NAV

3'-phospho-5'-adenylyl sulfate

Identification

Generic Name
3'-phospho-5'-adenylyl sulfate
DrugBank Accession Number
DB02902
Background

3'-phospho-5'-adenylyl sulfate is a key intermediate in the formation by living cells of sulfate esters of phenols, alcohols, steroids, sulfated polysaccharides, and simple esters, such as choline sulfate. It is formed from sulfate ion and ATP in a two-step process. This compound also is an important step in the process of sulfur fixation in plants and microorganisms.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 507.264
Monoisotopic: 506.986229305
Chemical Formula
C10H15N5O13P2S
Synonyms
  • 3'-phosphoadenosine 5'-phosphosulfate
  • 3'-phosphoadenylyl sulfate
  • PAPS
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UEstrogen sulfotransferaseNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound 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.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside 3',5'-bisphosphates
Alternative Parents
Purine ribonucleoside monophosphates / Ribonucleoside 3'-phosphates / Pentose phosphates / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Aminopyrimidines and derivatives / Monoalkyl phosphates / N-substituted imidazoles / Imidolactams
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Substituents
6-aminopurine / Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound / Heteroaromatic compound
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Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
acyl sulfate, adenosine bisphosphate, purine ribonucleoside bisphosphate (CHEBI:17980) / Coenzymes (C00053)
Affected organisms
Not Available

Chemical Identifiers

UNII
5TH3ERG159
CAS number
482-67-7
InChI Key
GACDQMDRPRGCTN-KQYNXXCUSA-N
InChI
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
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
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

References

General References
Not Available
Human Metabolome Database
HMDB0001134
KEGG Compound
C00053
PubChem Compound
10214
PubChem Substance
46508242
ChemSpider
9799
ChEBI
17980
ZINC
ZINC000004228233
PDBe Ligand
PPS
Wikipedia
3%27-Phosphoadenosine-5%27-phosphosulfate
PDB Entries
1bux / 1hy3 / 1m8p / 2ofx / 2zyt / 2zyu / 2zyv / 3cr7 / 3f3m / 4ifb …
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.05 mg/mLALOGPS
logP-0.65ALOGPS
logP-6Chemaxon
logS-2ALOGPS
pKa (Strongest Acidic)-2.1Chemaxon
pKa (Strongest Basic)4.88Chemaxon
Physiological Charge-4Chemaxon
Hydrogen Acceptor Count14Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area275.97 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity94.93 m3·mol-1Chemaxon
Polarizability39.26 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5522
Blood Brain Barrier+0.8264
Caco-2 permeable-0.6488
P-glycoprotein substrateNon-substrate0.784
P-glycoprotein inhibitor INon-inhibitor0.8107
P-glycoprotein inhibitor IINon-inhibitor0.9341
Renal organic cation transporterNon-inhibitor0.9405
CYP450 2C9 substrateNon-substrate0.8365
CYP450 2D6 substrateNon-substrate0.8154
CYP450 3A4 substrateNon-substrate0.5865
CYP450 1A2 substrateNon-inhibitor0.7933
CYP450 2C9 inhibitorNon-inhibitor0.8363
CYP450 2D6 inhibitorNon-inhibitor0.8632
CYP450 2C19 inhibitorNon-inhibitor0.8337
CYP450 3A4 inhibitorNon-inhibitor0.9186
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9638
Ames testNon AMES toxic0.6924
CarcinogenicityNon-carcinogens0.633
BiodegradationNot ready biodegradable0.886
Rat acute toxicity2.5116 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9623
hERG inhibition (predictor II)Non-inhibitor0.7247
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0002-8930200000-a2821e129c20bee87c33
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0000090000-8c0c7c8c4c2bfd461a65
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0000090000-928173710acff5cde828
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01t9-0101900000-67acfd871cc65163f291
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a70-5000940000-24e0aa2c7f12a734ac46
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0059-0509310000-a358a3174d7cb668da7a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01rt-8501900000-8041e54d5a96e80a944f
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-221.9937175
predicted
DarkChem Lite v0.1.0
[M-H]-221.6003175
predicted
DarkChem Lite v0.1.0
[M-H]-181.62938
predicted
DeepCCS 1.0 (2019)
[M+H]+222.8994175
predicted
DarkChem Lite v0.1.0
[M+H]+222.1665175
predicted
DarkChem Lite v0.1.0
[M+H]+183.73494
predicted
DeepCCS 1.0 (2019)
[M+Na]+223.5289175
predicted
DarkChem Lite v0.1.0
[M+Na]+223.1561175
predicted
DarkChem Lite v0.1.0
[M+Na]+190.83214
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Estrogen sulfotransferase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
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. May play a role in the regulation of estrogen r...
Gene Name
SULT1E1
Uniprot ID
P49888
Uniprot Name
Estrogen sulfotransferase
Molecular Weight
35126.185 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52