Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000222
Identification
Name: Adenosine phosphosulfate
Description:Adenosine phosphosulfate (also known as APS) is the initial compound formed by the action of ATP sulfurylase (or PAPS synthetase) on sulfate ions after sulfate uptake. PAPS synthetase 1 is a bifunctional enzyme with both ATP sulfurylase and APS kinase activity, which mediates two steps in the sulfate activation pathway. The first step is the transfer of a sulfate group to ATP to yield adenosine 5'-phosphosulfate (APS), and the second step is the transfer of a phosphate group from ATP to APS yielding 3'-phosphoadenylylsulfate (PAPS).
Structure
Thumb
Synonyms:
  • Adenosine 5'-phosphosulfate
  • Adenosine 5'-phosphosulfuric acid
  • Adenosine 5'-phosphosulphate
  • Adenosine 5'-phosphosulphuric acid
  • Adenosine 5'-sulfatophosphate
  • Adenosine 5'-sulfatophosphoric acid
  • Adenosine 5'-sulphatophosphate
  • Adenosine 5'-sulphatophosphoric acid
  • Adenosine Phosphosulfate
  • Adenosine phosphosulfuric acid
  • Adenosine Phosphosulphate
  • Adenosine phosphosulphuric acid
  • Adenosine sulfatophosphate
  • Adenosine sulfatophosphoric acid
  • Adenosine sulphatophosphate
  • Adenosine sulphatophosphoric acid
  • Adenylate monoanhydride with sulfate
  • Adenylate monoanhydride with sulfurate
  • Adenylate monoanhydride with sulfuric acid
  • Adenylate monoanhydride with sulphate
  • Adenylate monoanhydride with sulphurate
  • Adenylate monoanhydride with sulphuric acid
  • Adenylic acid monoanhydride with sulfurate
  • Adenylic acid monoanhydride with sulfuric acid
  • Adenylic acid monoanhydride with sulphuric acid
  • Adenylyl sulfate
  • Adenylyl sulfuric acid
  • Adenylyl sulphate
  • Adenylyl sulphuric acid
  • Adenylyl-sulfate
  • Adenylyl-sulfuric acid
  • Adenylyl-sulphate
  • Adenylyl-sulphuric acid
  • AMPS
  • APS
  • Phosphosulfate
  • Phosphosulfuric acid
  • Phosphosulphate
  • Phosphosulphuric acid
  • Sulfatophosphate
  • Sulfatophosphoric acid
  • Sulphatophosphate
  • Sulphatophosphoric acid
Chemical Formula: C10H14N5O10PS
Average Molecular Weight: 427.284
Monoisotopic Molecular Weight: 427.019898895
InChI Key: IRLPACMLTUPBCL-KQYNXXCUSA-N
InChI:InChI=1S/C10H14N5O10PS/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-26(18,19)25-27(20,21)22/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H2,11,12,13)(H,20,21,22)/t4-,6-,7-,10-/m1/s1
CAS number: 485-84-7
IUPAC Name:[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid
Traditional IUPAC Name: adenosine phosphosulfate
SMILES:NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleotides
Sub ClassPurine ribonucleotides
Direct Parent Purine ribonucleoside monophosphates
Alternative Parents
Substituents
  • 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
  • Heteroaromatic compound
  • Oxolane
  • Organic sulfuric acid or derivatives
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • 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
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.29 mg/mLALOGPS
logP-1.6ALOGPS
logP-5.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)-2.1ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area229.44 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity84.06 m3·mol-1ChemAxon
Polarizability35.24 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0912300000-29cd6f42fa9d4c6c4455View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901000000-018ae7ee1fc1b662ec07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-861a01467a0191dcd31aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0901600000-785b903b29133cefd0bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3900000000-d2245ba9a6f6bf6d0217View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9700000000-3f4588ade18801775becView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Al-Buheissi SZ, Patel HR, Meinl W, Hewer A, Bryan RL, Glatt H, Miller RA, Phillips DH: N-Acetyltransferase and sulfotransferase activity in human prostate: potential for carcinogen activation. Pharmacogenet Genomics. 2006 Jun;16(6):391-9. Pubmed: 16708048
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Chou HC, Lang NP, Kadlubar FF: Metabolic activation of N-hydroxy arylamines and N-hydroxy heterocyclic amines by human sulfotransferase(s). Cancer Res. 1995 Feb 1;55(3):525-9. Pubmed: 7834621
  • Eklund E, Roden L, Malmstrom M, Malmstrom A: Dermatan is a better substrate for 4-O-sulfation than chondroitin: implications in the generation of 4-O-sulfated, L-iduronate-rich galactosaminoglycans. Arch Biochem Biophys. 2000 Nov 15;383(2):171-7. Pubmed: 11185550
  • Eto Y, Tokoro T, Handa T, Herschkowitz NN, Rennert OM: Acid mucopolysaccharide (AMPS) abnormality in multiple sulfatase deficiency: chemical compositions of AMPS in urine and liver. Pediatr Res. 1982 May;16(5):395-9. Pubmed: 6212904
  • 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
  • Keogh JR, Wolf MF, Overend ME, Tang L, Eaton JW: Biocompatibility of sulphonated polyurethane surfaces. Biomaterials. 1996 Oct;17(20):1987-94. Pubmed: 8894093
  • 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
  • Mateos-Trigos G, Evans RJ, Heath MF: Effects of P2Y(1) and P2Y(12) receptor antagonists on ADP-induced shape change of equine platelets: comparison with human platelets. Platelets. 2002 Aug-Sep;13(5-6):285-92. Pubmed: 12189014
  • Raju U, Kadner S, Levitz M, Kaganowicz A, Blaustein A: Glucosiduronidation and esterification of androsterone by human breast tumors in vitro. Steroids. 1981 Apr;37(4):399-407. Pubmed: 7245287
  • Slomiany BL, Liau YH, Sarosiek J, Tsukada H, Mizuta K, Rosenthal W, Slomiany A: Sulfation of glycolipids by human gastric mucosa in disease. Digestion. 1987;36(4):246-52. Pubmed: 3475228
  • 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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID17709
HMDB IDHMDB01003
Pubchem Compound ID228
Kegg IDC00224
ChemSpider ID9821
Wikipediaamps
BioCyc IDAPS
EcoCyc IDAPS
Ligand ExpoADX