You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00256
NameAdenosine phosphosulfate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAdenosine 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
Thumb
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
CAS number485-84-7
WeightAverage: 427.284
Monoisotopic: 427.019898895
InChI KeyIRLPACMLTUPBCL-KQYNXXCUSA-N
InChIInChI=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 Nameadenosine phosphosulfate
Chemical FormulaC10H14N5O10PS
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 carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentCarotenes
Alternative Parents
Substituents
  • Carotene
  • Branched unsaturated hydrocarbon
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Acyclic olefin
  • Hydrocarbon
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.29 g/LALOGPS
logP-1.6ALOGPS
logP-5.6ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)-2.3ChemAxon
pKa (Strongest Basic)3.94ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area229.44 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity84.06 m³·mol⁻¹ChemAxon
Polarizability35.07 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Sulfur metabolismPW002483 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Purine metabolismec00230 Map00230
Sulfur metabolismec00920 Map00920
SMPDB Reactions
Adenosine triphosphate + hydron + SulfateAdenosine phosphosulfate + Pyrophosphate
Adenosine phosphosulfate + Adenosine triphosphatePhosphoadenosine phosphosulfate + ADP + hydron
Phosphoadenosine phosphosulfate + waterphosphate + Adenosine phosphosulfate
KEGG Reactions
Adenosine phosphosulfate + Adenosine triphosphatehydron + Phosphoadenosine phosphosulfate + ADP
Adenosine triphosphate + hydron + SulfatePyrophosphate + Adenosine phosphosulfate
hydron + Sulfate + ADPAdenosine phosphosulfate + phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-2911100000-c7b3ba6ec47b4fb3e832JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-055b-7693530000-45cc4add4821e6fea5efJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0912300000-29cd6f42fa9d4c6c4455JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901000000-018ae7ee1fc1b662ec07JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-861a01467a0191dcd31aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0901600000-785b903b29133cefd0bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3900000000-d2245ba9a6f6bf6d0217JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9700000000-3f4588ade18801775becJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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:
ResourceLink
CHEBI ID17709
HMDB IDHMDB01003
Pubchem Compound ID228
Kegg IDC00224
ChemSpider ID9821
FOODB IDFDB022362
Wikipediaamps
BioCyc IDAPS

Enzymes

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.
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.
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.