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Compound Detail

CHEMBL4297643

APILIMOD
🧪 Phase II
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🧪 Phase II
Cc1cccc(/C=N/Nc2cc(N3CCOCC3)nc(OCCc3ccccn3)n2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4297643
Name APILIMOD
Phase Phase II
Structure Type MOL
InChI Key HSKAZIJJKRAJAV-KOEQRZSOSA-N

Known Names

Apilimod STA 5326 Sta-5326
8
Targets
27
Activities
3
Assay Types
0
PK Parameters
20
Publications
3
Known Names
3
Indications
1
Mechanisms

Molecular Properties

418.5
MW (Da)
3.08
ALogP
8
HBA
1
HBD
84.8
PSA (Ų)
0.44
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -imod

Extended Properties

Molecular Formula C23H26N6O2
MW 418.50
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -2.06

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
1-phosphatidylinositol 3-phosphate 5-kinase inhibitor INHIBITOR 1-phosphatidylinositol 3-phosphate 5-kinase ✓ ✓

Indications

Crohn Disease Severe Acute Respiratory Syndrome Common Variable Immunodeficiency

Activity Summary

IC50 19 meas. best 9.51
EC50 6 meas. best 8.0
Kd 2 meas. best 10.12

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
1-phosphatidylinositol 3-phosphate 5-kinase
CHEMBL1938222
 Kd 10.12 10.12 0.1 1
1-phosphatidylinositol 3-phosphate 5-kinase
CHEMBL1938222
 IC50 9.51 8.296 0.3 10
SARS-CoV-2
CHEMBL4303835
 IC50 8.15 8.15 7.0 1
Marburgvirus
CHEMBL4296577
 EC50 8.0 8.0 10.0 1
Marburgvirus
CHEMBL4296577
 IC50 8.0 8.0 10.0 1
Ebolavirus
CHEMBL4434621
 EC50 8.0 8.0 10.0 1
Ebolavirus
CHEMBL4434621
 IC50 8.0 8.0 10.0 1
Murine hepatitis virus
CHEMBL613733
 IC50 7.8 7.8 15.7 2
SARS-CoV-2
CHEMBL4303835
 EC50 7.64 7.64 23.0 4
MDA-MB-231
CHEMBL400
 IC50 7.0 7.0 100.0 1
HeLa
CHEMBL399
 IC50 6.85 6.85 140.0 1
VCaP
CHEMBL4296508
 IC50 6.6 6.26 253.6 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
1-phosphatidylinositol 3-phosphate 5-kinase Kd = 0.075 nM 10.12 Binding affinity to human wild type partial length PIKFYVE (F1512 to C2098 resid... 36111834
1-phosphatidylinositol 3-phosphate 5-kinase IC50 = 0.312 nM 9.51 Inhibition of PIKFYVE in HEK293 cells by NanoBRET assay 36111834
1-phosphatidylinositol 3-phosphate 5-kinase IC50 = 0.309 nM 9.51 Inhibition of PIKFYVE in HEK293 cells by NanoBRET assay 36111834
1-phosphatidylinositol 3-phosphate 5-kinase IC50 = 3.4 nM 8.47 Inhibition of human GST tagged PIKFYVE (1493 to end residues) expressed in bacul... 36111834
1-phosphatidylinositol 3-phosphate 5-kinase IC50 = 4.0 nM 8.4 Inhibition of Nano-Luc fused PIKFYVE (unknown origin) expressed in HEK293T cells... 36826833
SARS-CoV-2 IC50 = 7.0 nM 8.15 Antiviral activity against SARS-CoV-2 in human A549-ACE2 cells assessed as inhib... 34081439
Marburgvirus EC50 = 10.0 nM 8.0 Antiviral activity against MARV 33539089
Marburgvirus IC50 = 10.0 nM 8.0 Antiviral activity against MARV infected in human MDM 33539089
Ebolavirus IC50 = 10.0 nM 8.0 Antiviral activity against EBOV infected in human MDM 33539089
Ebolavirus EC50 = 10.0 nM 8.0 Antiviral activity against EBOV 33539089
1-phosphatidylinositol 3-phosphate 5-kinase IC50 = 14.0 nM 7.85 Inhibition of N-terminal His-tagged human PIKfyve expressed in Sf9 insect cells ... 37981443
1-phosphatidylinositol 3-phosphate 5-kinase IC50 = 14.0 nM 7.85 Inhibition of PIKfyve (unknown origin) 37605297
1-phosphatidylinositol 3-phosphate 5-kinase IC50 = 14.0 nM 7.85 Inhibition of recombinant PIKFYVE (unknown origin) 36857133
1-phosphatidylinositol 3-phosphate 5-kinase IC50 = 14.0 nM 7.85 Inhibition of PIKFYVE (unknown origin) 33970631
1-phosphatidylinositol 3-phosphate 5-kinase IC50 = 14.0 nM 7.85 Inhibition of human PIKfyve (unknown origin) 33539089
1-phosphatidylinositol 3-phosphate 5-kinase IC50 = 15.0 nM 7.82 Inhibition of human PIKfyve in HEK293 lysate using di-C8 PI(3)P as substrate pre... 33539089
Murine hepatitis virus IC50 = 15.7 nM 7.8 Antiviral activity against MHV-nLuc infected in DBT cells assessed as effect on ... 36111834
Murine hepatitis virus IC50 = 15.85 nM 7.8 Antiviral activity against MHV-nLuc infected in DBT cells assessed as effect on ... 36111834
SARS-CoV-2 EC50 = 23.0 nM 7.64 Determination of antiviral efficacy in high-content imaging assay in Vero E6 cel... -
SARS-CoV-2 EC50 = 23.0 nM 7.64 Antiviral activity against SARSCoV-2 33539089

Literature References

PubMed DOI Target Context # Activities
36111834 10.1021/acs.jmedchem.2c00697 Unchecked 6
36111834 10.1021/acs.jmedchem.2c00697 1-phosphatidylinositol 3-phosphate 5-kinase 4
37605297 10.1021/acs.jmedchem.3c00912 VCaP 3
38117948 10.1021/acs.jmedchem.3c01039 MDA-MB-231 3
38117948 10.1021/acs.jmedchem.3c01039 HeLa 3
33539089 10.1021/acs.jmedchem.0c01467 SARS-CoV-2 3
33539089 10.1021/acs.jmedchem.0c01467 Ebolavirus 2
37605297 10.1021/acs.jmedchem.3c00912 Unchecked 2
34081439 10.1021/acs.jmedchem.1c00335 SARS-CoV-2 2
33539089 10.1021/acs.jmedchem.0c01467 Marburgvirus 2
33539089 10.1021/acs.jmedchem.0c01467 1-phosphatidylinositol 3-phosphate 5-kinase 2
36111834 10.1021/acs.jmedchem.2c00697 Murine hepatitis virus 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.1101/2020.04.16.044016 SARS-CoV-2 1
33539089 10.1021/acs.jmedchem.0c01467 Vero C1008 1
33970631 10.1021/acs.jmedchem.1c00302 1-phosphatidylinositol 3-phosphate 5-kinase 1
36826833 10.1021/acs.jmedchem.2c01834 1-phosphatidylinositol 3-phosphate 5-kinase 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1

Data from ChEMBL 36 via Core Engine