Sp-Adenosine-3',5'-Cyclic-Monophosphorothioate

Identification

Name
Sp-Adenosine-3',5'-Cyclic-Monophosphorothioate
Accession Number
DB01790  (EXPT02808, EXPT02940)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 345.272
Monoisotopic: 345.029675721
Chemical Formula
C10H12N5O5PS
InChI Key
SMPNJFHAPJOHPP-PUHOFUEYSA-N
InChI
InChI=1S/C10H12N5O5PS/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(19-10)1-18-21(17,22)20-7/h2-4,6-7,10,16H,1H2,(H,17,22)(H2,11,12,13)/t4-,6-,7-,10-,21-/m1/s1
IUPAC Name
(2R,4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinine-2-thione
SMILES
[H][[email protected]@]12CO[[email protected]@](O)(=S)O[[email protected]@]1([H])[[email protected]@]([H])(O)[[email protected]@]([H])(O2)N1C=NC2=C(N)N=CN=C12

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UcAMP-dependent protein kinase type I-alpha regulatory subunitNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
6858240
PubChem Substance
46504971
ChemSpider
23646829
ChEBI
84622
HET
RP1
PDB Entries
1ne4

Clinical Trials

Clinical Trials
Not Available

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 Solubility1.84 mg/mLALOGPS
logP-0.93ALOGPS
logP-3.1ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area137.77 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity78.28 m3·mol-1ChemAxon
Polarizability30.72 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8432
Blood Brain Barrier+0.8148
Caco-2 permeable-0.6508
P-glycoprotein substrateNon-substrate0.8147
P-glycoprotein inhibitor INon-inhibitor0.8482
P-glycoprotein inhibitor IINon-inhibitor0.9884
Renal organic cation transporterNon-inhibitor0.9177
CYP450 2C9 substrateNon-substrate0.8094
CYP450 2D6 substrateNon-substrate0.8223
CYP450 3A4 substrateNon-substrate0.5183
CYP450 1A2 substrateNon-inhibitor0.8435
CYP450 2C9 inhibitorNon-inhibitor0.835
CYP450 2D6 inhibitorNon-inhibitor0.9093
CYP450 2C19 inhibitorNon-inhibitor0.843
CYP450 3A4 inhibitorNon-inhibitor0.8399
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8992
Ames testNon AMES toxic0.614
CarcinogenicityNon-carcinogens0.8188
BiodegradationNot ready biodegradable0.9956
Rat acute toxicity2.4791 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9897
hERG inhibition (predictor II)Non-inhibitor0.7874
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as 3',5'-cyclic purine nucleoside phosphorothioates. These are 3',5'-cyclic purine nucleoside phosphate analogues, where a phosphate oxygen has been exchanged for sulphur generating a chiral phosphorothioate. In 3',5'-cyclic nucleoside phosphorothioate, the oxygen atoms at the 3'- and 5'-positions of the ribose are part of the phosphorothioate group.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Nucleoside and nucleotide analogues
Sub Class
3',5'-cyclic purine nucleoside phosphorothioates
Direct Parent
3',5'-cyclic purine nucleoside phosphorothioates
Alternative Parents
Glycosylamines / 6-aminopurines / Thiophosphate diesters / Aminopyrimidines and derivatives / N-substituted imidazoles / Monosaccharides / Imidolactams / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols
show 5 more
Substituents
3',5'-cyclic purine nucleoside phosphorothioate / Glycosyl compound / N-glycosyl compound / 6-aminopurine / Imidazopyrimidine / Purine / Aminopyrimidine / Thiophosphate diester / Monosaccharide / N-substituted imidazole
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
purines, nucleoside 3',5'-cyclic phosphorothioate (CHEBI:84622)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Regulatory subunit of the cAMP-dependent protein kinases involved in cAMP signaling in cells.
Gene Name
PRKAR1A
Uniprot ID
P10644
Uniprot Name
cAMP-dependent protein kinase type I-alpha regulatory subunit
Molecular Weight
42981.28 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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:48