosine polyphosphates (GpnGs) are found in human platelets, among a number of dinucleoside polyphosphates, which vary with respect to the number of phosphate groups and the nucleoside moieties; not only diguanosine polyphosphates (GpnG) are found, but also mixed dinucleoside polyphosphates containing one adenosine and one guanosine moiety (ApnG). The vasoactive nucleotides that can be detected in human plasma contain short (n=2-3)and long(n=4-6)polyphosphate chains. GpnGs have not yet been characterized so far with respect to their effects on kidney vasculature. (PMID: 11159696 , 11682456 , 11115507 ). |
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Structure | NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2NC(N)=NC3=O)[C@@H](O)[C@H]1O InChI=1S/C20H26N10O15P2/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(43-17)1-41-46(37,38)45-47(39,40)42-2-6-10(32)12(34)18(44-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1 |
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Synonyms | Value | Source |
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Diguanosine diphosphoric acid | Generator | Guanosine 5'-diphospho-5'-guanosine | HMDB, MeSH | {[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinate | Generator, HMDB |
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Chemical Formula | C20H26N10O15P2 |
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Average Molecular Weight | 708.426 |
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Monoisotopic Molecular Weight | 708.105433236 |
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IUPAC Name | {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid |
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Traditional Name | [(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)phosphinic acid |
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CAS Registry Number | 34692-44-9 |
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SMILES | NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2NC(N)=NC3=O)[C@@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C20H26N10O15P2/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(43-17)1-41-46(37,38)45-47(39,40)42-2-6-10(32)12(34)18(44-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1 |
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InChI Key | LFEYGVXBDRXHGF-MHARETSRSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | (5'->5')-dinucleotides |
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Sub Class | Not Available |
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Direct Parent | (5'->5')-dinucleotides |
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Alternative Parents | |
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Substituents | - (5'->5')-dinucleotide
- Purine nucleotide sugar
- Purine ribonucleoside diphosphate
- Purine ribonucleoside monophosphate
- Pentose-5-phosphate
- Pentose phosphate
- N-glycosyl compound
- Glycosyl compound
- Monosaccharide phosphate
- Organic pyrophosphate
- 6-oxopurine
- Hypoxanthine
- Purine
- Imidazopyrimidine
- Pyrimidone
- Monoalkyl phosphate
- Aminopyrimidine
- Monosaccharide
- N-substituted imidazole
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Pyrimidine
- Vinylogous amide
- Azole
- Tetrahydrofuran
- Imidazole
- Heteroaromatic compound
- Secondary alcohol
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Amine
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Primary amine
- Organonitrogen compound
- Organic nitrogen compound
- Alcohol
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (Non-derivatized) - 70eV, Positive | splash10-01ox-1283923000-6ccde279d587bebc2ea8 | 2017-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_1_5) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_4) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_5) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_6) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_7) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_8) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_9) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_10) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_11) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_12) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_13) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_14) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_15) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_16) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_17) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_18) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Diguanosine diphosphate GC-MS (TMS_2_19) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Diguanosine diphosphate 10V, Positive-QTOF | splash10-0udi-0910001200-2b06d795c59a08513af7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Diguanosine diphosphate 20V, Positive-QTOF | splash10-0udi-0900000000-6c71b326e2d27d1b653d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Diguanosine diphosphate 40V, Positive-QTOF | splash10-0udi-0900000000-1ef768e5dcf6f5c902ec | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Diguanosine diphosphate 10V, Negative-QTOF | splash10-0pb9-0800202900-a64860d40dcadb3a92cf | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Diguanosine diphosphate 20V, Negative-QTOF | splash10-0udi-1900100000-e68a64b14a70034882b7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Diguanosine diphosphate 40V, Negative-QTOF | splash10-0zfr-2900000000-73adfcc13c7f6cdfc64e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Diguanosine diphosphate 10V, Negative-QTOF | splash10-0a4i-0200000900-ef62c8bd6128b927138f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Diguanosine diphosphate 20V, Negative-QTOF | splash10-0ab9-1100019300-9c3f17212b4558d0153b | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Diguanosine diphosphate 40V, Negative-QTOF | splash10-0a6v-6907808000-f7b74c8f4e4857add2bb | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Diguanosine diphosphate 10V, Positive-QTOF | splash10-0udi-0900020300-252d80460c0b613ccbe2 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Diguanosine diphosphate 20V, Positive-QTOF | splash10-0zfu-0900041400-53e6215b251a1c1a5a74 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Diguanosine diphosphate 40V, Positive-QTOF | splash10-0udi-0932200000-92e72dc8af2dac31a11d | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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General References | - van der Giet M, Westhoff T, Cinkilic O, Jankowski J, Schluter H, Zidek W, Tepel M: The critical role of adenosine and guanosine in the affinity of dinucleoside polyphosphates to P(2X)-receptors in the isolated perfused rat kidney. Br J Pharmacol. 2001 Jan;132(2):467-74. [PubMed:11159696 ]
- Ralevic V, Jankowski J, Schluter H: Structure-activity relationships of diadenosine polyphosphates (Ap(n)As), adenosine polyphospho guanosines (Ap(n)Gs) and guanosine polyphospho guanosines (Gp(n)Gs) at P2 receptors in the rat mesenteric arterial bed. Br J Pharmacol. 2001 Nov;134(5):1073-83. [PubMed:11682456 ]
- Jankowski J, Hagemann J, Tepel M, van Der Giet M, Stephan N, Henning L, Gouni-Berthold I, Sachinidis A, Zidek W, Schluter H: Dinucleotides as growth-promoting extracellular mediators. Presence of dinucleoside diphosphates Ap2A, Ap2G, and Gp2G in releasable granules of platelets. J Biol Chem. 2001 Mar 23;276(12):8904-9. Epub 2000 Dec 13. [PubMed:11115507 ]
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