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Compound Detail

CHEMBL364123

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COc1ccc2c(C(=O)c3cc(OC)c(OC)c(OC)c3)c[nH]c2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL364123
Phase Preclinical
Structure Type MOL
InChI Key UZJVBXKFBQNDTQ-UHFFFAOYSA-N
15
Targets
30
Activities
1
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

341.4
MW (Da)
3.43
ALogP
5
HBA
1
HBD
69.8
PSA (Ų)
0.70
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 C19H19NO5
MW 341.36
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness 0.02

Activity Summary

IC50 30 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NCI-H460
CHEMBL396
 IC50 9.0 8.275 1.0 4
NUGC-3
CHEMBL614208
 IC50 9.0 9.0 1.0 1
HT-29
CHEMBL384
 IC50 8.96 8.595 1.1 2
KB
CHEMBL398
 IC50 8.75 8.384 1.8 5
MKN-45
CHEMBL614354
 IC50 8.49 8.3967 3.2 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.47 8.47 3.4 1
L1210
CHEMBL386
 IC50 8.46 8.46 3.5 1
CCRF-CEM
CHEMBL382
 IC50 8.44 8.44 3.6 1
FM3A
CHEMBL614297
 IC50 8.43 8.43 3.7 1
MES-SA
CHEMBL614343
 IC50 8.4 8.4 4.0 1
MCF7
CHEMBL387
 IC50 8.15 8.15 7.0 1
B16
CHEMBL381
 IC50 7.89 7.89 13.0 1
A549
CHEMBL392
 IC50 7.64 7.64 23.0 2
Tubulin beta-1 chain
CHEMBL1915
 IC50 5.66 5.66 2180.0 1
Unchecked
CHEMBL612545
 IC50 5.55 5.534 2800.0 5

Pharmacokinetic Data

Parameter Value Units Species
AUC 2712.0 ng.hr.mL-1 Rattus norvegicus
AUC 1311.0 ng.hr.mL-1 Rattus norvegicus
CL 0.525 mL.min-1.kg-1 Rattus norvegicus
Cmax 524.37 nM Rattus norvegicus
F 9.7 % Rattus norvegicus
T1/2 0.9 hr Rattus norvegicus
T1/2 2.8 hr Rattus norvegicus
Tmax 4.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NCI-H460 IC50 = 1.0 nM 9.0 Cytotoxicity against human H460 cells after 72 hrs by methylene blue dye assay 19586033
NUGC-3 IC50 = 1.0 nM 9.0 Concentration required for the 50% inhibition of human stomach cancer (NUGC3) ce... 15293996
HT-29 IC50 = 1.1 nM 8.96 Cytotoxicity against human HT-29 cells after 72 hrs by methylene blue dye assay 19586033
KB IC50 = 1.78 nM 8.75 Cytotoxicity against human KB cells after 72 hrs by methylene blue dye assay 19586033
MKN-45 IC50 = 3.2 nM 8.49 Growth inhibition of human MKN45 cells after 72 hrs by methylene blue dye assay 19053773
NON-PROTEIN TARGET IC50 = 3.4 nM 8.47 Antiproliferative activity against human Molt4/C8 cells 18260616
L1210 IC50 = 3.5 nM 8.46 Antiproliferative activity against mouse L1210 cells 18260616
CCRF-CEM IC50 = 3.6 nM 8.44 Antiproliferative activity against human CEM cells 18260616
FM3A IC50 = 3.7 nM 8.43 Antiproliferative activity against mouse FM3A cells 18260616
MKN-45 IC50 = 4.0 nM 8.4 Concentration required for the 50% inhibition of human stomach cancer (MKN45) ce... 15293996
MES-SA IC50 = 4.0 nM 8.4 Concentration required for the 50% inhibition of human uterine cancer (MESSA) ce... 15293996
KB IC50 = 4.0 nM 8.4 Antiproliferative activity against human KB cells 19743863
KB IC50 = 4.6 nM 8.34 Growth inhibition of human KB cells after 72 hrs by methylene blue dye assay 19053773
MKN-45 IC50 = 5.0 nM 8.3 Cytotoxicity against human MKN45 cells after 72 hrs by methylene blue dye assay 21434659
HT-29 IC50 = 5.9 nM 8.23 Growth inhibition of human HT-29 cells after 72 hrs by methylene blue dye assay 19053773
KB IC50 = 6.0 nM 8.22 Cytotoxicity against human KB cells after 72 hrs by methylene blue dye assay 21434659
KB IC50 = 6.2 nM 8.21 Growth inhibition of human Pgp170 overexpressing multidrug resistant-KB-VIN10 ce... 19053773
MCF7 IC50 = 7.0 nM 8.15 Concentration required for the 50% inhibition of human breast cancer (MCF-7) cel... 15293996
NCI-H460 IC50 = 7.1 nM 8.15 Growth inhibition of human H460 cells after 72 hrs by methylene blue dye assay 19053773
NCI-H460 IC50 = 7.0 nM 8.15 Antiproliferative activity against human H460 cells 19743863

Literature References

PubMed DOI Target Context # Activities
21434659 10.1021/jm101027s Rattus norvegicus 9
19586033 10.1021/jm900060s KB 2
19053773 10.1021/jm8008635 Unchecked 2
19586033 10.1021/jm900060s Unchecked 2
19586033 10.1021/jm900060s ADMET 2
19586033 10.1021/jm900060s Liver microsomes 2
21434659 10.1021/jm101027s No relevant target 2
19053773 10.1021/jm8008635 KB 2
15231674 10.1158/0008-5472.can-03-3474 ATP-dependent translocase ABCB1 2
18260616 10.1021/jm7011547 Unchecked 2
18583138 10.1016/j.bmc.2008.06.002 Unchecked 2
18260616 10.1021/jm7011547 FM3A 1
18583138 10.1016/j.bmc.2008.06.002 B16 1
18260616 10.1021/jm7011547 CCRF-CEM 1
18260616 10.1021/jm7011547 NON-PROTEIN TARGET 1
18260616 10.1021/jm7011547 L1210 1
15293996 10.1021/jm049802l Tubulin beta-1 chain 1
15293996 10.1021/jm049802l MCF7 1
27886544 10.1016/j.ejmech.2016.11.033 A549 1
15293996 10.1021/jm049802l MES-SA 1

Data from ChEMBL 36 via Core Engine