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Compound Detail

CHEMBL5270408

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COc1c(Cl)cc([C@@H]2c3cc4c(cc3C[C@H]3C(=O)NC(=O)N23)OCCO4)cc1Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5270408
Phase Preclinical
Structure Type MOL
InChI Key GANPPQNYXDZLNS-WMLDXEAASA-N
6
Targets
8
Activities
2
Assay Types
7
PK Parameters
11
Publications
0
Known Names

Molecular Properties

435.3
MW (Da)
3.34
ALogP
5
HBA
1
HBD
77.1
PSA (Ų)
0.73
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H16Cl2N2O5
MW 435.26
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness -0.04

Activity Summary

IC50 7 meas. best 8.28
Kd 1 meas. best 5.35

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 8.28 8.195 5.2 2
K562
CHEMBL385
 IC50 8.2 8.2 6.3 1
HT-29
CHEMBL384
 IC50 8.08 8.08 8.3 1
HCT-116
CHEMBL394
 IC50 8.06 8.06 8.7 1
MCF7
CHEMBL387
 IC50 8.04 8.04 9.2 1
Tubulin
CHEMBL2111354
 IC50 5.6 5.6 2520.0 1
Tubulin
CHEMBL2111354
 Kd 5.35 5.35 4490.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6.527 ng.hr.mL-1 Rattus norvegicus
CL 66.66 mL.min-1.kg-1 Homo sapiens
CL 65.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 16750.91 nM Rattus norvegicus
T1/2 0.4347 hr Homo sapiens
T1/2 1.59 hr Rattus norvegicus
Tmax 0.11 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 5.2 nM 8.28 Antiproliferative activity against paclitaxel-resistant human A549/TxR cells mea... 36471625
K562 IC50 = 6.3 nM 8.2 Antiproliferative activity against human K562 cells measured after 72 hrs by MTT... 36471625
Unchecked IC50 = 7.8 nM 8.11 Antiproliferative activity against paclitaxel-resistant human MCF7/TxR cells mea... 36471625
HT-29 IC50 = 8.3 nM 8.08 Antiproliferative activity against human HT-29 cells measured after 72 hrs by MT... 36471625
HCT-116 IC50 = 8.7 nM 8.06 Antiproliferative activity against human HCT-116 cells measured after 72 hrs by ... 36471625
MCF7 IC50 = 9.2 nM 8.04 Antiproliferative activity against human MCF7 cells measured after 72 hrs by MTT... 36471625
Tubulin IC50 = 2520.0 nM 5.6 Inhibition of porcine brain tubulin assessed as changes in the fluorescence inte... 36471625
Tubulin Kd = 4490.0 nM 5.35 Binding affinity to porcine brain tubulin assessed as changes in the fluorescenc... 36471625

Literature References

PubMed DOI Target Context # Activities
36471625 10.1021/acs.jmedchem.2c01595 MCF7 30
36471625 10.1021/acs.jmedchem.2c01595 ADMET 28
36471625 10.1021/acs.jmedchem.2c01595 Unchecked 12
36471625 10.1021/acs.jmedchem.2c01595 Tubulin 5
36471625 10.1021/acs.jmedchem.2c01595 ATP-dependent translocase ABCB1 2
36471625 10.1021/acs.jmedchem.2c01595 K562 1
36471625 10.1021/acs.jmedchem.2c01595 HT-29 1
36471625 10.1021/acs.jmedchem.2c01595 HCT-116 1
36471625 10.1021/acs.jmedchem.2c01595 No relevant target 1
36471625 10.1021/acs.jmedchem.2c01595 Tubulin beta 1
36471625 10.1021/acs.jmedchem.2c01595 A549 1

Data from ChEMBL 36 via Core Engine