P. aeruginosa Metabolome Database: Phosphoadenosine phosphosulfate (PAMDB000269)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000269

Identification

Name:

Phosphoadenosine phosphosulfate

Description:

3'-Phosphoadenosine-5'-phosphosulfate is a key intermediate in the formation by living cells of sulfate esters of phenols, alcohols, sulfated polysaccharides, and simple esters, such as choline sulfate. It is formed from a sulfate ion and ATP in a two-step process. This compound also is an important intermediate in the process of sulfur fixation in plants and microorganisms.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

3'-Phospho-5'-adenylyl sulfate
3'-phospho-5'-Adenylyl sulfuric acid
3'-Phospho-5'-adenylyl sulphate
3'-phospho-5'-Adenylyl sulphuric acid
3'-Phosphoadenosine 5'-phosphosulfate
3'-Phosphoadenosine 5'-phosphosulfuric acid
3'-Phosphoadenosine 5'-phosphosulphate
3'-Phosphoadenosine 5'-phosphosulphuric acid
3'-Phosphoadenosine-5'-phosphosulfate
3'-Phosphoadenosine-5'-phosphosulfuric acid
3'-Phosphoadenosine-5'-phosphosulphate
3'-Phosphoadenosine-5'-phosphosulphuric acid
3'-Phosphoadenylyl sulfate
3'-Phosphoadenylyl sulfuric acid
3'-Phosphoadenylyl sulphate
3'-Phosphoadenylyl sulphuric acid
3'-Phosphoadenylyl-sulfate
3'-Phosphoadenylyl-sulfuric acid
3'-Phosphoadenylyl-sulphate
3'-Phosphoadenylyl-sulphuric acid
5-Phosphoadenosine 3-phosphosulfate
5-Phosphoadenosine 3-phosphosulfuric acid
5-Phosphoadenosine 3-phosphosulphate
5-Phosphoadenosine 3-phosphosulphuric acid
PAPS
Phosphoadenosine Phosphosulfate
Phosphoadenosine phosphosulfuric acid
Phosphoadenosine Phosphosulphate
Phosphoadenosine phosphosulphuric acid

Chemical Formula:

C₁₀H₁₅N₅O₁₃P₂S

Average Molecular Weight:

507.264

Monoisotopic Molecular Weight:

506.986229305

InChI Key:

GACDQMDRPRGCTN-KQYNXXCUSA-N

InChI:

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

CAS number:

482-67-7

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:

3'-phosphoadenylyl sulfate

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

Chemical Taxonomy

Taxonomy Description

This compound 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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside 3',5'-bisphosphates

Alternative Parents

Substituents

Purine ribonucleoside 3',5'-bisphosphate
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
Saccharide
Heteroaromatic compound
Oxolane
Organic sulfuric acid or derivatives
Imidazole
Azole
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acyl sulfate (CHEBI:17980 )
adenosine bisphosphate (CHEBI:17980 )
purine ribonucleoside bisphosphate (CHEBI:17980 )
Coenzymes (C00053 )

Physical Properties

State:

Solid

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	5.05 mg/mL	ALOGPS
logP	-0.65	ALOGPS
logP	-7.1	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	-2.1	ChemAxon
pKa (Strongest Basic)	4.94	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	275.97 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	94.93 m³·mol^-1	ChemAxon
Polarizability	39.36 Å³	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:

Pathways:

Metabolic pathways pae01100
Microbial metabolism in diverse environments pae01120
Purine metabolism pae00230
Selenoamino acid metabolism pae00450
Sulfur metabolism pae00920

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2901410000-afa8a71104e69c842868	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900200000-8f9317ccb6340a4317c4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-e2c92e775605a11d728e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a7i-4900240000-500302d146b6d356a0b8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-5900100000-07e0047589df3afabbbd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9500000000-517ff9b08c8f8999b922	View in MoNA

References

References:

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
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
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
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
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
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
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
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
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
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
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
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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

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

Links

External Links:

Resource	Link
CHEBI ID	17980
HMDB ID	HMDB01134
Pubchem Compound ID	990
Kegg ID	C00053
ChemSpider ID	9799
Wikipedia	Phosphoadenosine phosphosulfate
BioCyc ID	PAPS
EcoCyc ID	PAPS
Ligand Expo	PPS

Enzymes

Protein Details

• Adenylyl-sulfate kinase

General function:: Involved in adenylylsulfate kinase activity
Specific function:: Catalyzes the synthesis of activated sulfate
Gene Name:: cysC
Locus Tag:: PA1393
Molecular weight:: 22.1 kDa

Reactions

ATP + adenylyl sulfate = ADP + 3'-phosphoadenylyl sulfate.

Protein Details

• Phosphoadenosine phosphosulfate reductase

General function:: Involved in phosphoadenylyl-sulfate reductase (thioredoxin) activity
Specific function:: Reduction of activated sulfate into sulfite
Gene Name:: cysH
Locus Tag:: PA1756
Molecular weight:: 30.2 kDa

Reactions

Adenosine 3',5'-bisphosphate + sulfite + thioredoxin disulfide = 3'-phosphoadenylyl sulfate + thioredoxin.

Protein Details

• 3'(2'),5'-bisphosphate nucleotidase cysQ

General function:: Involved in magnesium ion binding
Specific function:: Converts 3'(2')-phosphoadenosine 5'-phosphate (PAP) to AMP. May also convert adenosine 3'-phosphate 5'-phosphosulfate (PAPS) to adenosine 5'-phosphosulfate (APS). Has 10000-fold lower activity towards inositol 1,4-bisphosphate (Ins(1,4)P2)
Gene Name:: cysQ
Locus Tag:: PA5175
Molecular weight:: 29.8 kDa

Reactions

Adenosine 3',5'-bisphosphate + H(2)O = adenosine 5'-phosphate + phosphate.

Protein Details

• Putative aliphatic sulfonates transport permease protein ssuC

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:: ssuC
Locus Tag:: PA3443
Molecular weight:: 28.5 kDa

Protein Details

• Glutaredoxin-4

General function:: Involved in electron carrier activity
Specific function:: Monothiol glutaredoxin involved in the biogenesis of iron-sulfur clusters (Probable)
Gene Name:: grxD
Locus Tag:: PA3533
Molecular weight:: 11.8 kDa

Protein Details

• Glutaredoxin-3

General function:: Involved in electron carrier activity
Specific function:: The disulfide bond functions as an electron carrier in the glutathione-dependent synthesis of deoxyribonucleotides by the enzyme ribonucleotide reductase. In addition, it is also involved in reducing some disulfides in a coupled system with glutathione reductase
Gene Name:: grxC
Locus Tag:: PA5129
Molecular weight:: 9.2 kDa

Protein Details

• Thioredoxin-1

General function:: Involved in electron carrier activity
Specific function:: Participates in various redox reactions through the reversible oxidation of its active center dithiol to a disulfide and catalyzes dithiol-disulfide exchange reactions
Gene Name:: trxA
Locus Tag:: PA5240
Molecular weight:: 11.9 kDa

Transporters

Protein Details

• Putative aliphatic sulfonates transport permease protein ssuC

General function:: Involved in transporter activity
Specific function:: Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:: ssuC
Locus Tag:: PA3443
Molecular weight:: 28.5 kDa

Phosphoadenosine phosphosulfate (PAMDB000269)

Structure for Phosphoadenosine phosphosulfate (PAMDB000269)

Enzymes

Reactions

Reactions

Reactions

Transporters