Record Information
Version1.0
Created at2020-04-17 19:14:10 UTC
Updated at2020-11-18 16:39:26 UTC
CannabisDB IDCDB005148
Secondary Accession NumbersNot Available
Cannabis Compound 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. 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. Phosphoadenosine phosphosulfate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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
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
Chemical FormulaC10H15N5O13P2S
Average Molecular Weight507.26
Monoisotopic Molecular Weight506.9862
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
Disposition

Source:

Biological location:

Role

Industrial application:

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-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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPhosphoadenosine phosphosulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-8930200000-a2821e129c20bee87c33Spectrum
Predicted GC-MSPhosphoadenosine phosphosulfate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9441110000-619798b0c3242743c13aSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2901410000-afa8a71104e69c842868Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900200000-8f9317ccb6340a4317c4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-e2c92e775605a11d728eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a7i-4900240000-500302d146b6d356a0b8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-5900100000-07e0047589df3afabbbdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9500000000-517ff9b08c8f8999b922Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 3ENPP36q22O14638 details
Carbohydrate sulfotransferase 11CHST1112qQ9NPF2 details
Carbohydrate sulfotransferase 3CHST310q22.1Q7LGC8 details
Carbohydrate sulfotransferase 13CHST133q21.3Q8NET6 details
Carbohydrate sulfotransferase 12CHST127p22Q9NRB3 details
Galactosylceramide sulfotransferaseGAL3ST122q12.2Q99999 details
Heparan sulfate glucosamine 3-O-sulfotransferase 3B1HS3ST3B117p12Q9Y662 details
Heparan sulfate glucosamine 3-O-sulfotransferase 3A1HS3ST3A117p12Q9Y663 details
Sulfotransferase 1A1SULT1A116p12.1P50225 details
3'(2'),5'-bisphosphate nucleotidase 1BPNT11q41O95861 details
Heparan sulfate glucosamine 3-O-sulfotransferase 1HS3ST14p16O14792 details
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1PAPSS14q24O43252 details
Estrogen sulfotransferaseSULT1E14q13.1P49888 details
Bile salt sulfotransferaseSULT2A119q13.3Q06520 details
Carbohydrate sulfotransferase 1CHST111p11.2O43916 details
Heparan sulfate glucosamine 3-O-sulfotransferase 4HS3ST416p11.2Q9Y661 details
Sulfotransferase 1A2SULT1A216p12.1P50226 details
Heparan sulfate glucosamine 3-O-sulfotransferase 5HS3ST56q21Q8IZT8 details
Heparan sulfate glucosamine 3-O-sulfotransferase 2HS3ST216p12Q9Y278 details
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2PAPSS210q24O95340 details
Protein-tyrosine sulfotransferase 2TPST222q12.1O60704 details
Sulfotransferase family cytosolic 2B member 1SULT2B119q13.3O00204 details
Sulfotransferase 1A3/1A4SULT1A316p11.2P50224 details
Carbohydrate sulfotransferase 7CHST7Xp11.23Q9NS84 details
Carbohydrate sulfotransferase 14CHST1415q15.1Q8NCH0 details
Heparan-sulfate 6-O-sulfotransferase 1HS6ST12q21O60243 details
Heparan-sulfate 6-O-sulfotransferase 2HS6ST2Xq26.2Q96MM7 details
Adenosine 3'-phospho 5'-phosphosulfate transporter 1SLC35B26p12.1-p11.2Q8TB61 details
Heparan-sulfate 6-O-sulfotransferase 3HS6ST313q32.1Q8IZP7 details
Carbohydrate sulfotransferase 15CHST1510q26Q7LFX5 details
Inositol monophosphatase 3IMPAD18q12.1Q9NX62 details
Tyrosylprotein sulfotransferase 1TPST17q11.21A4D2M0 details
Heparan sulfate glucosamine 3-O-sulfotransferase 6HS3ST6Q96QI5 details
Bifunctional heparan sulfate N-deacetylase/N-sulfotransferase 1NDST15q33.1P52848 details
Bifunctional heparan sulfate N-deacetylase/N-sulfotransferase 2NDST210q22P52849 details
Bifunctional heparan sulfate N-deacetylase/N-sulfotransferase 3NDST34q26O95803 details
Bifunctional heparan sulfate N-deacetylase/N-sulfotransferase 4NDST44q26Q9H3R1 details
Sulfotransferase 1C3SULT1C32q12.3Q6IMI6 details
Sulfotransferase 6B1SULT6B1Q6IMI4 details
Protein-tyrosine sulfotransferase 1TPST17q11.21O60507 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 3ENPP36q22O14638 details
Inositol monophosphatase 3IMPAD18q12.1Q9NX62 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 3ENPP36q22O14638 details
Carbohydrate sulfotransferase 11CHST1112qQ9NPF2 details
Bifunctional heparan sulfate N-deacetylase/N-sulfotransferase 1NDST15q33.1P52848 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001134
DrugBank IDDB02902
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022445
KNApSAcK IDC00007446
Chemspider ID9799
KEGG Compound IDC00053
BioCyc IDPAPS
BiGG ID33679
Wikipedia Link3'-Phosphoadenosine-5'-phosphosulfate
METLIN ID6028
PubChem Compound10214
PDB IDNot Available
ChEBI ID17980
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 48 proteins in total.

Enzymes

General function:
Involved in catalytic activity
Specific function:
Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular weight:
104923.58
General function:
Involved in catalytic activity
Specific function:
Cleaves a variety of phosphodiester and phosphosulfate bonds including deoxynucleotides, nucleotide sugars, and NAD (By similarity).
Gene Name:
ENPP3
Uniprot ID:
O14638
Molecular weight:
100123.54
General function:
Involved in sulfotransferase activity
Specific function:
Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Can also sulfate Gal residues in desulfated dermatan sulfate. Preferentially sulfates in GlcA->GalNAc unit than in IdoA->GalNAc unit. Does not form 4, 6-di-O-sulfated GalNAc when chondroitin sulfate C is used as an acceptor.
Gene Name:
CHST11
Uniprot ID:
Q9NPF2
Molecular weight:
41002.97
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the transfer of sulfate to position 6 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Can also sulfate Gal residues of keratan sulfate, another glycosaminoglycan, and the Gal residues in sialyl N-acetyllactosamine (sialyl LacNAc) oligosaccharides. May play a role in the maintenance of naive T-lymphocytes in the spleen.
Gene Name:
CHST3
Uniprot ID:
Q7LGC8
Molecular weight:
54705.5
General function:
Involved in sulfotransferase activity
Specific function:
Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Transfers sulfate to the C4 hydroxyl of beta1,4-linked GalNAc that is substituted with a beta-linked glucuronic acid at the C-3 hydroxyl. No activity toward dermatan.
Gene Name:
CHST13
Uniprot ID:
Q8NET6
Molecular weight:
38919.34
General function:
Involved in sulfotransferase activity
Specific function:
Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of chondroitin and desulfated dermatan sulfate. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Activity toward partially desulfated dermatan sulfate is however lower. Does not form 4, 6-di-O-sulfated GalNAc when chondroitin sulfate C is used as an acceptor.
Gene Name:
CHST12
Uniprot ID:
Q9NRB3
Molecular weight:
48413.945
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 galactosylceramide sulfate (sulfatide), a major lipid component of the myelin sheath and of monogalactosylalkylacylglycerol sulfate (seminolipid), present in spermatocytes (By similarity). Also acts on lactosylceramide, galactosyl 1-alkyl-2-sn-glycerol and galactosyl diacylglycerol (in vitro).
Gene Name:
GAL3ST1
Uniprot ID:
Q99999
Molecular weight:
48763.63
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) to catalyze the transfer of a sulfo group to an N-unsubstituted glucosamine linked to a 2-O-sulfo iduronic acid unit on heparan sulfate. Catalyzes the O-sulfation of glucosamine in IdoUA2S-GlcNS and also in IdoUA2S-GlcNH2. The substrate-specific O-sulfation generates an enzyme-modified heparan sulfate which acts as a binding receptor to Herpes simplex virus-1 (HSV-1) and permits its entry. Unlike 3-OST-1, does not convert non-anticoagulant heparan sulfate to anticoagulant heparan sulfate.
Gene Name:
HS3ST3B1
Uniprot ID:
Q9Y662
Molecular weight:
43323.605
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) to catalyze the transfer of a sulfo group to an N-unsubstituted glucosamine linked to a 2-O-sulfo iduronic acid unit on heparan sulfate. Catalyzes the O-sulfation of glucosamine in IdoUA2S-GlcNS and also in IdoUA2S-GlcNH2. The substrate-specific O-sulfation generates an enzyme-modified heparan sulfate which acts as a binding receptor to Herpes simplex virus-1 (HSV-1) and permits its entry. Unlike 3-OST-1, does not convert non-anticoagulant heparan sulfate to anticoagulant heparan sulfate.
Gene Name:
HS3ST3A1
Uniprot ID:
Q9Y663
Molecular weight:
44899.155
General function:
Involved in 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.
Gene Name:
SULT1A1
Uniprot ID:
P50225
Molecular weight:
34165.13

Only showing the first 10 proteins. There are 48 proteins in total.