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Compound Detail

CHEMBL4438309

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CCn1nc(C)cc1C(=O)/N=c1\[nH]c2cc(C(N)=O)cc(OC)c2n1C/C=C/Cn1/c(=N/C(=O)c2cc(C)nn2CC)[nH]c2cc(C(N)=O)cc(OCCCN3CCOCC3)c21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4438309
Phase Preclinical
Structure Type MOL
InChI Key JGLMVXWAHNTPRF-CMDGGOBGSA-N
4
Targets
21
Activities
2
Assay Types
9
PK Parameters
20
Publications
0
Known Names

Molecular Properties

850.0
MW (Da)
2.35
ALogP
14
HBA
4
HBD
253.1
PSA (Ų)
0.08
QED
2
Ro5 Violations
16
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C42H51N13O7
MW 849.95
Aromatic Rings 6
Heavy Atoms 62
NP-Likeness -0.96

Activity Summary

EC50 17 meas. best 7.96
IC50 4 meas. best 8.59

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Stimulator of interferon genes protein
CHEMBL4523311
 IC50 8.59 8.59 2.6 1
Stimulator of interferon genes protein
CHEMBL4523377
 IC50 8.41 8.28 3.9 2
Stimulator of interferon genes protein
CHEMBL4523377
 EC50 7.96 7.172 11.0 10
Stimulator of interferon genes protein
CHEMBL4523311
 EC50 7.27 6.26 54.0 4
Unchecked
CHEMBL612545
 EC50 6.7 6.7 200.0 2
Cyclic GMP-AMP synthase
CHEMBL4523383
 IC50 6.57 6.57 270.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 657.0 ng.hr.mL-1 Rattus norvegicus
AUC 666.0 ng.hr.mL-1 Rattus norvegicus
AUC 657.0 ng.hr.mL-1 Mus musculus
AUC 666.0 ng.hr.mL-1 Mus musculus
CL 26.0 mL.min-1.kg-1 Rattus norvegicus
CL 26.0 mL.min-1.kg-1 Mus musculus
MRT 0.633 hr Rattus norvegicus
T1/2 1.14 hr Rattus norvegicus
T1/2 1.14 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Stimulator of interferon genes protein IC50 = 2.6 nM 8.59 Displacement of fluorescein-labelled probe from wild type mouse His-tagged STING... 35108011
Stimulator of interferon genes protein IC50 = 3.9 nM 8.41 Displacement of fluorescein-labelled probe from human cytoplasmic domain of STIN... 35108011
Stimulator of interferon genes protein IC50 = 7.1 nM 8.15 Displacement of fluorescein-labelled probe from wild type human His-tagged STING... 35108011
Stimulator of interferon genes protein EC50 = 11.0 nM 7.96 Binding affinity to human STING G230A/R293Q double mutant cytoplasmic domain (15... 35108011
Stimulator of interferon genes protein EC50 = 11.0 nM 7.96 Binding affinity to wild type human His-tagged STING cytoplasmic domain (155 to ... 35108011
Stimulator of interferon genes protein EC50 = 35.0 nM 7.46 Agonist activity at STING in human THP1 Dual cells assessed as IRF reporter acti... 35108011
Stimulator of interferon genes protein EC50 = 54.0 nM 7.27 Binding affinity to wild type mouse His-tagged STING cytoplasmic domain (155 to ... 35108011
Stimulator of interferon genes protein EC50 = 55.0 nM 7.26 Agonist activity at STING in human THP1-Dual cells assessed as NF-kappaB reporte... 35108011
Stimulator of interferon genes protein EC50 = 130.0 nM 6.89 Induction of STING in human PBMC assessed as increase in IFNbeta secretion 31419779
Stimulator of interferon genes protein EC50 = 130.0 nM 6.89 Inhibition of wild type human STING by SPA assay 31820978
Stimulator of interferon genes protein EC50 = 130.0 nM 6.89 Activation of STING in human peripheral mononuclear blood 33470814
Stimulator of interferon genes protein EC50 = 130.0 nM 6.89 Agonist activity at human wild type haplotype STING in human PBMC cells assessed... 35963129
Stimulator of interferon genes protein EC50 = 160.0 nM 6.8 Inhibition of human STING HAQ mutant by SPA assay 31820978
Stimulator of interferon genes protein EC50 = 186.0 nM 6.73 Agonist activity at mouse STING 35671593
Stimulator of interferon genes protein EC50 = 190.0 nM 6.72 Agonist activity at human STING HAQ mutant 35671593
Unchecked EC50 = 200.0 nM 6.7 Agonist activity at human STING R232H mutant 35671593
Unchecked EC50 = 200.0 nM 6.7 Inhibition of human STING H232 mutant by SPA assay 31820978
Cyclic GMP-AMP synthase IC50 = 270.0 nM 6.57 Inhibition of mouse cGAS by ATP consumption assay 37360395
Stimulator of interferon genes protein EC50 = 3000.0 nM 5.52 Activation of mouse STING expressed in RAW-Lucia ISG cells incubated for 24 hrs ... 33470814
Stimulator of interferon genes protein EC50 = 3000.0 nM 5.52 Agonist activity at STING in mouse RAW-Lucia ISG cells assessed as ISG activatio... 35671593

Literature References

PubMed DOI Target Context # Activities
35671593 10.1016/j.ejmech.2022.114482 Stimulator of interferon genes protein 17
33470814 10.1021/acs.jmedchem.0c01900 Stimulator of interferon genes protein 13
35108011 10.1021/acs.jmedchem.1c01986 Stimulator of interferon genes protein 12
33470814 10.1021/acs.jmedchem.0c01900 ADMET 6
35108011 10.1021/acs.jmedchem.1c01986 ADMET 5
35671593 10.1016/j.ejmech.2022.114482 ADMET 5
35315650 10.1021/acs.jmedchem.1c01795 Unchecked 4
33470814 10.1021/acs.jmedchem.0c01900 Unchecked 3
31820978 10.1021/acs.jmedchem.9b01039 Stimulator of interferon genes protein 2
35315650 10.1021/acs.jmedchem.1c01795 Stimulator of interferon genes protein 2
35963129 10.1016/j.ejmech.2022.114627 Stimulator of interferon genes protein 1
37360395 10.1039/d3md00061c Stimulator of interferon genes protein 1
37360395 10.1039/d3md00061c Cyclic GMP-AMP synthase 1
35315650 10.1021/acs.jmedchem.1c01795 Nuclear factor NF-kappa-B complex 1
35315650 10.1021/acs.jmedchem.1c01795 THP1-Dual 1
35671593 10.1016/j.ejmech.2022.114482 Unchecked 1
31419779 10.1016/j.ejmech.2019.111591 Stimulator of interferon genes protein 1
33470814 10.1021/acs.jmedchem.0c01900 4T1 1
31820978 10.1021/acs.jmedchem.9b01039 Unchecked 1
31419779 10.1016/j.ejmech.2019.111591 Unchecked 1

Data from ChEMBL 36 via Core Engine