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Compound Detail

CHEMBL176140

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CS(=O)(=O)c1ccccc1-c1ccc(NC(=O)c2cc(C(F)(F)F)nn2-c2cccc(CN)c2)c(F)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL176140
Phase Preclinical
Structure Type MOL
InChI Key ZLUOAFAJSUPHOG-UHFFFAOYSA-N
9
Targets
18
Activities
3
Assay Types
7
PK Parameters
20
Publications
0
Known Names

Molecular Properties

532.5
MW (Da)
4.81
ALogP
6
HBA
2
HBD
107.1
PSA (Ų)
0.35
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H20F4N4O3S
MW 532.52
Aromatic Rings 4
Heavy Atoms 37
NP-Likeness -1.75

Activity Summary

Ki 16 meas. best 9.82
EC50 1 meas. best 6.86
IC50 1 meas. best 6.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Coagulation factor X
CHEMBL244
 Ki 9.82 9.76 0.1 5
Serine protease 1
CHEMBL209
 Ki 7.22 7.22 60.0 1
Trypsin
CHEMBL2095204
 Ki 7.22 7.22 60.0 2
Unchecked
CHEMBL612545
 Ki 7.22 7.22 60.0 1
Kallikrein-1
CHEMBL2319
 Ki 7.21 7.21 61.0 1
Oryctolagus cuniculus
CHEMBL374
 EC50 6.86 6.86 137.0 1
Oryctolagus cuniculus
CHEMBL374
 IC50 6.82 6.82 150.0 1
Vitamin K-dependent protein C
CHEMBL4444
 Ki 5.75 5.75 1800.0 1
Coagulation factor IX
CHEMBL2016
 Ki 5.66 5.66 2200.0 1
Prothrombin
CHEMBL204
 Ki 5.22 5.22 6000.0 4

Pharmacokinetic Data

Parameter Value Units Species
CL 4.0 mL.min-1.kg-1 Canis lupus familiaris
CL 4.0 mL.min-1.kg-1 Canis lupus familiaris
F 57.0 % Canis lupus familiaris
F 57.0 % Canis lupus familiaris
T1/2 7.5 hr Canis lupus familiaris
T1/2 2.067 hr Homo sapiens
T1/2 7.5 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Coagulation factor X Ki = 0.15 nM 9.82 Binding affinity against human Coagulation factor Xa 15771420
Coagulation factor X Ki = 0.15 nM 9.82 Inhibition of human factor 10a 20100660
Coagulation factor X Ki = 0.15 nM 9.82 Inhibition of factor 10a 20503967
Coagulation factor X Ki = 0.15 nM 9.82 Binding affinity to human FXa assessed as inhibition constant 27322757
Coagulation factor X Ki = 0.3 nM 9.52 Inhibition of human factor 10a 17174550
Serine protease 1 Ki = 60.0 nM 7.22 Binding affinity determined against human trypsin 15771420
Trypsin Ki = 60.0 nM 7.22 Inhibition of trypsin 17174550
Trypsin Ki = 60.0 nM 7.22 Inhibition of human trypsin 20100660
Unchecked Ki = 60.0 nM 7.22 Inhibition of trypsin 20503967
Kallikrein-1 Ki = 61.0 nM 7.21 Binding affinity determined against human kallikrein 15771420
Oryctolagus cuniculus EC50 = 137.0 nM 6.86 Antithrombotic activity in iv dosed rabbit assessed as restoration of integrated... 20503967
Oryctolagus cuniculus IC50 = 150.0 nM 6.82 Antithrombotic activity in iv dosed rabbit assessed as reduction in thrombus wei... 20503967
Vitamin K-dependent protein C Ki = 1800.0 nM 5.75 Binding affinity determined against human activated protein C 15771420
Coagulation factor IX Ki = 2200.0 nM 5.66 Binding affinity against human Coagulation factor IX 15771420
Prothrombin Ki = 6000.0 nM 5.22 Binding affinity against human thrombin 15771420
Prothrombin Ki = 6000.0 nM 5.22 Inhibition of thrombin 17174550
Prothrombin Ki = 6000.0 nM 5.22 Inhibition of human factor 2a 20100660
Prothrombin Ki = 6000.0 nM 5.22 Inhibition of thrombin 20503967

Literature References

PubMed DOI Target Context # Activities
20503967 10.1021/jm100146h Canis familiaris 4
17174550 10.1016/j.bmcl.2006.11.071 Canis familiaris 4
20503967 10.1021/jm100146h Oryctolagus cuniculus 2
17174550 10.1016/j.bmcl.2006.11.071 Unchecked 2
17174550 10.1016/j.bmcl.2006.11.071 Coagulation factor X 1
17174550 10.1016/j.bmcl.2006.11.071 Tissue-type plasminogen activator 1
27322757 10.1016/j.ejmech.2016.05.039 Coagulation factor X 1
17174550 10.1016/j.bmcl.2006.11.071 Vitamin K-dependent protein C 1
17174550 10.1016/j.bmcl.2006.11.071 Plasma kallikrein 1
17174550 10.1016/j.bmcl.2006.11.071 Trypsin 1
17174550 10.1016/j.bmcl.2006.11.071 Prothrombin 1
15771420 10.1021/jm0497949 Coagulation factor X 1
15771420 10.1021/jm0497949 Vitamin K-dependent protein C 1
15771420 10.1021/jm0497949 Urokinase-type plasminogen activator 1
15771420 10.1021/jm0497949 Chymotrypsinogen B 1
15771420 10.1021/jm0497949 Coagulation factor VII 1
15771420 10.1021/jm0497949 Coagulation factor IX 1
15771420 10.1021/jm0497949 Prothrombin 1
15771420 10.1021/jm0497949 Kallikrein-1 1
15771420 10.1021/jm0497949 Serine protease 1 1

Data from ChEMBL 36 via Core Engine