2'3'-cGAMP

Ligand id: 9207

Name: 2'3'-cGAMP

Structure and Physico-chemical Properties

2D Structure
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Calculated Physico-chemical Properties
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

Molecular properties generated using the CDK

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.

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View interactive charts of activity data from GtoPdb and ChEMBL (where available) across species

Classification
Compound class Synthetic organic
Synonyms
cyclic [G(2',5')pA(3',5')p] | cyclic GMP-AMP | Cyclic guanosine monophosphate-adenosine monophosphate
Comments
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].
Database Links
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

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