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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 | 2020-05-14 21:41:43 UTC |
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HMDB ID | HMDB0000061 |
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Secondary Accession Numbers | - HMDB0001468
- HMDB00061
- HMDB01468
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Metabolite Identification |
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Common Name | Adenosine 3',5'-diphosphate |
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Description | Adenosine 3', 5'-diphosphate or PAP is a nucleotide that is closely related to ADP. It has two phosphate groups attached to the 5' and 3' positions of the pentose sugar ribose (instead of pyrophosphoric acid at the 5' position, as found in ADP), and the nucleobase adenine. PAP is converted to PAPS by Sulfotransferase and then back to PAP after the sulfotransferase reaction. Sulfotransferase (STs) catalyze the transfer reaction of the sulfate group from the ubiquitous donor 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to an acceptor group of numerous substrates. This reaction, often referred to as sulfuryl transfer, sulfation, or sulfonation, is widely observed from bacteria to humans and plays a key role in various biological processes such as cell communication, growth and development, and defense. PAP also appears to a role in bipolar depression. Phosphatases converting 3'-phosphoadenosine 5'-phosphate (PAP) into adenosine 5'-phosphate are of fundamental importance in living cells as the accumulation of PAP is toxic to several cellular systems. These enzymes are lithium-sensitive and we have characterized a human PAP phosphatase as a potential target of lithium therapy. |
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Structure | |
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Synonyms | Value | Source |
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3'-Phosphoadenylate | ChEBI | Adenosine 3',5'-bisphosphate | ChEBI | PAP | ChEBI | Phosphoadenosine phosphate | ChEBI | 3'-Phosphoadenylic acid | Generator | Adenosine 3',5'-bisphosphoric acid | Generator | Phosphoadenosine phosphoric acid | Generator | Adenosine 3',5'-diphosphoric acid | Generator | 3'-Phosphoryl-AMP | HMDB | 3,5-ADP | HMDB | 3,5-Diphosphoadenosine | HMDB | 3-Phosphoadenosine 5-phosphate | HMDB | 5-(Dihydrogen phosphate) 3-adenylate | HMDB | 5-(Dihydrogen phosphate)3'-adenylic acid | HMDB | Adenosine 3,5-bis | HMDB | Adenosine 3,5-bisphosphate | HMDB | Adenosine 3'-phosphate-5'-phosphate, disodium salt | HMDB | 3'-Phosphoadenosine 5'-phosphate | HMDB | Adenosine 3'-phosphate-5'-phosphate, monosodium salt | HMDB | 3',5'-ADP | HMDB | Adenosine 3'-phosphate-5'-phosphate | HMDB |
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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)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid |
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Traditional Name | adenosine 3',5'-bisphosphate |
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CAS Registry Number | 1053-73-2 |
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SMILES | NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]3O)C2=NC=N1 |
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InChI Identifier | InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(17,18)19/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1 |
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InChI Key | WHTCPDAXWFLDIH-KQYNXXCUSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as purine ribonucleoside 3',5'-bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of 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 3',5'-bisphosphates |
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Alternative Parents | |
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Substituents | - Purine ribonucleoside 3',5'-bisphosphate
- Purine ribonucleoside monophosphate
- Pentose phosphate
- Ribonucleoside 3'-phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- 6-aminopurine
- Pentose monosaccharide
- Monosaccharide phosphate
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Monoalkyl phosphate
- Organic phosphoric acid derivative
- N-substituted imidazole
- Phosphoric acid ester
- Monosaccharide
- Imidolactam
- Pyrimidine
- Alkyl phosphate
- Imidazole
- Azole
- Tetrahydrofuran
- Heteroaromatic compound
- Secondary alcohol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Amine
- Alcohol
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- 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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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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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 | 614.5 mg/mL | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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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 | splash10-0002-9332100000-c2cf1343058e5c460684 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0002-9141400000-8e8cf251eecd6d39cf02 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive | splash10-000i-0913100000-4559e980fc823f06cda1 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive | splash10-000i-0910000000-164b37f4075a5627b64d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive | splash10-000i-1900000000-0f28c9a19c771609202d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0902300000-77268ef9fe8672f81e9f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-6986eb10675f363acf42 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1900000000-493254661a51349997bd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-7801900000-b4b0af4deca129a6a12c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0059-9800000000-4a1ffcf05d9938fe121e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9200000000-fb4a5bf16d0e5bcaa1e0 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Cellular Cytoplasm | Detected and Quantified | 137 uM | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB01812 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB030650 |
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KNApSAcK ID | C00019352 |
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Chemspider ID | 140102 |
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KEGG Compound ID | C00054 |
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BioCyc ID | 3-5-ADP |
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BiGG ID | 33684 |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 159296 |
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PDB ID | Not Available |
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ChEBI ID | 17985 |
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Food Biomarker Ontology | Not Available |
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VMH ID | PAP |
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MarkerDB ID | |
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References |
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Synthesis Reference | Tsunako, Mitsutomo; Kotone, Akira. Preparation of nucleoside-2',5'- and 3',5'-diphosphoric acids. Jpn. Kokai Tokkyo Koho (1991), 13 pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Lewis AJ, Otake Y, Walle UK, Walle T: Sulphonation of N-hydroxy-2-acetylaminofluorene by human dehydroepiandrosterone sulphotransferase. Xenobiotica. 2000 Mar;30(3):253-61. [PubMed:10752640 ]
- Gasmi L, McLennan AG: The mouse Nudt7 gene encodes a peroxisomal nudix hydrolase specific for coenzyme A and its derivatives. Biochem J. 2001 Jul 1;357(Pt 1):33-8. [PubMed:11415433 ]
- Leonidas DD, Chavali GB, Oikonomakos NG, Chrysina ED, Kosmopoulou MN, Vlassi M, Frankling C, Acharya KR: High-resolution crystal structures of ribonuclease A complexed with adenylic and uridylic nucleotide inhibitors. Implications for structure-based design of ribonucleolytic inhibitors. Protein Sci. 2003 Nov;12(11):2559-74. [PubMed:14573867 ]
- Turner NA, Moake JL, McIntire LV: Blockade of adenosine diphosphate receptors P2Y(12) and P2Y(1) is required to inhibit platelet aggregation in whole blood under flow. Blood. 2001 Dec 1;98(12):3340-5. [PubMed:11719372 ]
- Traut TW: Physiological concentrations of purines and pyrimidines. Mol Cell Biochem. 1994 Nov 9;140(1):1-22. [PubMed:7877593 ]
- Russo N, Acharya KR, Vallee BL, Shapiro R: A combined kinetic and modeling study of the catalytic center subsites of human angiogenin. Proc Natl Acad Sci U S A. 1996 Jan 23;93(2):804-8. [PubMed:8570639 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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