Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000269
Name: Phosphoadenosine phosphosulfate
Description:3'-Phosphoadenosine-5'-phosphosulfate is a key intermediate in the formation by living cells of sulfate esters of phenols, alcohols, sulfated polysaccharides, and simple esters, such as choline sulfate. It is formed from a sulfate ion and ATP in a two-step process. This compound also is an important intermediate in the process of sulfur fixation in plants and microorganisms.
  • 3'-Phospho-5'-adenylyl sulfate
  • 3'-phospho-5'-Adenylyl sulfuric acid
  • 3'-Phospho-5'-adenylyl sulphate
  • 3'-phospho-5'-Adenylyl sulphuric acid
  • 3'-Phosphoadenosine 5'-phosphosulfate
  • 3'-Phosphoadenosine 5'-phosphosulfuric acid
  • 3'-Phosphoadenosine 5'-phosphosulphate
  • 3'-Phosphoadenosine 5'-phosphosulphuric acid
  • 3'-Phosphoadenosine-5'-phosphosulfate
  • 3'-Phosphoadenosine-5'-phosphosulfuric acid
  • 3'-Phosphoadenosine-5'-phosphosulphate
  • 3'-Phosphoadenosine-5'-phosphosulphuric acid
  • 3'-Phosphoadenylyl sulfate
  • 3'-Phosphoadenylyl sulfuric acid
  • 3'-Phosphoadenylyl sulphate
  • 3'-Phosphoadenylyl sulphuric acid
  • 3'-Phosphoadenylyl-sulfate
  • 3'-Phosphoadenylyl-sulfuric acid
  • 3'-Phosphoadenylyl-sulphate
  • 3'-Phosphoadenylyl-sulphuric acid
  • 5-Phosphoadenosine 3-phosphosulfate
  • 5-Phosphoadenosine 3-phosphosulfuric acid
  • 5-Phosphoadenosine 3-phosphosulphate
  • 5-Phosphoadenosine 3-phosphosulphuric acid
  • PAPS
  • Phosphoadenosine Phosphosulfate
  • Phosphoadenosine phosphosulfuric acid
  • Phosphoadenosine Phosphosulphate
  • Phosphoadenosine phosphosulphuric acid
Chemical Formula: C10H15N5O13P2S
Average Molecular Weight: 507.264
Monoisotopic Molecular Weight: 506.986229305
CAS number: 482-67-7
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
Traditional IUPAC Name: 3'-phosphoadenylyl sulfate
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleotides
Sub ClassPurine ribonucleotides
Direct Parent Purine ribonucleoside 3',5'-bisphosphates
Alternative Parents
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside monophosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Organic sulfuric acid or derivatives
  • Imidazole
  • Azole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Melting point: Not Available
Experimental Properties:
Predicted Properties
Water Solubility5.05 mg/mLALOGPS
pKa (Strongest Acidic)-2.1ChemAxon
pKa (Strongest Basic)4.94ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area275.97 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity94.93 m3·mol-1ChemAxon
Polarizability39.36 Å3ChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2901410000-afa8a71104e69c842868View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900200000-8f9317ccb6340a4317c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-e2c92e775605a11d728eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a7i-4900240000-500302d146b6d356a0b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-5900100000-07e0047589df3afabbbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9500000000-517ff9b08c8f8999b922View in MoNA
  • 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
  • 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
  • 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
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • 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
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. Journal of the American Chemical Society (1995),
Material Safety Data Sheet (MSDS) Not Available
External Links:
Pubchem Compound ID990
Kegg IDC00053
ChemSpider ID9799
WikipediaPhosphoadenosine phosphosulfate
Ligand ExpoPPS


General function:
Involved in adenylylsulfate kinase activity
Specific function:
Catalyzes the synthesis of activated sulfate
Gene Name:
Locus Tag:
Molecular weight:
22.1 kDa
ATP + adenylyl sulfate = ADP + 3'-phosphoadenylyl sulfate.
General function:
Involved in phosphoadenylyl-sulfate reductase (thioredoxin) activity
Specific function:
Reduction of activated sulfate into sulfite
Gene Name:
Locus Tag:
Molecular weight:
30.2 kDa
Adenosine 3',5'-bisphosphate + sulfite + thioredoxin disulfide = 3'-phosphoadenylyl sulfate + thioredoxin.
General function:
Involved in magnesium ion binding
Specific function:
Converts 3'(2')-phosphoadenosine 5'-phosphate (PAP) to AMP. May also convert adenosine 3'-phosphate 5'-phosphosulfate (PAPS) to adenosine 5'-phosphosulfate (APS). Has 10000-fold lower activity towards inositol 1,4-bisphosphate (Ins(1,4)P2)
Gene Name:
Locus Tag:
Molecular weight:
29.8 kDa
Adenosine 3',5'-bisphosphate + H(2)O = adenosine 5'-phosphate + phosphate.
General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
Locus Tag:
Molecular weight:
28.5 kDa
General function:
Involved in electron carrier activity
Specific function:
Monothiol glutaredoxin involved in the biogenesis of iron-sulfur clusters (Probable)
Gene Name:
Locus Tag:
Molecular weight:
11.8 kDa
General function:
Involved in electron carrier activity
Specific function:
The disulfide bond functions as an electron carrier in the glutathione-dependent synthesis of deoxyribonucleotides by the enzyme ribonucleotide reductase. In addition, it is also involved in reducing some disulfides in a coupled system with glutathione reductase
Gene Name:
Locus Tag:
Molecular weight:
9.2 kDa
General function:
Involved in electron carrier activity
Specific function:
Participates in various redox reactions through the reversible oxidation of its active center dithiol to a disulfide and catalyzes dithiol-disulfide exchange reactions
Gene Name:
Locus Tag:
Molecular weight:
11.9 kDa


General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
Locus Tag:
Molecular weight:
28.5 kDa