Record Information
Version2.0
Creation Date2012-05-31 13:46:04 -0600
Update Date2015-06-03 15:53:46 -0600
Secondary Accession Numbers
  • ECMDB01134
Identification
Name:Phosphoadenosine phosphosulfate
Description3'-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.
Structure
Thumb
Synonyms:
  • 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
Weight:Average: 507.264
Monoisotopic: 506.986229305
InChI Key:GACDQMDRPRGCTN-KQYNXXCUSA-N
InChI: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
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
SMILES:NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](OP(O)(O)=O)[C@H]1O
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside 3',5'-bisphosphates
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.05 g/LALOGPS
logP-0.65ALOGPS
logP-7.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)-2.1ChemAxon
pKa (Strongest Basic)4.94ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area275.97 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity94.93 m³·mol⁻¹ChemAxon
Polarizability39.36 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
glutaredoxin + Phosphoadenosine phosphosulfate > glutaredoxin +2 Hydrogen ion + Adenosine 3',5'-diphosphate + Sulfite
Phosphoadenosine phosphosulfate + Reduced Thioredoxin >2 Hydrogen ion + Adenosine 3',5'-diphosphate + Sulfite + Oxidized Thioredoxin
Adenosine phosphosulfate + Adenosine triphosphate <> ADP + Hydrogen ion + Phosphoadenosine phosphosulfate
Phosphoadenosine phosphosulfate + Water <> Adenosine phosphosulfate + Phosphate
Adenosine triphosphate + Adenosine phosphosulfate <> ADP + Phosphoadenosine phosphosulfate
Thioredoxin + Phosphoadenosine phosphosulfate + Thioredoxin disulfide <> Thioredoxin disulfide + Sulfite + Adenosine 3',5'-diphosphate + Thioredoxin
Adenosine phosphosulfate + Adenosine triphosphate > Hydrogen ion + Phosphoadenosine phosphosulfate + ADP
Adenosine triphosphate + Adenosine phosphosulfate > ADP + Phosphoadenosine phosphosulfate
Adenosine 3',5'-diphosphate + Sulfite + thioredoxin disulfide > Phosphoadenosine phosphosulfate + thioredoxin
Phosphoadenosine phosphosulfate + reduced thioredoxin > Sulfite +2 Hydrogen ion + Adenosine 3',5'-diphosphate +2 oxidized thioredoxin + Sulfite + Adenosine 3',5'-diphosphate
Phosphoadenosine phosphosulfate + reduced thioredoxin > Sulfite + oxidized thioredoxin + Hydrogen ion + Adenosine 3',5'-diphosphate + Sulfite + Adenosine 3',5'-diphosphate
Adenosine phosphosulfate + Adenosine triphosphate > Phosphoadenosine phosphosulfate + Adenosine diphosphate + Hydrogen ion + ADP
Adenosine phosphosulfate + Adenosine triphosphate <> ADP + Hydrogen ion + Phosphoadenosine phosphosulfate
Thioredoxin + Phosphoadenosine phosphosulfate + Thioredoxin disulfide <> Sulfite + Adenosine 3',5'-diphosphate
Phosphoadenosine phosphosulfate + Water <> Adenosine phosphosulfate + Phosphate
Phosphoadenosine phosphosulfate + Water <> Adenosine phosphosulfate + Phosphate
SMPDB Pathways:
Sulfur metabolismPW000922 ThumbThumb?image type=greyscaleThumb?image type=simple
cysteine biosynthesisPW000800 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (butanesulfonate)PW000923 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (ethanesulfonate)PW000925 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (isethionate)PW000926 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (methanesulfonate)PW000927 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (propanesulfonate)PW000924 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-8930200000-a2821e129c20bee87c33View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9441110000-619798b0c3242743c13aView in MoNA
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
References
References:
  • 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:
ResourceLink
CHEBI ID17980
HMDB IDHMDB01134
Pubchem Compound ID990
Kegg IDC00053
ChemSpider ID9799
WikipediaPhosphoadenosine phosphosulfate
BioCyc IDPAPS
EcoCyc IDPAPS
Ligand ExpoPPS

Enzymes

General function:
Involved in adenylylsulfate kinase activity
Specific function:
Catalyzes the synthesis of activated sulfate
Gene Name:
cysC
Uniprot ID:
P0A6J1
Molecular weight:
22321
Reactions
ATP + adenylyl sulfate = ADP + 3'-phosphoadenylyl sulfate.
General function:
Involved in electron carrier activity
Specific function:
Efficient electron donor for the essential enzyme ribonucleotide reductase. Is also able to reduce the interchain disulfide bridges of insulin
Gene Name:
trxC
Uniprot ID:
P0AGG4
Molecular weight:
15555
Reactions
Protein dithiol + NAD(P)(+) = protein disulfide + NAD(P)H.
General function:
Involved in phosphoadenylyl-sulfate reductase (thioredoxin) activity
Specific function:
Reduction of activated sulfate into sulfite
Gene Name:
cysH
Uniprot ID:
P17854
Molecular weight:
27976
Reactions
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:
cysQ
Uniprot ID:
P22255
Molecular weight:
27176
Reactions
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:
ssuC
Uniprot ID:
P75851
Molecular weight:
28925
General function:
Involved in electron carrier activity
Specific function:
Monothiol glutaredoxin involved in the biogenesis of iron-sulfur clusters (Probable)
Gene Name:
grxD
Uniprot ID:
P0AC69
Molecular weight:
12879
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:
grxC
Uniprot ID:
P0AC62
Molecular weight:
9137
General function:
Involved in protein binding
Specific function:
Involved in reducing some disulfides in a coupled system with glutathione reductase. Does not act as hydrogen donor for ribonucleotide reductase
Gene Name:
grxB
Uniprot ID:
P0AC59
Molecular weight:
24350
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:
grxA
Uniprot ID:
P68688
Molecular weight:
9685
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:
trxA
Uniprot ID:
P0AA25
Molecular weight:
11807

Transporters

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:
ssuC
Uniprot ID:
P75851
Molecular weight:
28925