NAV
Explore a selection of essential drug information below, or:
Unlock enhanced features & extensive drug insights. Create a free account.
Explore the full scope of our drug knowledge tailored for pharmaceutical research needs in our data library. Learn more.

(Rp)-cAMPS

Explore a selection of our essential drug information below, or:

CREATE FREE ACCOUNT
Full Drug Profiles
Unlock enhanced features & extensive drug insights, including detailed interaction data & regulatory status. Create a free account.
SUBSCRIBERECOMMENDED FOR PHARMA
Data Packages
Explore the full scope of our drug knowledge tailored for pharmaceutical research needs in our data library. Learn more.

Overview

Structure
DrugBank ID
DB01790
Type
Small Molecule
US Approved
NO
Other Approved
NO
Patents
0
Indicated Conditions
0
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

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
Get Early Access To DrugBank+
Be among the first to try our new AI-powered, game-changing platform. DrugBank+ is here to streamline your pharmaceutical research and deliver faster insights and smarter decisions.
Join the Waitlist
Get Early Access To DrugBank+
Join the Waitlist

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available
Unlock the secrets to drugging the undruggable
Discover how groundbreaking research is turning "undruggable" targets into therapeutic opportunities.
Download eBook
Unlock the secrets to drugging the undruggable
Download eBook

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
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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Unlock 175K+ rows when you subscribe.View sample data

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

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. cAMP-dependent protein kinase type I-alpha regulatory subunit
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Regulatory subunit of the cAMP-dependent protein kinases involved in cAMP signaling in cells
Specific Function
cAMP binding
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