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Record Information |
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Version | 4.0 |
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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 | 2020-06-25 20:15:15 UTC |
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HMDB ID | HMDB0001134 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Phosphoadenosine phosphosulfate |
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Description | Phosphoadenosine phosphosulfate, also known as 3'-phospho-5'-adenylyl sulfate or PAPS, 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. Phosphoadenosine phosphosulfate is a strong basic compound (based on its pKa). Phosphoadenosine phosphosulfate exists in all living species, ranging from bacteria to humans. Within humans, phosphoadenosine phosphosulfate participates in a number of enzymatic reactions. In particular, galactosylceramide (D18:1/18:0) and phosphoadenosine phosphosulfate can be converted into 3-O-sulfogalactosylceramide (D18:1/18:0) and adenosine 3',5'-diphosphate through its interaction with the enzyme galactosylceramide sulfotransferase. In addition, galabiosylceramide (D18:1/18:0) and phosphoadenosine phosphosulfate can be converted into adenosine 3',5'-diphosphate and galabiosylceramide sulfate (D18:1/18:0) through its interaction with the enzyme galactosylceramide sulfotransferase. An adenosine bisphosphate having monophosphate groups at the 3'- and 5'-positions and a sulfo group attached to the phosphate at position 5'. In humans, phosphoadenosine phosphosulfate is involved in globoid cell leukodystrophy. |
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Structure | |
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Synonyms | Value | Source |
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3'-Phosphoadenosine 5'-phosphosulfate | ChEBI | 3'-Phosphoadenylyl sulfate | ChEBI | PAPS | ChEBI | 3'-Phospho-5'-adenylyl sulfate | Kegg | 3'-Phosphoadenosine 5'-phosphosulfuric acid | Generator | 3'-Phosphoadenosine 5'-phosphosulphate | Generator | 3'-Phosphoadenosine 5'-phosphosulphuric acid | Generator | 3'-Phosphoadenylyl sulfuric acid | Generator | 3'-Phosphoadenylyl sulphate | Generator | 3'-Phosphoadenylyl sulphuric acid | Generator | 3'-Phospho-5'-adenylyl sulfuric acid | Generator | 3'-Phospho-5'-adenylyl sulphate | Generator | 3'-Phospho-5'-adenylyl sulphuric acid | Generator | Phosphoadenosine phosphosulfuric acid | Generator | Phosphoadenosine phosphosulphate | Generator | Phosphoadenosine phosphosulphuric acid | Generator | 3'-Phosphoadenosine-5'-phosphosulfate | HMDB | 3'-Phosphoadenosine-5'-phosphosulphate | HMDB | 3'-Phosphoadenylyl-sulfate | HMDB | 3'-Phosphoadenylyl-sulphate | HMDB | 5-Phosphoadenosine 3-phosphosulfate | HMDB | 5-Phosphoadenosine 3-phosphosulphate | HMDB | Adenosine 3' phosphate 5' phosphosulfate | HMDB | Adenosine-3'-phosphate-5'-phosphosulfate | HMDB | Phosphosulfate, phosphoadenosine | HMDB | 3’-Phosphoadenosine 5’-phosphosulfate | HMDB | 3’-Phosphoadenosine 5’-phosphosulphate | HMDB | 3’-Phosphoadenylyl sulfate | HMDB | 3’-Phosphoadenylyl sulphate | HMDB | 5'-Adenylyl sulfate 3'-phosphate | HMDB | 5'-Adenylyl sulphate 3'-phosphate | HMDB | 5’-Adenylyl sulfate 3’-phosphate | HMDB | 5’-Adenylyl sulphate 3’-phosphate | HMDB | Adenosine 3'-phosphate 5'-phosphosulfate | HMDB | Adenosine 3'-phosphate 5'-phosphosulphate | HMDB | Adenosine 3'-phosphate 5'-sulfatophosphate | HMDB | Adenosine 3’-phosphate 5’-phosphosulfate | HMDB | Adenosine 3’-phosphate 5’-phosphosulphate | HMDB | Adenosine 3’-phosphate 5’-sulfatophosphate | HMDB | Adenosine 5'-phosphosulfate 3'-phosphate | HMDB | Adenosine 5'-phosphosulphate 3'-phosphate | HMDB | Adenosine 5’-phosphosulfate 3’-phosphate | HMDB | Adenosine 5’-phosphosulphate 3’-phosphate | HMDB |
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Chemical Formula | C10H15N5O13P2S |
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Average Molecular Weight | 507.264 |
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Monoisotopic Molecular Weight | 506.986229305 |
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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}(hydroxy)phosphoryl)oxy]sulfonic acid |
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Traditional Name | 3'-phosphoadenylyl sulfate |
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CAS Registry Number | 482-67-7 |
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SMILES | NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](OP(O)(O)=O)[C@H]3O)C2=NC=N1 |
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InChI Identifier | InChI=1S/C10H15N5O13P2S/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(27-29(17,18)19)4(26-10)1-25-30(20,21)28-31(22,23)24/h2-4,6-7,10,16H,1H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)(H,22,23,24)/t4-,6-,7-,10-/m1/s1 |
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InChI Key | GACDQMDRPRGCTN-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
- Ribonucleoside 3'-phosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- 6-aminopurine
- Monosaccharide phosphate
- Pentose monosaccharide
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Monoalkyl phosphate
- Monosaccharide
- N-substituted imidazole
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Imidolactam
- Alkyl phosphate
- Pyrimidine
- Tetrahydrofuran
- Organic sulfuric acid or derivatives
- Azole
- Imidazole
- Heteroaromatic compound
- Secondary alcohol
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Organooxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Organic oxygen compound
- Primary amine
- Amine
- Organonitrogen compound
- Organopnictogen 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 | 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 | Not Available | 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 | splash10-0002-8930200000-a2821e129c20bee87c33 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0002-9441110000-619798b0c3242743c13a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-2901410000-afa8a71104e69c842868 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900200000-8f9317ccb6340a4317c4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1900000000-e2c92e775605a11d728e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a7i-4900240000-500302d146b6d356a0b8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0059-5900100000-07e0047589df3afabbbd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9500000000-517ff9b08c8f8999b922 | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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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 | DB02902 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022445 |
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KNApSAcK ID | C00007446 |
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Chemspider ID | 9799 |
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KEGG Compound ID | C00053 |
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BioCyc ID | PAPS |
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BiGG ID | 33679 |
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Wikipedia Link | 3'-Phosphoadenosine-5'-phosphosulfate |
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METLIN ID | 6028 |
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PubChem Compound | 10214 |
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PDB ID | Not Available |
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ChEBI ID | 17980 |
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Food Biomarker Ontology | Not Available |
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VMH ID | PAPS |
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MarkerDB ID | |
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References |
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Synthesis Reference | Lin, Chun-Hung; Shen, Gwo-Jenn; Garcia-Junceda, Eduardo; Wong, Chi-Huey. Enzymic Synthesis and Regeneration of 3'-Phosphoadenosine 5'-Phosphosulfate (PAPS) for Regioselective Sulfation of Oligosaccharides. J. Am. Chem. Soc., 1995, 117 (30), pp 8031-8032 |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Emmi L, Bergamini C, Spinelli A, Liotta F, Marchione T, Caldini A, Fanelli A, De Cristofaro MT, Dal Pozzo G: Possible pathogenetic role of activated platelets in the primary antiphospholipid syndrome involving the central nervous system. Ann N Y Acad Sci. 1997 Aug 14;823:188-200. [PubMed:9292045 ]
- Fanelli A, Bergamini C, Rapi S, Caldini A, Spinelli A, Buggiani A, Emmi L: Flow cytometric detection of circulating activated platelets in primary antiphospholipid syndrome. Correlation with thrombocytopenia and anticardiolipin antibodies. Lupus. 1997;6(3):261-7. [PubMed:9104734 ]
- Joseph JE, Harrison P, Mackie IJ, Isenberg DA, Machin SJ: Increased circulating platelet-leucocyte complexes and platelet activation in patients with antiphospholipid syndrome, systemic lupus erythematosus and rheumatoid arthritis. Br J Haematol. 2001 Nov;115(2):451-9. [PubMed:11703349 ]
- Suarez IM, Diaz RA, Aguayo Canela D, Pujol de la Llave E: Correction of severe thrombocytopenia with chloroquine in the primary antiphospholipid syndrome. Lupus. 1996 Feb;5(1):81-3. [PubMed:8646233 ]
- Khoo BY, Sit KH, Wong KP: Does PAPS generation determine the overall sulfate conjugation in human platelets? Life Sci. 1988;42(23):2389-95. [PubMed:3131608 ]
- Wong KP, Khoo BY, Sit KH: Biosynthesis of PAPS in vitro by human liver. Measurement by two independent assay procedures. Biochem Pharmacol. 1991 Jan 1;41(1):63-9. [PubMed:1846073 ]
- Cappiello M, Franchi M, Rane A, Pacifici GM: Sulphotransferase and its substrate: adenosine-3'-phosphate-5'-phosphosulphate in human fetal liver and placenta. Dev Pharmacol Ther. 1990;14(1):62-5. [PubMed:2311482 ]
- Cappiello M, Franchi M, Giuliani L, Pacifici GM: Distribution of 2-naphthol sulphotransferase and its endogenous substrate adenosine 3'-phosphate 5'-phosphosulphate in human tissues. Eur J Clin Pharmacol. 1989;37(3):317-20. [PubMed:2612547 ]
- Carlier M, Squifflet JP, Pirson Y, Gribomont B, Alexandre GP: Maximal hydration during anesthesia increases pulmonary arterial pressures and improves early function of human renal transplants. Transplantation. 1982 Oct;34(4):201-4. [PubMed:6755828 ]
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