Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:58 UTC
HMDB IDHMDB01134
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhosphoadenosine phosphosulfate
Description3'-Phosphoadenosine-5'-phosphosulfate. Key intermediate in the formation by living cells of sulfate esters of phenols, alcohols, steroids, sulfated polysaccharides, and simple esters, such as choline sulfate. It is formed from sulfate ion and ATP in a two-step process. This compound also is an important step in the process of sulfur fixation in plants and microorganisms.
Structure
Thumb
Synonyms
  1. 3'-Phospho-5'-adenylyl sulfate
  2. 3'-Phospho-5'-adenylyl sulphate
  3. 3'-Phosphoadenosine 5'-phosphosulfate
  4. 3'-Phosphoadenosine 5'-phosphosulphate
  5. 3'-Phosphoadenosine-5'-phosphosulfate
  6. 3'-Phosphoadenosine-5'-phosphosulphate
  7. 3'-Phosphoadenylyl sulfate
  8. 3'-Phosphoadenylyl sulphate
  9. 3'-Phosphoadenylyl-sulfate
  10. 3'-Phosphoadenylyl-sulphate
  11. 5-Phosphoadenosine 3-phosphosulfate
  12. 5-Phosphoadenosine 3-phosphosulphate
  13. PAPS
  14. Phosphoadenosine Phosphosulfate
  15. Phosphoadenosine Phosphosulphate
Chemical FormulaC10H15N5O13P2S
Average Molecular Weight507.264
Monoisotopic Molecular Weight506.986229305
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{[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxysulfonic acid
CAS Registry Number482-67-7
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
InChI Identifier
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
InChI KeyGACDQMDRPRGCTN-KQYNXXCUSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleotides
Sub ClassPurine Ribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Coenzymes(KEGG)
  • acyl sulfate(ChEBI)
  • adenosine bisphosphate(ChEBI)
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Sulfuric Acid
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
Direct ParentPurine Ribonucleoside 3',5'-Bisphosphates
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Androgen and estrogen metabolism
  • Component of Chondroitin / Heparan sulfate biosynthesis
  • Component of Glycosphingolipid metabolism
  • Component of Sulfur metabolism
ApplicationNot Available
Cellular locations
  • Golgi apparatus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 area275.97ChemAxon
rotatable bond count8ChemAxon
refractivity94.93ChemAxon
polarizability39.36ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Golgi apparatus
Biofluid LocationsNot Available
Tissue Location
  • Kidney
  • Liver
  • Platelet
Pathways
NameSMPDB LinkKEGG Link
Sulfate/Sulfite MetabolismSMP00041map00920
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022445
KNApSAcK IDNot Available
Chemspider ID9799
KEGG Compound IDC00053
BioCyc IDPAPS
BiGG ID33679
Wikipedia LinkPhosphoadenosine phosphosulfate
NuGOwiki LinkHMDB01134
Metagene LinkHMDB01134
METLIN ID6028
PubChem Compound10214
PDB IDPPS
ChEBI ID17980
References
Synthesis ReferenceLin, 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
General References
  1. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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

Enzymes

Gene Name:
ENPP1
Uniprot ID:
P22413
Reactions
Phosphoadenosine phosphosulfate + Water unknown Oat gum + Adenosine 3',5'-diphosphatedetails
Gene Name:
ENPP3
Uniprot ID:
O14638
Reactions
Phosphoadenosine phosphosulfate + Water unknown Oat gum + Adenosine 3',5'-diphosphatedetails
Gene Name:
CHST11
Uniprot ID:
Q9NPF2
Reactions
Phosphoadenosine phosphosulfate + Chondroitin unknown Adenosine 3',5'-diphosphate + chondroitin 4'-sulfatedetails
Phosphoadenosine phosphosulfate + Chondroitin unknown Adenosine 3',5'-diphosphate + Chondroitin 4-sulfatedetails
Gene Name:
CHST3
Uniprot ID:
Q7LGC8
Reactions
Phosphoadenosine phosphosulfate + Chondroitin unknown Adenosine 3',5'-diphosphate + Chondroitin 6'-sulfatedetails
Gene Name:
CHST13
Uniprot ID:
Q8NET6
Reactions
Phosphoadenosine phosphosulfate + Chondroitin unknown Adenosine 3',5'-diphosphate + chondroitin 4'-sulfatedetails
Phosphoadenosine phosphosulfate + Chondroitin unknown Adenosine 3',5'-diphosphate + Chondroitin 4-sulfatedetails
Gene Name:
CHST12
Uniprot ID:
Q9NRB3
Reactions
Phosphoadenosine phosphosulfate + Chondroitin unknown Adenosine 3',5'-diphosphate + chondroitin 4'-sulfatedetails
Phosphoadenosine phosphosulfate + Chondroitin unknown Adenosine 3',5'-diphosphate + Chondroitin 4-sulfatedetails
Gene Name:
GAL3ST1
Uniprot ID:
Q99999
Reactions
Phosphoadenosine phosphosulfate + a galactosylceramide unknown Adenosine 3',5'-diphosphate + a galactosylceramidesulfatedetails
Phosphoadenosine phosphosulfate + monogalactosylalkylacylglycerol unknown Adenosine 3',5'-diphosphate + monogalactosylalkylacylglycerol sulfatedetails
Phosphoadenosine phosphosulfate + Galactosylceramide unknown Adenosine 3',5'-diphosphate + Sulfatidedetails
Phosphoadenosine phosphosulfate + Digalactosylceramide unknown Adenosine 3',5'-diphosphate + Digalactosylceramidesulfatedetails
Gene Name:
HS3ST3B1
Uniprot ID:
Q9Y662
Reactions
Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine unknown Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfatedetails
Gene Name:
HS3ST3A1
Uniprot ID:
Q9Y663
Reactions
Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine unknown Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfatedetails
Gene Name:
SULT1A1
Uniprot ID:
P50225
Reactions
Phosphoadenosine phosphosulfate + a phenol unknown Adenosine 3',5'-diphosphate + an aryl sulfatedetails
Phosphoadenosine phosphosulfate + Phenol unknown Adenosine 3',5'-diphosphate + Phenol sulphatedetails
Gene Name:
BPNT1
Uniprot ID:
O95861
Reactions
Phosphoadenosine phosphosulfate + Water unknown Adenosine phosphosulfate + Phosphoric aciddetails
Gene Name:
HS3ST1
Uniprot ID:
O14792
Reactions
Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine unknown Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfatedetails
Gene Name:
PAPSS1
Uniprot ID:
O43252
Reactions
Adenosine triphosphate + Adenosine phosphosulfate unknown ADP + Phosphoadenosine phosphosulfatedetails
Gene Name:
SULT1E1
Uniprot ID:
P49888
Reactions
Phosphoadenosine phosphosulfate + Estrone unknown Adenosine 3',5'-diphosphate + Estrone sulfatedetails
Gene Name:
SULT2A1
Uniprot ID:
Q06520
Reactions
Phosphoadenosine phosphosulfate + Lithocholic acid glycine conjugate unknown Adenosine 3',5'-diphosphate + Sulfolithocholylglycinedetails
Phosphoadenosine phosphosulfate + Lithocholyltaurine unknown Adenosine 3',5'-diphosphate + Taurolithocholic acid 3-sulfatedetails
7-Hydroxymethyl-12-methylbenz[a]anthracene + Phosphoadenosine phosphosulfate unknown 7-Hydroxymethyl-12-methylbenz[a]anthracene sulfate + Adenosine 3',5'-diphosphatedetails
Gene Name:
CHST1
Uniprot ID:
O43916
Reactions
Phosphoadenosine phosphosulfate + Keratan unknown Adenosine 3',5'-diphosphate + Keratandetails
Gene Name:
HS3ST4
Uniprot ID:
Q9Y661
Reactions
Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine unknown Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfatedetails
Gene Name:
SULT1A2
Uniprot ID:
P50226
Reactions
Phosphoadenosine phosphosulfate + a phenol unknown Adenosine 3',5'-diphosphate + an aryl sulfatedetails
Phosphoadenosine phosphosulfate + Phenol unknown Adenosine 3',5'-diphosphate + Phenol sulphatedetails
Gene Name:
HS3ST5
Uniprot ID:
Q8IZT8
Reactions
Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine unknown Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfatedetails
Gene Name:
HS3ST2
Uniprot ID:
Q9Y278
Reactions
Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine unknown Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfatedetails
Gene Name:
PAPSS2
Uniprot ID:
O95340
Reactions
Adenosine triphosphate + Adenosine phosphosulfate unknown ADP + Phosphoadenosine phosphosulfatedetails
Gene Name:
TPST2
Uniprot ID:
O60704
Reactions
Phosphoadenosine phosphosulfate + protein tyrosine unknown Adenosine 3',5'-diphosphate + protein tyrosine-O-sulfatedetails
Gene Name:
SULT2B1
Uniprot ID:
O00204
Reactions
Phosphoadenosine phosphosulfate + an alcohol unknown Adenosine 3',5'-diphosphate + an alkyl sulfatedetails
Alcohol + Phosphoadenosine phosphosulfate unknown Alkyl sulfate + Adenosine 3',5'-diphosphatedetails
Phosphoadenosine phosphosulfate + Dehydroepiandrosterone unknown Adenosine 3',5'-diphosphate + Dehydroepiandrosterone sulfatedetails
Cholesterol + Phosphoadenosine phosphosulfate unknown Cholesterol sulfate + Adenosine 3',5'-diphosphatedetails
Pregnenolone + Phosphoadenosine phosphosulfate unknown 3beta-Hydroxypregn-5-en-20-one sulfate + Adenosine 3',5'-diphosphatedetails
Gene Name:
SULT1A3
Uniprot ID:
P50224
Reactions
Phosphoadenosine phosphosulfate + a phenol unknown Adenosine 3',5'-diphosphate + an aryl sulfatedetails
Phosphoadenosine phosphosulfate + Phenol unknown Adenosine 3',5'-diphosphate + Phenol sulphatedetails
Gene Name:
CHST7
Uniprot ID:
Q9NS84
Reactions
Phosphoadenosine phosphosulfate + Chondroitin unknown Adenosine 3',5'-diphosphate + Chondroitin 6'-sulfatedetails
Gene Name:
CHST14
Uniprot ID:
Q8NCH0
Reactions
Phosphoadenosine phosphosulfate + [dermatan]-N-acetyl-D-galactosamine unknown Adenosine 3',5'-diphosphate + [dermatan]- 4-O-sulfo-N-acetyl-D-galactosaminedetails
Gene Name:
HS6ST1
Uniprot ID:
O60243
Reactions
Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine unknown Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 6-sulfatedetails
Gene Name:
HS6ST2
Uniprot ID:
Q96MM7
Reactions
Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine unknown Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 6-sulfatedetails
Gene Name:
HS6ST3
Uniprot ID:
Q8IZP7
Reactions
Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine unknown Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 6-sulfatedetails
Gene Name:
CHST15
Uniprot ID:
Q7LFX5
Gene Name:
IMPAD1
Uniprot ID:
Q9NX62
Reactions
Phosphoadenosine phosphosulfate + Water unknown Adenosine phosphosulfate + Phosphoric aciddetails
Gene Name:
TPST1
Uniprot ID:
A4D2M0
Gene Name:
HS3ST6
Uniprot ID:
Q96QI5
Reactions
Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine unknown Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfatedetails
Gene Name:
NDST1
Uniprot ID:
P52848
Reactions
Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine unknown Adenosine 3',5'-diphosphate + [heparan sulfate]-N-sulfoglucosaminedetails
Gene Name:
NDST2
Uniprot ID:
P52849
Reactions
Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine unknown Adenosine 3',5'-diphosphate + [heparan sulfate]-N-sulfoglucosaminedetails
Gene Name:
NDST3
Uniprot ID:
O95803
Reactions
Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine unknown Adenosine 3',5'-diphosphate + [heparan sulfate]-N-sulfoglucosaminedetails
Gene Name:
NDST4
Uniprot ID:
Q9H3R1
Reactions
Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine unknown Adenosine 3',5'-diphosphate + [heparan sulfate]-N-sulfoglucosaminedetails
Gene Name:
SULT1C3
Uniprot ID:
Q6IMI6
Reactions
Phosphoadenosine phosphosulfate + an alcohol unknown Adenosine 3',5'-diphosphate + an alkyl sulfatedetails
Gene Name:
SULT6B1
Uniprot ID:
Q6IMI4
Reactions
Phosphoadenosine phosphosulfate + Thyroxine unknown Adenosine 3',5'-diphosphate + thyroxine-sulfatedetails
Gene Name:
TPST1
Uniprot ID:
O60507
Reactions
Phosphoadenosine phosphosulfate + protein tyrosine unknown Adenosine 3',5'-diphosphate + protein tyrosine-O-sulfatedetails