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Human Metabolome Database Version 3.5

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Showing metabocard for Phosphoadenosine phosphosulfate (HMDB01134)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:58 -0700
HMDB ID HMDB01134
Secondary Accession Numbers None
Metabolite Identification
Common Name Phosphoadenosine phosphosulfate
Description 3'-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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3'-Phospho-5'-adenylyl sulfate
  2. 3'-Phosphoadenosine 5'-phosphosulfate
  3. 3'-Phosphoadenosine-5'-phosphosulfate
  4. 3'-Phosphoadenylyl sulfate
  5. 3'-Phosphoadenylyl-sulfate
  6. 5-Phosphoadenosine 3-phosphosulfate
  7. PAPS
  8. Phosphoadenosine Phosphosulfate
Chemical Formula C10H15N5O13P2S
Average Molecular Weight 507.264
Monoisotopic Molecular Weight 506.986229305
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 Number 482-67-7
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 Key GACDQMDRPRGCTN-KQYNXXCUSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleotides
Sub Class Purine 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 Parent Purine Ribonucleoside 3',5'-Bisphosphates
Ontology
Status Expected 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
Application Not Available
Cellular locations
  • Golgi apparatus
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 5.05 g/L ALOGPS
LogP -0.65 ALOGPS
LogP -7.1 ChemAxon
LogS -2.00 ALOGPS
pKa (strongest acidic) -2.1 ChemAxon
pKa (strongest basic) 4.94 ChemAxon
Hydrogen Acceptor Count 14 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 275.97 A2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 94.93 ChemAxon
Polarizability 39.36 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Golgi apparatus
Biofluid Locations Not Available
Tissue Location
  • Kidney
  • Liver
  • Platelet
Pathways
Name SMPDB Link KEGG Link
Sulfate/Sulfite Metabolism SMP00041 map00920 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022445
KNApSAcK ID Not Available
Chemspider ID 9799 Link_out
KEGG Compound ID C00053 Link_out
BioCyc ID PAPS Link_out
BiGG ID 33679 Link_out
Wikipedia Link Phosphoadenosine phosphosulfate Link_out
NuGOwiki Link HMDB01134 Link_out
Metagene Link HMDB01134 Link_out
METLIN ID 6028 Link_out
PubChem Compound 10214 Link_out
PDB ID PPS Link_out
ChEBI ID 17980 Link_out
References
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
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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
Enzymes
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 1
Reactions:
  • a dinucleotide + H2O = 2 mononucleotides [RN:R00056]
Gene Name: ENPP1
Uniprot ID: P22413 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 3
Reactions:
  • a dinucleotide + H2O = 2 mononucleotides [RN:R00056]
Gene Name: ENPP3
Uniprot ID: O14638 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carbohydrate sulfotransferase 3
Reactions:
  • 3'-phosphoadenylyl sulfate + chondroitin = adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate [RN:R02181]
Gene Name: CHST3
Uniprot ID: Q7LGC8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carbohydrate sulfotransferase 13
Reactions:
  • 3'-phosphoadenylyl sulfate + chondroitin = adenosine 3',5'-bisphosphate + chondroitin 4'-sulfate [RN:R02180]
Gene Name: CHST13
Uniprot ID: Q8NET6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carbohydrate sulfotransferase 12
Reactions:
  • 3'-phosphoadenylyl sulfate + chondroitin = adenosine 3',5'-bisphosphate + chondroitin 4'-sulfate [RN:R02180]
Gene Name: CHST12
Uniprot ID: Q9NRB3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Galactosylceramide sulfotransferase
Reactions:
  • 3'-phosphoadenylyl sulfate + a galactosylceramide = adenosine 3',5'-bisphosphate + a galactosylceramidesulfate [RN:R04017 R06279]
Gene Name: GAL3ST1
Uniprot ID: Q99999 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Heparan sulfate glucosamine 3-O-sulfotransferase 3B1
Reactions:
  • 3'-phosphoadenylyl sulfate + [heparan sulfate]-glucosamine = adenosine 3',5'-bisphosphate + [heparan sulfate]-glucosamine 3-sulfate [RN:R05798]
Gene Name: HS3ST3B1
Uniprot ID: Q9Y662 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3'(2'),5'-bisphosphate nucleotidase 1
Reactions:
  • adenosine 3',5'-bisphosphate + H2O = adenosine 5'-phosphate + phosphate [RN:R00188]
Gene Name: BPNT1
Uniprot ID: O95861 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Heparan sulfate glucosamine 3-O-sulfotransferase 1
Reactions:
  • 3'-phosphoadenylyl sulfate + [heparan sulfate]-glucosamine = adenosine 3',5'-bisphosphate + [heparan sulfate]-glucosamine 3-sulfate [RN:R05798]
Gene Name: HS3ST1
Uniprot ID: O14792 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1
Reactions:
  • ATP + sulfate = diphosphate + adenylyl sulfate [RN:R00529]
Gene Name: PAPSS1
Uniprot ID: O43252 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Estrogen sulfotransferase
Reactions:
  • 3'-phosphoadenylyl sulfate + estrone = adenosine 3',5'-bisphosphate + estrone 3-sulfate [RN:R02350]
Gene Name: SULT1E1
Uniprot ID: P49888 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sulfotransferase 1A2
Reactions:
  • 3'-phosphoadenylyl sulfate + a phenol = adenosine 3',5'-bisphosphate + an aryl sulfate [RN:R01242]
Gene Name: SULT1A2
Uniprot ID: P50226 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Heparan sulfate glucosamine 3-O-sulfotransferase 5
Reactions:
  • 3'-phosphoadenylyl sulfate + [heparan sulfate]-glucosamine = adenosine 3',5'-bisphosphate + [heparan sulfate]-glucosamine 3-sulfate [RN:R05798]
Gene Name: HS3ST5
Uniprot ID: Q8IZT8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Heparan sulfate glucosamine 3-O-sulfotransferase 2
Reactions:
  • 3'-phosphoadenylyl sulfate + [heparan sulfate]-glucosamine = adenosine 3',5'-bisphosphate + [heparan sulfate]-glucosamine 3-sulfate [RN:R05798]
Gene Name: HS3ST2
Uniprot ID: Q9Y278 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2
Reactions:
  • ATP + sulfate = diphosphate + adenylyl sulfate [RN:R00529]
Gene Name: PAPSS2
Uniprot ID: O95340 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein-tyrosine sulfotransferase 2
Reactions:
  • 3'-phosphoadenylyl sulfate + protein tyrosine = adenosine 3',5'-bisphosphate + protein tyrosine-O-sulfate [RN:R02586]
Gene Name: TPST2
Uniprot ID: O60704 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sulfotransferase family cytosolic 2B member 1
Reactions:
  • 3'-phosphoadenylyl sulfate + an alcohol = adenosine 3',5'-bisphosphate + an alkyl sulfate [RN:R00629]
Gene Name: SULT2B1
Uniprot ID: O00204 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sulfotransferase 1A3/1A4
Reactions:
  • 3'-phosphoadenylyl sulfate + a phenol = adenosine 3',5'-bisphosphate + an aryl sulfate [RN:R01242]
Gene Name: SULT1A3
Uniprot ID: P50224 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carbohydrate sulfotransferase 7
Reactions:
  • 3'-phosphoadenylyl sulfate + chondroitin = adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate [RN:R02181]
Gene Name: CHST7
Uniprot ID: Q9NS84 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Heparan-sulfate 6-O-sulfotransferase 1
Reactions:
    Gene Name: HS6ST1
    Uniprot ID: O60243 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Heparan-sulfate 6-O-sulfotransferase 2
    Reactions:
      Gene Name: HS6ST2
      Uniprot ID: Q96MM7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Adenosine 3'-phospho 5'-phosphosulfate transporter 1
      Reactions:
        Gene Name: SLC35B2
        Uniprot ID: Q8TB61 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Heparan-sulfate 6-O-sulfotransferase 3
        Reactions:
          Gene Name: HS6ST3
          Uniprot ID: Q8IZP7 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Carbohydrate sulfotransferase 15
          Reactions:
          • (1) 3'-phosphoadenylyl sulfate + dermatan = adenosine 3',5'-bisphosphate + dermatan 6'-sulfate [RN:R07288]
          • (2) 3'-phosphoadenylyl sulfate + chondroitin = adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate [RN:R02181]
          Gene Name: CHST15
          Uniprot ID: Q7LFX5 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Tyrosylprotein sulfotransferase 1
          Reactions:
            Gene Name: TPST1
            Uniprot ID: A4D2M0 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Adenosine 3'-phospho 5'-phosphosulfate transporter 2
            Reactions:
              Gene Name: SLC35B3
              Uniprot ID: Q9H1N7 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA