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Compound Detail

CHEMBL559015

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

Basic Information

ChEMBL ID CHEMBL559015
Phase Preclinical
Structure Type MOL
InChI Key LJBVKRYJJZQKGE-UHFFFAOYSA-N
Parent Compound CHEMBL176140
Active Moiety CHEMBL176140
10
Targets
18
Activities
2
Assay Types
6
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 C25H21ClF4N4O3S
MW 568.98
Aromatic Rings 4
Heavy Atoms 37
NP-Likeness -1.75

Activity Summary

Ki 15 meas. best 9.52
IC50 3 meas. best 8.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Coagulation factor X
CHEMBL5062
 Ki 9.52 9.52 0.3 2
Coagulation factor X
CHEMBL244
 IC50 8.62 8.62 2.4 1
Serine protease 1
CHEMBL209
 Ki 7.22 7.22 60.0 1
Trypsin
CHEMBL2095204
 Ki 7.22 7.22 60.0 1
Plasma kallikrein
CHEMBL2000
 Ki 7.21 7.21 61.0 2
Coagulation factor X
CHEMBL244
 Ki 6.82 6.82 150.0 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 2
Coagulation factor IX
CHEMBL2016
 Ki 5.66 5.66 2200.0 2
Prothrombin
CHEMBL204
 Ki 5.22 5.22 6000.0 2
Complement factor H
CHEMBL4629
 IC50 4.36 4.36 44000.0 1

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 % Eutheria
T1/2 7.5 hr Canis lupus familiaris
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 = 0.3 nM 9.52 In vitro activity against rabbit factor Xa 11170646
Coagulation factor X Ki = 0.3 nM 9.52 Tested in vitro for inhibition of rabbit Coagulation factor X 14640539
Coagulation factor X IC50 = 2.4 nM 8.62 Inhibition of human factor 10a using S-2222 chromogenic substrate assessed as hy... 25523211
Trypsin Ki = 60.0 nM 7.22 In vitro activity against human trypsin. 11170646
Serine protease 1 Ki = 60.0 nM 7.22 Tested in vitro for inhibition of human trypsin 14640539
Plasma kallikrein Ki = 61.0 nM 7.21 In vitro activity against human Plasma kallikrein. 11170646
Plasma kallikrein Ki = 61.0 nM 7.21 Tested in vitro for inhibition of human plasma Kallikriene 14640539
Oryctolagus cuniculus IC50 = 150.0 nM 6.82 Inhibition of thrombus formation in rabbits. 11170646
Coagulation factor X Ki = 150.0 nM 6.82 Binding affinity against human coagulation factor X 11170646
Vitamin K-dependent protein C Ki = 1800.0 nM 5.75 In vitro activity against human Activated protein C 11170646
Vitamin K-dependent protein C Ki = 1800.0 nM 5.75 Tested in vitro for inhibition of human activated protein C 14640539
Coagulation factor IX Ki = 2200.0 nM 5.66 In vitro activity against human factor IXa 11170646
Coagulation factor IX Ki = 2200.0 nM 5.66 Tested in vitro for inhibition of human Coagulation factor IX 14640539
Prothrombin Ki = 6000.0 nM 5.22 In vitro activity against human thrombin. 11170646
Prothrombin Ki = 6000.0 nM 5.22 In vitro for inhibition of human thrombin 14640539
Complement factor H IC50 = 44000.0 nM 4.36 In vitro activity against human Complement factor I 11170646

Literature References

PubMed DOI Target Context # Activities
14640539 10.1021/jm030212h Canis familiaris 4
11170646 10.1021/jm000409z Homo sapiens 3
11170646 10.1021/jm000409z Canis familiaris 3
14640539 10.1021/jm030212h NON-PROTEIN TARGET 2
14640539 10.1021/jm030212h ADMET 2
14640539 10.1021/jm030212h Coagulation factor X 2
11170646 10.1021/jm000409z Oryctolagus cuniculus 2
25523211 10.1016/j.bmc.2014.11.042 Plasma 2
11170646 10.1021/jm000409z Coagulation factor X 2
11170646 10.1021/jm000409z Tissue-type plasminogen activator 1
14640539 10.1021/jm030212h Prothrombin 1
11170646 10.1021/jm000409z Complement factor H 1
11170646 10.1021/jm000409z Plasminogen 1
11170646 10.1021/jm000409z Urokinase-type plasminogen activator 1
11170646 10.1021/jm000409z Chymotrypsinogen B 1
11170646 10.1021/jm000409z Coagulation factor VII 1
11170646 10.1021/jm000409z Coagulation factor IX 1
11170646 10.1021/jm000409z Vitamin K-dependent protein C 1
11170646 10.1021/jm000409z Plasma kallikrein 1
11170646 10.1021/jm000409z Trypsin 1

Data from ChEMBL 36 via Core Engine