Record Information
Version1.0
Creation date2011-09-21 00:14:07 UTC
Update date2020-09-17 15:40:42 UTC
Primary IDFDB022445
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhosphoadenosine phosphosulfate
DescriptionPhosphoadenosine phosphosulfate, also known as 3'-phospho-5'-adenylyl sulfate or PAPS, 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. Phosphoadenosine phosphosulfate is a strong basic compound (based on its pKa). Phosphoadenosine phosphosulfate exists in all living species, ranging from bacteria to humans. Within humans, phosphoadenosine phosphosulfate participates in a number of enzymatic reactions. In particular, galactosylceramide (D18:1/18:0) and phosphoadenosine phosphosulfate can be converted into 3-O-sulfogalactosylceramide (D18:1/18:0) and adenosine 3',5'-diphosphate through its interaction with the enzyme galactosylceramide sulfotransferase. In addition, galabiosylceramide (D18:1/18:0) and phosphoadenosine phosphosulfate can be converted into adenosine 3',5'-diphosphate and galabiosylceramide sulfate (D18:1/18:0) through its interaction with the enzyme galactosylceramide sulfotransferase. An adenosine bisphosphate having monophosphate groups at the 3'- and 5'-positions and a sulfo group attached to the phosphate at position 5'. In humans, phosphoadenosine phosphosulfate is involved in globoid cell leukodystrophy.
CAS Number482-67-7
Structure
Thumb
Synonyms
SynonymSource
3'-Phosphoadenosine 5'-phosphosulfateChEBI
3'-Phosphoadenylyl sulfateChEBI
PAPSChEBI
3'-Phospho-5'-adenylyl sulfateKegg
3'-Phosphoadenosine 5'-phosphosulfuric acidGenerator
3'-Phosphoadenosine 5'-phosphosulphateGenerator
3'-Phosphoadenosine 5'-phosphosulphuric acidGenerator
3'-Phosphoadenylyl sulfuric acidGenerator
3'-Phosphoadenylyl sulphateGenerator
3'-Phosphoadenylyl sulphuric acidGenerator
3'-Phospho-5'-adenylyl sulfuric acidGenerator
3'-Phospho-5'-adenylyl sulphateGenerator
3'-Phospho-5'-adenylyl sulphuric acidGenerator
Phosphoadenosine phosphosulfuric acidGenerator
Phosphoadenosine phosphosulphateGenerator
Phosphoadenosine phosphosulphuric acidGenerator
3'-Phosphoadenosine-5'-phosphosulfateHMDB
3'-Phosphoadenosine-5'-phosphosulphateHMDB
3'-Phosphoadenylyl-sulfateHMDB
3'-Phosphoadenylyl-sulphateHMDB
5-Phosphoadenosine 3-phosphosulfateHMDB
5-Phosphoadenosine 3-phosphosulphateHMDB
Adenosine 3' phosphate 5' phosphosulfateHMDB
Adenosine-3'-phosphate-5'-phosphosulfateHMDB
Phosphosulfate, phosphoadenosineHMDB
3’-Phosphoadenosine 5’-phosphosulfateHMDB
3’-Phosphoadenosine 5’-phosphosulphateHMDB
3’-Phosphoadenylyl sulfateHMDB
3’-Phosphoadenylyl sulphateHMDB
5'-Adenylyl sulfate 3'-phosphateHMDB
5'-Adenylyl sulphate 3'-phosphateHMDB
5’-Adenylyl sulfate 3’-phosphateHMDB
5’-Adenylyl sulphate 3’-phosphateHMDB
Adenosine 3'-phosphate 5'-phosphosulfateHMDB
Adenosine 3'-phosphate 5'-phosphosulphateHMDB
Adenosine 3'-phosphate 5'-sulfatophosphateHMDB
Adenosine 3’-phosphate 5’-phosphosulfateHMDB
Adenosine 3’-phosphate 5’-phosphosulphateHMDB
Adenosine 3’-phosphate 5’-sulfatophosphateHMDB
Adenosine 5'-phosphosulfate 3'-phosphateHMDB
Adenosine 5'-phosphosulphate 3'-phosphateHMDB
Adenosine 5’-phosphosulfate 3’-phosphateHMDB
Adenosine 5’-phosphosulphate 3’-phosphateHMDB
3'-O-5'-Adenylyl sulfateChEBI
3'-O-5'-Adenylyl sulfuric acidGenerator
3'-O-5'-Adenylyl sulphateGenerator
3'-O-5'-Adenylyl sulphuric acidGenerator
3'-Oadenosine 5'-OsulfateChEBI
3'-Oadenosine 5'-Osulfuric acidGenerator
3'-Oadenosine 5'-OsulphateGenerator
3'-Oadenosine 5'-Osulphuric acidGenerator
3'-Oadenosine-5'-OsulfateHMDB
3'-Oadenosine-5'-OsulphateHMDB
3'-Oadenylyl sulfateChEBI
3'-Oadenylyl sulfuric acidGenerator
3'-Oadenylyl sulphateGenerator
3'-Oadenylyl sulphuric acidGenerator
3'-Oadenylyl-sulfateHMDB
3'-Oadenylyl-sulphateHMDB
3'-phosphoadenosine-5'-phosphosulfatehmdb
3'-phosphoadenylyl-sulfatehmdb
5-Oadenosine 3-OsulfateHMDB
5-Oadenosine 3-OsulphateHMDB
5-phosphoadenosine 3-phosphosulfatehmdb
Oadenosine OsulfateHMDB
Oadenosine OsulphateHMDB
Phosphoadenosine Phosphosulfatehmdb
Phosphoadenosine phosphosulfic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility5.05 g/LALOGPS
logP-0.65ALOGPS
logP-5.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)-2.4ChemAxon
pKa (Strongest Basic)3.94ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area275.97 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity94.93 m³·mol⁻¹ChemAxon
Polarizability39.26 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H15N5O13P2S
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
InChI IdentifierInChI=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
InChI KeyGACDQMDRPRGCTN-KQYNXXCUSA-N
Isomeric SMILESNC1=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
Average Molecular Weight507.264
Monoisotopic Molecular Weight506.986229305
Classification
Description 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside 3',5'-bisphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside monophosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Tetrahydrofuran
  • Organic sulfuric acid or derivatives
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Primary amine
  • Amine
  • Organonitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-8930200000-a2821e129c20bee87c33JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9441110000-619798b0c3242743c13aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2901410000-afa8a71104e69c842868JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900200000-8f9317ccb6340a4317c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-e2c92e775605a11d728eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a7i-4900240000-500302d146b6d356a0b8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-5900100000-07e0047589df3afabbbdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9500000000-517ff9b08c8f8999b922JSpectraViewer
ChemSpider ID9799
ChEMBL IDNot Available
KEGG Compound IDC00053
Pubchem Compound ID10214
Pubchem Substance IDNot Available
ChEBI ID17980
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01134
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33679
KNApSAcK IDNot Available
HET IDPPS
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPhosphoadenosine phosphosulfate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Sulfotransferase family cytosolic 2B member 1SULT2B1O00204
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1PAPSS1O43252
Sulfotransferase 1A1SULT1A1P50225
Sulfotransferase 1A2SULT1A2P50226
Sulfotransferase 1A3/1A4SULT1A3P50224
Galactosylceramide sulfotransferaseGAL3ST1Q99999
Adenosine 3'-phospho 5'-phosphosulfate transporter 1SLC35B2Q8TB61
Estrogen sulfotransferaseSULT1E1P49888
Heparan sulfate glucosamine 3-O-sulfotransferase 3A1HS3ST3A1Q9Y663
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2PAPSS2O95340
Carbohydrate sulfotransferase 3CHST3Q7LGC8
Carbohydrate sulfotransferase 1CHST1O43916
Carbohydrate sulfotransferase 7CHST7Q9NS84
Bile salt sulfotransferaseSULT2A1Q06520
Carbohydrate sulfotransferase 11CHST11Q9NPF2
Carbohydrate sulfotransferase 13CHST13Q8NET6
Carbohydrate sulfotransferase 12CHST12Q9NRB3
Heparan sulfate glucosamine 3-O-sulfotransferase 3B1HS3ST3B1Q9Y662
Heparan sulfate glucosamine 3-O-sulfotransferase 1HS3ST1O14792
Heparan sulfate glucosamine 3-O-sulfotransferase 4HS3ST4Q9Y661
Heparan sulfate glucosamine 3-O-sulfotransferase 5HS3ST5Q8IZT8
Heparan sulfate glucosamine 3-O-sulfotransferase 2HS3ST2Q9Y278
Protein-tyrosine sulfotransferase 2TPST2O60704
Carbohydrate sulfotransferase 14CHST14Q8NCH0
Heparan-sulfate 6-O-sulfotransferase 1HS6ST1O60243
Heparan-sulfate 6-O-sulfotransferase 2HS6ST2Q96MM7
Heparan-sulfate 6-O-sulfotransferase 3HS6ST3Q8IZP7
Carbohydrate sulfotransferase 15CHST15Q7LFX5
Tyrosylprotein sulfotransferase 1TPST1A4D2M0
Pathways
NameSMPDB LinkKEGG Link
Sulfate/Sulfite MetabolismSMP00041 map00920
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference