Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 05:36:26 UTC |
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Update Date | 2016-11-09 01:21:16 UTC |
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Accession Number | CHEM035250 |
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Identification |
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Common Name | dADP |
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Class | Small Molecule |
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Description | Deoxyadenosine diphosphate has been identified in the mononuclear cells of a patient affected with in inherited adenosine deaminase deficiency (OMIM 102700) (PMID 6980023), and in in mononuclear cells of hemodialyzed patients. (PMID 11461945) [HMDB]. dADP is found in many foods, some of which are medlar, oil palm, greenthread tea, and green vegetables. |
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Contaminant Sources | |
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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2'-Deoxyadenosine-5'-diphosphate | HMDB | Deoxyadenosine diphosphate | HMDB |
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Chemical Formula | C10H15N5O9P2 |
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Average Molecular Mass | 411.202 g/mol |
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Monoisotopic Mass | 411.035 g/mol |
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CAS Registry Number | 2793-06-8 |
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IUPAC Name | [({[(2R,3S)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid |
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Traditional Name | {[(2R,3S)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid |
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SMILES | NC1=NC=NC2=C1N=CN2C1C[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-GFCOJPQKSA-N |
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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 | |
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Substituents | - Purine 2'-deoxyribonucleoside diphosphate
- 6-aminopurine
- Organic pyrophosphate
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Monoalkyl phosphate
- N-substituted imidazole
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Pyrimidine
- Alkyl phosphate
- Imidolactam
- Heteroaromatic compound
- Azole
- Tetrahydrofuran
- Imidazole
- Secondary alcohol
- Azacycle
- Organoheterocyclic compound
- Oxacycle
- Organic oxygen compound
- Organic oxide
- Alcohol
- Organic nitrogen compound
- Organopnictogen compound
- Organonitrogen compound
- Organooxygen compound
- Amine
- Primary amine
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-002g-6912000000-79e00145ccc9b13e6929 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-004m-6911200000-e5bf41ca8aa765fc86ea | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0901000000-8ca1882bf2be011f491e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-85ff133b10a7cade586c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-0900000000-61ac8ef338ec6bb84314 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0602900000-ae11f56ebe4579143453 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0560-4900000000-672539848df9fba4f8bf | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9100000000-2485964b0c6e0be9f916 | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0001508 |
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FooDB ID | FDB022662 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | 34254 |
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BioCyc ID | Not Available |
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METLIN ID | 6286 |
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PDB ID | Not Available |
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Wikipedia Link | Deoxyadenosine diphosphate |
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Chemspider ID | Not Available |
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ChEBI ID | 16174 |
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PubChem Compound ID | 53477733 |
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Kegg Compound ID | C00206 |
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YMDB ID | YMDB00901 |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. Nara, Takashi; Misawa, Masanaru. Bacterial phosphorylation of 5'-deoxyadenosine monophosphate to di- or triphosphate. Jpn. Tokkyo Koho (1971), 2 pp. | 2. Cartwright PH, Ilchyshyn A, Ilderton E, Yardley HJ: Modulation of phospholipase A2 activity in extracts of lesion-free psoriatic epidermis by alkaline phosphatase and a protein phosphatase inhibitor. Br J Dermatol. 1988 Mar;118(3):333-8. | 3. Doherty M, Belcher C, Regan M, Jones A, Ledingham J: Association between synovial fluid levels of inorganic pyrophosphate and short term radiographic outcome of knee osteoarthritis. Ann Rheum Dis. 1996 Jul;55(7):432-6. | 4. Chen SD, Kao CH, Poon SK: Radionuclide imaging in primary amyloidosis with liver involvement. Clin Nucl Med. 1998 Jun;23(6):374-6. | 5. Yepes M, Moore E, Brown SA, Hanscom HN, Smith EP, Lawrence DA, Winkles JA: Progressive ankylosis (Ank) protein is expressed by neurons and Ank immunohistochemical reactivity is increased by limbic seizures. Lab Invest. 2003 Jul;83(7):1025-32. | 6. Blackburn MR, Datta SK, Kellems RE: Adenosine deaminase-deficient mice generated using a two-stage genetic engineering strategy exhibit a combined immunodeficiency. J Biol Chem. 1998 Feb 27;273(9):5093-100. | 7. Beltran J, Marty-Delfaut E, Bencardino J, Rosenberg ZS, Steiner G, Aparisi F, Padron M: Chondrocalcinosis of the hyaline cartilage of the knee: MRI manifestations. Skeletal Radiol. 1998 Jul;27(7):369-74. | 8. Grubenmann CE, Frank CG, Kjaergaard S, Berger EG, Aebi M, Hennet T: ALG12 mannosyltransferase defect in congenital disorder of glycosylation type lg. Hum Mol Genet. 2002 Sep 15;11(19):2331-9. | 9. Rother E, Brandl R, Baker DL, Goyal P, Gebhard H, Tigyi G, Siess W: Subtype-selective antagonists of lysophosphatidic Acid receptors inhibit platelet activation triggered by the lipid core of atherosclerotic plaques. Circulation. 2003 Aug 12;108(6):741-7. Epub 2003 Jul 28. | 10. Collins ML, Eng S, Hoh R, Hellerstein MK: Measurement of mitochondrial DNA synthesis in vivo using a stable isotope-mass spectrometric technique. J Appl Physiol (1985). 2003 Jun;94(6):2203-11. Epub 2003 Jan 31. | 11. Cavusoglu Y, Entok E, Gorenek B, Kudaiberdieva G, Unalir A, Goktekin O, Birdane A, Ata N, Timuralp B: Reversible myoglobinuric renal failure following rhabdomyolysis as a rare complication of cardioversion. Pacing Clin Electrophysiol. 2003 Feb;26(2 Pt 1):645-6. | 12. Zaka R, Williams CJ: Role of the progressive ankylosis gene in cartilage mineralization. Curr Opin Rheumatol. 2006 Mar;18(2):181-6. | 13. Johnson K, Hashimoto S, Lotz M, Pritzker K, Goding J, Terkeltaub R: Up-regulated expression of the phosphodiesterase nucleotide pyrophosphatase family member PC-1 is a marker and pathogenic factor for knee meniscal cartilage matrix calcification. Arthritis Rheum. 2001 May;44(5):1071-81. | 14. Imbach T, Schenk B, Schollen E, Burda P, Stutz A, Grunewald S, Bailie NM, King MD, Jaeken J, Matthijs G, Berger EG, Aebi M, Hennet T: Deficiency of dolichol-phosphate-mannose synthase-1 causes congenital disorder of glycosylation type Ie. J Clin Invest. 2000 Jan;105(2):233-9. | 15. Ryan LM, Rosenthal AK: Metabolism of extracellular pyrophosphate. Curr Opin Rheumatol. 2003 May;15(3):311-4. | 16. Simmonds HA, Webster DR, Perrett D, Reiter S, Levinsky RJ: Formation and degradation of deoxyadenosine nucleotides in inherited adenosine deaminase deficiency. Biosci Rep. 1982 May;2(5):303-14. | 17. Sampol J, Dussol B, Fenouillet E, Capo C, Mege JL, Halimi G, Bechis G, Brunet P, Rochat H, Berland Y, Guieu R: High adenosine and deoxyadenosine concentrations in mononuclear cells of hemodialyzed patients. J Am Soc Nephrol. 2001 Aug;12(8):1721-8. |
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