P. aeruginosa Metabolome Database: Adenosine phosphosulfate (PAMDB000222)

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

PAMDB000222

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

🔍MOL SDF PDB SMILES InChI View Structure

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 Description

This 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 Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine 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

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 mg/mL	ALOGPS
logP	-1.6	ALOGPS
logP	-5.8	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	-2.1	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	229.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.06 m³·mol^-1	ChemAxon
Polarizability	35.24 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
Monobactam biosynthesis pae00261
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-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
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not 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)

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

Adenosine phosphosulfate (PAMDB000222)

Structure for Adenosine phosphosulfate (PAMDB000222)