2'3'-cGAMP   Click here for help

GtoPdb Ligand ID: 9207

Synonyms: cyclic [G(2',5')pA(3',5')p] | cyclic GMP-AMP | Cyclic guanosine monophosphate-adenosine monophosphate
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: 2'3'-cGAMP is produced in mammalian cells by the action of cGAS (cGAMP synthase) in response to double-stranded DNA in the cytoplasm. It acts as an agonist of the human STING protein [2], but not of mouse Sting. 2'3'-cGAMP functions as a second messenger that binds to and activates the endoplasmic reticulum protein STING to trigger type-I IFNs production [1].
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 20
Hydrogen bond donors 7
Rotatable bonds 2
Topological polar surface area 349.27
Molecular weight 674.1
XLogP -3.71
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES Nc1nc(=O)c2c([nH]1)n(cn2)C1OC2C(C1OP(=O)(O)OCC1C(OP(=O)(OC2)O)C(C(O1)n1cnc2c1ncnc2N)O)O
Isomeric SMILES Nc1nc(=O)c2c([nH]1)n(cn2)[C@@H]1O[C@H]2[C@H]([C@H]1OP(=O)(O)OC[C@@H]1[C@@H](OP(=O)(OC2)O)[C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O
InChI InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1
InChI Key XRILCFTWUCUKJR-INFSMZHSSA-N
Classification Click here for help
Compound class Synthetic organic
Synonyms Click here for help
cyclic [G(2',5')pA(3',5')p] | cyclic GMP-AMP | Cyclic guanosine monophosphate-adenosine monophosphate
Database Links Click here for help
GtoPdb PubChem SID 315661283
PubChem CID 71563406
RCSB PDB Ligand 1SY
Search Google for chemical match using the InChIKey XRILCFTWUCUKJR-INFSMZHSSA-N
Search Google for chemicals with the same backbone XRILCFTWUCUKJR
Search UniChem for chemical match using the InChIKey XRILCFTWUCUKJR-INFSMZHSSA-N
Search UniChem for chemicals with the same backbone XRILCFTWUCUKJR
SynPHARM 83677 (in complex with transmembrane protein 173)

Product suppliers

View disclaimer

Sponsored products disclaimer

Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

✖

Tocris
2',3'-cGAMP sodium salt
Cat. No. 5945