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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
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
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
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.