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].
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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
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
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SynPHARM 83677 (in complex with transmembrane protein 173)

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