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Compound Detail

CHEMBL3787587

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O=C(NCc1cc(Cl)ccc1-n1cnnn1)[C@@H]1CC=NN1C(=O)[C@H](O)c1ccc(F)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3787587
Phase Preclinical
Structure Type MOL
InChI Key GMKHQRCPNMGCIX-ZWKOTPCHSA-N
14
Targets
17
Activities
2
Assay Types
10
PK Parameters
20
Publications
0
Known Names

Molecular Properties

457.9
MW (Da)
1.39
ALogP
8
HBA
2
HBD
125.6
PSA (Ų)
0.58
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H17ClFN7O3
MW 457.85
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -1.86

Activity Summary

IC50 16 meas. best 8.52
Ki 1 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 9.52 9.52 0.3 1
Unchecked
CHEMBL612545
 IC50 8.52 8.52 3.0 1
Prothrombin
CHEMBL204
 IC50 8.4 8.4 4.0 1
Plasma
CHEMBL613652
 IC50 7.89 7.89 13.0 1
Rattus norvegicus
CHEMBL376
 IC50 6.75 6.525 180.0 2
Trypsin-3
CHEMBL4551
 IC50 6.39 6.39 410.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.15 6.115 710.0 2
Serine protease 1
CHEMBL209
 IC50 5.8 5.8 1600.0 1
Coagulation factor X
CHEMBL244
 IC50 5.57 5.57 2700.0 1
Tissue-type plasminogen activator
CHEMBL1873
 IC50 5.51 5.51 3100.0 1
Coagulation factor XI
CHEMBL2820
 IC50 5.34 5.34 4600.0 1
Thromboxane A2 receptor
CHEMBL2069
 IC50 4.86 4.86 13700.0 1
Coagulation factor IX
CHEMBL2016
 IC50 4.77 4.77 17000.0 1
Plasma kallikrein
CHEMBL2000
 IC50 4.72 4.72 19000.0 1
Coagulation factor VII
CHEMBL3991
 IC50 4.29 4.29 51000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 12.0 mL.min-1.g-1 Homo sapiens
CL 15.0 mL.min-1.g-1 Rattus norvegicus
CL 25.0 mL.min-1.kg-1 Rattus norvegicus
F 75.0 % Rattus norvegicus
Fu 0.13 - Cavia porcellus
Fu 0.34 - Homo sapiens
Fu 0.26 - Canis lupus familiaris
Fu 0.33 - Mus musculus
Fu 0.36 - Rattus norvegicus
T1/2 2.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.3 nM 9.52 Inhibition of human alpha thrombin after 40 mins using S-2366 chromogenic substr... -
Unchecked IC50 = 3.0 nM 8.52 Inhibition of human alpha thrombin after 40 mins using S-2366 chromogenic substr... -
Prothrombin IC50 = 4.0 nM 8.4 Inhibition of thrombin (unknown origin) -
Plasma IC50 = 13.0 nM 7.89 Anticoagulant activity in rat citrated plasma assessed as thrombin clotting time... -
Rattus norvegicus IC50 = 180.0 nM 6.75 Anticoagulant activity in rat plasma assessed as inhibition of venous thrombosis -
Trypsin-3 IC50 = 410.0 nM 6.39 Inhibition of trypsin 4 (unknown origin) -
Rattus norvegicus IC50 = 500.0 nM 6.3 Anticoagulant activity in rat plasma assessed as inhibition of arterial thrombos... -
NON-PROTEIN TARGET IC50 = 710.0 nM 6.15 Anticoagulant activity in human citrated plasma assessed as concentration requir... -
NON-PROTEIN TARGET IC50 = 830.0 nM 6.08 Anticoagulant activity in rat plasma assessed as concentration required to doubl... -
Serine protease 1 IC50 = 1600.0 nM 5.8 Inhibition of trypsin 1 (unknown origin) -
Coagulation factor X IC50 = 2700.0 nM 5.57 Inhibition of F10a (unknown origin) -
Tissue-type plasminogen activator IC50 = 3100.0 nM 5.51 Inhibition of tPA (unknown origin) -
Coagulation factor XI IC50 = 4600.0 nM 5.34 Inhibition of F11a (unknown origin) -
Thromboxane A2 receptor IC50 = 13700.0 nM 4.86 Binding affinity to thromboxane A2 receptor (unknown origin) -
Coagulation factor IX IC50 = 17000.0 nM 4.77 Inhibition of F9a (unknown origin) -
Plasma kallikrein IC50 = 19000.0 nM 4.72 Inhibition of kallikrein (unknown origin) -
Coagulation factor VII IC50 = 51000.0 nM 4.29 Inhibition of F7a (unknown origin) -

Literature References

PubMed DOI Target Context # Activities
- 10.1039/C5MD00479A Unchecked 18
- 10.1039/C5MD00479A Rattus norvegicus 7
- 10.1039/C5MD00479A Molecular identity unknown 5
- 10.1039/C5MD00479A Mus musculus 5
- 10.1039/C5MD00479A Thromboxane A2 receptor 3
- 10.1039/C5MD00479A NON-PROTEIN TARGET 2
- 10.1039/C5MD00479A Liver microsome 2
- 10.1039/C5MD00479A Homo sapiens 1
- 10.1039/C5MD00479A Tissue-type plasminogen activator 1
- 10.1039/C5MD00479A Plasma kallikrein 1
- 10.1039/C5MD00479A Coagulation factor XI 1
- 10.1039/C5MD00479A Coagulation factor X 1
- 10.1039/C5MD00479A Coagulation factor IX 1
- 10.1039/C5MD00479A Coagulation factor VII 1
- 10.1039/C5MD00479A Trypsin-3 1
- 10.1039/C5MD00479A Serine protease 1 1
- 10.1039/C5MD00479A Prothrombin 1
- 10.1039/C5MD00479A No relevant target 1
- 10.1039/C5MD00479A Cytochrome P450 3A4 1
- 10.1039/C5MD00479A Plasma 1

Data from ChEMBL 36 via Core Engine