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 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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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
Selectivity at other protein targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
stimulator of interferon response cGAMP interactor 1 Ligand is endogenous in the given species Hs Agonist Agonist 8.3 – 8.4 pKd - 2
pKd 8.3 – 8.4 (Kd 4.59x10-9 – 3.79x10-9 M) [2]