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Compound Detail

CHEMBL144647

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COc1cc2c(c(N)c1OC)C(=O)/C(=C/c1cc(C)c(O)c(C)c1)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL144647
Phase Preclinical
Structure Type MOL
InChI Key KJTPWUVVLPCPJD-VGOFMYFVSA-N
7
Targets
11
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

339.4
MW (Da)
3.43
ALogP
5
HBA
2
HBD
81.8
PSA (Ų)
0.66
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H21NO4
MW 339.39
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness 0.52

Activity Summary

IC50 11 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Jurkat
CHEMBL397
 IC50 9.0 8.8 1.0 3
HL60/ADR
CHEMBL4296430
 IC50 8.7 8.7 2.0 1
Unchecked
CHEMBL612545
 IC50 8.7 8.7 2.0 3
MES-SA/Dx5
CHEMBL613827
 IC50 8.7 8.7 2.0 1
NCI/ADR-RES
CHEMBL613829
 IC50 8.7 8.7 2.0 1
KB 3-1
CHEMBL614590
 IC50 8.7 8.7 2.0 1
Tubulin
CHEMBL2094134
 IC50 5.77 5.77 1700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Jurkat IC50 = 1.0 nM 9.0 Cytotoxicity against human Jurkat cells assessed as growth inhibition 23961916
Jurkat IC50 = 1.0 nM 9.0 Cytotoxicity against human Jurkat cells assessed as growth inhibition 23961916
NCI/ADR-RES IC50 = 2.0 nM 8.7 Antiproliferative activity against multi drug resistant human NCI-ADR-RES cells ... 36126323
MES-SA/Dx5 IC50 = 2.0 nM 8.7 Antiproliferative activity against multi drug resistant human MES-SA/Dx5 cells a... 36126323
Unchecked IC50 = 2.0 nM 8.7 Antiproliferative activity against doxorubicin resistant human MDA-MB-231-Dox ce... 36126323
HL60/ADR IC50 = 2.0 nM 8.7 Antiproliferative activity against drug resistant human HL60/ADR cells assessed ... 36126323
Unchecked IC50 = 2.0 nM 8.7 Antiproliferative activity against multidrug resistant human CEM/VLB100 cells as... 36126323
KB 3-1 IC50 = 2.0 nM 8.7 Antiproliferative activity against multidrug resistant human KB-3-1 cells assess... 36126323
Unchecked IC50 = 2.0 nM 8.7 Antiproliferative activity against multidrug resistant human MV522/MDR1 cells as... 36126323
Jurkat IC50 = 4.0 nM 8.4 In vitro test for antitumor activity against human Jurkat cell line using a form... 10743954
Tubulin IC50 = 1700.0 nM 5.77 Inhibition of bovine brain tubulin polymerization preincubated for 30 mins follo... 36126323

Literature References

PubMed DOI Target Context # Activities
36126323 10.1021/acs.jmedchem.2c01150 Unchecked 3
23961916 10.1021/jm400954h Jurkat 2
10743954 10.1016/s0960-894x(00)00032-9 NCI-H596 1
36126323 10.1021/acs.jmedchem.2c01150 Tubulin 1
36126323 10.1021/acs.jmedchem.2c01150 HL60/ADR 1
36126323 10.1021/acs.jmedchem.2c01150 MES-SA/Dx5 1
36126323 10.1021/acs.jmedchem.2c01150 NCI/ADR-RES 1
10743954 10.1016/s0960-894x(00)00032-9 NIH3T3 1
10743954 10.1016/s0960-894x(00)00032-9 A549 1
10743954 10.1016/s0960-894x(00)00032-9 MCF7 1
10743954 10.1016/s0960-894x(00)00032-9 NCI-H292 1
10743954 10.1016/s0960-894x(00)00032-9 Jurkat 1
10743954 10.1016/s0960-894x(00)00032-9 HL-60 1
10743954 10.1016/s0960-894x(00)00032-9 K562 1
10743954 10.1016/s0960-894x(00)00032-9 WI-38 1
10743954 10.1016/s0960-894x(00)00032-9 WIL2 1
10743954 10.1016/s0960-894x(00)00032-9 MOLT-4 1
10743954 10.1016/s0960-894x(00)00032-9 B16 1
10743954 10.1016/s0960-894x(00)00032-9 L1210 1
10743954 10.1016/s0960-894x(00)00032-9 CCRF-CEM 1

Data from ChEMBL 36 via Core Engine