Adenosine-3',5'-cyclic phosphorothioate
PubChem CID
6858240
Structure
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.
Chemical Structure Depiction
(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)
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)
SMPNJFHAPJOHPP-JOILOJCLSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
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)
C10H12N5O5PS
Computed by PubChem 2.2 (PubChem release 2021.10.14)
23645-17-2
73208-40-9
- (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
- Sp-Camps
- RP-cAMPS
- Cyclic apt
- (RP)-Camps
- RP-Camp-S
- SP-Camp-S
- (R)-p-Camps
- 3,5'-Camps
- R(p)-cAMPS
- 71774-13-5
- Adenosine-3',5'-cyclic phosphorothioate
- Adenosine 3',5'-monothionophosphate
- Adenosine-3',5'-monophosphorothioate
- Cyclic adenosine 3,'5'-phosphorothioate
- p-Adenosine 3',5'-cyclic phosphorothiate
- Adenosine 3',5'-cyclic monophosphorothioate
- 23645-17-2
- (Sp)-cAMPS
- CHEBI:84615
- CHEBI:84622
- 73208-40-9
- DTXSID20178316
- Adenosine, cyclic 3',5'-(hydrogen phosphorothioate)
- ADENOSINE-3',5'-CYCLIC -MONOPHOSPHOROTHIOATE
- (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
- SP-ADENOSINE-3',5'-CYCLIC-MONOPHOSPHOROTHIOATE
- Sp-cAMPS (sodium salt)
- 6-(6-AMINO-PURIN-9-YL)-2-THIOXO-TETRAHYDRO-2-FURO[3,2-D][1,3,2]DIOXAPHOSPHININE-2,7-DIOL
- GTPL5262
- SCHEMBL4159569
- CHEMBL1235719
- CHEMBL1236010
- SCHEMBL22370431
- DTXCID50100807
- DTXSID30993936
- CHEBI:191063
- EX-A10492A
- AKOS040745140
- AKOS040749365
- DB01790
- HY-100530A
- HY-100530B
- NCGC00182722-01
- NCGC00485585-01
- CS-0019676
- CS-0107084
- (Rp)-adenosine-3',5'-cyclic monophosphorothioate
- (Sp)-adenosine-3',5'-cyclic monophosphorothioate
- Q27088619
- Q27157921
- RP-ADENOSINE-3',5'-CYCLIC-MONOPHOSPHOROTHIOATE
- adenosine-3',5'-cyclic monophosphorothioate, Rp-isomer
- adenosine-3',5'-cyclic monophosphorothioate, Sp-isomer
- Adenosine, cyclic 3',5'-[hydrogen [p(s)]-phosphorothioate]
- Adenosine- 3', 5'- cyclic monophosphorothioate, Rp- isomer
- Adenosine cyclic 3a(2),5a(2)-[hydrogen [P(R)]-phosphorothioate]
- (2R,4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-7-hydroxy-2-sulfanyltetrahydro-2H,4H-2lambda(5)-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
- (2R,4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-sulfide
- (2S,4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-7-hydroxy-2-sulfanyltetrahydro-2H,4H-2lambda(5)-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
- (2S,4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-sulfide
- (4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-hydroxy-2-sulanylidene-4a,6,7,7a-tetrahydro-4H-uro[3,2-d][1,3,2]dioxaphosphinin-7-ol
- RP1
Property Name
Property Value
Reference
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)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Protein Kinase Inhibitors
Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)
- ChEBI
- ChEMBLLICENSEAccess 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.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- ChemIDplusAdenosine-3',5'-cyclic phosphorothioatehttps://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0023645172ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSToxAdenosine-3',5'-cyclic phosphorothioatehttps://comptox.epa.gov/dashboard/DTXSID20178316Adenosine cyclic 3',5'-[hydrogen [P(R)]-phosphorothioate]https://comptox.epa.gov/dashboard/DTXSID30993936CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- ClinicalTrials.govLICENSEThe 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
- Comparative Toxicogenomics Database (CTD)LICENSEIt 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.jspadenosine-3',5'-cyclic phosphorothioatehttps://ctdbase.org/detail.go?type=chem&acc=C016957
- DrugBankLICENSECreative 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(Rp)-cAMPShttps://www.drugbank.ca/drugs/DB01790
- IUPHAR/BPS Guide to PHARMACOLOGYLICENSEThe 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#licenseGuide to Pharmacology Target Classificationhttps://www.guidetopharmacology.org/targets.jsp
- Therapeutic Target Database (TTD)
- Japan Chemical Substance Dictionary (Nikkaji)
- Metabolomics Workbench
- Protein Data Bank in Europe (PDBe)
- WikidataAdenosine-3',5'-cyclic phosphorothioatehttps://www.wikidata.org/wiki/Q83048706
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks 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.htmladenosine-3',5'-cyclic phosphorothioatehttps://www.ncbi.nlm.nih.gov/mesh/67016957Protein Kinase Inhibitorshttps://www.ncbi.nlm.nih.gov/mesh/68047428
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- NCBI
CONTENTS