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: Metabolite
Comment: 2'3'-cGAMP is produced in mammalian cells by the action of cyclic guanosine monophosphate (GMP)-adenosine monophosphate (AMP) synthase (cGAS) upon detection of double-stranded DNA in the cytosol that originates for example, from tumours or viruses. It is the endogenous agonist of the human STING protein [2], but appears not to activate mouse Sting. STING activation at the endoplasmic reticulum triggers type-I IFNs production by the innate immune response [1].
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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 across species
2D Structure
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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.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Wu J, Sun L, Chen X, Du F, Shi H, Chen C, Chen ZJ. (2013)
Cyclic GMP-AMP is an endogenous second messenger in innate immune signaling by cytosolic DNA.
Science, 339 (6121): 826-30. [PMID:23258412]
2. Zhang X, Shi H, Wu J, Zhang X, Sun L, Chen C, Chen ZJ. (2013)
Cyclic GMP-AMP containing mixed phosphodiester linkages is an endogenous high-affinity ligand for STING.
Mol Cell, 51 (2): 226-35. [PMID:23747010]