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Compound Detail

CHEMBL4086008

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CN(C/C=C/c1ccc(-c2ccccc2)cc1)Cc1coc2ccccc12.Cl

Basic Information

ChEMBL ID CHEMBL4086008
Phase Preclinical
Structure Type MOL
InChI Key QDPAOFJRNBDFSD-USRGLUTNSA-N
Parent Compound CHEMBL4116938
Active Moiety CHEMBL4116938
13
Targets
26
Activities
1
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

353.5
MW (Da)
6.25
ALogP
2
HBA
0
HBD
16.4
PSA (Ų)
0.41
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 C25H24ClNO
MW 389.93
Aromatic Rings 4
Heavy Atoms 27
NP-Likeness -0.33

Activity Summary

IC50 26 meas. best 10.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
IC50 10.7 8.911 0.0 10
4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming)
CHEMBL4105905
IC50 9.1 9.1 0.8 1
4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming)
CHEMBL3813586
IC50 8.74 7.9467 1.8 3
4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming)
CHEMBL4105865
IC50 8.72 8.72 1.9 1
4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming)
CHEMBL3832958
IC50 8.1 8.1 7.9 1
Cytochrome P450 2D6
CHEMBL289
IC50 5.5 5.5 3200.0 1
Cytochrome P450 1A2
CHEMBL3356
IC50 5.24 5.24 5700.0 1
Cytochrome P450 2C9
CHEMBL3397
IC50 5.0 5.0 10000.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 5.0 5.0 10000.0 2
Cytochrome P450 2C19
CHEMBL3622
IC50 5.0 5.0 10000.0 1
Cytochrome P450 2C8
CHEMBL3721
IC50 5.0 5.0 10000.0 1
Cytochrome P450 2B6
CHEMBL4729
IC50 5.0 5.0 10000.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 4.46 4.46 34800.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2805.48 ng.hr.mL-1 Rattus norvegicus
AUC 898.7 ng.hr.mL-1 Rattus norvegicus
AUC 974951.4 ng.hr.mL-1 Rattus norvegicus
AUC 2862.41 ng.hr.mL-1 Rattus norvegicus
AUC 930.33 ng.hr.mL-1 Rattus norvegicus
AUC 1086152.29 ng.hr.mL-1 Rattus norvegicus
AUC 1067.27 ng.hr.mL-1 Mus musculus
AUC 4528.41 ng.hr.mL-1 Mus musculus
AUC 1089.95 ng.hr.mL-1 Mus musculus
AUC 4556.4 ng.hr.mL-1 Mus musculus
CL 1230.0 mL.min-1.g-1 Homo sapiens
CL 31600.0 mL.min-1.g-1 Homo sapiens
CL 29.17 mL.min-1.kg-1 Rattus norvegicus
CL 30.67 mL.min-1.kg-1 Mus musculus
Cmax 13039.3 nM Rattus norvegicus
Cmax 601.47 nM Rattus norvegicus
Cmax 369140.24 nM Rattus norvegicus
Cmax 6308.88 nM Mus musculus
Cmax 2266.67 nM Mus musculus
F 16.3 % Rattus norvegicus
F 83.84 % Mus musculus
T1/2 0.845 hr Homo sapiens
T1/2 2.46 hr Rattus norvegicus
T1/2 1.29 hr Rattus norvegicus
T1/2 7.61 hr Rattus norvegicus
T1/2 2.05 hr Mus musculus
T1/2 3.35 hr Mus musculus
Tmax 0.08 hr Rattus norvegicus
Tmax 2.0 hr Rattus norvegicus
Tmax 3.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 0.02 nM 10.7 Inhibition of CrtN in methicillin-resistant Staphylococcus aureus HS663 assessed... 29243920
Unchecked IC50 = 0.2 nM 9.7 Inhibition of CrtN in methicillin-resistant Staphylococcus aureus XN108 assessed... 29243920
4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming) IC50 = 0.8 nM 9.1 Inhibition of CrtN in methicillin-resistant Staphylococcus aureus Mu50 assessed ... 29243920
Unchecked IC50 = 1.0 nM 9.0 Inhibition of CrtN in methicillin-resistant Staphylococcus aureus NF65Y assessed... 29243920
Unchecked IC50 = 1.2 nM 8.92 Inhibition of CrtN in methicillin-resistant Staphylococcus aureus NRS100 assesse... 29243920
Unchecked IC50 = 1.6 nM 8.8 Inhibition of CrtN in methicillin-resistant Staphylococcus aureus LRSA202 assess... 29243920
Unchecked IC50 = 1.7 nM 8.77 Inhibition of CrtN in methicillin-resistant Staphylococcus aureus NRS70 assessed... 29243920
Unchecked IC50 = 1.8 nM 8.74 Inhibition of CrtN in methicillin-resistant Staphylococcus aureus LRSA56 assesse... 29243920
4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming) IC50 = 1.8 nM 8.74 Inhibition of CrtN in Staphylococcus aureus Newman after 12 resistant developmen... 29243920
4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming) IC50 = 1.9 nM 8.72 Inhibition of CrtN in methicillin-resistant Staphylococcus aureus LAC USA300 ass... 29243920
4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming) IC50 = 2.0 nM 8.7 Inhibition of CrtN in Staphylococcus aureus Newman assessed as reduction in stap... 29243920
Unchecked IC50 = 5.6 nM 8.25 Inhibition of CrtN in methicillin-resistant Staphylococcus aureus NRS108 assesse... 29243920
Unchecked IC50 = 5.6 nM 8.25 Inhibition of CrtN in methicillin-resistant Staphylococcus aureus NRS271 assesse... 29243920
4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming) IC50 = 7.9 nM 8.1 Inhibition of CrtN in methicillin-resistant Staphylococcus aureus USA400 MW2 ass... 29243920
Unchecked IC50 = 10.5 nM 7.98 Inhibition of CrtN in methicillin-resistant Staphylococcus aureus LRSA205 assess... 29243920
4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming) IC50 = 400.0 nM 6.4 Inhibition of Staphylococcus aureus Newman 6His-tagged CrtN expressed in Escheri... 29243920
Cytochrome P450 2D6 IC50 = 3200.0 nM 5.5 Inhibition of CYP2D6 in human liver microsomes using dextromethorphan as substra... 29243920
Cytochrome P450 1A2 IC50 = 5700.0 nM 5.24 Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate upt... 29243920
Cytochrome P450 2B6 IC50 = 10000.0 nM 5.0 Inhibition of CYP2B6 in human liver microsomes using bupropion as substrate upto... 29243920
Cytochrome P450 2C8 IC50 = 10000.0 nM 5.0 Inhibition of CYP2C8 in human liver microsomes using paclitaxel as substrate upt... 29243920

Literature References

PubMed DOI Target Context # Activities
29243920 10.1021/acs.jmedchem.7b01300 Staphylococcus aureus 62
29243920 10.1021/acs.jmedchem.7b01300 Rattus norvegicus 26
29243920 10.1021/acs.jmedchem.7b01300 4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming) 13
29243920 10.1021/acs.jmedchem.7b01300 Mus musculus 12
29243920 10.1021/acs.jmedchem.7b01300 Unchecked 10
29243920 10.1021/acs.jmedchem.7b01300 Liver 3
29243920 10.1021/acs.jmedchem.7b01300 Cytochrome P450 3A4 2
29243920 10.1021/acs.jmedchem.7b01300 Voltage-gated inwardly rectifying potassium channel KCNH2 1
29243920 10.1021/acs.jmedchem.7b01300 Trichophyton rubrum 1
29243920 10.1021/acs.jmedchem.7b01300 Nannizzia gypsea 1
29243920 10.1021/acs.jmedchem.7b01300 Trichophyton verrucosum 1
29243920 10.1021/acs.jmedchem.7b01300 Trichophyton mentagrophytes 1
29243920 10.1021/acs.jmedchem.7b01300 Cytochrome P450 1A2 1
29243920 10.1021/acs.jmedchem.7b01300 Cytochrome P450 2B6 1
29243920 10.1021/acs.jmedchem.7b01300 Cytochrome P450 2C8 1
29243920 10.1021/acs.jmedchem.7b01300 Cytochrome P450 2C9 1
29243920 10.1021/acs.jmedchem.7b01300 Cytochrome P450 2C19 1
29243920 10.1021/acs.jmedchem.7b01300 Enterococcus faecium 1
29243920 10.1021/acs.jmedchem.7b01300 No relevant target 1
29243920 10.1021/acs.jmedchem.7b01300 HepG2 1

Data from ChEMBL 36 via Core Engine