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Compound Detail

CHEMBL4173075

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CS(=O)(=O)c1ccc(Oc2cc(F)cc(C#N)c2)c2c1[C@H](O)C(F)(F)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4173075
Phase Preclinical
Structure Type MOL
InChI Key ONBSHRSJOPSEGS-INIZCTEOSA-N
5
Targets
18
Activities
3
Assay Types
17
PK Parameters
20
Publications
0
Known Names

Molecular Properties

383.4
MW (Da)
3.12
ALogP
5
HBA
1
HBD
87.4
PSA (Ų)
0.88
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C17H12F3NO4S
MW 383.35
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -0.88

Activity Summary

IC50 9 meas. best 8.7
EC50 8 meas. best 7.57
Kd 1 meas. best 7.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aryl hydrocarbon receptor nuclear translocator/Endothelial PAS domain-containing protein 1
CHEMBL3885518
 IC50 8.7 8.7 2.0 1
Endothelial PAS domain-containing protein 1
CHEMBL1744522
 IC50 8.07 7.7767 8.5 6
Endothelial PAS domain-containing protein 1
CHEMBL1744522
 Kd 7.77 7.77 17.0 1
Endothelial PAS domain-containing protein 1
CHEMBL1744522
 EC50 7.57 7.334 27.0 5
Vascular endothelial growth factor A, long form
CHEMBL1783
 EC50 7.38 7.38 42.0 3
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.64 4.64 23000.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.34 4.34 46000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6298.44 ng.hr.mL-1 Mus musculus
AUC 1962.75 ng.hr.mL-1 Rattus norvegicus
AUC 2376.77 ng.hr.mL-1 Canis lupus familiaris
CL 19.9 mL.min-1.kg-1 Mus musculus
CL 29.2 mL.min-1.kg-1 Mus musculus
CL 34.6 mL.min-1.kg-1 Rattus norvegicus
CL 21.5 mL.min-1.kg-1 Canis lupus familiaris
CL 4.7 mL.min-1.kg-1 Homo sapiens
CL 22.6 mL.min-1.kg-1 Rattus norvegicus
CL 5.0 mL.min-1.kg-1 Canis lupus familiaris
CL 5.4 mL.min-1.kg-1 Macaca mulatta
F 110.0 % Mus musculus
F 40.0 % Rattus norvegicus
F 87.0 % Canis lupus familiaris
T1/2 3.3 hr Mus musculus
T1/2 3.3 hr Rattus norvegicus
T1/2 11.0 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aryl hydrocarbon receptor nuclear translocator/Endothelial PAS domain-containing protein 1 IC50 = 2.0 nM 8.7 Inhibition of human recombinant N-terminal His6Gb1-TEV-GEFKGL-tagged HIF-2alpha ... 37403966
Endothelial PAS domain-containing protein 1 IC50 = 8.5 nM 8.07 Scintillation Proximity Assay (SPA): HIF-2a: The total assay volume was about 10... -
Endothelial PAS domain-containing protein 1 IC50 = 12.0 nM 7.92 Inhibition of N-(3-Chlorophenyl-4,6-t2)-4-nitrobenzo[c][1,2,5]oxadiazol-5-amine ... 31282155
Endothelial PAS domain-containing protein 1 IC50 = 12.0 nM 7.92 Binding affinity to His-tagged HIF-2alpha PAS-B domain (unknown origin) after 2 ... 30289716
Endothelial PAS domain-containing protein 1 Kd = 17.0 nM 7.77 Binding affinity to human recombinant HIF-2alpha (240 to 350 residues) assessed ... 37403966
Endothelial PAS domain-containing protein 1 IC50 = 17.0 nM 7.77 Scintillation Proximity Assay (SPA): HIF-2a: The total assay volume was about 10... -
Endothelial PAS domain-containing protein 1 EC50 = 27.0 nM 7.57 Inhibition of HIF-2alpha (unknown origin) expressed in human 786-O cells measure... 31282155
Endothelial PAS domain-containing protein 1 IC50 = 27.0 nM 7.57 Inhibition of HIF-2alpha transcriptional activity in human 786-0 cells transfect... 37403966
Endothelial PAS domain-containing protein 1 EC50 = 27.0 nM 7.57 Antagonist activity at HIF-2alpha in human 786-O cells co-expressing HIF respons... 30289716
Endothelial PAS domain-containing protein 1 IC50 = 39.0 nM 7.41 Inhibition of HIF-2alpha transcriptional activity in human 786-0 cells assessed ... 37403966
Endothelial PAS domain-containing protein 1 EC50 = 41.0 nM 7.39 Antagonist activity at HIF-2alpha in human 786-O cells assessed as reduction in ... 30289716
Vascular endothelial growth factor A, long form EC50 = 42.0 nM 7.38 ELISA Assay: VEGF: Four hours later, serial dilutions of 10x compound stocks wer... -
Vascular endothelial growth factor A, long form EC50 = 42.0 nM 7.38 ELISA Assay: About 7500 of 786-0 cells in 180 μL of growth medium were seeded in... -
Vascular endothelial growth factor A, long form EC50 = 42.0 nM 7.38 ELISA Assay: Four hours later, serial dilutions of 10× compound stocks were made... -
Endothelial PAS domain-containing protein 1 EC50 = 46.0 nM 7.34 Inhibition of HIF-2alpha (unknown origin) expressed in human 786-O cells assesse... 31282155
Endothelial PAS domain-containing protein 1 EC50 = 158.0 nM 6.8 Antagonist activity at HIF-2alpha in human 786-O cells assessed as free plasma a... 30289716
Cytochrome P450 2C9 IC50 = 23000.0 nM 4.64 Inhibition of of CYP2C9 in human liver microsomes using diclofenac as substrate ... 30289716
Cytochrome P450 2C19 IC50 = 46000.0 nM 4.34 Inhibition of of CYP2C19 in human liver microsomes using S-mephenytoin as substr... 30289716

Literature References

PubMed DOI Target Context # Activities
31282155 10.1021/acs.jmedchem.9b00719 ADMET 15
30289716 10.1021/acs.jmedchem.8b01196 ADMET 13
30289716 10.1021/acs.jmedchem.8b01196 Mus musculus 11
31282155 10.1021/acs.jmedchem.9b00719 Endothelial PAS domain-containing protein 1 5
31282155 10.1021/acs.jmedchem.9b00719 UDP-glucuronosyltransferase 2B17 5
30289716 10.1021/acs.jmedchem.8b01196 Canis familiaris 5
30289716 10.1021/acs.jmedchem.8b01196 Rattus norvegicus 5
30289716 10.1021/acs.jmedchem.8b01196 Endothelial PAS domain-containing protein 1 4
37403966 10.1021/acs.jmedchem.3c00332 Endothelial PAS domain-containing protein 1 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
30289716 10.1021/acs.jmedchem.8b01196 786-0 2
37403966 10.1021/acs.jmedchem.3c00332 J774.A1 2
31282155 10.1021/acs.jmedchem.9b00719 No relevant target 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
30289716 10.1021/acs.jmedchem.8b01196 No relevant target 1
30289716 10.1021/acs.jmedchem.8b01196 Cytochrome P450 2B6 1
30289716 10.1021/acs.jmedchem.8b01196 Cytochrome P450 2C8 1
30289716 10.1021/acs.jmedchem.8b01196 Cytochrome P450 2D6 1
30289716 10.1021/acs.jmedchem.8b01196 Cytochrome P450 3A4 1
30289716 10.1021/acs.jmedchem.8b01196 Cytochrome P450 2C19 1

Data from ChEMBL 36 via Core Engine