ECMDB: Adenosine phosphosulfate (ECMDB01003) (M2MDB000222)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)XML

Proteins (1080)

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

MOL SDF PDB SMILES InChI

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

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 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.06 m³·mol⁻¹	ChemAxon
Polarizability	35.07 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:

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

Enzymes

Protein Details

1. Adenylyl-sulfate kinase

General function:: Involved in adenylylsulfate kinase activity
Specific function:: Catalyzes the synthesis of activated sulfate
Gene Name:: cysC
Uniprot ID:: P0A6J1
Molecular weight:: 22321

Reactions

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

Protein Details

2. Sulfate adenylyltransferase subunit 2

General function:: Involved in catalytic activity
Specific function:: ATP + sulfate = diphosphate + adenylyl sulfate
Gene Name:: cysD
Uniprot ID:: P21156
Molecular weight:: 35188

Reactions

ATP + sulfate = diphosphate + adenylyl sulfate.

Protein Details

3. 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
Uniprot ID:: P22255
Molecular weight:: 27176

Reactions

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

Protein Details

4. Sulfate adenylyltransferase subunit 1

General function:: Involved in GTPase activity
Specific function:: May be the GTPase, regulating ATP sulfurylase activity
Gene Name:: cysN
Uniprot ID:: P23845
Molecular weight:: 52558

Reactions

ATP + sulfate = diphosphate + adenylyl sulfate.

Adenosine phosphosulfate (ECMDB01003) (M2MDB000222)

Structure for #<Compound:0xa8eb0b24>

Enzymes

Reactions

Reactions

Reactions

Reactions