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Compound Detail

CHEMBL221655

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O=C(CCCCC[C@H](NC(=O)c1cc2ccccc2[nH]1)C(=O)Nc1cccc2cccnc12)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL221655
Phase Preclinical
Structure Type MOL
InChI Key IYQNLKIVMPPKFV-NRFANRHFSA-N
20
Targets
31
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

473.5
MW (Da)
3.91
ALogP
5
HBA
5
HBD
136.2
PSA (Ų)
0.14
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C26H27N5O4
MW 473.53
Aromatic Rings 4
Heavy Atoms 35
NP-Likeness -0.77

Activity Summary

IC50 31 meas. best 7.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 7.89 7.2933 13.0 9
SK-MEL-5
CHEMBL614922
 IC50 7.75 7.75 18.0 1
MCF7
CHEMBL387
 IC50 7.72 7.72 19.0 1
T47D
CHEMBL614361
 IC50 7.72 7.72 19.0 1
C180-13S
CHEMBL613540
 IC50 7.7 7.7 20.0 1
MM96L
CHEMBL614170
 IC50 7.68 7.68 21.0 1
DU-145
CHEMBL613508
 IC50 7.66 7.66 22.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.58 7.45 26.0 2
SK-MEL-28
CHEMBL614919
 IC50 7.48 7.48 33.0 1
Histone deacetylase 1
CHEMBL325
 IC50 7.32 7.32 48.0 1
HOP-62
CHEMBL614643
 IC50 7.2 7.2 63.0 1
A549
CHEMBL392
 IC50 7.16 7.16 69.0 1
Histone deacetylase
CHEMBL1293190
 IC50 7.11 7.11 78.0 1
HT-29
CHEMBL384
 IC50 7.1 7.1 79.0 1
COLO 205
CHEMBL614561
 IC50 6.99 6.99 102.0 1
Histone deacetylase 6
CHEMBL1865
 IC50 6.97 6.97 107.0 1
PC-3
CHEMBL390
 IC50 6.83 6.83 148.0 1
Plasmodium vivax
CHEMBL613013
 IC50 6.67 6.5733 214.0 3
NFF
CHEMBL614198
 IC50 6.47 6.47 337.0 1
ADMET
CHEMBL612558
 IC50 6.47 6.47 337.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 13.0 nM 7.89 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 as... 21135175
Plasmodium falciparum IC50 = 13.0 nM 7.89 Antiplasmodial activity against CQ-sensitive Plasmodium falciparum 3D7 25593097
Plasmodium falciparum IC50 = 13.0 nM 7.89 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 in... 18212103
SK-MEL-5 IC50 = 18.0 nM 7.75 Antiproliferative activity against human SK-Mel-5 cells 17181145
MCF7 IC50 = 19.0 nM 7.72 Antiproliferative activity against human MCF7 cells 17181145
T47D IC50 = 19.0 nM 7.72 Antiproliferative activity against human T-47D cells 17181145
C180-13S IC50 = 20.0 nM 7.7 Antiproliferative activity against human C180-13S cells 17181145
MM96L IC50 = 21.0 nM 7.68 Antiproliferative activity against human MM96L cells 17181145
DU-145 IC50 = 22.0 nM 7.66 Antiproliferative activity against human DU145 cells 17181145
NON-PROTEIN TARGET IC50 = 26.0 nM 7.58 Antiproliferative activity against human H520 cells 17181145
SK-MEL-28 IC50 = 33.0 nM 7.48 Antiproliferative activity against human SK-Mel-28 cells 17181145
Plasmodium falciparum IC50 = 33.0 nM 7.48 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Dd2 in... 18212103
Plasmodium falciparum IC50 = 33.0 nM 7.48 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Dd2 as... 21135175
Plasmodium falciparum IC50 = 33.0 nM 7.48 Antiplasmodial activity against CQ-resistant Plasmodium falciparum Dd2 25593097
Histone deacetylase 1 IC50 = 48.0 nM 7.32 Inhibition of recombinant human HDAC1 using Cbz-Lys(TFAc)-AMC as substrate by fl... 20947351
NON-PROTEIN TARGET IC50 = 48.0 nM 7.32 Antiproliferative activity against human JAM cells 17181145
HOP-62 IC50 = 63.0 nM 7.2 Antiproliferative activity against human HOP62 cells 17181145
A549 IC50 = 69.0 nM 7.16 Antiproliferative activity against human A549 cells 17181145
Histone deacetylase IC50 = 78.0 nM 7.11 Inhibition of Plasmodium falciparum 3D7 HDAC1 in infected-human erythrocytes ass... 20951583
HT-29 IC50 = 79.0 nM 7.1 Antiproliferative activity against human HT29 cells 17181145

Literature References

PubMed DOI Target Context # Activities
17181145 10.1021/jm050214x NFF 13
18212103 10.1128/aac.00757-07 Plasmodium falciparum 9
21135175 10.1128/aac.01220-10 Plasmodium falciparum 5
21135175 10.1128/aac.01220-10 Plasmodium vivax 3
17181145 10.1021/jm050214x NON-PROTEIN TARGET 2
20951583 10.1016/j.bmcl.2010.09.096 Histone deacetylase 2
18212103 10.1128/aac.00757-07 Unchecked 2
17181145 10.1021/jm050214x SK-MEL-5 2
25593097 10.1016/j.bmc.2014.12.018 Plasmodium falciparum 2
17181145 10.1021/jm050214x HOP-62 2
17181145 10.1021/jm050214x A549 2
17181145 10.1021/jm050214x SK-MEL-28 1
17181145 10.1021/jm050214x MCF7 1
17181145 10.1021/jm050214x T47D 1
17181145 10.1021/jm050214x C180-13S 1
17181145 10.1021/jm050214x PC-3 1
17181145 10.1021/jm050214x DU-145 1
18212103 10.1128/aac.00757-07 ADMET 1
20947351 10.1016/j.bmcl.2010.09.100 Histone deacetylase 1 1
17181145 10.1021/jm050214x Unchecked 1

Data from ChEMBL 36 via Core Engine