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Adenosine-3',5'-cyclic phosphorothioate

PubChem CID
6858240
Structure
Adenosine-3',5'-cyclic phosphorothioate_small.png
Adenosine-3',5'-cyclic phosphorothioate_3D_Structure.png
Molecular Formula
Synonyms
  • Sp-Camps
  • RP-cAMPS
  • Cyclic apt
  • (RP)-Camps
  • RP-Camp-S
Molecular Weight
345.27 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2006-07-03
  • Modify:
    2025-01-18
Description
(Sp)-cAMPS is a nucleoside 3',5'-cyclic phosphorothioate having adenine as the nucleobase (the Sp-stereoisomer). It has a role as a protein kinase agonist. It is a member of purines and a nucleoside 3',5'-cyclic phosphorothioate. It is functionally related to a 3',5'-cyclic AMP.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Adenosine-3',5'-cyclic phosphorothioate.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-hydroxy-2-sulfanylidene-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

SMPNJFHAPJOHPP-JOILOJCLSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=S)(O1)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C10H12N5O5PS
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

23645-17-2
73208-40-9

2.3.2 ChEBI ID

2.3.3 ChEMBL ID

2.3.4 DrugBank ID

2.3.5 DSSTox Substance ID

2.3.6 Metabolomics Workbench ID

2.3.7 Nikkaji Number

2.3.8 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • (R)-p-cAMPS
  • (RP)-cAMPS
  • 3,5'-cAMPS
  • adenosine 3',5'-cyclic monophosphorothioate
  • adenosine 3',5'-monothionophosphate
  • adenosine-3',5'-cyclic phosphorothioate
  • adenosine-3',5'-monophosphorothioate
  • cyclic adenosine 3,'5'-phosphorothioate
  • cyclic APT
  • p-adenosine 3',5'-cyclic phosphorothiate
  • R(p)-cAMPS
  • RP-cAMP-S
  • SP-cAMP-S
  • Sp-cAMPS

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
345.27 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-0.8
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
345.02967667 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
345.02967667 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
170 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
22
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
502
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
4
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

5 Chemical Vendors

6 Drug and Medication Information

6.1 Clinical Trials

6.1.1 ClinicalTrials.gov

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Protein Kinase Inhibitors
Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)

8 Associated Disorders and Diseases

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Chemical Co-Occurrences in Literature

9.4 Chemical-Gene Co-Occurrences in Literature

9.5 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 Chemical Co-Occurrences in Patents

10.3 Chemical-Disease Co-Occurrences in Patents

10.4 Chemical-Gene Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Protein Bound 3D Structures

11.1.1 Ligands from Protein Bound 3D Structures

1 of 2
View All
PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

11.2 Chemical-Target Interactions

12 Biological Test Results

12.1 BioAssay Results

13 Classification

13.1 MeSH Tree

13.2 ChEBI Ontology

13.3 ChemIDplus

13.4 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

13.5 ChEMBL Target Tree

13.6 EPA DSSTox Classification

13.7 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. ChEBI
  2. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. EPA DSSTox
    Adenosine-3',5'-cyclic phosphorothioate
    https://comptox.epa.gov/dashboard/DTXSID20178316
    Adenosine cyclic 3',5'-[hydrogen [P(R)]-phosphorothioate]
    https://comptox.epa.gov/dashboard/DTXSID30993936
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  6. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
    adenosine-3',5'-cyclic phosphorothioate
    https://ctdbase.org/detail.go?type=chem&acc=C016957
  7. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  8. IUPHAR/BPS Guide to PHARMACOLOGY
    LICENSE
    The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)
    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  9. Therapeutic Target Database (TTD)
  10. Japan Chemical Substance Dictionary (Nikkaji)
  11. Metabolomics Workbench
  12. Protein Data Bank in Europe (PDBe)
  13. Wikidata
    Adenosine-3',5'-cyclic phosphorothioate
    https://www.wikidata.org/wiki/Q83048706
  14. PubChem
  15. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    adenosine-3',5'-cyclic phosphorothioate
    https://www.ncbi.nlm.nih.gov/mesh/67016957
  16. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  17. NCBI
CONTENTS