Phosphoadenosine phosphosulfate (YMDB00120)

Identification
YMDB IDYMDB00120
NamePhosphoadenosine phosphosulfate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPhosphoadenosine 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 3'-Phospho-5'-adenylyl sulfate
  • 3'-Phosphoadenosine 5'-phosphosulfate
  • 3'-phosphoadenosine-5'-phosphosulfate
  • 3'-Phosphoadenylyl sulfate
  • 3'-phosphoadenylyl-sulfate
  • 5-phosphoadenosine 3-phosphosulfate
  • PAPS
  • Phosphoadenosine Phosphosulfate
  • Phosphoadenosine phosphosulfic acid
  • 3'-Phosphoadenosine 5'-phosphosulfuric acid
  • 3'-Phosphoadenosine 5'-phosphosulphate
  • 3'-Phosphoadenosine 5'-phosphosulphuric acid
  • 3'-Phosphoadenylyl sulfuric acid
  • 3'-Phosphoadenylyl sulphate
  • 3'-Phosphoadenylyl sulphuric acid
  • 3'-Phospho-5'-adenylyl sulfuric acid
  • 3'-Phospho-5'-adenylyl sulphate
  • 3'-Phospho-5'-adenylyl sulphuric acid
  • Phosphoadenosine phosphosulfuric acid
  • Phosphoadenosine phosphosulphate
  • Phosphoadenosine phosphosulphuric acid
  • 3'-Phosphoadenosine-5'-phosphosulphate
  • 3'-Phosphoadenylyl-sulphate
  • 5-Phosphoadenosine 3-phosphosulphate
  • Adenosine 3' phosphate 5' phosphosulfate
  • Adenosine-3'-phosphate-5'-phosphosulfate
  • Phosphosulfate, phosphoadenosine
  • 3’-Phosphoadenosine 5’-phosphosulfate
  • 3’-Phosphoadenosine 5’-phosphosulphate
  • 3’-Phosphoadenylyl sulfate
  • 3’-Phosphoadenylyl sulphate
  • 5'-Adenylyl sulfate 3'-phosphate
  • 5'-Adenylyl sulphate 3'-phosphate
  • 5’-Adenylyl sulfate 3’-phosphate
  • 5’-Adenylyl sulphate 3’-phosphate
  • Adenosine 3'-phosphate 5'-phosphosulfate
  • Adenosine 3'-phosphate 5'-phosphosulphate
  • Adenosine 3'-phosphate 5'-sulfatophosphate
  • Adenosine 3’-phosphate 5’-phosphosulfate
  • Adenosine 3’-phosphate 5’-phosphosulphate
  • Adenosine 3’-phosphate 5’-sulfatophosphate
  • Adenosine 5'-phosphosulfate 3'-phosphate
  • Adenosine 5'-phosphosulphate 3'-phosphate
  • Adenosine 5’-phosphosulfate 3’-phosphate
  • Adenosine 5’-phosphosulphate 3’-phosphate
CAS number485-84-7
WeightAverage: 507.264
Monoisotopic: 506.986229305
InChI KeyGACDQMDRPRGCTN-KQYNXXCUSA-N
InChIInChI=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
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 Name3'-phosphoadenylyl sulfate
Chemical FormulaC10H15N5O13P2S
SMILES[H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(=O)(O[H])OS(=O)(=O)O[H])[C@@]1([H])OP(=O)(O[H])O[H])N1C([H])=NC2=C1N=C([H])N=C2N([H])[H]
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.05 g/LALOGPS
logP-0.65ALOGPS
logP-5.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)-2.4ChemAxon
pKa (Strongest Basic)3.94ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area275.97 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity94.93 m³·mol⁻¹ChemAxon
Polarizability39.26 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Sulfur metabolismPW002483 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Purine metabolismec00230 Map00230
Sulfur metabolismec00920 Map00920
SMPDB Reactions
Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate → 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphate
Galabiosylceramide (d18:1/22:0) + Phosphoadenosine phosphosulfate → Galabiosylceramide-sulfate + Adenosine 3',5'-diphosphate
Adenosine phosphosulfate + Adenosine triphosphate → Phosphoadenosine phosphosulfate + ADP + hydron
Phosphoadenosine phosphosulfate + water ↔ phosphate + Adenosine phosphosulfate
Phosphoadenosine phosphosulfate + reduced thioredoxin → Sulfite + oxidized thioredoxin + hydron + Adenosine 3',5'-diphosphate
KEGG Reactions
Adenosine phosphosulfate + Adenosine triphosphate → hydron + Phosphoadenosine phosphosulfate + ADP
thioredoxin dithiol + Phosphoadenosine phosphosulfate → Adenosine 3',5'-diphosphate + Sulfite + thioredoxin disulfide + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-8930200000-a2821e129c20bee87c33JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9441110000-619798b0c3242743c13aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2901410000-afa8a71104e69c842868JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900200000-8f9317ccb6340a4317c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-e2c92e775605a11d728eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a7i-4900240000-500302d146b6d356a0b8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-5900100000-07e0047589df3afabbbdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9500000000-517ff9b08c8f8999b922JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000090000-ba006402f6f0af41d779JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ri-0402920000-7d549a97dd2276b8b754JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qi-0439100000-94b8e2004e4fb012c91dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-63709bad7395f9f33accJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-94a8fdc8360cf2577ca6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003s-8900000000-0b1152e8f0b7373e9349JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Schwenn, J. D., Krone, F. A., Husmann, K. (1988). "Yeast PAPS reductase: properties and requirements of the purified enzyme." Arch Microbiol 150:313-319.3060034
  • Thomas, D., Barbey, R., Surdin-Kerjan, Y. (1990). "Gene-enzyme relationship in the sulfate assimilation pathway of Saccharomyces cerevisiae. Study of the 3'-phosphoadenylylsulfate reductase structural gene." J Biol Chem 265:15518-15524.2203779
  • Korch, C., Mountain, H. A., Bystrom, A. S. (1991). "Cloning, nucleotide sequence, and regulation of MET14, the gene encoding the APS kinase of Saccharomyces cerevisiae." Mol Gen Genet 229:96-108.1654509
  • Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
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),
External Links:
ResourceLink
CHEBI ID17709
HMDB IDHMDB01003
Pubchem Compound ID990
Kegg IDC00053
ChemSpider ID9799
FOODB IDFDB022445
Wikipediaamps
BioCyc IDAPS

Enzymes

Protein Details
1. Adenylyl-sulfate kinase
General function:
Involved in ATP binding
Specific function:
Catalyzes the synthesis of activated sulfate
Gene Name:
MET14
Uniprot ID:
Q02196
Molecular weight:
23060.09961
Reactions
ATP + adenylyl sulfate → ADP + 3'-phosphoadenylyl sulfate.
Protein Details
2. Phosphoadenosine phosphosulfate reductase
General function:
Involved in phosphoadenylyl-sulfate reductase (thioredoxin) activity
Specific function:
The NADP dependent reduction of PAPS into sulfite involves thioredoxin which probably plays the role of a thiol carrier
Gene Name:
MET16
Uniprot ID:
P18408
Molecular weight:
30380.09961
Reactions
Adenosine 3',5'-bisphosphate + sulfite + thioredoxin disulfide → 3'-phosphoadenylyl sulfate + thioredoxin.