Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-10-09 21:01:36 UTC |
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HMDB ID | HMDB0001341 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | ADP |
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Description | ADP, also known as H3ADP or magnesium ADP, belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP is a strong basic compound (based on its pKa). Adenosine diphosphate, abbreviated ADP, is a nucleotide. ADP exists in all living species, ranging from bacteria to humans. In humans, ADP is involved in d4-gdi signaling pathway. ADP is a potentially toxic compound. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. |
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Structure | |
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Synonyms | Value | Source |
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5'-Adenylphosphoric acid | ChEBI | Adenosine 5'-diphosphate | ChEBI | ADENOSINE-5'-diphosphATE | ChEBI | H3ADP | ChEBI | 5'-Adenylphosphate | Generator | Adenosine 5'-diphosphoric acid | Generator | ADENOSINE-5'-diphosphoric acid | Generator | Adenosindiphosphorsaeure | HMDB | Adenosine 5'-pyrophosphate | HMDB | Adenosine diphosphate | HMDB | Adenosine pyrophosphate | HMDB | Adenosine-5-diphosphate | HMDB | Adenosine-diphosphate | HMDB | 5'-Pyrophosphate, adenosine | HMDB | Adenosine 5' pyrophosphate | HMDB | Diphosphate, adenosine | HMDB | Magnesium ADP | HMDB | MgADP | HMDB | Pyrophosphate, adenosine | HMDB | ADP, Magnesium | HMDB | Adenosine diphosphoric acid | HMDB | ADP | MeSH |
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Chemical Formula | C10H15N5O10P2 |
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Average Molecular Weight | 427.2011 |
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Monoisotopic Molecular Weight | 427.029414749 |
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IUPAC Name | [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid |
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Traditional Name | adenosine-diphosphate |
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CAS Registry Number | 58-64-0 |
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SMILES | NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1 |
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InChI Key | XTWYTFMLZFPYCI-KQYNXXCUSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. |
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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 ribonucleotides |
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Direct Parent | Purine ribonucleoside diphosphates |
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Alternative Parents | |
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Substituents | - Purine ribonucleoside diphosphate
- Purine ribonucleoside monophosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- 6-aminopurine
- Monosaccharide phosphate
- Organic pyrophosphate
- Pentose monosaccharide
- Imidazopyrimidine
- Purine
- Monoalkyl phosphate
- Aminopyrimidine
- Alkyl phosphate
- Monosaccharide
- N-substituted imidazole
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Imidolactam
- Pyrimidine
- Azole
- Heteroaromatic compound
- Imidazole
- Tetrahydrofuran
- Secondary alcohol
- 1,2-diol
- Azacycle
- Oxacycle
- Organoheterocyclic compound
- Alcohol
- Organonitrogen compound
- Organic oxide
- Organic nitrogen compound
- Organooxygen compound
- Organopnictogen compound
- Organic oxygen compound
- Primary amine
- Amine
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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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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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004i-5931200000-d741fb674f63c06ad31c | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-004j-9814310000-161f4ca9b901a0d2af95 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-0301900000-f65eba52a00479514d8e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000i-0900000000-cdad0c415295c75e0b67 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000i-1900000000-1f27fdf6dbd77cbe927d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004i-0102981000-79c6771fae3255f75825 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004i-0209000000-24c7ad0d0646786963be | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004i-0009000000-d266bbe08f0bcb8102b4 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0000090000-8a788ef5a2c7ccc534e1 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-004i-6900600000-fe2194fd2a27df917e5b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-004i-0209000000-24c7ad0d0646786963be | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-004i-6900600000-fe2194fd2a27df917e5b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-002k-0809500000-7fdcfab442e6730d4fea | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-000b-0809400000-73322c322a5e1ac31635 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-000b-0809200000-2c8f8cd308e88cb92e57 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0911300000-0b0c309b755e7b5adfdb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-1d631dbd3ed3927f1194 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1900000000-0e5039d8b3a6bd79b7d6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0059-0900700000-ae031f4329b6e38885e8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-3900000000-4c42d87cdde0e1918071 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9200000000-3eb64003e08db733f0e2 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Disease References | Rachialgia |
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- Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. [PubMed:15993662 ]
| Subarachnoid hemorrhage |
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- Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. [PubMed:15993662 ]
| Epilepsy |
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- Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. [PubMed:15993662 ]
| Stroke |
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- Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. [PubMed:15993662 ]
| Neuroinfection |
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- Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. [PubMed:15993662 ]
| Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
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General References | - Quinton TM, Kim S, Jin J, Kunapuli SP: Lipid rafts are required in Galpha(i) signaling downstream of the P2Y12 receptor during ADP-mediated platelet activation. J Thromb Haemost. 2005 May;3(5):1036-41. [PubMed:15869601 ]
- Saxena R, Gupta M, Gupta S, Kannan M, Ahmed RP, Choudhry VP: Inherited heterogenous defect in platelet aggregation selectively with ADP and epinephrine--a series of 25 cases. Indian J Pathol Microbiol. 2005 Jul;48(3):345-8. [PubMed:16761747 ]
- Corsonello A, Malara A, De Domenico D, Damiano MC, Mirone S, Loddo S, Ientile R, Corica F: Effects of magnesium sulphate on leptin-dependent platelet aggregation: an ex vivo study. Magnes Res. 2005 Mar;18(1):7-11. [PubMed:15945611 ]
- Cuisset T, Frere C, Quilici J, Barbou F, Morange PE, Hovasse T, Bonnet JL, Alessi MC: High post-treatment platelet reactivity identified low-responders to dual antiplatelet therapy at increased risk of recurrent cardiovascular events after stenting for acute coronary syndrome. J Thromb Haemost. 2006 Mar;4(3):542-9. Epub 2005 Dec 22. [PubMed:16371119 ]
- Imura Y, Stassen JM, Bunting S, Stockmans F, Collen D: Antithrombotic properties of L-cysteine, N-(mercaptoacetyl)-D-Tyr-Arg-Gly-Asp-sulfoxide (G4120) in a hamster platelet-rich femoral vein thrombosis model. Blood. 1992 Sep 1;80(5):1247-53. [PubMed:1515641 ]
- Cuisset T, Frere C, Quilici J, Morange PE, Nait-Saidi L, Carvajal J, Lehmann A, Lambert M, Bonnet JL, Alessi MC: Benefit of a 600-mg loading dose of clopidogrel on platelet reactivity and clinical outcomes in patients with non-ST-segment elevation acute coronary syndrome undergoing coronary stenting. J Am Coll Cardiol. 2006 Oct 3;48(7):1339-45. Epub 2006 Sep 12. [PubMed:17010792 ]
- Vigue C, Vigue L, Huszar G: Adenosine triphosphate (ATP) concentrations and ATP/adenosine diphosphate ratios in human sperm of normospermic, oligospermic, and asthenospermic specimens and in their swim-up fractions: lack of correlation between ATP parameters and sperm creatine kinase concentrations. J Androl. 1992 Jul-Aug;13(4):305-11. [PubMed:1399831 ]
- Smith SM, Judge HM, Peters G, Storey RF: Multiple antiplatelet effects of clopidogrel are not modulated by statin type in patients undergoing percutaneous coronary intervention. Platelets. 2004 Dec;15(8):465-74. [PubMed:15763887 ]
- Ji Q, Ghaly M, Hjemdahl P, Tornvall P, Li N: Contrast medium attenuates platelet activation and platelet-leukocyte cross-talk. Thromb Haemost. 2005 May;93(5):922-6. [PubMed:15886810 ]
- Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
- Morshedi M, Oehninger S, Blackmore P, Bocca S, Coddington C, Hodgen G: Investigation of some biochemical and functional effects of cryopreservation of human spermatozoa using an automated freezing-quick-thawing method. Int J Androl. 1995 Dec;18(6):279-86. [PubMed:8719843 ]
- Hua J, Suguro S, Iwabuchi K, Tsutsumi-Ishii Y, Sakamoto K, Nagaoka I: Glucosamine, a naturally occurring amino monosaccharide, suppresses the ADP-mediated platelet activation in humans. Inflamm Res. 2004 Dec;53(12):680-8. [PubMed:15654516 ]
- Shabanova EY, Mindukshev IV, Malakhovskaya EA, Vivulanets EV, Petrishchev NN, Krivchenko AI: Cooperative type of platelet hypersensitivity to ADP. Bull Exp Biol Med. 2005 Sep;140(3):282-4. [PubMed:16307036 ]
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