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Compound Detail

CHEMBL1231573

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Nc1nc2c(ncn2[C@@H]2O[C@@H]3COP(=O)(O)O[C@H]4[C@@H](O)[C@H](n5cnc6c(=O)[nH]c(N)nc65)O[C@@H]4COP(=O)(O)O[C@H]3[C@H]2O)c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1231573
Phase Preclinical
Structure Type MOL
InChI Key PKFDLKSEZWEFGL-MHARETSRSA-N
4
Targets
19
Activities
4
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

690.4
MW (Da)
-3.05
ALogP
20
HBA
8
HBD
349.6
PSA (Ų)
0.10
QED
3
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H24N10O14P2
MW 690.42
Aromatic Rings 4
Heavy Atoms 46
NP-Likeness 0.60

Activity Summary

EC50 9 meas. best 6.05
Kd 5 meas. best 6.96
IC50 4 meas. best 7.7
Ki 1 meas. best 4.81

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cyclic di-GMP phosphodiesterase RocR
CHEMBL2396510
 IC50 7.7 7.7 20.0 1
Stimulator of interferon genes protein
CHEMBL4523311
 Kd 6.96 6.96 110.0 1
Stimulator of interferon genes protein
CHEMBL4523377
 EC50 6.05 5.79 890.0 6
Stimulator of interferon genes protein
CHEMBL4523377
 Kd 5.92 5.76 1210.0 4
Unchecked
CHEMBL612545
 IC50 5.3 4.9067 5000.0 3
Unchecked
CHEMBL612545
 EC50 5.08 5.08 8400.0 2
Unchecked
CHEMBL612545
 Ki 4.81 4.81 15420.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cyclic di-GMP phosphodiesterase RocR IC50 = 20.0 nM 7.7 Competitive binding affinity to Pseudomonas aeruginosa PAO1 His6-tagged RocR exp... 23685177
Stimulator of interferon genes protein Kd = 110.0 nM 6.96 Binding affinity to mouse C-terminal STING domain (139 to 378 residues) by isoth... 32206239
Stimulator of interferon genes protein EC50 = 890.0 nM 6.05 Activation of human STING HAQ mutant expressed in digitonin treated HEK293T cell... 34019405
Stimulator of interferon genes protein EC50 = 900.0 nM 6.05 Activation of recombinant human STING haplotype R71H/G230A/R293Q mutant expresse... 31715099
Stimulator of interferon genes protein EC50 = 1050.0 nM 5.98 Activation of human STING QA mutant expressed in digitonin treated HEK293T cells... 34019405
Stimulator of interferon genes protein EC50 = 1100.0 nM 5.96 Activation of recombinant human STING haplotype G230A/R293Q mutant expressed in ... 31715099
Stimulator of interferon genes protein Kd = 1210.0 nM 5.92 Agonist activity at wild type human STING C-terminal domain (139 to 379 residues... 35671593
Stimulator of interferon genes protein Kd = 1210.0 nM 5.92 Binding affinity to human STING expressed in Escherichia coli by isothermal titr... 32206239
Stimulator of interferon genes protein Kd = 1210.0 nM 5.92 Binding affinity to wild type human STING (139 to 379 residues) by ITC assay 31820978
Stimulator of interferon genes protein EC50 = 4500.0 nM 5.35 Activation of recombinant human wild-type STING expressed in 293T cells measured... 31715099
Stimulator of interferon genes protein EC50 = 4470.0 nM 5.35 Activation of wild-type human STING expressed in digitonin treated HEK293T cells... 34019405
Unchecked IC50 = 5000.0 nM 5.3 Inhibition of Caulobacter crescentus PleD 26426545
Stimulator of interferon genes protein Kd = 5200.0 nM 5.28 Binding affinity to human C-terminal STING domain (139 to 379 residues) by isoth... 32206239
Unchecked IC50 = 7690.0 nM 5.11 Competitive binding affinity to Pseudomonas aeruginosa Alg44 PilZ domain after 5... 23685177
Unchecked EC50 = 8410.0 nM 5.08 Activation of human STING REF mutant expressed in digitonin treated HEK293T cell... 34019405
Unchecked EC50 = 8400.0 nM 5.08 Activation of recombinant human STING haplotype R232H mutant expressed in 293T c... 31715099
Unchecked Ki = 15420.0 nM 4.81 Allosteric inhibition of Pseudomonas aeruginosa WspR using [32P]-GTP as substrat... 23685177
Unchecked IC50 = 48910.0 nM 4.31 Competitive binding affinity to Pseudomonas aeruginosa WspR after 5 mins in pres... 23685177

Literature References

PubMed DOI Target Context # Activities
31715099 10.1021/acs.jmedchem.9b01062 Stimulator of interferon genes protein 14
23685177 10.1016/j.bmc.2013.04.050 Unchecked 6
31715099 10.1021/acs.jmedchem.9b01062 Unchecked 3
32206239 10.1039/C8MD00555A Stimulator of interferon genes protein 3
34019405 10.1021/acs.jmedchem.1c00301 Stimulator of interferon genes protein 3
23685177 10.1016/j.bmc.2013.04.050 Cyclic di-GMP phosphodiesterase RocR 2
33271284 10.1016/j.bmcl.2020.127713 Escherichia coli 2
33271284 10.1016/j.bmcl.2020.127713 Pseudomonas aeruginosa 2
33271284 10.1016/j.bmcl.2020.127713 Staphylococcus aureus 2
33271284 10.1016/j.bmcl.2020.127713 Streptococcus mutans 2
34019405 10.1021/acs.jmedchem.1c00301 Unchecked 2
26426545 10.1021/acs.jmedchem.5b01184 Unchecked 1
31715099 10.1021/acs.jmedchem.9b01062 Monocyte 1
31820978 10.1021/acs.jmedchem.9b01039 Stimulator of interferon genes protein 1
35671593 10.1016/j.ejmech.2022.114482 Stimulator of interferon genes protein 1

Data from ChEMBL 36 via Core Engine