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Identification
NameSp-Adenosine-3',5'-Cyclic-Monophosphorothioate
Accession NumberDB01790  (EXPT02808, EXPT02940)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 345.272
Monoisotopic: 345.029675721
Chemical FormulaC10H12N5O5PS
InChI KeySMPNJFHAPJOHPP-BTQOAJACSA-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
(2S,4aR,6S,7S,7aR)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinine-2-thione
SMILES
NC1=NC=NC2=C1N=CN2[[email protected]]1O[C@@H]2CO[P@](O)(=S)O[C@@H]2[C@@H]1O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
cAMP-dependent protein kinase type I-alpha regulatory subunitProteinunknownNot AvailableHumanP10644 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.84 mg/mLALOGPS
logP-0.93ALOGPS
logP-2.9ChemAxon
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
Polarizability30.53 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassNucleoside and nucleotide analogues
Direct Parent3',5'-cyclic purine nucleoside phosphorothioates
Alternative Parents
Substituents
  • 3',5'-cyclic purine nucleoside phosphorothioate
  • N-glycosyl compound
  • Glycosyl compound
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Thiophosphate diester
  • N-substituted imidazole
  • Imidolactam
  • Organic thiophosphoric acid or derivatives
  • Pyrimidine
  • Thiophosphoric acid ester
  • Primary aromatic amine
  • Monosaccharide
  • Imidazole
  • Oxolane
  • Heteroaromatic compound
  • Azole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23