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Record Information
Version	2.0
Creation Date	2012-05-31 13:03:16 -0600
Update Date	2015-09-13 12:56:09 -0600
Secondary Accession Numbers	ECMDB01003
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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb1305c30> Close
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
Weight:	Average: 427.284 Monoisotopic: 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
Description	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 Class	Nucleosides, nucleotides, and analogues
Class	Purine nucleotides
Sub Class	Purine ribonucleotides
Direct Parent	Purine ribonucleoside monophosphates
Alternative Parents	Pentose phosphates Glycosylamines 6-aminopurines Monosaccharide phosphates Monoalkyl phosphates Aminopyrimidines and derivatives N-substituted imidazoles Imidolactams Organic sulfuric acids and derivatives Heteroaromatic compounds Tetrahydrofurans 1,2-diols Secondary alcohols Oxacyclic compounds Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Primary amines
Substituents	Purine ribonucleoside monophosphate Pentose phosphate Pentose-5-phosphate Glycosyl compound N-glycosyl compound 6-aminopurine Monosaccharide phosphate Pentose monosaccharide Imidazopyrimidine Purine Monoalkyl phosphate Aminopyrimidine Alkyl phosphate Pyrimidine Monosaccharide Imidolactam Phosphoric acid ester N-substituted imidazole Organic phosphoric acid derivative Tetrahydrofuran Heteroaromatic compound Azole Imidazole Organic sulfuric acid or derivatives Secondary alcohol 1,2-diol Oxacycle Azacycle Organoheterocyclic compound Organic nitrogen compound Organic oxide Organonitrogen compound Organopnictogen compound Organic oxygen compound Organooxygen compound Hydrocarbon derivative Amine Alcohol Primary amine Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	adenosine 5'-phosphate (CHEBI:17709 ) acyl sulfate (CHEBI:17709 ) acyl monophosphate (CHEBI:17709 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 3.29 g/L ALOGPS logP -1.6 ALOGPS logP -5.6 ChemAxon logS -2.1 ALOGPS pKa (Strongest Acidic) -2.3 ChemAxon pKa (Strongest Basic) 3.94 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 12 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 229.44 Ų ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 84.06 m³·mol⁻¹ ChemAxon Polarizability 35.07 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Adenosine triphosphate + Guanosine triphosphate + Water + Sulfate > Adenosine phosphosulfate + Guanosine diphosphate + Phosphate + Pyrophosphate Adenosine phosphosulfate + Adenosine triphosphate <> ADP + Hydrogen ion + Phosphoadenosine phosphosulfate Phosphoadenosine phosphosulfate + Water <> Adenosine phosphosulfate + Phosphate Adenosine triphosphate + Adenosine phosphosulfate <> ADP + Phosphoadenosine phosphosulfate Adenosine triphosphate + Sulfate <> Pyrophosphate + Adenosine phosphosulfate Adenosine phosphosulfate + Adenosine triphosphate > Hydrogen ion + Phosphoadenosine phosphosulfate + ADP Hydrogen ion + Sulfate + Adenosine triphosphate > Adenosine phosphosulfate + Pyrophosphate Adenosine triphosphate + Adenosine phosphosulfate > ADP + Phosphoadenosine phosphosulfate Adenosine triphosphate + Sulfate > Pyrophosphate + Adenosine phosphosulfate Adenosine phosphosulfate + Adenosine triphosphate > Phosphoadenosine phosphosulfate + Adenosine diphosphate + Hydrogen ion + ADP Adenosine triphosphate + Hydrogen ion + Sulfate + Sulfate > Adenosine phosphosulfate + Pyrophosphate Adenosine phosphosulfate + Adenosine triphosphate <> ADP + Hydrogen ion + Phosphoadenosine phosphosulfate Adenosine triphosphate + Sulfate <> Pyrophosphate + Adenosine phosphosulfate Phosphoadenosine phosphosulfate + Water <> Adenosine phosphosulfate + Phosphate Adenosine triphosphate + Sulfate <> Pyrophosphate + Adenosine phosphosulfate Phosphoadenosine phosphosulfate + Water <> Adenosine phosphosulfate + Phosphate
SMPDB Pathways:	Sulfur metabolism PW000922 cysteine biosynthesis PW000800 sulfur metabolism (butanesulfonate) PW000923 sulfur metabolism (ethanesulfonate) PW000925 sulfur metabolism (isethionate) PW000926 sulfur metabolism (methanesulfonate) PW000927 sulfur metabolism (propanesulfonate) PW000924
KEGG Pathways:	Metabolic pathways eco01100 Microbial metabolism in diverse environments ec01120 Monobactam biosynthesis eco00261 Purine metabolism ec00230 Selenoamino acid metabolism ec00450 Sulfur metabolism ec00920
EcoCyc Pathways:	sulfate activation for sulfonation PWY-5340
Concentrations
	Concentration Strain Media Growth Status Growth System Temperature Details 7± 0 uM K12 NCM3722 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 Find out more about how we convert literature concentrations.
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-004i-2911100000-c7b3ba6ec47b4fb3e832 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-055b-7693530000-45cc4add4821e6fea5ef View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-0912300000-29cd6f42fa9d4c6c4455 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0901000000-018ae7ee1fc1b662ec07 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-1900000000-861a01467a0191dcd31a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0059-0901600000-785b903b29133cefd0bc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-003r-3900000000-d2245ba9a6f6bf6d0217 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-056r-9700000000-3f4588ade18801775bec View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004i-0200900000-b10f97ec4ef8bff7823c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0911000000-4563fb5a2cb7fd85ab98 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-0900000000-5a937b62fdf69d198700 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-0100900000-a398ce6fc250a971f068 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-056r-6900300000-d9d41d4bc70263df8221 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004j-9200000000-979bc3001281c5d76962 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
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)
Links
External Links:	Resource Link CHEBI ID 17709 HMDB ID HMDB01003 Pubchem Compound ID 228 Kegg ID C00224 ChemSpider ID 9821 Wikipedia amps BioCyc ID APS EcoCyc ID APS Ligand Expo ADX

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