Adenosine phosphosulfate (YMDB00256)

Identification

YMDB ID

YMDB00256

Name

Adenosine phosphosulfate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Adenosine phosphosulfate (APS) is the initial compound formed by the action of ATP sulfurylase (PAPS synthetase) on sulfate ions after sulfate uptake in the sulfate-activation pathway. It is an intermediate in the sulfate reduction pathway. Plants, fungi, and many bacteria reduce inorganic sulfate to sulfide to cover their need for the element. Before the sulfur can be assimilated into biosynthetic pathways it needs to be reduced to hydrogen sulfide. [Biocyc SULFMETII-PWY]

Structure

MOL SDF PDB SMILES InChI

Synonyms

3-phospho-5-adenylyl sulfate
3-phosphoadenosine 5-phosphosulfate
3'-Phospho-5'-adenylyl sulfate
3'-Phosphoadenosine 5'-phosphosulfate
3'-phosphoadenosine-5'-phosphosulfate
3'-Phosphoadenylyl sulfate
3'-phosphoadenylyl-sulfate
5-phosphoadenosine 3-phosphosulfate
Adenosine 5'-phosphosulfate
adenosine 5'-sulphatophosphate
Adenosine Phosphosulfate
Adenosine phosphosulfic acid
adenosine sulfatophosphate
ADENOSINE-5'-PHOSPHOSULFATE
adenylic acid monoanhydride with sulfurate
adenylic acid monoanhydride with sulfuric acid
adenylyl sulfate
adenylyl-sulfate
Adenylylsulfate
AMPS
APS
paps
Phosphoadenosine Phosphosulfate
Phosphoadenosine phosphosulfic acid
phosphoadenosine-5'-phosphosulfate
phosphosulfate
sulfatophosphate
5'-Adenylyl sulfate
Adenosine 5'-phosphosulfuric acid
Adenosine 5'-phosphosulphate
Adenosine 5'-phosphosulphuric acid
ADENOSINE-5'-phosphosulfuric acid
ADENOSINE-5'-phosphosulphate
ADENOSINE-5'-phosphosulphuric acid
Adenylylsulfuric acid
Adenylylsulphate
Adenylylsulphuric acid
5'-Adenylyl sulfuric acid
5'-Adenylyl sulphate
5'-Adenylyl sulphuric acid
Adenosine phosphosulfuric acid
Adenosine phosphosulphate
Adenosine phosphosulphuric acid
Adenylyl sulphate
Adenylyl-sulphate
Phosphosulphate
5'-Phosphosulfate, adenosine
Adenosine 5' phosphosulfate
Phospho adenylsulfate
Phospho-adenylsulfate
Phosphosulfate, adenosine
Sulfate, adenylyl
5’-Adenylyl sulfate
5’-Adenylyl sulphate
Adenosine 5'-monophosphosulfate
Adenosine 5'-monophosphosulphate
Adenosine 5'-sulfatophosphate
Adenosine 5’-monophosphosulfate
Adenosine 5’-monophosphosulphate
Adenosine 5’-phosphosulfate
Adenosine 5’-phosphosulphate
Adenosine 5’-sulfatophosphate

CAS number

485-84-7

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

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

Chemical Formula

C₁₀H₁₄N₅O₁₀PS

SMILES

[H]O[C@]1([H])[C@]([H])(O[H])[C@]([H])(O[C@@]1([H])N1C([H])=NC2=C1N=C([H])N=C2N([H])[H])C([H])([H])OP(=O)(O[H])OS(=O)(=O)O[H]

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

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

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

Organoleptic Properties

Not Available

SMPDB Pathways

Sulfur metabolism

PW002483

KEGG Pathways

Purine metabolism	ec00230
Sulfur metabolism	ec00920

SMPDB Reactions

Adenosine triphosphate + hydron + Sulfate → Adenosine phosphosulfate + Pyrophosphate

Adenosine phosphosulfate + Adenosine triphosphate → Phosphoadenosine phosphosulfate + ADP + hydron

Phosphoadenosine phosphosulfate + water ↔ phosphate + Adenosine phosphosulfate

KEGG Reactions

Adenosine phosphosulfate + Adenosine triphosphate → hydron + Phosphoadenosine phosphosulfate + ADP

Adenosine triphosphate + hydron + Sulfate → Pyrophosphate + Adenosine phosphosulfate

hydron + Sulfate + ADP ↔ Adenosine phosphosulfate + phosphate

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-2911100000-c7b3ba6ec47b4fb3e832	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-055b-7693530000-45cc4add4821e6fea5ef	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0912300000-29cd6f42fa9d4c6c4455	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0901000000-018ae7ee1fc1b662ec07	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-861a01467a0191dcd31a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-0901600000-785b903b29133cefd0bc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-3900000000-d2245ba9a6f6bf6d0217	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9700000000-3f4588ade18801775bec	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0200900000-b10f97ec4ef8bff7823c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0911000000-4563fb5a2cb7fd85ab98	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900000000-5a937b62fdf69d198700	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0100900000-a398ce6fc250a971f068	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-6900300000-d9d41d4bc70263df8221	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004j-9200000000-979bc3001281c5d76962	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Plateau, P., Fromant, M., Schmitter, J. M., Buhler, J. M., Blanquet, S. (1989). "Isolation, characterization, and inactivation of the APA1 gene encoding yeast diadenosine 5',5'''-P1,P4-tetraphosphate phosphorylase." J Bacteriol 171:6437-6445.2556364
Masselot, M., Surdin-Kerjan, Y. (1977). "Methionine biosynthesis in Saccharomyces cerevisiae. II. Gene-enzyme relationships in the sulfate assimilation pathway." Mol Gen Genet 154:23-30.197388
Korch, C., Mountain, H. A., Bystrom, A. S. (1991). "Cloning, nucleotide sequence, and regulation of MET14, the gene encoding the APS kinase of Saccharomyces cerevisiae." Mol Gen Genet 229:96-108.1654509

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	17709
HMDB ID	HMDB01003
Pubchem Compound ID	228
Kegg ID	C00224
ChemSpider ID	9821
FOODB ID	FDB022362
Wikipedia	amps
BioCyc ID	APS

Enzymes

Protein Details

1. Sulfate adenylyltransferase

General function:: Involved in sulfate adenylyltransferase (ATP) activity
Specific function:: Catalyzes the first intracellular reaction of sulfate assimilation, forming adenosine-5'-phosphosulfate (APS) from inorganic sulfate and ATP. Plays an important role in sulfate activation as a component of the biosynthesis pathway of sulfur- containing amino acids
Gene Name:: MET3
Uniprot ID:: P08536
Molecular weight:: 57724.0

Reactions

ATP + sulfate → diphosphate + adenylyl sulfate.

Protein Details

2. Protein APA1

General function:: Involved in ATP adenylyltransferase activity
Specific function:: Ap4A phosphorylase catabolizes Ap4N nucleotides (where N is A,C,G or U). Additionally this enzyme catalyzes the conversion of adenosine-5-phosphosulfate (AMPs) plus Pi to ADP plus sulfate, the exchange of NDP and phosphate and the synthesis of Ap4A from AMPs plus ATP
Gene Name:: APA1
Uniprot ID:: P16550
Molecular weight:: 36492.19922

Reactions

ADP + ATP → phosphate + P(1),P(4)-bis(5'-adenosyl) tetraphosphate.
ADP + sulfate → phosphate + adenylyl sulfate.
Adenylylsulfate + ATP → P(1),P(4)-bis(5'-adenosyl)tetraphosphate + sulfate.

Protein Details

3. Adenylyl-sulfate kinase

General function:: Involved in ATP binding
Specific function:: Catalyzes the synthesis of activated sulfate
Gene Name:: MET14
Uniprot ID:: Q02196
Molecular weight:: 23060.09961

Reactions

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

Structure for #<Compound:0xaf895670>

Enzymes

Reactions

Reactions

Reactions