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CHEMBL3902498

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Cc1cc2ccc1[C@@H](C)COC(=O)Nc1ccc(S(=O)(=O)C3CC3)c(c1)CN(C)C(=O)[C@@H]2Nc1ccc2c(N)ncc(F)c2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3902498
Phase Preclinical
Structure Type MOL
InChI Key ZVYUEFHDJYEETD-WWOZWPLTSA-N
15
Targets
17
Activities
2
Assay Types
9
PK Parameters
17
Publications
0
Known Names

Molecular Properties

631.7
MW (Da)
5.68
ALogP
8
HBA
3
HBD
143.7
PSA (Ų)
0.26
QED
2
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C33H34FN5O5S
MW 631.73
Aromatic Rings 4
Heavy Atoms 45
NP-Likeness -0.25

Activity Summary

Ki 16 meas. best 9.37
EC50 1 meas. best 6.44

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Coagulation factor VII/tissue factor
CHEMBL2095194
 Ki 9.37 9.37 0.4 1
Coagulation factor VII
CHEMBL3991
 Ki 9.37 7.78 0.4 2
Vitamin K-dependent protein C
CHEMBL4444
 Ki 6.72 6.72 190.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 6.44 6.44 360.0 1
Plasma kallikrein
CHEMBL2000
 Ki 6.28 6.28 520.0 1
Kallikrein-1
CHEMBL2319
 Ki 6.19 6.19 650.0 1
Plasminogen
CHEMBL1801
 Ki 5.82 5.82 1500.0 1
Coagulation factor IX
CHEMBL2016
 Ki 5.8 5.8 1600.0 1
Unchecked
CHEMBL612545
 Ki 5.52 5.145 3000.0 2
Coagulation factor XI
CHEMBL2820
 Ki 5.47 5.47 3400.0 1
Coagulation factor X
CHEMBL244
 Ki 5.4 5.4 4000.0 1
Coagulation factor XII
CHEMBL2821
 Ki 5.12 5.12 7500.0 1
Tissue-type plasminogen activator
CHEMBL1873
 Ki 5.04 5.04 9100.0 1
Prothrombin
CHEMBL204
 Ki 4.96 4.96 11000.0 1
Urokinase-type plasminogen activator
CHEMBL3286
 Ki 4.82 4.82 15000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 8.0 mL.min-1.kg-1 Canis lupus familiaris
F 40.0 % Canis lupus familiaris
Fu 0.026 - Oryctolagus cuniculus
Fu 0.014 - Canis lupus familiaris
Fu 0.023 - Homo sapiens
T1/2 8.0 hr Canis lupus familiaris
T1/2 0.03167 hr Rattus norvegicus
T1/2 0.4333 hr Canis lupus familiaris
T1/2 0.75 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Coagulation factor VII/tissue factor Ki = 0.43 nM 9.37 Inhibition of full-length human TF/recombinant human factor 7a assessed as decre... 27455395
Coagulation factor VII Ki = 0.43 nM 9.37 In Vitro Assay: FVIIa-Xase Ki (37° C.): S2765 (0.5 mM), PCPS (25 μM), calcium ch... -
Vitamin K-dependent protein C Ki = 190.0 nM 6.72 Inhibition of human activated protein C using pyroGlu-Pro-Arg-pNA as substrate a... 27455395
NON-PROTEIN TARGET EC50 = 360.0 nM 6.44 Antithrombotic activity in iv dosed New Zealand White rabbit electrically-induce... 27455395
Plasma kallikrein Ki = 520.0 nM 6.28 Inhibition of human plasma kallikrein using H-(D)-Pro-Phe-Arg-pNA as substrate a... 27455395
Kallikrein-1 Ki = 650.0 nM 6.19 Inhibition of human HK1 using H-D-Val-Leu-Arg-AFC as substrate assessed as relea... 27455395
Coagulation factor VII Ki = 650.0 nM 6.19 In Vitro Assay: Tissue kallikrein-1 (37° C) activity was determined in reactions... -
Plasminogen Ki = 1500.0 nM 5.82 Inhibition of human plasmin using H-(D)-Val-Leu-LyspNA as substrate assessed as ... 27455395
Coagulation factor IX Ki = 1600.0 nM 5.8 Inhibition of human factor 9a using methylsulfonyl-D-cyclohexylglycyl-Gly-Arg-AM... 27455395
Unchecked Ki = 3000.0 nM 5.52 Inhibition of trypsin (unknown origin) using N-benzoyl-Ile-Glu-(OH,OMe)-Gly-Arg-... 27455395
Coagulation factor XI Ki = 3400.0 nM 5.47 Inhibition of human factor 11a using pyroGlu-Pro-Arg-pNA as substrate assessed a... 27455395
Coagulation factor X Ki = 4000.0 nM 5.4 Inhibition of human factor 10a using N-benzoyl-Ile-Glu-(OH,OMe)-Gly-Arg-pNA as s... 27455395
Coagulation factor XII Ki = 7500.0 nM 5.12 Inhibition of human factor 12a using H-(D)-CHT-Gly-Arg-pNA as substrate assessed... 27455395
Tissue-type plasminogen activator Ki = 9100.0 nM 5.04 Inhibition of human recombinant tPA using methylsulfonyl-D-cyclohexylalanylGly-A... 27455395
Prothrombin Ki = 11000.0 nM 4.96 Inhibition of alpha-thrombin (unknown origin) using pyroGlu-Pro-Arg-pNA as subst... 27455395
Urokinase-type plasminogen activator Ki = 15000.0 nM 4.82 Inhibition of human urokinase using pyro-Glu-Gly-Arg-pNA as substrate assessed a... 27455395
Unchecked Ki = 17000.0 nM 4.77 Inhibition of chymotrypsin (unknown origin) using MeO-SucArg-Pro-Tyr-pNA as subs... 27455395

Literature References

PubMed DOI Target Context # Activities
27455395 10.1021/acs.jmedchem.6b00469 Unchecked 17
27455395 10.1021/acs.jmedchem.6b00469 ADMET 11
27455395 10.1021/acs.jmedchem.6b00469 NON-PROTEIN TARGET 3
27455395 10.1021/acs.jmedchem.6b00469 Coagulation factor VII/tissue factor 2
27455395 10.1021/acs.jmedchem.6b00469 No relevant target 1
27455395 10.1021/acs.jmedchem.6b00469 Kallikrein-1 1
27455395 10.1021/acs.jmedchem.6b00469 Coagulation factor IX 1
27455395 10.1021/acs.jmedchem.6b00469 Coagulation factor XII 1
27455395 10.1021/acs.jmedchem.6b00469 Plasma kallikrein 1
27455395 10.1021/acs.jmedchem.6b00469 Vitamin K-dependent protein C 1
27455395 10.1021/acs.jmedchem.6b00469 Plasminogen 1
27455395 10.1021/acs.jmedchem.6b00469 Tissue-type plasminogen activator 1
27455395 10.1021/acs.jmedchem.6b00469 Urokinase-type plasminogen activator 1
27455395 10.1021/acs.jmedchem.6b00469 Voltage-gated inwardly rectifying potassium channel KCNH2 1
27455395 10.1021/acs.jmedchem.6b00469 Coagulation factor X 1
27455395 10.1021/acs.jmedchem.6b00469 Coagulation factor XI 1
27455395 10.1021/acs.jmedchem.6b00469 Prothrombin 1

Data from ChEMBL 36 via Core Engine