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Record Information
Version1.0
Creation Date2016-09-30 22:41:33 UTC
Update Date2020-05-21 16:28:36 UTC
BMDB IDBMDB0001134
Secondary Accession Numbers
  • BMDB01134
Metabolite Identification
Common 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.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC10H15N5O13P2S
Average Molecular Weight507.264
Monoisotopic Molecular Weight506.986229305
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
Traditional Name3'-phosphoadenylyl sulfate
CAS Registry Number482-67-7
SMILES
NC1=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
InChI Identifier
InChI=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
Chemical Taxonomy
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Golgi
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.65ALOGPS
logP-7.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)-2.1ChemAxon
pKa (Strongest Basic)4.94ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area275.97 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity94.93 m³·mol⁻¹ChemAxon
Polarizability39.36 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-8930200000-a2821e129c20bee87c33View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9441110000-619798b0c3242743c13aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2901410000-afa8a71104e69c842868View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900200000-8f9317ccb6340a4317c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-e2c92e775605a11d728eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a7i-4900240000-500302d146b6d356a0b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-5900100000-07e0047589df3afabbbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9500000000-517ff9b08c8f8999b922View in MoNA
Biological Properties
Cellular Locations
  • Golgi
Biospecimen Locations
  • Kidney
  • Liver
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001134
DrugBank IDDB02902
Phenol Explorer Compound IDNot Available
FooDB IDFDB022445
KNApSAcK IDC00007446
Chemspider ID9799
KEGG Compound IDC00053
BioCyc IDNot Available
BiGG ID33679
Wikipedia Link3'-Phosphoadenosine-5'-phosphosulfate
METLIN ID6028
PubChem Compound10214
PDB IDNot Available
ChEBI ID17980
References
Synthesis ReferenceLin, Chun-Hung; Shen, Gwo-Jenn; Garcia-Junceda, Eduardo; Wong, Chi-Huey. Enzymic Synthesis and Regeneration of 3'-Phosphoadenosine 5'-Phosphosulfate (PAPS) for Regioselective Sulfation of Oligosaccharides. J. Am. Chem. Soc., 1995, 117 (30), pp 8031-8032
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in galactosylceramide sulfotransferase activity
Specific function:
Catalyzes the sulfation of membrane glycolipids. Seems to prefer beta-glycosides at the non-reducing termini of sugar chains attached to a lipid moiety. Catalyzes the synthesis of HSO3-3-galactosylceramide (sulfatide), a major lipid component of the myelin sheath and of HSO3-3-monogalactosylalkylacylglycerol (seminolipid), present in spermatocytes. Also acts on lactosylceramide, galactosyl 1-alkyl-2-sn-glycerol and galactosyl diacylglycerol (in vitro) (By similarity).
Gene Name:
GAL3ST1
Uniprot ID:
A6QNK1
Molecular weight:
48754.0
Reactions
Galactosylceramide (d18:1/16:0) + Phosphoadenosine phosphosulfate → 3-O-Sulfogalactosylceramide (d18:1/24:0) + Adenosine 3',5'-diphosphatedetails
Galabiosylceramide (d18:1/22:0) + Phosphoadenosine phosphosulfate → Galabiosylceramide-sulfate + Adenosine 3',5'-diphosphatedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Converts adenosine 3'-phosphate 5'-phosphosulfate (PAPS) to adenosine 5'-phosphosulfate (APS) and 3'(2')-phosphoadenosine 5'- phosphate (PAP) to AMP. Has 1000-fold lower activity towards inositol 1,4-bisphosphate (Ins(1,4)P2) and inositol 1,3,4-trisphosphate (Ins(1,3,4)P3), but does not hydrolyze Ins(1)P, Ins(3,4)P2, Ins(1,3,4,5)P4 or InsP6 (By similarity).
Gene Name:
BPNT1
Uniprot ID:
Q3ZCK3
Molecular weight:
33328.0
Reactions
Phosphoadenosine phosphosulfate + Water → Adenosine phosphosulfate + Hydrogen phosphatedetails
General function:
Involved in protein-tyrosine sulfotransferase activity
Specific function:
Catalyzes the O-sulfation of tyrosine residues within acidic motifs of polypeptides, using 3'-phosphoadenylyl sulfate (PAPS) as cosubstrate.
Gene Name:
TPST2
Uniprot ID:
Q3SYY2
Molecular weight:
41967.0
General function:
Involved in aryl sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estrogen sulfotransferase activity. responsible for the sulfonation and activation of minoxidil. Is Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk (By similarity).
Gene Name:
SULT1A1
Uniprot ID:
P50227
Molecular weight:
34184.0
Reactions
Phosphoadenosine phosphosulfate + Phenol → Adenosine 3',5'-diphosphate + Phenol sulphatedetails
Phosphoadenosine phosphosulfate + Dehydroepiandrosterone → Adenosine 3',5'-diphosphate + DHEA sulfatedetails
General function:
Involved in [heparan sulfate]-glucosamine N-sulfotransf
Specific function:
Essential bifunctional enzyme that catalyzes both the N-deacetylation and the N-sulfation of glucosamine (GlcNAc) of the glycosaminoglycan in heparan sulfate. Modifies the GlcNAc-GlcA disaccharide repeating sugar backbone to make N-sulfated heparosan, a prerequisite substrate for later modifications in heparin biosynthesis. Plays a role in determining the extent and pattern of sulfation of heparan sulfate. Required for the exosomal release of SDCBP, CD63 and syndecan (By similarity).
Gene Name:
NDST2
Uniprot ID:
O97583
Molecular weight:
100897.0
General function:
Involved in estrone sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone (PubMed:1900200) (By similarity). Is a key enzyme in estrogen homeostasis, the sulfation of estrogens leads to their inactivation. Also sulfates dehydroepiandrosterone (DHEA), pregnenolone, (24S)-hydroxycholesterol and xenobiotic compounds like ethinylestradiol, equalenin, diethyl stilbesterol and 1-naphthol at significantly lower efficiency. Does not sulfonate cortisol, testosterone and dopamine (By similarity).
Gene Name:
SULT1E1
Uniprot ID:
P19217
Molecular weight:
34640.0
Reactions
Estrone + Phosphoadenosine phosphosulfate → Estrone sulfate + Adenosine 3',5'-diphosphatedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
PAPSS2
Uniprot ID:
Q0VC88
Molecular weight:
69672.0
Reactions
Adenosine triphosphate + Adenosine phosphosulfate → ADP + Phosphoadenosine phosphosulfatedetails