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Compound Detail

CHEMBL3629567

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O=C(N[C@@H](Cn1ccnc1)c1ccc(-c2ccc(F)cc2)cc1F)c1ccc(-c2nnc(-c3ccccc3)o2)cc1

Basic Information

ChEMBL ID CHEMBL3629567
Phase Preclinical
Structure Type MOL
InChI Key YTJXXDVLDUKYHV-LJAQVGFWSA-N
9
Targets
14
Activities
3
Assay Types
10
PK Parameters
18
Publications
0
Known Names

Molecular Properties

547.6
MW (Da)
6.72
ALogP
6
HBA
1
HBD
85.8
PSA (Ų)
0.23
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C32H23F2N5O2
MW 547.57
Aromatic Rings 6
Heavy Atoms 41
NP-Likeness -1.28

Activity Summary

EC50 6 meas. best 9.0
IC50 4 meas. best 9.1
Kd 4 meas. best 8.17

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma cruzi
CHEMBL368
IC50 9.1 9.1 0.8 1
Trypanosoma cruzi
CHEMBL368
EC50 9.0 8.91 1.0 2
Sterol 14-alpha demethylase
CHEMBL1075110
Kd 8.17 8.17 6.8 1
Putative lanosterol 14-alpha-demethylase
CHEMBL4295531
Kd 8.08 8.08 8.4 1
Unchecked
CHEMBL612545
Kd 8.0 8.0 10.0 1
Lanosterol 14-alpha demethylase
CHEMBL3849
Kd 7.05 7.05 90.0 1
Unchecked
CHEMBL612545
IC50 5.23 4.885 5940.0 2
MCF7
CHEMBL387
EC50 5.0 5.0 10000.0 1
A549
CHEMBL392
EC50 5.0 5.0 10000.0 1
MDA-MB-436
CHEMBL4296465
EC50 5.0 5.0 10000.0 1
A-431
CHEMBL614069
EC50 5.0 5.0 10000.0 1
Lanosterol 14-alpha demethylase
CHEMBL3849
IC50 4.61 4.61 24400.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 29.9 mL.min-1.kg-1 Homo sapiens
CL 12.3 mL.min-1.kg-1 Homo sapiens
CL 17.7 mL.min-1.kg-1 Rattus norvegicus
CL 14.2 mL.min-1.kg-1 Rattus norvegicus
CL 145.0 mL.min-1.kg-1 Mus musculus
CL 55.6 mL.min-1.kg-1 Mus musculus
Cmax 24000.0 nM Mus musculus
T1/2 0.7 hr Homo sapiens
T1/2 2.633 hr Rattus norvegicus
T1/2 0.6333 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma cruzi IC50 = 0.8 nM 9.1 Antiparasitic activity against Trypanosoma cruzi Tulahuen strain amastigotes 32818869
Trypanosoma cruzi EC50 = 1.0 nM 9.0 Antiparasitic activity against GFP-expressing Trypanosoma cruzi Tulahuen amastig... 30451500
Trypanosoma cruzi EC50 = 1.5 nM 8.82 Antiparasitic activity against GFP-expressing Trypanosoma cruzi Y amastigote for... 30451500
Sterol 14-alpha demethylase Kd = 6.8 nM 8.17 Binding affinity to Trypanosoma cruzi Y CYP51A expressed in Escherichia coli 30451500
Putative lanosterol 14-alpha-demethylase Kd = 8.4 nM 8.08 Binding affinity to Leishmania infantum CYP51 expressed in Escherichia coli 30451500
Unchecked Kd = 10.0 nM 8.0 Binding affinity to Naegleria fowleri CYP51 expressed in Escherichia coli HMS-17... 34842434
Lanosterol 14-alpha demethylase Kd = 90.0 nM 7.05 Binding affinity to recombinant full length human CYP51 expressed in Escherichia... 31663733
Unchecked IC50 = 5940.0 nM 5.23 Inhibition of Naegleria fowleri CYP51 catalytic activity using [3-3H]sterol subs... 34842434
A549 EC50 = 10000.0 nM 5.0 Antiproliferative activity against human A549 cells assessed as reduction in cel... 31663733
MCF7 EC50 = 10000.0 nM 5.0 Antiproliferative activity against human MCF7 cells assessed as reduction in cel... 31663733
MDA-MB-436 EC50 = 10000.0 nM 5.0 Antiproliferative activity against human MDA-MB-436 cells assessed as reduction ... 31663733
A-431 EC50 = 10000.0 nM 5.0 Antiproliferative activity against human A431 cells assessed as reduction in cel... 31663733
Lanosterol 14-alpha demethylase IC50 = 24400.0 nM 4.61 Inhibition of recombinant full length human CYP51 expressed in Escherichia coli ... 31663733
Unchecked IC50 = 28900.0 nM 4.54 Catalytic inhibition of Acanthamoeba castellanii CYP51 expressed in Escherichia ... 38683753

Literature References

Data from ChEMBL 36 via Core Engine