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Compound Detail

CHEMBL468935

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Nc1cccc(-c2csc(NC(=O)CCCCCCC(=O)NO)n2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL468935
Phase Preclinical
Structure Type MOL
InChI Key DRRQFLRBTKPRMM-UHFFFAOYSA-N
7
Targets
32
Activities
1
Assay Types
10
PK Parameters
20
Publications
0
Known Names

Molecular Properties

362.5
MW (Da)
3.18
ALogP
6
HBA
4
HBD
117.3
PSA (Ų)
0.24
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H22N4O3S
MW 362.46
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -1.30

Activity Summary

IC50 32 meas. best 9.76

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 9.76 9.1679 0.2 19
Histone deacetylase 6
CHEMBL1865
 IC50 8.52 8.52 3.0 1
Histone deacetylase
CHEMBL2093865
 IC50 8.41 8.255 3.9 2
Histone deacetylase 1
CHEMBL325
 IC50 8.4 8.4 4.0 1
Unchecked
CHEMBL612545
 IC50 7.98 7.98 10.4 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.0 6.4957 100.0 7
RAW
CHEMBL614631
 IC50 6.22 6.22 600.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3690.0 ng.hr.mL-1 Mus musculus
AUC 3603.0 ng.hr.mL-1 Mus musculus
Cmax 6897.31 nM Mus musculus
Cmax 1111.85 nM Mus musculus
T1/2 0.1833 hr Mus musculus
T1/2 1.0 hr Homo sapiens
T1/2 3.5 hr Mus musculus
T1/2 8.5 hr Mus musculus
Tmax 0.83 hr Mus musculus
Tmax 1.3 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.175 nM 9.76 Antiparasitic activity against chloroquine-resistant/verapamil-insensitive Plasm... -
Plasmodium falciparum IC50 = 0.23 nM 9.64 Inhibition of HDAC in Plasmodium falciparum 3D7 by fluorescent activity assay 19223622
Plasmodium falciparum IC50 = 0.4 nM 9.4 Antimalarial activity against Plasmodium falciparum 7G8 assessed as parasite gro... 19223622
Plasmodium falciparum IC50 = 0.59 nM 9.23 Antimalarial activity against Plasmodium falciparum infected in mouse RAW264.7 c... 18644969
Plasmodium falciparum IC50 = 0.6 nM 9.22 Antimalarial activity against drug-resistant Plasmodium falciparum TM90C2A 18644969
Plasmodium falciparum IC50 = 0.6 nM 9.22 Antimalarial activity against chloroquine-resistant Plasmodium falciparum FCB1 a... 19223622
Plasmodium falciparum IC50 = 0.6 nM 9.22 Antimalarial activity against Plasmodium falciparum FCR3 assessed as parasite gr... 19223622
Plasmodium falciparum IC50 = 0.6 nM 9.22 Antimalarial activity against Plasmodium falciparum Dd2 assessed as parasite gro... 19223622
Plasmodium falciparum IC50 = 0.6 nM 9.22 Antimalarial activity against Plasmodium falciparum 24904967
Plasmodium falciparum IC50 = 0.6 nM 9.22 Antiparasitic activity against chloroquine-resistant/verapamil-sensitive Plasmod... -
Plasmodium falciparum IC50 = 0.6 nM 9.22 Antiparasitic activity against chloroquine-resistant/verapamil-sensitive Plasmod... -
Plasmodium falciparum IC50 = 0.8 nM 9.1 Antimalarial activity against drug-resistant Plasmodium falciparum D6 infected i... 18644969
Plasmodium falciparum IC50 = 0.9 nM 9.05 Antimalarial activity against Plasmodium falciparum HB3 assessed as parasite gro... 19223622
Plasmodium falciparum IC50 = 0.9 nM 9.05 Antiparasitic activity against chloroquine-sensitive Plasmodium falciparum HB3 -
Plasmodium falciparum IC50 = 1.0 nM 9.0 Antimalarial activity against sPlasmodium falciparum VS/1 assessed as parasite g... 19223622
Plasmodium falciparum IC50 = 1.25 nM 8.9 Antiparasitic activity against chloroquine-sensitive Plasmodium falciparum 3D7 -
Plasmodium falciparum IC50 = 1.25 nM 8.9 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 as... 19223622
Plasmodium falciparum IC50 = 1.5 nM 8.82 Antimalarial activity against drug-resistant Plasmodium falciparum TM91C235 18644969
Plasmodium falciparum IC50 = 1.6 nM 8.8 Antimalarial activity against drug-resistant Plasmodium falciparum W2 18644969
Histone deacetylase 6 IC50 = 3.0 nM 8.52 Inhibition of human recombinant HDAC6 19419863

Literature References

PubMed DOI Target Context # Activities
18644969 10.1128/aac.00439-08 Plasmodium berghei 53
18644969 10.1128/aac.00439-08 Plasmodium falciparum 18
18644969 10.1128/aac.00439-08 Mus musculus 18
19223622 10.1128/aac.00729-08 Plasmodium falciparum 15
19223622 10.1128/aac.00729-08 Plasmodium berghei 11
19223622 10.1128/aac.00729-08 Mus musculus 10
18644969 10.1128/aac.00439-08 Unchecked 2
24904967 10.1016/j.ejmech.2014.05.050 Unchecked 1
19419863 10.1016/j.bmcl.2009.04.058 Histone deacetylase 1 1
24904967 10.1016/j.ejmech.2014.05.050 RAW 1
24904967 10.1016/j.ejmech.2014.05.050 Plasmodium falciparum 1
19223622 10.1128/aac.00729-08 Histone deacetylase 1
19223622 10.1128/aac.00729-08 Unchecked 1
18644969 10.1128/aac.00439-08 Vero 1
18644969 10.1128/aac.00439-08 RAW264.7 1
18644969 10.1128/aac.00439-08 Liver microsomes 1
18644969 10.1128/aac.00439-08 ADMET 1
18644969 10.1128/aac.00439-08 Histone deacetylase 1
19419863 10.1016/j.bmcl.2009.04.058 Histone deacetylase 6 1
19419863 10.1016/j.bmcl.2009.04.058 Histone deacetylase 3 1

Data from ChEMBL 36 via Core Engine