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Compound Detail

CHEMBL3323240

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COc1ccc2c(c1OC)C(=O)O[C@@H]2[C@H]1c2c(c(Br)c3c(c2OC)OCO3)CCN1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3323240
Phase Preclinical
Structure Type MOL
InChI Key PLMUFLAOTAHIIZ-SJORKVTESA-N
13
Targets
16
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

492.3
MW (Da)
3.64
ALogP
8
HBA
0
HBD
75.7
PSA (Ų)
0.60
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H22BrNO7
MW 492.32
Aromatic Rings 2
Heavy Atoms 31
NP-Likeness 1.26

Activity Summary

IC50 14 meas. best 5.85
EC50 1 meas. best 5.11
Kd 1 meas. best 4.27

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.85 5.6667 1400.0 3
HeLa
CHEMBL399
 IC50 5.58 5.58 2600.0 1
CCRF-CEM
CHEMBL382
 IC50 5.55 5.55 2800.0 1
Jurkat
CHEMBL397
 IC50 5.52 5.52 3000.0 1
HeLa
CHEMBL399
 EC50 5.11 5.11 7700.0 1
JeKo-1
CHEMBL4296445
 IC50 4.94 4.94 11500.0 1
MOLM-13
CHEMBL3706572
 IC50 4.82 4.82 15280.0 1
NB-4
CHEMBL614188
 IC50 4.79 4.79 16270.0 1
HT-29
CHEMBL384
 IC50 4.73 4.73 18700.0 1
LoVo
CHEMBL614721
 IC50 4.37 4.37 42800.0 1
Tubulin
CHEMBL2095182
 Kd 4.27 4.27 54000.0 1
A549
CHEMBL392
 IC50 4.13 4.13 73900.0 1
IGROV-1
CHEMBL613984
 IC50 4.11 4.11 78200.0 1
PBL
CHEMBL614233
 IC50 4.04 4.04 92200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 1400.0 nM 5.85 Antiproliferative activity against human RS4:11 cells assessed as reduction in c... 25050880
NON-PROTEIN TARGET IC50 = 1800.0 nM 5.75 Antiproliferative activity against human SEM cells assessed as reduction in cell... 25050880
HeLa IC50 = 2600.0 nM 5.58 Antiproliferative activity against human HeLa cells assessed as reduction in cel... 25050880
CCRF-CEM IC50 = 2800.0 nM 5.55 Antiproliferative activity against human CEM cells assessed as reduction in cell... 25050880
Jurkat IC50 = 3000.0 nM 5.52 Antiproliferative activity against human Jurkat cells assessed as reduction in c... 25050880
NON-PROTEIN TARGET IC50 = 4000.0 nM 5.4 Cytotoxicity against human Non-small cell lung cancer cell 25811651
HeLa EC50 = 7700.0 nM 5.11 Antimitotic activity against human HeLa cells 25811651
JeKo-1 IC50 = 11500.0 nM 4.94 Antiproliferative activity against human JeKo-1 cells assessed as inhibition of ... 38352836
MOLM-13 IC50 = 15280.0 nM 4.82 Antiproliferative activity against human MOLM-13 cells assessed as inhibition of... 38352836
NB-4 IC50 = 16270.0 nM 4.79 Antiproliferative activity against human NB4 cells assessed as inhibition of cel... 38352836
HT-29 IC50 = 18700.0 nM 4.73 Antiproliferative activity against human HT-29 cells assessed as reduction in ce... 25050880
LoVo IC50 = 42800.0 nM 4.37 Antiproliferative activity against human LoVo cells assessed as reduction in cel... 25050880
Tubulin Kd = 54000.0 nM 4.27 Binding affinity to tubulin (unknown origin) 25811651
A549 IC50 = 73900.0 nM 4.13 Antiproliferative activity against human A549 cells assessed as reduction in cel... 25050880
IGROV-1 IC50 = 78200.0 nM 4.11 Antiproliferative activity against human IGROV1 cells assessed as reduction in c... 25050880
PBL IC50 = 92200.0 nM 4.04 Cytotoxicity against PHA-stimulated human PBLs assessed as reduction in cell gro... 25050880

Literature References

PubMed DOI Target Context # Activities
25050880 10.1016/j.ejmech.2014.07.050 HeLa 28
38352836 10.1021/acsmedchemlett.3c00462 MOLM-13 9
25811651 10.1021/jm501180v Tubulin 4
25050880 10.1016/j.ejmech.2014.07.050 Tubulin 4
25811651 10.1021/jm501180v CCRF-CEM 4
25050880 10.1016/j.ejmech.2014.07.050 NON-PROTEIN TARGET 3
25050880 10.1016/j.ejmech.2014.07.050 Jurkat 2
38352836 10.1021/acsmedchemlett.3c00462 JeKo-1 2
38352836 10.1021/acsmedchemlett.3c00462 NB-4 2
25811651 10.1021/jm501180v HeLa 2
25811651 10.1021/jm501180v Molecular identity unknown 2
25811651 10.1021/jm501180v Unchecked 2
25811651 10.1021/jm501180v NON-PROTEIN TARGET 2
25050880 10.1016/j.ejmech.2014.07.050 PBL 2
25050880 10.1016/j.ejmech.2014.07.050 IGROV-1 1
25050880 10.1016/j.ejmech.2014.07.050 A549 1
25050880 10.1016/j.ejmech.2014.07.050 HT-29 1
25050880 10.1016/j.ejmech.2014.07.050 LoVo 1
25050880 10.1016/j.ejmech.2014.07.050 CCRF-CEM 1
38352836 10.1021/acsmedchemlett.3c00462 A549 1

Data from ChEMBL 36 via Core Engine