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Compound Detail

CHEMBL3318100

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COc1cc(C(=O)c2ccn(-c3cccc(N)c3)c2)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3318100
Phase Preclinical
Structure Type MOL
InChI Key RLKGRFCJEXIHGX-UHFFFAOYSA-N
13
Targets
17
Activities
1
Assay Types
13
PK Parameters
20
Publications
0
Known Names

Molecular Properties

352.4
MW (Da)
3.32
ALogP
6
HBA
1
HBD
75.7
PSA (Ų)
0.54
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 C20H20N2O4
MW 352.39
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -0.54

Activity Summary

IC50 17 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NCI/ADR-RES
CHEMBL613829
 IC50 9.0 9.0 1.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.74 7.896 1.8 5
A549
CHEMBL392
 IC50 8.0 8.0 10.0 1
MCF7
CHEMBL387
 IC50 7.82 7.82 15.0 1
K562
CHEMBL385
 IC50 7.7 7.7 20.0 1
LAMA-84
CHEMBL2366090
 IC50 7.55 7.55 28.0 1
KU812 cell line
CHEMBL613997
 IC50 7.55 7.55 28.0 1
HeLa
CHEMBL399
 IC50 7.52 7.52 30.0 1
HT-29
CHEMBL384
 IC50 7.22 7.22 60.0 1
RD
CHEMBL614144
 IC50 7.02 7.02 95.3 1
HepG2
CHEMBL395
 IC50 6.56 6.56 274.5 1
Molecular identity unknown
CHEMBL612546
 IC50 6.17 6.17 676.0 1
Tubulin
CHEMBL2095182
 IC50 5.85 5.85 1400.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1027.67 ng.hr.mL-1 Mus musculus
AUC 1031.77 ng.hr.mL-1 Mus musculus
AUC 1324.02 ng.hr.mL-1 Mus musculus
AUC 1469.72 ng.hr.mL-1 Mus musculus
CL 80.8 mL.min-1.kg-1 Mus musculus
Cmax 9659.75 nM Mus musculus
Cmax 5014.33 nM Mus musculus
F 49.0 % Mus musculus
MRT 0.5167 hr Mus musculus
MRT 2.417 hr Mus musculus
T1/2 1.233 hr Mus musculus
T1/2 2.983 hr Mus musculus
Tmax 0.08333 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NCI/ADR-RES IC50 = 1.0 nM 9.0 Cytotoxicity against human NCI/ADR-RES cells assessed as growth inhibition after... 25025991
NON-PROTEIN TARGET IC50 = 1.8 nM 8.74 Cytotoxicity against human MESSA cells assessed as growth inhibition after 72 hr... 25025991
NON-PROTEIN TARGET IC50 = 4.6 nM 8.34 Cytotoxicity against human MESSA/DX5 cells assessed as growth inhibition after 7... 25025991
NON-PROTEIN TARGET IC50 = 7.0 nM 8.15 Cytotoxicity against human OVCAR8 cells assessed as growth inhibition after 96 h... 25025991
NON-PROTEIN TARGET IC50 = 9.8 nM 8.01 Cytotoxicity against human PC3 cells assessed as growth inhibition after 48 hrs ... 25025991
A549 IC50 = 10.0 nM 8.0 Cytotoxicity against human A549 cells assessed as growth inhibition after 48 hrs... 25025991
MCF7 IC50 = 15.0 nM 7.82 Cytotoxicity against human MCF7 cells after 96 hrs by Giemsa staining-based ligh... 25025991
K562 IC50 = 20.0 nM 7.7 Cytotoxicity against human K562 cells assessed as growth inhibition after 96 hrs... 25025991
KU812 cell line IC50 = 28.0 nM 7.55 Antiproliferative activity against human KU812 cells expressing BCR/ABL assessed... 28523104
LAMA-84 IC50 = 28.0 nM 7.55 Antiproliferative activity against human LAMA-84 cells expressing BCR/ABL assess... 28523104
HeLa IC50 = 30.0 nM 7.52 Cytotoxicity against human HeLa cells assessed as growth inhibition after 48 hrs... 25025991
HT-29 IC50 = 60.0 nM 7.22 Cytotoxicity against human HT-29 cells assessed as growth inhibition after 48 hr... 25025991
RD IC50 = 95.3 nM 7.02 Cytotoxicity against human RD cells assessed as growth inhibition after 48 hrs b... 25025991
HepG2 IC50 = 274.5 nM 6.56 Cytotoxicity against human HepG2 cells assessed as growth inhibition after 48 hr... 25025991
NON-PROTEIN TARGET IC50 = 580.0 nM 6.24 Cytotoxicity against human D283 cells 25025991
Molecular identity unknown IC50 = 676.0 nM 6.17 Inhibition of hedgehog signaling in mouse NIH/3T3 Shh-Light II cells after 48 hr... 25025991
Tubulin IC50 = 1400.0 nM 5.85 Inhibition of tubulin (unknown origin) polymerization incubated 15 mins prior to... 25025991

Literature References

PubMed DOI Target Context # Activities
25025991 10.1021/jm500561a Mus musculus 19
25025991 10.1021/jm500561a HeLa 10
25025991 10.1021/jm500561a RD 6
25025991 10.1021/jm500561a HepG2 5
25025991 10.1021/jm500561a NON-PROTEIN TARGET 5
25025991 10.1021/jm500561a Molecular identity unknown 5
25025991 10.1021/jm500561a K562 2
25025991 10.1021/jm500561a ADMET 2
26132075 10.1021/acs.jmedchem.5b00310 HeLa 2
25025991 10.1021/jm500561a Tubulin 2
25025991 10.1021/jm500561a MCF7 2
28523104 10.1021/acsmedchemlett.7b00022 LAMA-84 1
28523104 10.1021/acsmedchemlett.7b00022 KU812 cell line 1
25025991 10.1021/jm500561a NCI/ADR-RES 1
25025991 10.1021/jm500561a A549 1
25025991 10.1021/jm500561a HT-29 1
25025991 10.1021/jm500561a Cytochrome P450 3A4 1
25025991 10.1021/jm500561a Cytochrome P450 2D6 1
25025991 10.1021/jm500561a Cytochrome P450 2C9 1
25025991 10.1021/jm500561a Cytochrome P450 2C19 1

Data from ChEMBL 36 via Core Engine