NAV

(Rp)-cAMPS

Identification

Generic Name
(Rp)-cAMPS
DrugBank Accession Number
DB01790
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 345.272
Monoisotopic: 345.029675721
Chemical Formula
C10H12N5O5PS
Synonyms
  • (Rp)-adenosine-3',5'-cyclic monophosphorothioate
  • adenosine-3',5'-cyclic monophosphorothioate, Rp-isomer
  • Rp-cAMPS
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UcAMP-dependent protein kinase type I-alpha regulatory subunitNot 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
Chemical TaxonomyProvided by Classyfire
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 / 6-aminopurine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound / Heteroaromatic compound
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
purines, nucleoside 3',5'-cyclic phosphorothioate (CHEBI:84622)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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)-7-hydroxy-2-sulfanyl-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
SMILES
NC1=C2N=CN([C@@H]3O[C@@H]4CO[P@](S)(=O)O[C@H]4[C@H]3O)C2=NC=N1

References

General References
Not Available
PubChem Compound
6858240
PubChem Substance
46504971
ChemSpider
23646829
ChEBI
84622
ZINC
ZINC000014806300
PDBe Ligand
RP1
PDB Entries
1ne4

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
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 Solubility1.5 mg/mLALOGPS
logP-0.63ALOGPS
logP-3.2Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.97Chemaxon
pKa (Strongest Basic)3.94Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area134.61 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity74.28 m3·mol-1Chemaxon
Polarizability30.69 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-MSsplash10-0fu6-2901000000-7fb238f77280c9323b5b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-4e865df0df91e857c0f2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-c1c73cdad662e872336c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0109000000-76d62fc41aa603ba5d0c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-3059000000-2b3bf02b5a34a239f1cd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-882741b16d9e39a676d3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ue9-2937000000-c779989fe5e1b64f09e8
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-170.96788
predicted
DeepCCS 1.0 (2019)
[M+H]+172.8633
predicted
DeepCCS 1.0 (2019)
[M+Na]+178.79117
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. cAMP-dependent protein kinase type I-alpha regulatory subunit
Kind
Protein
Organism
Humans
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. [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]
  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. [Article]

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